Remarkable potential of the α-aminophosphonate/phosphinate structural motif in medicinal chemistry

Journal of Medicinal Chemistry

Volumn 54, Issue 17, 2011, Pages 5955-5980

  Mucha, Artur ^a   Kafarski, Paweł ^a   Berlicki, Łukasz ^a  

^a WROCLAW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE TRIPHOSPHATE; ALAFOSFALIN; ALENDRONIC ACID; ALPHA AMINOPHOSPHONATE; BESTATIN; CLODRONIC ACID; COLLAGENASE 3; CYTOSOL AMINOPEPTIDASE; DITHIOCARBAMIC ACID; ETIDRONIC ACID; FOSINOPRIL; GLUTAMIC ACID; HUMAN IMMUNODEFICIENCY VIRUS PROTEINASE; INCADRONIC ACID; INTERSTITIAL COLLAGENASE; LEUCINE; MATRIX METALLOPROTEINASE; MATRIX METALLOPROTEINASE 14; MEMBRANE METALLOENDOPEPTIDASE; METALLOPROTEINASE; PAMIDRONIC ACID; PARACETAMOL; PEPSIN A; PHOSPHINIC ACID DERIVATIVE; PHOSPHORAMIDIC ACID; PYRIDOXAL 5 PHOSPHATE; RALOXIFENE; RENIN; RISEDRONIC ACID; SCAFFOLD PROTEIN; THREONINE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VANCOMYCIN; ZOLEDRONIC ACID;

BACILLUS ANTHRACIS; BREAST TUMOR; CARBOXY TERMINAL SEQUENCE; CATALYSIS; CELL SURVIVAL; DIZZINESS; DRUG TOLERABILITY; ESTERIFICATION; FATIGUE; GASTROINTESTINAL DISEASE; HEADACHE; HUMAN; MALARIA FALCIPARUM; NONHUMAN; PLASMODIUM CHABAUDI INFECTION; PROTEIN INTERACTION; PROTEIN STRUCTURE; REVIEW; STREPTOMYCES;

AMINO ACID MOTIFS; CHEMISTRY, PHARMACEUTICAL; HUMANS; PHOSPHINIC ACIDS; PHOSPHONIC ACIDS;

EID: 80052377713     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm200587f     Document Type: Review

References (229)

1. Hiroguchi, M.; Kandatsu, M. Isolation of 2-Aminoethanephosphonic Acid from Rumen Protozoa Nature 1959, 184, 901-902
2. Mastalerz, P. Inhibition of Glutamine Synthetase by Phosphonic Analogues of Glutamic Acid Arch. Immunol. Ter. Dosw. 1959, 7, 201-210
3. Kukhar, V. P.; Hudson, H. R. Aminophosphonic and Aminophosphinic Acids: Chemistry and Biological Activity; John Wiley & Sons: Chichester, U.K., 2000.
4. Kafarski, P.; Lejczak, B. Biological Activity of Aminophosphonic Acids Phosphorus, Sulfur Silicon Relat. Elem. 1991, 63, 193-215
5. Collinsová, M.; Jiráček, J. Phosphinic Acid Compounds in Biochemistry, Biology and Medicine Curr. Med. Chem. 2000, 7, 629-647 (Pubitemid 30396421)
6. Kafarski, P.; Lejczak, B. Aminophosphonic Acids of Potential Medical Importance Curr. Med. Chem.: Anti-Cancer Agents 2001, 1, 301-312
7. Berlicki, Ł.; Kafarski, P. Computer-Aided Analysis and Design of Phosphonic and Phosphinic Enzyme Inhibitors as Potential Drugs and Agrochemicals Curr. Org. Chem. 2005, 9, 1829-1850 (Pubitemid 41672457)
8. Wardle, N. J.; Bligh, S. W. A.; Hudson, H. R. ω-Phosphinyl-α- amino Acids: Synthesis, Development towards Use as Therapeutic Agents Curr. Org. Chem. 2007, 11, 1635-1651
9. Ecker, S. J.; Erion, M. D. Prodrugs of Phosphates and Phosphonates J. Med. Chem. 2008, 51, 2328-2345 (Pubitemid 351628494)
10. Lejczak, B.; Kafarski, P. Biological Activity of Aminophosphonic Acids and Their Short Peptides Top. Heterocycl. Chem. 2009, 20, 31-63
11. Orsini, F.; Sello, G.; Sisti, M. Aminophosphonic Acids and Derivatives. Synthesis and Biological Applications Curr. Med. Chem. 2010, 17, 264-289
12. Azema, L.; Baron, R.; Ladame, S. Targeting Enzymes with Phosphonate-Based Inhibitors: Mimics of Tetrahedral Transition States and Stable Isosteric Analogues of Phosphates Curr. Enzyme Inhib. 2006, 2, 61-72 (Pubitemid 44082963)
13. Macchiarulo, A.; Pellicciari, R. Exploring the Other Side of Biologically Relevant Chemical Space: Insights into Carboxylic, Sulfonic and Phosphonic acid Bioisosteric Relationships J. Mol. Graphics Modell. 2007, 26, 728-739 (Pubitemid 47615556)
14. Sun, L.; Chiu, D.; Kowal, D.; Simon, R.; Smeyne, M.; Zukin, R. S.; Olney, J.; Baudy, R.; Lin, S. Characterization of Two Novel N -Methyl- d -aspartate Antagonists: EAA-090 (2-[8,9-Dioxo-2,6-diazabicyclo[5.2.0]non-1(7)-en2-yl] ethylphosphonic Acid) and EAB-318 (R -α-Amino-5-chloro-1-(phosphonomethyl) -1 H -benzimidazole-2-propanoic Acid Hydrochloride) J. Pharmacol. Exp. Ther. 2004, 310, 563-570 (Pubitemid 38988900)
15. Badet, B.; Inagaki, K.; Soda, K.; Walsh, C. T. Time-Dependent Inhibition of Bacillus stearothermophilus Alanine Racemase by (1-Aminoethyl)phosphonate Isomers by Isomerization to Noncovalent Slowly Dissociating Enzyme-(1- aminoethyl)phosphonate Complexes Biochemistry 1986, 25, 3275-3282 (Pubitemid 16056970)
16. Stamper, C. G. F.; Morollo, A. A.; Ringe, D. Reaction of Alanine Racemase with 1-Aminoethylphosphonic Acid Forms a Stable External Aldimine Biochemistry 1998, 37, 10438-10445 (Pubitemid 28357566)
17. Shaw, J. P.; Petsko, G. A.; Ringe, D. Determination of the Structure of Alanine Racemase from Bacillus stearothermophilus at 1.9 Å Biochemistry 1997, 36, 1329-1342 (Pubitemid 27074957)
18. Au, K.; Ren, J.; Walter, T. S.; Harlos, K.; Nettleship, J. E.; Owens, R. J.; Stuart, D. I.; Esnouf, R. M. Structures of an Alanine Racemase from Bacillus anthracis (BA0252) in the Presence and Absence of (R)-1-Aminoethylphosphonic acid (L-Ala-P) Acta Crystallogr., Sect. F: Struct. Biol. Cryst. Commun. 2008, 64, 327-333 (Pubitemid 351631214)
19. Watanabe, A.; Kurosawa, Y.; Yoshimura, T.; Kurihata, T.; Soda, K.; Esaki, N. Role of Lysine 39 of Alanine Racemase from Bacillus stearothermophilus That Binds Pyridoxal 5′-Phosphate, Chemical Rescue Studies of Lys39-Ala Mutant J. Biol. Chem. 1999, 274, 4189-4194
20. Barreteau, H.; Kovač, A.; Boniface, A.; Sova, M.; Gobec, S.; Blanot, D. Cytoplasmic Steps of Peptidoglycan Biosynthesis FEMS Microbiol. Rev. 2008, 32, 168-207 (Pubitemid 351257820)
21. Tytgat, I.; Colacino, E.; Tulkens, P. M.; Poupaert, J. H.; Prévost, M.; Van Bambeke, F. DD-Ligases as a Potential Target for Antibiotics: Past, Present and Future Curr. Med. Chem. 2009, 16, 2566-2580
22. Ellsworth, B. A.; Tom, N. J.; Bartlett, P. A. Synthesis and Evaluation of Inhibitors of Bacterial d -Alanine: d -alanine Ligases Chem. Biol. 1996, 3, 37-44 (Pubitemid 126682707)
23. Fan, C.; Park, I. S.; Walsh, C. T.; Knox, J. R. d -Alanine: d -alanine Ligase: Phosphonate and Phosphinate Intermediates with Wild Type and the Y216F Mutant Biochemistry 1997, 36, 2531-2538 (Pubitemid 27106645)
24. Wu, D.; Zhang, L.; Kong, Y.; Du, J.; Chen, S.; Chen, J.; Ding, J.; Jiang, H.; Shen, X. Enzymatic Characterization and Crystal Structure Analysis of the d -Alanine- d -alanine Ligase from Helicobacter pylori Proteins 2008, 72, 1148-1160
25. Neuhaus, F. C. Role of Arg301 in Substrate Orientation and Catalysis in Subsite 2 of d -Alanine: d -alanine (d -Lactate) Ligase from Leuconostoc mesenteroides: A Molecular Docking Study J. Mol. Graphics Modell. 2010, 28, 728-734
26. Kuzin, A. P.; Sun, T.; Jorczak-Baillass, J.; Healy, V. L.; Walsh, C. T.; Knox, J. R. Enzymes of Vancomycin Resistance: The Structure of d -Alanine- d -Lactate Ligase of Naturally Resistant Leuconostoc mesenteroides Structure 2000, 8, 463-470 (Pubitemid 30304544)
27. Seto, H.; Kuzuyama, T. Bioactive Natural Products with Carbon-Phosphorus Bond and Their Biosynthesis Nat. Prod. Rep. 1999, 16, 589-596 (Pubitemid 29501613)
28. Akif, M.; Ntai, I.; Sturrock, D.; Isaac, R. E.; Bachmann, B. O.; Acharya, K. R. Crystal Structure of a Phosphonotripeptide K-26 in Complex with Angiotensin Converting Enzyme Homologue (AnCE) from Drosophila melanogaster Biochem. Biophys. Res. Commun. 2010, 398, 532-536
29. Ntai, I.; Bachmann, B. Identification of ACE Pharmacophore in the Phosphonopeptide Metabolite K-26 Bioorg. Med. Chem. Lett. 2008, 18, 3068-3071 (Pubitemid 351680387)
30. Johnson, R. D.; Gordee, R. S.; Kastner, R. M.; Larsen, S. H.; Ose, E. E. Antibiotic A53868 and Process for Production Thereof. U.K. Patent 2,127,413, 1984; Eli Lilly.
31. Chem. Abstr. 1984, 101, 88837.
32. Whitteck, J. T.; Ni, W.; Griffin, B. M.; Eliot, A. C.; Thomas, P. M.; Kelleher, N. L.; Metcalf, W. W.; van der Donk, W. A. Reassignment of the Structure of the Antibiotic A53868 Reveals an Unusual Amino Dehydrophosphonic Acid Angew. Chem., Int. Ed. 2007, 46, 9089-9909
33. Kuemin, M.; van der Donk, W. A. Structure-Activity Relationships of the Phosphonate Antibiotic Dehydrophos Chem. Commun. 2010, 46, 7694-7696
34. Allen, J. G.; Havas, L.; Leicht, E.; Lenox-Smith, I.; Nisbet, L. J. Phosphonopeptides as Antibacterial Agents: Metabolism and Pharmacokinetics of Alafosfalin in Animals and Humans Antimicrob. Agents Chemother. 1979, 16, 306-313 (Pubitemid 10224022)
35. Pauling, L. Chemical Achievement and Hope for the Future Am. Sci. 1948, 36, 51-58
36. Wolfenden, R. Transition State Analogues for Enzyme Catalysis Nature 1969, 223, 704-705
37. Kafarski, P.; Lejczak, B. The Biological Activity of Phosphono- and Phosphinopeptides. In Aminophosphonic and Aminophosphinic Acids. Chemistry and Biological Activity; Kukhar, V. P.; Hudson, H. R., Eds.; John Wiley & Sons: Chichester, U.K., 2000; pp 407-442.
38. Peyman, A. Aminophosphonic and Aminophosphinic Acids in the Design and Synthesis of HIV Protease Inhibitors. In Aminophosphonic and Aminophosphinic Acids. Chemistry and Biological Activity; Kukhar, V. P.; Hudson, H. R., Eds.; John Wiley & Sons: Chichester, U.K., 2000; pp 559-577.
39. Holden, H. M.; Tronrud, D. E.; Monzingo, A. F.; Weaver, L. H.; Matthews, B. W. Slow- and Fast-Binding Inhibitors of Thermolysin Display Different Modes of Binding: Crystallographic Analysis of Extended Phosphonamidate Transition-State Analogs Biochemistry 1987, 26, 8542-8553
40. Matthews, B. W. Structural Basis of the Action of Thermolysin and Related Zinc Peptidases Acc. Chem. Res. 1988, 21, 333-340
41. Mucha, A.; Dra̧g, M.; Dalton, J. P.; Kafarski, P. Metallo-aminopeptidase Inhibitors Biochimie 2010, 92, 1509-1529
42. Matsui, M.; Fowler, J. H.; Walling, L. L. Leucine Aminopeptidases: Diversity in Structure and Function Biol. Chem. 2006, 387, 1535-1544 (Pubitemid 44837577)
43. Grembecka, J.; Kafarski, P. Leucine Aminopeptidase as a Target for Inhibitor Design Mini-Rev. Med. Chem. 2001, 1, 133-144
44. Luan, Y.; Xu, W. The Structure and Main Functions of Aminopeptidase N Curr. Med. Chem. 2007, 14, 639-647 (Pubitemid 46477717)
45. Zhang, X.; Xu, W. Aminopeptidase N (APN/CD13) as a Target for Anti-Cancer Agent Design Curr. Med. Chem. 2008, 15, 2850-2865
46. Stack, C. M.; Lowther, J.; Cunningham, E.; Donnelly, S.; Gardiner, D. L.; Trenholme, K. R.; Skinner-Adams, T. S.; Teuscher, F.; Grembecka, J.; Mucha, A.; Kafarski, P.; Lua, L.; Bell, A.; Dalton, J. P. Characterization of the Plasmodium falciparum M17 Leucyl Aminopeptidase. A Protease Involved in Amino Acid Regulation with Potential for Antimalarial Drug Development J. Biol. Chem. 2007, 282, 2069-2080 (Pubitemid 47076702)
47. Skinner-Adams, T. S.; Stack, C. M.; Trenholme, K. R.; Brown, C. L.; Grembecka, J.; Lowther, J.; Mucha, A.; Drag, M.; Kafarski, P.; McGowan, S.; Whisstock, J. C.; Gardiner, D. L.; Dalton, J. P. Plasmodium falciparum Neutral Aminopeptidases: New Targets for Anti-Malarials Trends Biochem. Sci. 2010, 35, 53-61
48. Giannousis, P. P.; Bartlett, P. A. Phosphorus Amino Acid Analogues as Inhibitors of Leucine Aminopeptidase J. Med. Chem. 1987, 30, 1603-1609 (Pubitemid 17135907)
49. Lejczak, B.; Kafarski, P.; Zygmunt, J. Inhibition of Aminopeptidases by Aminophosphonates Biochemistry 1989, 28, 3549-3555 (Pubitemid 19121952)
50. Dra̧g, M.; Grembecka, J.; Pawełczak, M.; Kafarski, P. alpha-Aminoalkylphosphonates as a Tool in Experimental Optimization of P1 Side Chain Shape of Potential Inhibitors in S1 Pocket of Leucine and Neutral Aminopeptidases Eur. J. Med. Chem. 2005, 40, 764-771 (Pubitemid 41191117)
51. Pícha, J.; Liboska, R.; Buděšínský, M.; Jiráček, J.; Pawełczak, M.; Mucha, A. Unusual Activity Pattern of Leucine Aminopeptidase Inhibitors Based on Phosphorus Containing Derivatives of Methionine and Norleucine J. Enzyme Inhib. Med. Chem. 2011, 26, 155-161
52. Dra̧g, M.; Bogyo, M.; Ellman, J. A.; Salvesen, G. S. Aminopeptidase Fingerprints. An Integrated Approach for Identification of Good Substrates and Optimal Inhibitors J. Biol. Chem. 2010, 285, 3310-3318
53. Strater, N.; Lipscomb, W. N. Transition State Analogue l -Leucinephosphonic Acid Bound to Bovine Lens Leucine Aminopeptidase: X-ray Structure at 1.65 Å Resolution in a New Crystal Form Biochemistry 1995, 34, 9200-9210
54. Grembecka, J.; Mucha, A.; Cierpicki, T.; Kafarski, P. The Most Potent Organophosphorus Inhibitors of Leucine Aminopeptidase. Structure-based Design, Chemistry, and Activity J. Med. Chem. 2003, 46, 2641-2655 (Pubitemid 36702533)
55. Morgan, B.; Scholtz, J. M.; Ballinger, M. D.; Zipkin, I. D.; Bartlett, P. A. Differential Binding Energy: A Detailed Evaluation of the Influence of Hydrogen-Bonding and Hydrophobic Groups on the Inhibition of Thermolysin by Phosphorus-Containing Inhibitors J. Am. Chem. Soc. 1991, 113, 297-307
56. Mucha, A.; Grembecka, J.; Cierpicki, T.; Kafarski, P. Hydrolysis of the Phosphonamidate Bond in Phosphono Dipeptide Analogues: The Influence of the Nature of the N-Terminal Functional Group Eur. J. Org. Chem. 2003, 4797-4803
57. Mucha, A.; Laemmerhofer, M.; Lindner, W.; Pawełczak, M.; Kafarski, P. Individual Stereoisomers of Phosphinic Dipeptide Inhibitor of Leucine Aminopeptidase Bioorg. Med. Chem. Lett. 2008, 18, 1550-1554 (Pubitemid 351318263)
58. Skinner-Adams, T. S.; Lowther, J.; Teuscher, F.; Stack, C. M.; Grembecka, J.; Mucha, A.; Kafarski, P.; Trenholme, K. R.; Dalton, J. P.; Gardiner, D. L. Identification of Phosphinate Dipeptide Analog Inhibitors Directed against the Plasmodium falciparum M17 Leucine Aminopeptidase as Lead Antimalarial Compounds J. Med. Chem. 2007, 50, 6024-6031
59. McGowan, S.; Porter, C. J.; Lowther., J.; Stack, C. M.; Golding, S. J.; Skinner-Adams, T. S.; Trenholme, K. R.; Teuscher, F.; Donnelly, S. M.; Grembecka, J.; Mucha, A.; Kafarski, P.; Degori, R.; Buckle, A. M.; Gardiner, D. L.; Whisstock, J. C.; Dalton, J. P. Structural Basis for the Inhibition of the Essential Plasmodium falciparum M1 Neutral Aminopeptidase Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 2537-2542
60. McGowan, S.; Oellig, C. A.; Birru, W. A.; Caradoc-Davies, T. T.; Stack, C. M.; Lowther, J.; Skinner-Adams, T.; Mucha, A.; Kafarski, P.; Grembecka, J.; Trenholme, K. R.; Buckle, A. M.; Gardiner, D. L.; Dalton, J. P.; Whisstock, J. C. Structure of the Plasmodium falciparum M17 Aminopeptidase and Significance for the Design of Drugs Targeting the Neutral Exopeptidases Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 2449-2454
61. Chen, H.; Noble, F.; Mothé, A.; Meudal, H.; Coric, P.; Danascimento, S.; Roques, B. P.; George, P.; Fournié-Zaluski, M.-C. Phosphinic Derivatives as New Dual Enkephalin-Degrading Enzyme Inhibitors: Synthesis, Biological Properties, and Antinociceptive Activities J. Med. Chem. 2000, 43, 1398-1408 (Pubitemid 30212580)
62. Fournié-Zaluski, M.-C.; Poras, H.; Roques, B. P.; Nakajima, Y.; Ito, K.; Yoshimoto, T. Structure of Aminopeptidase N from Escherichia coli Complexed with the Transition-State Analogue Aminophosphinic Inhibitor PL250 Acta Crystallogr., Sect. D: Biol. Crystallogr. 2009, 65, 814-822
63. Dra̧g, M.; Grzywa, R.; Oleksyszyn, J. Novel Hydroxamic Acid Related Phosphinates: Inhibitor of Neutral Aminopeptidase N (APN) Bioorg. Med. Chem. Lett. 2007, 17, 1516-1519 (Pubitemid 46274368)
64. Grzywa, R.; Oleksyszyn, J. First Synthesis of α-Aminoalkyl-(N- substituted)-thiocarbamoylphosphinates. Inhibitors of Aminopeptidase N (APN/CD13) with the new Zinc-Binding Group Bioorg. Med. Chem. Lett. 2008, 18, 3734-3736 (Pubitemid 351795637)
65. Grzywa, R.; Oleksyszyn, J.; Salvesen, G. S.; Dra̧g, M. Identification of Very Potent Inhibitor of Human Aminopeptidase N (CD13) Bioorg. Med. Chem. Lett. 2010, 20, 2497-2499
66. Zitka, O.; Kukacka, J.; Krizkov, S.; Huska, D.; Adam, V.; Masarik, M.; Prusa, R.; Kizek, R. Matrix Metalloproteinases Curr. Med. Chem. 2010, 17, 3751-3768
67. Kessenbrock, K.; Plaks, V.; Werb, Z. Matrix Metalloproteinases: Regulators of the Tumor Microenvironment Cell 2010, 141, 52-67
68. Li, N.-G.; Shi, Z.-H.; Tang, Y.-P.; Duan, J.-A. Selective Matrix Metalloproteinase Inhibitors for Cancer Curr. Med. Chem. 2009, 16, 3805-3827
69. Konstantinopoulos, P. A.; Karamouzis, M. V.; Papatsoris, A. G.; Papavassiliou, A. G. Matrix Metalloproteinase Inhibitors As Anticancer Agents Int. J. Biochem. Cell Biol. 2008, 40, 1156-1168
70. Coussens, L. M.; Fingleton, B.; Matrisian, L. M. Matrix Metalloproteinases and Cancer: Trials and Tribulations Science 2002, 295, 2387-2392 (Pubitemid 34270240)
71. Devel, L.; Czarny, B.; Beau, F.; Georgiadis, D.; Stura, E.; Dive, V. Third Generation of Matrix Metalloprotease Inhibitors: Gain in Selectivity by Targeting the Depth of the S1′ Cavity Biochimie 2010, 92, 1501-1508
72. Nuti, E.; Tuccinardi, T.; Rossello, A. Matrix Metalloproteinase Inhibitors: New Challenges in the Era of Post Broad-Spectrum Inhibitors Curr. Pharm. Des. 2007, 13, 2087-2100 (Pubitemid 47040490)
73. Veerendhar, A.; Reich, R.; Breuer, E. Phosphorus Based Inhibitors of Matrix Metalloproteinases C. R. Chim. 2010, 13, 1191-1202
74. Dive, V.; Georgiadis, D.; Matziari, M.; Makaritis, A.; Beau, F.; Cuniasse, P.; Yiotakis, A. Phosphinic Peptides As Zinc Metalloproteinase Inhibitors Cell. Mol. Life Sci. 2004, 61, 2010-2019 (Pubitemid 39149891)
75. Yiotakis, A.; Vassiliou, S.; Jiráček, J.; Dive, V. Protection of the Hydroxyphosphinyl Function of Phosphinic Dipeptides by Adamantyl. Application to the Solid-Phase Synthesis of Phosphinic Peptides J. Org. Chem. 1996, 61, 6601-6605 (Pubitemid 26328647)
76. Yiotakis, A.; Georgiadis, D.; Matziari, M.; Makaritis, A.; Dive, V. Phosphinic Peptides: Synthetic Approaches and Biochemical Evaluation as Zn-Metalloprotease Inhibitors Curr. Org. Chem. 2004, 8, 1135-1158 (Pubitemid 38976459)
77. Vassiliou, S.; Mucha, A.; Cuniasse, P.; Georgiadis, D.; Lucet-Levannier, K.; Beau, F.; Kannan, R.; Murphy, G.; Knäuper, V.; Rio, M.-C.; Basset, P.; Yiotakis, A.; Dive, V. Phosphinic Pseudo-Tripeptides as Potent Inhibitors of Matrix Metalloproteinases: A Structure-Activity Study J. Med. Chem. 1999, 42, 2610-2620 (Pubitemid 29344301)
78. Matziari, M.; Dive, V.; Yiotakis, A. Matrix Metalloproteinase 11 (MMP-11; Stromelysin-3) and Synthetic Inhibitors Med. Res. Rev. 2007, 27, 528-552 (Pubitemid 46984659)
79. Cuniasse, P.; Devel, L.; Makaritis, A.; Beau, F.; Georgiadis, D.; Matziari, M.; Yiotakis, A.; Dive, V. Future Challenges Facing the Development of Specific Active-Site-Directed Synthetic Inhibitors of MMPs Biochimie 2005, 87, 393-402 (Pubitemid 40387619)
80. Matziari, M.; Beau, F.; Cuniasse, P.; Dive, V.; Yiotakis, A. Evaluation of P-1′-Diversified Phosphinic Peptides Leads to the Development of Highly Selective Inhibitors of MMP-11 J. Med. Chem. 2004, 47, 325-336 (Pubitemid 38057877)
81. Matziari, M.; Georgiadis, D.; Dive, V.; Yiotakis, A. Convenient Synthesis and Diversification of Dehydroalaninyl Phosphinic Peptide Analogues Org. Lett. 2001, 3, 659-662
82. Dive, V.; Andarawewa, K. L.; Boulay, A.; Matziari, M.; Beau, F.; Guerin, E.; Rousseau, B.; Yiotakis, A.; Rio, M.-C. Dosing and Scheduling Influence the Antitumor Efficacy of a Phosphinic Peptide Inhibitor of Matrix Metalloproteinases Int. J. Cancer 2005, 113, 775-781 (Pubitemid 40101259)
83. Gall, A. L.; Ruff, M.; Kannan, R.; Cuniasse, P.; Yiotakis, A.; Dive, V.; Rio, M. C.; Basset, P.; Moras, D. Crystal Structure of the Stromelysin-3 (MMP-11) Catalytic Domain Complexed with a Phosphinic Inhibitor Mimicking the Transition-State J. Mol. Biol. 2001, 307, 577-586 (Pubitemid 33027678)
84. Bernstein, K. E.; Shen, X. Z.; Gonzalez-Villalobos, R. A.; Billet, S.; Okwan-Duodu, D.; Ong, F. S.; Fuchs, S. Different in Vivo Functions of the Two Catalytic Domains of Angiotensin-Converting Enzyme (ACE) Curr. Opin. Pharmacol. 2011, 11, 105-111
85. Dive, V.; Cotton, J.; Yiotakis, A.; Michaud, A.; Vassiliou, S.; Jiráček, J.; Vazeux, G.; Chauvet, M.-T.; Cuniasse, P.; Corvol, P. RXP 407, a Phosphinic Peptide, Is a Potent Inhibitor of Angiotensin I Converting Enzyme Able To Differentiate between Its Two Active Sites Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 4330-4335 (Pubitemid 29190336)
86. Junot, C.; Gonzales, M.-F.; Ezan, E.; Cotton, J.; Vazeux, G.; Michaud, A.; Azizi, M.; Vassiliou, S.; Yiotakis, A.; Corvol, P.; Dive, V. RXP 407, a Selective Inhibitor of the N-Domain of Angiotensin I-Converting Enzyme, Blocks in Vivo the Degradation of Hemoregulatory Peptide Acetyl-Ser-Asp-Lys-Pro with No Effect on Angiotensin I Hydrolysis J. Pharmacol. Exp. Ther. 2001, 297, 606-611 (Pubitemid 32377991)
87. Georgiadis, D.; Beau, F.; Czarny, B.; Cotton, J.; Yiotakis, A.; Dive, V. Roles of the Two Active Sites of Somatic Angiotensin-Converting Enzyme in the Cleavage of Angiotensin I and Bradykinin Insights from Selective Inhibitors Circ. Res. 2003, 93, 148-154 (Pubitemid 36919702)
88. Anthony, C. S.; Corradi, H. R.; Schwager, S. L. U.; Redelinghuys, P.; Georgiadis, D.; Dive, V.; Acharya, K. R.; Sturrock, E. D. The N Domain of Human Angiotensin-I-Converting Enzyme. The Role of N-Glycosylation and the Crystal Structure in Complex with an N Domain-Specific Phosphinic Inhibitor, RXP407 J. Biol. Chem. 2010, 285, 35685-35693
89. Georgiadis, D.; Cuniasse, P.; Cotton, J.; Yiotakis, A.; Dive, V. Structural Determinants of RXPA380, a Potent and Highly Selective Inhibitor of the Angiotensin-Converting Enzyme C-Domain Biochemistry 2004, 43, 8048-8054 (Pubitemid 38808259)
90. Corradi, H. R.; Chitapi, I.; Sewell, B. T.; Georgiadis, D.; Dive, V.; Sturrock, E. D.; Acharya, K. R. The Structure of Testis Angiotensin-Converting Enzyme in Complex with the C Domain-Specific Inhibitor RXPA380 Biochemistry 2007, 46, 5473-5478 (Pubitemid 46717270)
91. Kröger, W. L.; Douglas, R. G.; O'Neill, H. G.; Dive, V.; Sturrock, E. D. Investigating the Domain Specificity of Phosphinic Inhibitors RXPA380 and RXP407 in Angiotensin-Converting Enzyme Biochemistry 2009, 48, 8405-8412
92. Jullien, N.; Makritis, A.; Georgiadis, D.; Beau, F.; Yiotakis, A.; Dive, V. Phosphinic Tripeptides as Dual Angiotensin-Converting Enzyme C-Domain and Endothelin-Converting Enzyme-1 Inhibitors J. Med. Chem. 2010, 53, 208-220
93. Akif, M.; Georgiadis, D.; Mahajan, A.; Dive, V.; Sturrock, E. D.; Isaac, R. E.; Acharya, K. R. High-Resolution Crystal Structures of Drosophila Melanogaster Angiotensin-Converting Enzyme in Complex with Novel Inhibitors and Antihypertensive Drugs J. Mol. Biol. 2010, 400, 502-517
94. Krapcho, J.; Turk, C.; Cushman, D. W.; Powell, J. R.; DeForrest, J. M.; Spitzmiller, E. R.; Karanewsky, D. S.; Duggan, M. E.; Rovnyak, G. C.; Schwartz, J.; Natarajan, S.; Godfrey, J. D.; Ryono, D. E.; Neubeck, R.; Atwal, K. S.; Petrillo, E. W. Angiotensin-Converting Enzyme Inhibitors. Mercaptan, Carboxyalkyl Dipeptide, and Phosphinic Acid Inhibitors Incorporating 4-Substituted Prolines J. Med. Chem. 1988, 31, 1148-1160
95. Murdoch, D.; McTavish, D. Fosinopril. A Review of Its Pharmacodynamic and Pharmacokinetic Properties, and Therapeutic Potential in Essential Hypertension Drugs 1992, 43, 123-140
96. Ding, P. Y.; Chu, K. M.; Hu, O. Y.; Huang, G. M.; Jeng, J. J.; Chang, A.; Delaney, C. L.; MacAskill, M.; Yang, B. C.; Jemal, M.; Smith, R.; Liao, W. C. Fosinopril: Pharmacokinetics and Pharmacodynamics in Chinese Subjects J. Clin. Pharmacol. 1999, 39, 155-160 (Pubitemid 29068160)
97. Krajewska, B.; Ureases, I. Functional, Catalytic and Kinetic Properties: A Review J. Mol. Catal. B 2009, 59, 9-21
98. Mobley, H. L. T.; Island, M. D.; Hausinger, R. P. Molecular Biology of Microbial Ureases Microbiol. Rev. 1995, 59, 451-480
99. Burne, R. A.; Chen, Y. M. Bacterial Ureases in Infectious Diseases Microbes Infect. 2000, 2, 533-542 (Pubitemid 30387207)
100. Follmer, C. Ureases as a Target for the Treatment of Gastric and Urinary Infections J. Clin. Pathol. 2010, 63, 424-430
101. Kosikowska, P.; Berlicki, Ł. Urease Inhibitors as Potential Drugs for Gastric and Urinary Tract Infections: A Patent Review Expert Opin. Ther. Pat. 2011, 21, 945-957
102. Amtul, Z.; Atta-ur-Rahman; Siddiqui, R. A.; Choudhary, M. I. Chemistry and Mechanism of Urease Inhibition Curr. Med. Chem. 2002, 9, 1323-1348 (Pubitemid 34759887)
103. Pope, A. J.; Toseland, C. D.; Rushant, B.; Richardson, S.; McVey, M.; Hills, J. Effect of Potent Urease Inhibitor, Fluorofamide, on Helicobacter sp. in Vivo and in Vitro Dig. Dis. Sci. 1998, 43, 109-119 (Pubitemid 28081650)
104. Vassiliou, S.; Grabowiecka, A.; Kosikowska, P.; Yiotakis, A.; Kafarski, P.; Berlicki, Ł. Design, Synthesis and Evaluation of Novel Organophosphorus Inhibitors of Bacterial Ureases J. Med. Chem. 2008, 51, 5736-5744
105. Berlicki, Ł.; Bochno, M.; Grabowiecka, A.; Białas, A.; Kosikowska, P.; Kafarski, P. N-Substituted Aminomethanephosphonic and Aminomethane- P -methylphosphinic Acids as Inhibitors of Ureases. Amino Acids 2011, DOI: 10.1007/s00726-011-0920-4.
106. Vassiliou, S.; Kosikowska, P.; Grabowiecka, A.; Yiotakis, A.; Kafarski, P.; Berlicki, Ł. Computer-Aided Optimization of Phosphinic Inhibitors of Bacterial Ureases J. Med. Chem. 2010, 53, 5597-5606
107. Bailie, N. C.; Osborne, C. A.; Leininger, J. R.; Fletcher, T. F.; Johnston, S. D.; Ogburn, P. N.; Griffith, D. P. Teratogenic Effect of Acetohydroxamic Acid in Clinically Normal Beagles Am. J. Vet. Res. 1986, 47, 2604-2611 (Pubitemid 17222324)
108. Bajgar, J. Organophosphates/Nerve Agent Poisoning: Mechanism of Action, Diagnosis, Prophylaxis, and Treatment Adv. Clin. Chem. 2004, 38, 151-216
109. Oleksyszyn, J.; Powers, J. C. Amino Acid and Peptide Phosphonate as Specific Inhibitors of Serine Peptidases. In Methods in Enzymology; Barrett, A. J., Ed.; Academic Press: San Diego, CA, 1994; Vol. 244, pp 423-441.
110. Oleksyszyn, J. Aminophosphonic and Aminophosphinic Acid Derivatives in the Design of Transition State Analogue Inhibitors: Biomedical Opportunities and Limitations. In Aminophosphonic and Aminophosphinic Acids. Chemistry and Biological Activity; Kukhar, V. P.; Hudson, H. R., Eds.; John Wiley & Sons: Chichester, U.K., 2000; pp 537-557.
111. Sieńczyk, M.; Oleksyszyn, J. Irreversible Inhibition of Serine Proteases: Design and in Vivo Activity of Diaryl α-Aminophosphonate Derivatives Curr. Med. Chem. 2009, 16, 1673-1687
112. Bertrand, J. A.; Oleksyszyn, J.; Kam, C. M.; Boduszek, B.; Presnell, S.; Plaskon, R. R.; Suddath, F. L.; Powers, J. C.; Williams, L. D. Inhibition of Trypsin and Thrombin by Amino(4-amidinophenyl)methanephosphonate Diphenyl Ester Derivatives: X-ray Structures and Molecular Models Biochemistry 1996, 35, 3147-3155
113. Oleksyszyn, J.; Powers, J. C. Irreversible Inhibition of Serine Proteases by Peptide Derivatives of (alpha-Aminoalkyl)phosphonate diphenyl esters Biochemistry 1991, 30, 485-493
114. Bartlett, P. A.; Lamden, L. A. Inhibition of Chymotrypsin by Phosphonate and Phosphonamidate Peptide Analogs Bioorg. Chem. 1986, 14, 356-377 (Pubitemid 17225820)
115. Sampson, N. S.; Bartlett, P. A. Peptidic Phosphonylating Agents as Irreversible Inhibitors of Serine Proteases and Models of the Tetrahedral Intermediates Biochemistry 1991, 30, 2255-2263
116. Bone, R.; Sampson, N. S.; Bartlett, P. A.; Agard, D. A. Crystal Structures of alpha-Lytic Protease Complexes with Irreversibly Bound Phosphonate Esters Biochemistry 1991, 30, 2263-2272
117. Skordalakes, E.; Dodson, G. G.; Green, D. S.; Goodwin, C. A.; Scully, M. F.; Hudson, H. R.; Kakkar, V. V.; Deadman, J. J. Inhibition of Human alpha-Thrombin by a Phosphonate Tripeptide Proceeds via a Metastable Pentacoordinated Phosphorus Intermediate J. Mol. Biol. 2001, 311, 549-555 (Pubitemid 32821157)
118. Rahil, J.; Pratt, R. F. Mechanism of Inhibition of the Class C beta-Lactamase of Enterobacter cloacae P99 by Phosphonate Monoesters Biochemistry 1992, 31, 5869-5878
119. Lobkovsky, E.; Billings, E. M.; Moews, P. C.; Rahil, J.; Pratt, R. F.; Knox, J. R. Crystallographic Structure of a Phosphonate Derivative of the Enterobacter cloacae P99 Cephalosporinase: Mechanistic Interpretation of a beta-Lactamase Transition-State Analog Biochemistry 1994, 33, 6762-6772 (Pubitemid 24190798)
120. Ulisse, S.; Baldini, E.; Sorrenti, S.; D'Armiento, M. The Urokinase Plasminogen Activator System: A Target for Anti-Cancer Therapy Curr. Cancer Drug Targets 2009, 9, 32-71
121. Dass, K.; Ahmad, A.; Azmi, A. S.; Sarkar, S. H.; Sarkar, F. H. Evolving Role of uPA/uPAR System in Human Cancers Cancer Treat. Rev. 2008, 34, 122-136
122. Mekkawy, A. H.; Morris, D. L.; Pourgholami, M. H. Urokinase Plasminogen Activator System as a Potential Target for Cancer Therapy Future Oncol. 2009, 5, 1487-1499
123. Hildenbrand, R.; Allgayer, H.; Marx, A.; Stroebel, P. Modulators of the Urokinase-Type Plasminogen Activation System for Cancer Expert Opin. Invest. Drugs 2010, 19, 641-652
124. Joossens, J.; Van der Veken, P.; Lambeir, A.-M.; Augustyns, K.; Haemers, A. Development of Irreversible Diphenyl Phosphonate Inhibitors for Urokinase Plasminogen Activator J. Med. Chem. 2004, 47, 2411-2413 (Pubitemid 38580077)
125. Joossens, J.; Ali, O. M.; El-Sayed, I.; Surpateanu, G.; Van der Veken, P.; Lambeir, A.-M.; Setyono-Han, B.; Foekens, J. A.; Schneider, A.; Schmalix, W.; Haemers, A.; Augustyns, K. Small, Potent, and Selective Diaryl Phosphonate Inhibitors for Urokinase-Type Plasminogen Activator with in Vivo Antimetastatic Properties J. Med. Chem. 2007, 50, 6638-6646
126. Sieńczyk, M.; Oleksyszyn, J. Inhibition of Trypsin and Urokinase by Cbz-amino(4-guanidinophenyl)methanephosphonate Aromatic Ester Derivatives: The Influence of the Ester Group on Their Biological Activity Bioorg. Med. Chem. Lett. 2006, 16, 2886-2890 (Pubitemid 44316651)
127. Havale, S. H.; Pal, M. Medicinal Chemistry Approaches to the Inhibition of Dipeptidyl Peptidase-4 for the Treatment of Type 2 Diabetes Bioorg. Med. Chem. 2009, 17, 1783-1802
128. Gwaltney, S. L. Medicinal Chemistry Approaches to the Inhibition of Dipeptidyl Peptidase IV Curr. Top. Med. Chem. 2008, 8, 1545-1552
129. Gupta, R.; Walunj, S. S.; Tokala, R. K.; Parsa, K. V.; Singh, S. K.; Pal, M. Emerging Drug Candidates of Dipeptidyl Peptidase IV (DPP IV) Inhibitor Class for the Treatment of Type 2 Diabetes Curr. Drug Targets 2009, 10, 71-87
130. Doupis, J.; Veves, A. DPP4 Inhibitors: A New Approach in Diabetes Treatment Adv. Ther. 2008, 25, 627-643
131. Ohnuma, K.; Takahashi, N.; Yamochi, T.; Hosono, O.; Dang, N. H.; Morimoto, C. Role of CD26/Dipeptidyl Peptidase IV in Human T Cell Activation and Function Front. Biosci. 2008, 13, 2299-2310 (Pubitemid 351589255)
132. Thompson, M. A.; Ohnuma, K.; Abe, M.; Morimoto, C.; Dang, N. H. CD26/Dipeptidyl Peptidase IV as a Novel Therapeutic Target for Cancer and Immune Disorders Mini-Rev. Med. Chem. 2007, 7, 253-273 (Pubitemid 46488249)
133. Boduszek, B.; Oleksyszyn, J.; Kam, C. M.; Selzler, J.; Smith, R. E.; Powers, J. C. Dipeptide Phosphonates as Inhibitors of Dipeptidyl Peptidase IV J. Med. Chem. 1994, 37, 3969-3976 (Pubitemid 24379686)
134. Belyaev, A.; Zhang, X.; Augustyns, K.; Lambeir, A.-M.; De Meester, I.; Vedernikova, I.; Scharpe, S.; Haemers, A. Structure-Activity Relationship of Diaryl Phosphonate Esters as Potent Irreversible Dipeptidyl Peptidase IV Inhibitors J. Med. Chem. 1999, 42, 1041-1052 (Pubitemid 29153433)
135. Augustyns, K.; Van der Veken, P.; Senten, K.; Haemers, A. The Therapeutic Potential of Inhibitors of Dipeptidyl Peptidase IV (DPP IV) and Related Proline-Specific Dipeptidyl Aminopeptidases Curr. Med. Chem. 2005, 12, 971-998 (Pubitemid 40443851)
136. Van der Veken, P.; Haemers, A.; Augustyns, K. Prolyl Peptidases Related to Dipeptidyl Peptidase IV: Potential of Specific Inhibitors in Drug Discovery Curr. Top. Med. Chem. 2007, 7, 621-635 (Pubitemid 46488284)
137. Jung, F. J.; Yang, L.; De Meester, I.; Augustyns, K.; Cardell, M.; Hillinger, S.; Vogt, P.; Lardinois, D.; Scharpé, S.; Weder, W.; Korom, S. CD26/Dipeptidylpeptidase IV-Targeted Therapy of Acute Lung Rejection in Rats J. Heart Lung Transplant. 2006, 25, 1109-1116 (Pubitemid 44311522)
138. Zhai, W.; Cardell, M.; De Meester, I.; Augustyns, K.; Hillinger, S.; Inci, I.; Arni, S.; Jungraithmayr, W.; Scharpé, S.; Weder, W.; Korom, S. Intragraft DPP IV Inhibition Attenuates Post-Transplant Pulmonary Ischemia/Reperfusion Injury after Extended Ischemia J. Heart Lung Transplant. 2007, 26, 174-180 (Pubitemid 46136044)
139. Gilmore, B. F.; Lynas, J. F.; Scott, C. J.; McGoohan, C.; Martin, L.; Walker, B. Dipeptide Proline Diphenyl Phosphonates Are Potent, Irreversible Inhibitors of Seprase (FAPα) Biochem. Biophys. Res. Commun. 2006, 346, 436-446 (Pubitemid 43902705)
140. Van der Veken, P.; Soroka, A.; Brandt, I.; Chen, Y.-S.; Maes, M.-B.; Lambeir, A.-M.; Chen, X.; Haemers, A.; Scharpé, S.; Augustyns, K.; De Meester, I. Irreversible Inhibition of Dipeptidyl Peptidase 8 by Dipeptide-Derived Diaryl Phosphonates J. Med. Chem. 2007, 50, 5568-5570 (Pubitemid 350106012)
141. Juillerat-Jeanneret, L.; Gerber-Lemaire., S. The Prolyl-aminodipeptidases and Their Inhibitors as Therapeutic Targets for Fibrogenic Disorders Mini-Rev. Med. Chem. 2009, 9, 215-226
142. Singh, J.; Petter, R. C.; Baillie, T. A.; Whitty, A. The Resurgence of Covalent Drugs Nat. Rev. Drug Discovery 2011, 10, 307-317
143. Kiss, T.; Lázár, I. Structure and Stability Constants of Metal Complexes in Solution. In Aminophosphonic and Aminophosphinic Acids. Chemistry and Biological Activity; Kukhar, V. P.; Hudson, H. R., Eds.; John Wiley & Sons: Chichester, U.K., 2000; pp 285-325.
144. Fleisch, H.; Russel, R. G. G.; Staruman, F. Effect of Pyrophosphate and Hydroxyapatite and Its Implications in Calcium Homeostasis Nature 1966, 212, 901-903
145. Russell, R. G. G. Bisphosphonates: From Bench to Bedside Ann. N.Y. Acad. Sci. 2006, 1068, 367-401 (Pubitemid 43824169)
146. Shaw, N. J.; Bishop, N. J. Bisphosphonate Treatment of Bone Disease Arch. Dis. Child. 2005, 90, 494-499 (Pubitemid 40627446)
147. Wu, S.; Dahut, W. L.; Gulley, J. L. The Use of Bisphosphonates in Cancer Patients Acta Oncol. 2007, 46, 581-591 (Pubitemid 46911914)
148. Mukherjee, S.; Song, Y.; Oldfield, E. NMR Investigations of the Static and Dynamic Structures of Bisphosphonates on Human Bone: A Molecular Model J. Am. Chem. Soc. 2008, 130, 1264-1273 (Pubitemid 351171005)
149. Mönkkönen, H.; Kuokkanen, J.; Holen, I.; Evans, A.; Lefley, D. V.; Jauhiainen, M.; Auriola, S.; Mönkkönen, J. Bisphosphonate-Induced ATP Analog Formation and Its Effect on Inhibition of Cancer Cell Growth Anti-Cancer Drugs 2008, 19, 391-399
150. Clezardin, P.; Ebetino, F. H.; Fournier, P. G. Bisphosphonates and Cancer-Induced Bone Disease: Beyond Their Antireserptive Activity Cancer Res. 2005, 65, 4971-4974 (Pubitemid 40827299)
151. Usui, T.; Oiso, Y.; Tomito, A.; Ogata, E.; Uchida, T.; Ikeda, K. Pharmacokinetics of Incadronate, a New Bisphosphonate, in Healty Volunteers and Patients with Malignancy-Associated Hypercalcemia Int. J. Clin. Pharmacol. Ther. 1997, 35, 239-244 (Pubitemid 27268172)
152. Kim, S.; Lee, J.; Kim, H.; Im, Y.; Kim, T.; Ryoo, B.; Park, Y.; Park, J.; Park, K.; Katoh, H. Clinical Evaluation of Incadronate in Korean Patients with Malignancy-Associated Hypercalcemia: An Open-Label, Multicenter Study Curr. Ther. Res. 2007, 68, 193-204 (Pubitemid 47268442)
153. Shipman, C. M.; Croucher, P. I.; Russell, R. G. G.; Helfrich, M. H.; Rogers, M. J. The Bisphosphonate Incadronate (YM175) Causes Apoptosis of Human Myeloma Cells in Vitro by Inhibiting Mevalonate Pathway Cancer Res. 1998, 58, 5294-5297 (Pubitemid 28551102)
154. Tanvetyanon, T.; Stiff, P. J. Management of the Adverse Efects Associated with Intravenous Bisphosphonates Ann. Oncol. 2006, 17, 897-907 (Pubitemid 43785797)
155. Drake, M. T.; Clarke, B. L.; Khosla, S. Bisphosphonates: Mechanism of Action and Role in Clinical Practice Mayo Clin. Proc. 2008, 83, 1032-1045
156. Dunford, J. E.; Thompson, K.; Coxon, F. P.; Luckman, S. P.; Hahn, F. M.; Poulter, C. D.; Ebetino, F. H.; Rogers, M. J. Structure-Activity Relationships for Inhibition of Farnesyl Diphosphate Synthase in Vitro and Inhibition of Bone Resorption in Vivo by Nitrogen-Containing Bisphosphonates J. Pharmacol. Exp. Ther. 2001, 296, 235-242 (Pubitemid 32112446)
157. Russell, R. G.; Xia, Z.; Dunford, J. E.; Oppermann, U.; Kwaasi, A.; Hulley, P. A.; Kavanagh, K. L.; Triffitt, J. T.; Lundy, M. W.; Phipps, R. J.; Barnett, B. L.; Coxon, F. P.; Rogers, M. J.; Watts, N. B.; Ebetino, F. H. Bisphosphonates: An Update on Mechanisms of Action and How These Relate to Clinical Efficacy Ann. N.Y. Acad. Sci. 2007, 1117, 209-257 (Pubitemid 350191297)
158. Frith, J. C.; Mönkkönen, J.; Auriola, S.; Mönkkönen, H.; Rogers, M. J. The Molecular Mechanism of Action of the Antiresorptive and Antiinflammatory Drug Clodronate: Evidence for the Formation in Vivo of a Metabolite That Inhibits Bone Resorption and Causes Osteoclast and Macrophage Apoptosis Arthritis Rheum. 2001, 44, 2201-2210 (Pubitemid 33644066)
159. Frith, J. C.; Mönkkönen, J.; Blackburn, G. M.; Russell, R. G.; Rogers, M. J. Clodronate and Liposome-Encapsulated Clodronate Are Metabolized to a Toxic ATP Analog, Adenosine 5′-(beta,gamma-Dichloromethylene) Triphosphate, by Mammalian Cells in Vitro J. Bone Miner. Res. 1997, 12, 1358-1367 (Pubitemid 27375378)
160. van Beek, E.; Pieterman, E.; Cohen, L.; Löwik, C.; Papapoulos, S. Farnesyl Pyrophosphate Synthase Is the Molecular Target of Nitrogen-Containing Bisphosphonates Biochem. Biophys. Res. Commun. 1999, 264, 108-111 (Pubitemid 29500472)
161. Grove, J. E.; Brown, R. J.; Watts, D. J. The Intracellular Target for the Antiresorptive Aminobisphosphonate Drugs in Dictyostelium discoideum is the Enzyme Farnesyl Diphosphate Synthase J. Bone Miner. Res. 2000, 15, 971-981 (Pubitemid 30233423)
162. Bergstrom, J. D.; Bostedor, R. G.; Masarachia, P. J.; Reszka, A. A.; Rodan, G. Alendronate is a Specific, Nanomolar Inhibitor of Farnesyl Diphosphate Synthase Arch. Biochem. Biophys. 2000, 373, 231-241 (Pubitemid 30046509)
163. van Beek, E.; Pieterman, E.; Cohen, L.; Löwik, C.; Papapoulos, S. Nitrogen-Containing Bisphosphonates Inhibit Isopentenyl Pyrophosphate Isomerase/Farnesyl Pyrophosphate Synthase Activity with Relative Potencies Corresponding to Their Antiresorptive Potencies in Vitro and in Vivo Biochem. Biophys. Res. Commun. 1999, 255, 491-494 (Pubitemid 29292287)
164. Martin, M. B.; Arnold, W.; Heath, H. T., III; Urbina, J. A.; Oldfield, E. Nitrogen-Containing Bisphosphonates as Carbocation Transition State Analogs for Isoprenoid Biosynthesis Biochem. Biophys. Res. Commun. 1999, 263, 754-758 (Pubitemid 29490699)
165. Hosfield, D. J.; Zhang, Y.; Dougan, D. R.; Broun, A.; Tari, L. W.; Swanson, R. V.; Finn, J. Structural Basis for Bisphosphonate-Mediated Inhibition of Isoprenoid Biosynthesis J. Biol. Chem. 2004, 279, 8526-8529 (Pubitemid 38295905)
166. Rondeau, J. M.; Bitsch, F.; Bourgier, E.; Geiser, M.; Hemmig, R.; Kroemer, M.; Lehmann, S.; Ramage, P.; Rieffel, S.; Strauss, A.; Green, J. R.; Jahnke, W. Structural Basis for the Exceptional in Vivo Efficacy of Bisphosphonate Drugs ChemMedChem 2006, 1, 267-273 (Pubitemid 43700307)
167. Kavanagh, K. L.; Guo, K.; Dunford, J. E.; Wu, X.; Knapp, S.; Ebetino, F. H.; Rogers, M. J.; Russell, R. G.; Oppermann, U. The Molecular Mechanism of Nitrogen-Containing Bisphosphonates as Antiosteoporosis Drugs Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 7829-7834
168. Martin, M. B.; Grimley, J. S.; Lewis, J. C.; Heath, H. T., III; Bailey, B. N.; Kendrick, H.; Yardley, V.; Caldera, A.; Lira, R.; Urbina, J. A.; Moreno, S. N. J.; Docampo, R.; Croft, S. L.; Oldfield, E. Bisphosphonates Inhibit the Growth of Trypanosoma brucei, Trypanosoma cruzi, Leishmania donovani, Toxoplasma gondii, and Plasmodium falciparum: A Potential Route to Chemotherapy J. Med. Chem. 2001, 44, 909-916 (Pubitemid 32861615)
169. Ling, Y.; Sahota, G.; Odeh, S.; Chan, J. M. W.; Araujo, F. G.; Moreno, S. N. J.; Oldfield, E. Bisphosphonate Inhibitors of Toxoplasma gondi Growth: In Vitro, QSAR, and in Vivo Investigations J. Med. Chem. 2005, 48, 3130-3140 (Pubitemid 40628033)
170. Yardley, V.; Khan, A. A.; Martin, M. B.; Slifer, T. R.; Araujo, F. G.; Moreno, S. N.; Docampo, R.; Croft, S. L.; Oldfield, E. In Vivo Activities of Farnesyl Pyrophosphate Synthase Inhibitors against Leishmania donovani and Toxoplasma gondii Antimicrob. Agents Chemother. 2002, 46, 929-931 (Pubitemid 34157693)
171. Martin, M. B.; Sanders, J. M.; Kendrick, H.; de Luca-Fradley, K.; Lewis, J. C.; Grimley, J. S.; Van Brussel, E. M.; Olsen, J. R.; Meints, G. A.; Burzynska, A.; Kafarski, P.; Croft, S. L.; Oldfield, E. Activity of Bisphosphonates against Trypanosoma brucei rhodesiense J. Med. Chem. 2002, 45, 2904-2914 (Pubitemid 34721514)
172. Ghosh, S.; Chan, J. M. W.; Lea, C. R.; Meints, G. A.; Lewis, J. C.; Tovian, Z. S.; Flessner, R. M.; Loftus, T. C.; Bruchhaus, I.; Kendrick, H.; Croft, S. L.; Kemp, R. G.; Kobayashi, S.; Nozaki, T.; Oldfield, E. Effects of Bisphosphonates on the Growth of Entamoeba histolytica and Plasmodium Species in Vitro and in Vivo J. Med. Chem. 2004, 47, 175-187 (Pubitemid 38040501)
173. Sanders, J. M.; Gomez, A. O.; Mao, J.; Meints, G. A.; Van Brussel, E. M.; Burzynska, A.; Kafarski, P.; Gonzalez-Pacanowska, D.; Oldfield, E. 3-D QSAR Investigations of the Inhibition of Leishmania major Farnesyl Pyrophosphate Synthase by Bisphosphonates J. Med. Chem. 2003, 46, 5171-5183 (Pubitemid 37414187)
174. Kotsikorou, E.; Song, Y.; Chan, J. M.; Faelens, S.; Tovian, Z.; Broderick, E.; Bakalara, N.; Docampo, R.; Oldfield, E. Bisphosphonate Inhibition of the Exopolyphosphatase Activity of the Trypanosoma brucei Soluble Vacuolar Pyrophosphatase J. Med. Chem. 2005, 48, 6128-6139 (Pubitemid 41324620)
175. Hudock, M. P.; Sanz-Rodríguez, C. E.; Song, Y.; Chan, J. M.; Zhang, Y.; Odeh, S.; Kosztowski, T.; Leon-Rossell, A.; Concepción, J. L.; Yardley, V.; Croft, S. L.; Urbina, J. A.; Oldfield, E. Inhibition of Trypanosoma cruzi Hexokinase by Bisphosphonates J. Med. Chem. 2006, 49, 215-223 (Pubitemid 43077335)
176. Sanz-Rodríguez, C. E.; Concepción, J. L.; Pekerar, S.; Oldfield, E.; Urbina, J. A. Bisphosphonates as Inhibitors of Trypanosoma cruzi Hexokinase: Kinetic and Metabolic Studies J. Biol. Chem. 2007, 282, 12377-12387 (Pubitemid 47100604)
177. Yajima, S.; Hara, K.; Sanders, J. M.; Yin, F.; Ohsawa, K.; Wiesner, J.; Jomaa, H.; Oldfield, E. Crystallographic Structures of Two Bisphosphonate:1- deoxyxylulose-5-phosphate Reductoisomerase Complexes J. Am. Chem. Soc. 2004, 126, 10824-10825 (Pubitemid 39180551)
178. Szabo, C. M.; Matsumura, Y.; Fukura, S.; Martin, M. B.; Sanders, J. M.; Sengupta, S.; Cieslak, J. A.; Loftus, T. C.; Lea, C. R.; Lee, H.-J.; Koohang, A.; Coates, R. M.; Sagami, H.; Oldfield, E. Inhibition of Geranylgeranyl Diphosphate Synthase by Bisphosphonates and Diphosphates: A Potential Route to New Bone Antiresorption and Antiparasitic Agents J. Med. Chem. 2002, 45, 2185-2196 (Pubitemid 34525798)
179. Oldfield, E. Targeting Isoprenoid Biosynthesis for Drug Discovery: Bench to Bedside Acc. Chem. Res. 2010, 43, 1216-1226
180. Derenne, S.; Amiot, M.; Barille, S.; Collette, M.; Robillard, N.; Berthaud, P.; Harousseau, J. L.; Bataille, R. Zoledronate Is a Potent Inhibitor of Myeloma Cell Growth and Secretion of IL-6 and MMP-1 by the Tumoral Environment J. Bone Miner. Res. 1999, 14, 2048-2056 (Pubitemid 30026954)
181. Wilhelm, M.; Kunzmann, V.; Eckstein, S.; Reimer, P.; Weissinger, F.; Ruediger, T.; Tony, H. P. γΔ T Cells for Immune Therapy of Patients with Lymphoid Malignancies Blood 2003, 102, 200-206 (Pubitemid 36759655)
182. Dieli, F.; Vermijlen, D.; Fulfaro, F.; Caccamo, N.; Meraviglia, S.; Cicero, G.; Roberts, A.; Buccheri, S.; D'Asaro, M.; Gebbia, N.; Salerno, A.; Eberl, M.; Hayday, A. C. Targeting Human γΔ T Cells with Zoledronate and Interleukin-2 for Immunotherapy of Hormone-Refractory Prostate Cancer Cancer Res. 2007, 67, 7450-7457 (Pubitemid 47206575)
183. Gnant, M.; Mlineritsch, B.; Schippinger, W.; Luschin-Ebengreuth, G.; Postlberger, S.; Menzel, C.; Jakesz, R.; Seifert, M.; Hubalek, M.; Bjelic-Radisic, V.; Samonigg, H.; Tausch, C.; Eidtmann, H.; Steger, G.; Kwasny, W.; Dubsky, P.; Fridrik, M.; Fitzal, F.; Stierer, M.; Rucklinger, E.; Greil, R.; Marth, C. Endocrine Therapy plus Zoledronic Acid in Premenopausal Breast Cancer N. Engl. J. Med. 2009, 360, 679-691
184. Gao, Y. G.; Robinson, H.; Song, Y.; No, J. H.; Bergan, K.; Leon, A.; Cass, L.; Goddard, A.; Chang, T. K.; Lin, F. Y.; Van Beek, E.; Papapoulos, S.; Wang, A. H.; Kubo, T.; Ochi, M.; Mukkamala, D.; Oldfield, E. Lipophilic Bisphosphonates as Dual Farnesyl/Geranylgeranyl Diphosphate Synthase Inhibitors: An X-ray and NMR Investigation J. Am. Chem. Soc. 2009, 131, 5153-5162
185. Sanders, J. M.; Ghosh, S.; Chan, J. M. W.; Meints, G.; Wang, H.; Raker, A. M.; Song, Y.; Colantino, A.; Burzynska, A.; Kafarski, P.; Morita, C. T.; Oldfield, E. Quantitative Structure-Activity Relationships for gamma-delta-T Cell Activation by Bisphosphonates J. Med. Chem. 2004, 47, 375-384 (Pubitemid 38057881)
186. Zhang, Y.; Cao, R.; Yin, F.; Lin, F. Y.; Wang, H.; Krysiak, K.; No, J. H.; Mukkamala, D.; Houlihan, K.; Li, J.; Morita, C. T.; Oldfield, E. Lipophilic Pyridinium Bisphosphonates: Potent gammadelta T Cell Stimulators Angew. Chem., Int. Ed. 2010, 49, 1136-1138
187. Cremers, S. C.; Pillai, G.; Papapoulos, S. E. Pharmacokinetics/ Pharmacodynamics of Bisphosphonates: Use for Optimisation of Intermittent Therapy for Osteoporosis Clin. Pharmacokinet. 2005, 44, 551-570 (Pubitemid 40994085)
188. Kimmel, D. B. Mechanism of Action, Pharmacokinetic and Pharmacodynamic Profile, and Clinical Applications of Nitrogen-Containing Bisphosphonates J. Dent. Res. 2007, 86, 1022-1033
189. Chebbi, I.; Migianu-Griffoni, E.; Sainte-Catherine, O.; Lecouvey, M.; Seksek, O. In Vitro Assessment of Liposomal Neridronate on MDA-MB-231 Human Breast Cancer Cells Int. J. Pharm. 2010, 383, 116-122
190. Pignatello, R.; Cenni, E.; Micieli, D.; Fotia, C.; Salerno, M.; Granchi, D.; Avnet, S.; Sarpirtro, M. G.; Castelli, F.; Baldini, N. A Novel Biomaterial for Osteotropic Drug Nanocarriers: Synthesis and Biocompatibility Evaluation of a PLGA-ALE Conjugate Nanomedicine 2009, 4, 161-175
191. Morioka, M.; Kazimono, A.; Takikawa, H.; Mori, A.; Ueno, H.; Kadowaki, S.; Nakao, Y.; Kato, K.; Umezawa, K. Design, Synthesis, and Biological Evaluation of Novel Estradiol-Bisphosphonate Conjugates as Bone-Specific Estrogens Bioorg. Med. Chem. 2010, 18, 1142-1148
192. Wang, J.; Yang, C.; Ding, H.; Yan, X.; Wu, X.; Xie, Y. Synthesis of Novel Bone-Targeted Agents for Treatment of Osteoporosis Indian J. Chem. 2006, 45, 318-321 (Pubitemid 43479765)
193. Tanaka, K. S. E.; Dietrich, E.; Ciblat, S.; Métayer, C.; Arhin, F. F.; Sarmiento, I.; Moeck, G.; Parr, T. R., Jr.; Far, A. R. Synthesis and in Vitro Evaluation of Bisphosphonated Glycopeptide Prodrugs for the Treatment of Osteomyelitis Bioorg. Med. Chem. Lett. 2010, 20, 1355-1359
194. Doschak, M. R.; Kucharski, C. M.; Wright, J. E. I.; Zernicke, D. F.; Uluda, H. Improved Bone Delivery of Osteoprotegerin by Bisphosphonate Conjugation in a Rat Model of Osteoarthritis Mol. Pharmaceutics 2009, 6, 634-640
195. Gittens, S. A.; Bansal, G.; Kucharski, C.; Borden, M.; Uluda, H. Imparting Mineral Affinity to Fetuin by Bisphosphonate Conjugation: A Comparison of Three Bisphosphonate Conjugation Schemes Mol. Pharmaceutics 2005, 2, 392-406 (Pubitemid 41503680)
196. Davis, M. P.; Walsh, D. Epidemiology of Cancer Pain and Factors Influencing Poor Pain Control Am. J. Hospice Palliative Med. 2004, 21, 137-142 (Pubitemid 38560953)
197. Bauman, G.; Charette, M.; Reid, R.; Sathya, J. Radiopharmaceuticals for the Palliation of Painful Bone-Metastasis: A Systematic Review Radiother. Oncol. 2005, 75, 258-270
198. Kubíček., V.; Rudovský, J.; Kotek, J.; Hermann, P.; Van der Elst, L.; Muller, R. N.; Kolar, Z. I.; Wolterbeek, H. T.; Peters, J. A.; Lukeš, I. A Bisphosphonate Monoamide Analogue of DOTA: A Potential Agent for Bone Targeting J. Am. Chem. Soc. 2005, 127, 16477-16485 (Pubitemid 41740397)
199. 68Ga Tracers for Positron Emission Tomography Chem. - Eur. J. 2010, 16, 7174-7185
200. Tanwar, J.; Datta, A.; Tiwari, A. K.; Thirumal, M.; Chuttani, K.; Mishra, A. K. Preclinical Evaluation of DOP3P-AME-DOP3P: A Polyazamacrocyclic Methylene Phosphonate for Diagnosis and Therapy of Skeletal Matastases Bioconjugate Chem. 2010, 22, 244-255
201. Lacerda, S.; Marques, F.; Campello, P.; Gano, L.; Kubíček, V.; Hermann, P.; Santos, I. Chemical, Radiochemical and Biological Studies of Sm and Ho Complexes of H4dota Analogues Containing One Methylphosphonic/Phosphinic Acid Pedant Arm J. Labelled Compd. Radiopharm. 2010, 53, 36-43
202. 64Cu Small Animal PET Imaging Bioorg. Med. Chem. 2009, 17, 548-552
203. 68Ga-Bisphosphonates: First Human Study Eur. J. Nucl. Med. Mol. Imaging 2010, 37, 834-834
204. Murphy, G. The ADAMs: Signalling Scissors in the Tumour Microenvironment Nat. Rev. Cancer 2008, 8, 929-941
205. Rocks, N.; Paulissen, G.; El Hour, M.; Quesada, F.; Crahay, C.; Gueders, M.; Foidart, J.-M.; Noel, A.; Cataldo, D. Emerging Roles of ADAM and ADAMTS Metalloproteinases in Cancer Biochimie 2008, 90, 369-379 (Pubitemid 351172571)
206. Wagstaff, L.; Kelwick, R.; Decock, J.; Edwards, D. R. The Roles of ADAMTS Metalloproteinases in Tumorigenesis and Metastasis Front. Biosci. 2011, 16, 1861-1872
207. Huber, T.; Manzenrieder, F.; Kuttruff, C. A.; Dorner-Ciossek, C.; Kessler, H. Prolonged Stability by Cyclization: Macrocyclic Phosphino Dipeptide Isostere Inhibitors of β-Secretase (BACE1) Bioorg. Med. Chem. Lett. 2009, 19, 4427-4431
208. Manzenrieder, F.; Frank, A.; Huber, T.; Dorner-Ciossek, C.; Kessler, H. Synthesis and Biological Evaluation of Phosphino Dipeptide Isostere Inhibitor of Human β-Secretase (BACE1) Bioorg. Med. Chem. 2007, 15, 4136-4143 (Pubitemid 46678841)
209. Ga̧sowska, B.; Wojtasek, H.; Hurek, J.; Dra̧g, M.; Nowak, K.; Kafarski, P. Redox reaction between Amino-(3,4-dihydroxyphenyl)methylphosphonic Acid and Dopaquinone Is Responsible for the Apparent Inhibitory Effect on Tyrosinase Eur. J. Biochem. 2002, 269, 4098-4104 (Pubitemid 34994904)
210. Coudray, L.; Pennebaker, A. F.; Montchamp, J.-L. Synthesis and in Vitro Evaluation of Aspartate Transcarbamoylase Inhibitors Bioorg. Med. Chem. 2009, 17, 7680-7689
211. Flohr, A.; Aemissegger, A.; Hilvert, D. alpha-Functionalized Phosphonylphosphinates: Synthesis and Evaluation as Transcarbamoylase Inhibitors J. Med. Chem. 1999, 42, 2633-2640 (Pubitemid 29344303)
212. Collinsová, M.; Castro, C.; Garrow, T. A.; Yiotakis, A.; Dive, V.; Jiráček, J. Combining Combinatorial Chemistry and Affinity Chromatography: Highly Selective Inhibitors of Human Betaine: Homocysteine S -Methyltransferase Chem. Biol. 2003, 10, 113-122 (Pubitemid 36250969)
213. Jiráček, J.; Collinsová, M.; Rosenberg, I.; Budesinsky, M.; Protivinska, E.; Netusilova, H.; Garrow, T. A. S-Alkylated Homocysteine Derivatives: New Inhibitors of Human Betaine-Homocysteine S -Methyltransferase J. Med. Chem. 2006, 49, 3982-3989 (Pubitemid 43967895)
214. Makhaeva, G. F.; Aksinenko, A. Y.; Sokolov, V. B.; Baskin, I. I.; Palyulin, V. A.; Zefirov, N. S.; Hein, N. D.; Kampf, J. W.; Wijeyesakere, S. J.; Richardson, R. J. Kinetics and Mechanizm od Inhibition of Serie Esterases by Fluorinated Aminophosphonates Chem.-Biol. Interact. 2010, 187, 177-194
215. Steere, J. A.; Sampson, P. B.; Honek, J. F. Synthesis of an alpha-Aminophosphonate Nucleoside as an Inhibitor of S -Adenosyl- l -Homocysteine Hydrolase Bioorg. Med. Chem. Lett. 2002, 12, 457-460 (Pubitemid 34113924)
216. Khomutov, R. M.; Shchipanova, A. I.; Khurs, E. N. Phosphoanalogues of Amino Acids Involved in Methionine Metabolism as a New Source of Antiviral Compounds Dokl. Biochem. Biophys. 2009, 425, 84-86
217. Sheng, X. C.; Pyun, H.-J.; Chaudhary, K.; Wang, J.; Doerffler, E.; Fleury, M.; McMurtrie, D.; Chen, X.; Delaney, W. E., IV; Kim, C. U. Discovery of Novel Phosphonate Derivatives as Hepatitis C Virus NS3 Protease Inhibitors Bioorg. Med. Chem. Lett. 2009, 19, 3453-3457
218. Pyun, H.-J.; Chaudhary, K.; Somoza, J. R.; Sheng, X. C.; Kim, C. U. Synthesis and Resolution of Diethyl (1 S,2 S)-1-Amino-2-vinylcyclopropane-1- phosphonate for HCV NS3 Protease Inhibitors Tetrahedron Lett. 2009, 50, 3833-3835
219. Cherenok, S.; Vovk, A.; Muravyova, I.; Shivanyuk, A.; Kukhar, V.; Lipkowski, J.; Kalchenko, V. Calix[4]arene alpha-Aminophosphonic Acids: Asymmetric Synthesis and Enantioselective Inhibition of an Alkaline Phosphatase Org. Lett. 2006, 8, 549-552 (Pubitemid 43341957)
220. Morrison, M. J.; Li, N.; Pratt, R. F. Inverse Acyl Phosph(on)ates: Substrates or Inhibitors of β-Lactam-Recognizing Enzymes? Bioorg. Chem. 2001, 29, 271-281 (Pubitemid 34226223)
221. Liu, W.; Rogers, C. J.; Fisher, A. J.; Toney, M. D. Aminophosphonate Inhibitors of Dialkylglycine Decarboxylase: Structural Basis for Slow Binding Inhibition Biochemistry 2002, 41, 12320-12328
222. Asojo, O.; Friedman, J.; Adir, N.; Belakhov, V.; Shoham, Y.; Baasov, T. Crystal Structures of KDOP Synthase in Its Binary Complex with the Substrate Phosphoenolpyruvate and with Mechanism-Base Inhibitor Biochemistry 2001, 40, 6326-6334 (Pubitemid 32472721)
223. Cressina, E.; Lloyd, A. J.; De Pascale, G.; Mok, B. J.; Caddick, S.; Roper, D. I.; Dowson, C. G.; Bugg, T. D. H. Inhibition of tRNA-Dependent Ligase MurM from Straptococcus pneumoniae by Phosphonate and Sulfonamide Inhibitors Bioorg. Med. Chem. 2009, 17, 3443-3455
224. Berlicki, Ł.; Obojska, A.; Forlani, G.; Kafarski, P. Design, Synthesis, and Activity of Analogues of Phosphinothricin as Inhibitors of Glutamine Synthetase J. Med. Chem. 2005, 48, 6340-6349 (Pubitemid 41430483)
225. Hiratake, J.; Kato, H.; Oda, J. Mechanism-Based Inactivation of Glutathione Synthetase by Phosphinic Acid Transition-State Analog J. Am. Chem. Soc. 1994, 116, 12059-12060
226. Chen, S.; Coward, J. K. Investigations on New Strategies for the Facile Synthesis of Polyfunctionalized Phosphinates: Phosphinopeptide Analogues of Glutathionylspermidine J. Org. Chem. 1998, 63, 502-509 (Pubitemid 128499703)
227. Tanner, M. E.; Vaganay, S.; van Heijenoort, J.; Blanot, D. Phosphinate Inhibitors of the d -Glutamic Acid-Adding Enzyme of Peptidoglycan Biosynthesis J. Org. Chem. 1996, 61, 1756-1760 (Pubitemid 26106393)
228. Štrancar, K.; Blanot, D.; Gobec, S. Design, Synthesis and Structure-Activity Relationships of New Phosphinate Inhibitors of MurD Bioorg. Med. Chem. Lett. 2006, 16, 343-348 (Pubitemid 41680624)
229. Miller, D. J.; Hammond, S. M.; Anderluzzi, D.; Bugg, T. D. H. Aminoalkylphosphinate Inhibitors of d -Ala- d -Ala Adding Enzyme J. Chem. Soc., Perkin Trans. 1 1998, 131-142 (Pubitemid 128757891)