On the solubility and lipophilicity of metallacarborane pharmacophores

Molecular Pharmaceutics

Volumn 10, Issue 5, 2013, Pages 1751-1759

  Rak, Jakub ^a,b   Dejlová, Barbora ^a   Lampová, Hana ^a,b   Kaplánek, Robert ^a   Matějíček, Pavel ^c   Cígler, Petr ^d   Král, Vladimír ^a,b  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

^b Zentiva Prague   (Czech Republic)

^c CHARLES UNIVERSITY   (Czech Republic)

^d INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

cobalt bis(dicarbollide); HIV protease; inhibitor; lipophilicity; metallacarborane; P ow; serum albumin; solubility

Indexed keywords

CARBORANE DERIVATIVE; HUMAN IMMUNODEFICIENCY VIRUS PROTEINASE; HUMAN IMMUNODEFICIENCY VIRUS PROTEINASE INHIBITOR; HUMAN SERUM ALBUMIN; METALLACARBORANE; OCTANOL; SODIUM CHLORIDE; UNCLASSIFIED DRUG; WATER; BORON DERIVATIVE; COBALT; LIGAND; LIPID; ORGANOMETALLIC COMPOUND; SERUM ALBUMIN;

ARTICLE; CONTROLLED STUDY; DRUG DETERMINATION; DRUG SOLUBILITY; ENZYME INHIBITION; LIPOPHILICITY; PARTITION COEFFICIENT; PHARMACOPHORE; PLASMA; PRIORITY JOURNAL; ULTRAVIOLET SPECTROPHOTOMETRY; CHEMICAL STRUCTURE; CHEMISTRY; DRUG DEVELOPMENT; HUMAN; SOLUBILITY;

BORON COMPOUNDS; COBALT; DRUG DISCOVERY; HIV PROTEASE INHIBITORS; HUMANS; LIGANDS; LIPIDS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; SERUM ALBUMIN; SOLUBILITY;

EID: 84877297802     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp300565z     Document Type: Article

References (60)

1. Marson, C. M. New and unusual scaffolds in medicinal chemistry Chem. Soc. Rev. 2011, 40 (11) 5514-5533
2. Meggers, E. From conventional to unusual enzyme inhibitor scaffolds: the quest for target specificity Angew. Chem., Int. Ed. 2011, 50 (11) 2442-2448
3. Tjarks, W. The use of boron clusters in the rational design of boronated nucleosides for neutron capture therapy of cancer J. Organomet. Chem. 2000, 614, 37-47
4. Bregadze, V. I.; Sivaev, I. B.; Glazun, S. A. Polyhedral boron compounds as potential diagnostic and therapeutic antitumor agents Anti-Cancer Agents Med. Chem. 2006, 6 (2) 75-109
5. Crossley, E. L.; Ziolkowski, E. J.; Coderre, J. A.; Rendina, L. M. Boronated DNA-binding compounds as potential agents for boron neutron capture therapy Mini-Rev. Med. Chem. 2007, 7 (3) 303-313
6. Soloway, A. H.; Tjarks, W.; Barnum, B. A.; Rong, F. G.; Barth, R. F.; Codogni, I. M.; Wilson, J. G. The chemistry of neutron capture therapy Chem. Rev. 1998, 98 (4) 1515-1562
7. Hawthorne, M. F.; Maderna, A. Applications of radiolabeled boron clusters to the diagnosis and treatment of cancer Chem. Rev. 1999, 99 (12) 3421-3434
8. Cigler, P.; Kozisek, M.; Rezacova, P.; Brynda, J.; Otwinowski, Z.; Pokorna, J.; Plesek, J.; Gruner, B.; Doleckova-Maresova, L.; Masa, M.; Sedlacek, J.; Bodem, J.; Krausslich, H. G.; Kral, V.; Konvalinka, J. From nonpeptide toward noncarbon protease inhibitors: Metallacarboranes as specific and potent inhibitors of HIV protease Proc. Natl. Acad. Sci. U.S.A. 2005, 102 (43) 15394-15399
9. Kozisek, M.; Cigler, P.; Lepsik, M.; Fanfrlik, J.; Rezacova, P.; Brynda, J.; Pokorna, J.; Plesek, J.; Gruner, B.; Saskova, K. G.; Vaclavikova, J.; Kral, V.; Konvalinka, J. Inorganic polyhedral metallacarborane inhibitors of HIV protease: A new approach to overcoming antiviral resistance J. Med. Chem. 2008, 51 (15) 4839-4843
10. Rezacova, P.; Pokorna, J.; Brynda, J.; Kozisek, M.; Cigler, P.; Lepsik, M.; Fanfrlik, J.; Rezac, J.; Saskova, K. G.; Sieglova, I.; Plesek, J.; Sicha, V.; Gruner, B.; Oberwinkler, H.; Sedlacek, J.; Krausslich, H. G.; Hobza, P.; Kral, V.; Konvalinka, J. Design of HIV protease inhibitors based on inorganic polyhedral metallacarboranes J. Med. Chem. 2009, 52 (22) 7132-7141
11. Řezáčová, P.; Cígler, P.; Matějíček, P.; Lepšík, M.; Pokorná, J.; Grüner, B.; Konvalinka, J. Medicinal Application of Carboranes: Inhibition of HIV Protease. In Boron Science: New Technologies and Applications; Hosmane, N. S., Ed.; CRC Press: New York, 2011; pp 41-70.
12. Matejicek, P.; Cigler, P.; Prochazka, K.; Kral, V. Molecular assembly of metallacarboranes in water: Light scattering and microscopy study Langmuir 2006, 22 (2) 575-581
13. Scholz, M.; Bensdorf, K.; Gust, R.; Hey-Hawkins, E. Asborin: the carbaborane analogue of aspirin ChemMedChem 2009, 4 (5) 746-748
14. Scholz, M.; Steinhagen, M.; Heiker, J. T.; Beck-Sickinger, A. G.; Hey-Hawkins, E. Asborin inhibits aldo/keto reductase 1A1 ChemMedChem 2011, 6 (1) 89-93
15. Page, M. F. Z.; Jalisatgi, S. S.; Maderna, A.; Hawthorne, M. F. Design and synthesis of a candidate alpha-human thrombin irreversible inhibitor containing a hydrophobic carborane pharmacophore Synthesis 2008, 4, 555-563
16. Endo, Y.; Yoshimi, T.; Kimura, K.; Itai, A. Protein kinase C modulators bearing dicarba-closo-dodecaborane as a hydrophobic pharmacophore Bioorg. Med. Chem. Lett. 1999, 9 (17) 2561-2564
17. Tsuji, M.; Koiso, Y.; Takahashi, H.; Hashimoto, Y.; Endo, Y. Modulators of tumor necrosis factor alpha production bearing dicarba-closo-dodecaborane as a hydrophobic pharmacophore Biol. Pharm. Bull. 2000, 23 (4) 513-516
18. Lesnikowski, Z. J. Boron units as pharmacophores-new applications and opportunities of boron cluster chemistry Collect. Czech. Chem. Commun. 2007, 72 (12) 1646-1658
19. Satapathy, R.; Dash, B. P.; Maguire, J. A.; Hosmane, N. S. New developments in the medicinal chemistry of carboranes Collect. Czech. Chem. Commun. 2010, 75 (9) 995-1022
20. Issa, F.; Kassiou, M.; Rendina, L. M. Boron in drug discovery: carboranes as unique pharmacophores in biologically active compounds Chem. Rev. 2011, 111 (9) 5701-5722
21. Scholz, M.; Hey-Hawkins, E. Carbaboranes as pharmacophores: properties, synthesis, and application strategies Chem. Rev. 2011, 111 (11) 7035-7062
22. Grimes, R. N. Carboranes in Medicine. In Carboranes; Academic Press: New York, 2011; pp 1053-1082.
23. Sivaev, I. B.; Bregadze, V. V. Polyhedral boranes for medical applications: current status and perspectives Eur. J. Inorg. Chem. 2009, 11, 1433-1450
24. Chen, Z. F.; King, R. B. Spherical aromaticity: recent work on fullerenes, polyhedral boranes, and related structures Chem. Rev. 2005, 105 (10) 3613-3642
25. King, R. B. Three-dimensional aromaticity in polyhedral boranes and related molecules Chem. Rev. 2001, 101 (5) 1119-1152
26. Fanfrlik, J.; Lepsik, M.; Horinek, D.; Havlas, Z.; Hobza, P. Interaction of carboranes with biomolecules: formation of dihydrogen bonds Chemphyschem 2006, 7 (5) 1100-1105
27. Fanfrlik, J.; Hnyk, D.; Lepsik, M.; Hobza, P. Interaction of heteroboranes with biomolecules: Part 2. The effect of various metal vertices and exo-substitutions Phys. Chem. Chem. Phys. 2007, 9 (17) 2085-2093
28. Farras, P.; Juarez-Perez, E. J.; Lepsik, M.; Luque, R.; Nunez, R.; Teixidor, F. Metallacarboranes and their interactions: theoretical insights and their applicability Chem. Soc. Rev. 2012, 41 (9) 3445-3463
29. Matejicek, P.; Cigler, P.; Olejniczak, A. B.; Andrysiak, A.; Wojtczak, B.; Prochazka, K.; Lesnikowski, Z. J. Aggregation behavior of nucleoside-boron cluster conjugates in aqueous solutions Langmuir 2008, 24 (6) 2625-2630
30. Kubat, P.; Lang, K.; Cigler, P.; Kozisek, M.; Matejicek, P.; Janda, P.; Zelinger, Z.; Prochazka, K.; Kral, V. Tetraphenylporphyrin-cobalt(III) bis(1,2-dicarbollide) conjugates: From the solution characteristics to inhibition of HIV protease J. Phys. Chem. B 2007, 111 (17) 4539-4546
31. Hao, E.; Sibrian-Vazquez, M.; Serem, W.; Garno, J. C.; Fronczek, F. R.; Vicente, M. G. H. Synthesis, aggregation and cellular investigations of porphyrin-cobaltacarborane conjugates Chem.-Eur. J. 2007, 13 (32) 9035-9042
32. Bauduin, P.; Prevost, S.; Farras, P.; Teixidor, F.; Diat, O.; Zemb, T. A theta-shaped amphiphilic cobaltabisdicarbollide anion: transition from monolayer vesicles to micelles Angew. Chem., Int. Ed. 2011, 50 (23) 5298-5300
33. Rak, J.; Kaplanek, R.; Kral, V. Solubilization and deaggregation of cobalt bis(dicarbollide) derivatives in water by biocompatible excipients Bioorg. Med. Chem. Lett. 2010, 20 (3) 1045-1048
34. Rak, J.; Jakubek, M.; Kaplanek, R.; Matejicek, P.; Kral, V. Cobalt bis(dicarbollide) derivatives: solubilization and self-assembly suppression Eur. J. Med. Chem. 2011, 46 (4) 1140-1146
35. Fasano, M.; Curry, S.; Terreno, E.; Galliano, M.; Fanali, G.; Narciso, P.; Notari, S.; Ascenzi, P. The extraordinary ligand binding properties of human serum albumin IUBMB Life 2005, 57 (12) 787-796
36. Kalra, A.; Tugcu, N.; Cramer, S. M.; Garde, S. Salting-in and salting-out of hydrophobic solutes in aqueous salt solutions J. Phys. Chem. B 2001, 105 (27) 6380-6386
37. Lee, T. B.; Mckee, M. L. Dissolution Thermochemistry of Alkali Metal Dianion Salts (M2X1, M = Li+, Na+, and K+ with X = CO32-, SO42-, C8H82-, and B12H122-) Inorg. Chem. 2011, 50 (22) 11412-11422
38. Bockris, J. O.; Bowlerreed, J.; Kitchener, J. A. The salting-in effect Trans. Faraday Soc. 1951, 47 (2) 184-192
39. Tasleem, S.; Durani, S.; Anwar, M.; Niaz, M.; Muzaffar, K. Salting-out coefficients and activity coefficients of alkali and alkaline earth metals in aqueous and aqueous organic mixed solvents J. Chem. Soc. Pak. 2004, 26 (1) 39-43
40. Ivanov, I. M.; Volkov, V. V.; Kalish, N. K. Solvent-extraction and solvatation of alkali cations in form of salts cobalt(III) dicarbollide complexes Sibirskii Khim. Zh. 1991, 4, 78-81
41. Matejicek, P.; Zednik, J.; Uselova, K.; Plestil, J.; Fanfrlik, J.; Nykanen, A.; Ruokolainen, J.; Hobza, P.; Prochazka, K. Stimuli-responsive nanoparticles based on interaction of metallacarborane with poly(ethylene oxide) Macromolecules 2009, 42 (13) 4829-4837
42. Matejicek, P.; Brus, J.; Jigounov, A.; Plestil, J.; Uchman, M.; Prochazka, K.; Gradzielski, M. On the structure of polymeric composite of metallacarborane with poly(ethylene oxide) Macromolecules 2011, 44 (10) 3847-3855
43. Llop, J.; Masalles, C.; Vinas, C.; Teixidor, F.; Sillanpaa, R.; Kivekas, R. The [3,3 ′-Co(1,2-C2B9H11)(2)](-) anion as a platform for new materials: synthesis of its functionalized monosubstituted derivatives incorporating synthons for conducting organic polymers Dalton Trans. 2003, 4, 556-561
44. Uchman, M.; Cigler, P.; Gruner, B.; Prochazka, K.; Matejicek, P. Micelle-like nanoparticles of block copolymer poly(ethylene oxide)-block- poly(methacrylic acid) incorporating fluorescently substituted metallacarboranes designed as HIV protease inhibitor interaction probes J. Colloid Interface Sci. 2010, 348 (1) 129-136
45. Uchman, M.; Jurkiewicz, P.; Cigler, P.; Gruner, B.; Hof, M.; Prochazka, K.; Matejicek, P. Interaction of fluorescently substituted metallacarboranes with cyclodextrins and phospholipid bilayers: fluorescence and light scattering study Langmuir 2010, 26 (9) 6268-6275
46. Gruner, B.; Plesek, J.; Baca, J.; Cisarova, I.; Dozol, J. F.; Rouquette, H.; Vinas, C.; Selucky, P.; Rais, J. Cobalt bis(dicarbollide) ions with covalently bonded CMPO groups as selective extraction agents for lanthanide and actinide cations from highly acidic nuclear waste solutions New J. Chem. 2002, 26 (10) 1519-1527
47. Plesek, J.; Gruner, B.; Hermanek, S.; Baca, J.; Marecek, V.; Janchenova, J.; Lhotsky, A.; Holub, K.; Selucky, P.; Rais, J.; Cisarova, I.; Caslavsky, J. Synthesis of functionalized cobaltacarboranes based on the closo-[(1,2-C2B9H11) (2)-3,3 ′-Co](-) ion bearing polydentate ligands for separation of M3+ cations from nuclear waste solutions. Electrochemical and liquid-liquid extraction study of selective transfer of M3+ metal cations to an organic phase. Molecular structure of the closo-[(8-(2-CH3O-C5H4-O)-(CH2CH2O)(2)-1,2-C2B9H10)- (1′,2′-C2B9H11)-3,3′-Co]Na determined by X-ray diffraction analysis Polyhedron 2002, 21 (9-10) 975-986
48. Sivaev, I. B.; Starikova, Z. A.; Sjoberg, S.; Bregadze, V. I. Synthesis of functional derivatives of the [3,3′-Co(1,2-C2B2H11)(2)](-) anion J. Organomet. Chem. 2002, 649 (1-2) 1-8
49. Smallwood, I. M. Handbook of Organic Solvent Properties; John Wiley & Sons Inc.: New York, 1996; pp 101-103.
50. Semioshkin, A. A.; Sivaev, I. B.; Bregadze, V. I. Cyclic oxonium derivatives of polyhedral boron hydrides and their synthetic applications Dalton Trans. 2008, 8, 977-992
51. Grüner, B.; Rais, J.; Selucký, P.; Lučaní ková, M. Recent Progress in Extraction Agents Based on Cobalt Bis(dicarbollides) for Partitioning of Radionuclides from High-Level Nuclear Waste. In Boron Science: New Technologies and Applications; Hosmane, N. S., Ed.; CRC Press: New York, 2011; pp 463-490.
52. Chevrot, G.; Schurhammer, R.; Wipff, G. Surfactant behavior of "ellipsoidal" dicarbollide anions: A molecular dynamics study J. Phys. Chem. B 2006, 110 (19) 9488-9498
53. Chevrot, G.; Schurhammer, R.; Wipff, G. Synergistic effect of dicarbollide anions in liquid-liquid extraction: a molecular dynamics study at the octanol-water interface Phys. Chem. Chem. Phys. 2007, 9 (16) 1991-2003
54. Chevrot, G.; Schurhammer, R.; Wipff, G. Molecular dynamics study of dicarbollide anions in nitrobenzene solution and at its aqueous interface. Synergistic effect in the Eu(III) assisted extraction Phys. Chem. Chem. Phys. 2007, 9 (44) 5928-5938
55. Popov, A.; Borisova, T. Adsorption of dicarbollylcobaltate(III) anion {(pi-(3)-1,2-B9C2H11)(2)Co(III)(-)} at the water/1,2-dichloroethane interface. Influence of counterions' nature J. Colloid Interface Sci. 2001, 236 (1) 20-27
56. Zhao, Y. H.; Abraham, M. H. Octanol/water partition of ionic species, including 544 cations J. Org. Chem. 2005, 70 (7) 2633-2640
57. Waring, M. J. Lipophilicity in drug discovery Expert Opin. Drug Dis. 2010, 5 (3) 235-248
58. Oliferenko, P. V.; Oliferenko, A. A.; Poda, G.; Palyulin, V. A.; Zefirov, N. S.; Katritzky, A. R. New developments in hydrogen bonding acidity and basicity of small organic molecules for the prediction of physical and ADMET properties. Part 2. The universal solvation equation J. Chem. Inf. Model. 2009, 49 (3) 634-646
59. Edwards, M. P.; Price, D. A. Role of physicochemical properties and ligand lipophilicity efficiency in addressing drug safety risks Annu. Rep. Med. Chem. 2010, 45, 381-391
60. Leeson, P. D.; Springthorpe, B. The influence of drug-like concepts on decision-making in medicinal chemistry Nat. Rev. Drug Discovery 2007, 6 (11) 881-890