Synthesis and evaluation of selected key methyl ether derivatives of vancomycin aglycon

Journal of Medicinal Chemistry

Volumn 53, Issue 19, 2010, Pages 7229-7235

  Crane, Christine M ^a   Pierce, Joshua G ^a   Leung, Siegfried S F ^b   Tirado Rives, Julian ^b   Jorgensen, William L ^b   Boger, Dale L ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AGLYCONE; DIMETHYL ETHER; ORITAVANCIN; UNCLASSIFIED DRUG; VANCOMYCIN AGLYCON; VANCOMYCIN DERIVATIVE; ANTIINFECTIVE AGENT; ETHER DERIVATIVE; PEPTIDOGLYCAN; VANCOMYCIN;

ALKYLATION; ANTIMICROBIAL ACTIVITY; ARTICLE; BINDING AFFINITY; DERIVATIZATION; DRUG SCREENING; DRUG SYNTHESIS; ENTEROCOCCUS FAECALIS; METHYLATION; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; RING OPENING; STAPHYLOCOCCUS AUREUS; VANCOMYCIN RESISTANT ENTEROCOCCUS; ANALOGS AND DERIVATIVES; ANTIBIOTIC RESISTANCE; CHEMICAL PHENOMENA; CHEMISTRY; DRUG EFFECTS; MICROBIAL SENSITIVITY TEST; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS; THERMODYNAMICS;

ANTI-BACTERIAL AGENTS; DRUG RESISTANCE, BACTERIAL; ENTEROCOCCUS FAECALIS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; METHYL ETHERS; MICROBIAL SENSITIVITY TESTS; PEPTIDOGLYCAN; STAPHYLOCOCCUS AUREUS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; THERMODYNAMICS; VANCOMYCIN;

EID: 77957889946     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm100946e     Document Type: Article

References (54)

1. For reviews, see: Kahne, D.; Leimkuhler, C.; Lu, W.; Walsh, C. T. Glycopeptide and Lipoglycopeptide Antibiotics Chem. Rev. 2005, 105, 425-428
2. Hubbard, B. K.; Walsh, C. T. Vancomycin Assembly: Nature's Way Angew. Chem., Int. Ed. 2003, 42, 730-765
3. Williams, D. H.; Bardsley, B. The Vancomycin Group of Antibiotics and the Fight Against Resistant Bacteria Angew. Chem., Int. Ed. 1999, 38, 1172-1193
4. Malabarba, A.; Nicas, T. I.; Thompson, R. C. Structural Modifications of Glycopeptide Antibiotics Med. Res. Rev. 1997, 17, 69-137
5. For emerging vancomycin resistance in S. aureus see: Tenover, F. C.; Biddle, J. W.; Lancaster, M. V. Increasing Resistance to Vancomycin and Other Glycopeptides in Staphylococcus aureus Emerging Infect. Dis. 2001, 7, 327-332
6. Rotun, S. S.; McMath, V.; Schoonmaker, D. J.; Maupin, P. S.; Tenover, F. C.; Hill, B. C.; Ackman, D. M. Staphylococcus aureus with Reduced Susceptibility to Vancomycin Isolated from a Patient with Fatal B acteremia Emerging Infect. Dis. 1999, 5, 147-149
7. For reviews on glycopeptide resistance, see: Malabarba, A.; Ciabatti, R. Glycopeptide Derivatives Curr. Med. Chem. 2001, 8, 1759-1773
8. Pootoolal, J.; Neu, J.; Wright, G. D. Glycopeptide Antibiotic Resistance Annu. Rev. Pharmacol. Toxicol. 2002, 42, 381-408
9. Van Bambeke, F. V.; Laethem, Y. V.; Courvalin, P.; Tulkens, P. M. Glycopeptide Antibiotics: from Conventional to New Derivatives Drugs 2004, 64, 913-1028
10. Süssmuth, R. D. Vancomycin Resistance: Small Molecule Approaches Targeting the Bacterial Cell Wall Biosynthesis ChemBioChem 2002, 3, 295-298
11. Gao, Y. Glycopeptide Antibiotics and Development of Inhibitors to Overcome Vancomycin Resistance Nat. Prod. Rep. 2002, 19, 100-107
12. Healy, V. L.; Lessard, I. A.; Roper, D. I.; Knox, J. R.; Walsh, C. T. Vancomycin Resistance in Enterococci: Reprogramming of the d -Ala- d -Ala Ligases in Bacterial Peptidoglycan Biosynthesis Chem. Biol. 2000, 7, R109-R119
13. Walker, S.; Chen, L.; Helm, J.; Hu, Y.; Rew, Y.; Shin, D.; Boger, D. L. Chemistry and Biology of Ramoplanin: A Lipoglycodepsipeptide with Potent Antibiotic Activity Chem. Rev. 2005, 105, 449-476
14. von Nussbaum, F.; Brands, M.; Hinzen, B.; Weigand, S.; Häbich, D. Antibacterial Natural Products in Medicinal Chemistry - Exodus or Revival Angew. Chem., Int. Ed. 2006, 45, 5072-5129
15. Nicolaou, K. C.; Chen, J. S.; Edmonds, D. J.; Estrada, A. A. Recent Advances in the Chemistry and Biology of Naturally Occurring Antibiotics Angew. Chem., Int. Ed. 2009, 48, 660-719
16. McComas, C. C.; Crowley, B. M.; Boger, D. L. Partitioning the Loss in Vancomycin Binding Affinity for d -Ala- d -Lac into Lost H-Bond and Repulsive Lone Pair Contributions J. Am. Chem. Soc. 2003, 125, 9314-9315
17. 4]Vancomycin Aglycon: Reengineering Vancomycin for Dual d -Ala- d -Ala and d -Ala- d -Lac Binding J. Am. Chem. Soc. 2006, 128, 2885-2892
18. For related synthetic efforts, see: Boger, D. L.; Borzilleri, R. M.; Nukui, S.; Beresis, R. T. Synthesis of the Vancomycin CD and DE Ring Systems J. Org. Chem. 1997, 62, 4721-4736
19. Boger, D. L.; Miyazaki, S.; Kim, S. H.; Wu, J. H.; Loiseleur, O.; Castle, S. L. Diastereoselective Total Synthesis of the Vancomycin Aglycon with Ordered Atropisomer Equilibrations J. Am. Chem. Soc. 1999, 121, 3226-3227
20. Boger, D. L.; Miyazaki, S.; Kim, S. H.; Wu, J. H.; Castle, S. L.; Loiseleur, O.; Jin, Q. Total Synthesis of the Vancomycin Aglycon J. Am. Chem. Soc. 1999, 121, 10004-10011
21. Boger, D. L.; Kim, S. H.; Miyazaki, S.; Strittmatter, H.; Weng, J.-H.; Mori, Y.; Rogel, O.; Castle, S. L.; McAtee, J. J. Total Synthesis of the Teicoplanin Aglycon J. Am. Chem. Soc. 2000, 122, 7416-7417
22. Boger, D. L.; Kim, S. H.; Mori, Y.; Weng, J.-H.; Rogel, O.; Castle, S. L.; McAtee, J. J. First and Second Generation Total Synthesis of the Teicoplanin Aglycon J. Am. Chem. Soc. 2001, 123, 1862-1871
23. Crowley, B. M.; Mori, Y.; McComas, C. C.; Tang, D.; Boger, D. L. Total Synthesis of the Ristocetin Aglycon J. Am. Chem. Soc. 2004, 126, 4310-4317
24. Boger, D. L. Vancomycin, Teicoplanin, and Ramoplanin: Synthetic and Mechanistic Studies Med. Res. Rev. 2001, 21, 356-381
25. Garfunkle, J.; Kimball, F. S.; Trzupek, J. D.; Takazawa, S.; Shimamura, H.; Tomishima, M.; Boger, D. L. Total Synthesis of Chloropeptin II (Complestatin) and Chloropeptin I J. Am. Chem. Soc. 2009, 131, 16036-16038
26. Shimamura, H.; Breazzano, S. P.; Garfunkle, J.; Kimball, F. S.; Trzupek, J. D.; Boger, D. L. Total Synthesis of Complestatin, Development of a Pd(0)-Mediated Indole Annulation for Macrocyclization J. Am. Chem. Soc. 2010, 132, 7776-7783
27. Oritavancin (LY333328), a further glycosylated analogue of chlorobiphenyl vancomcyin, is under development for the treatment patients with serious bacterial infections. For a leading reference, see: Allen, N. E.; Nicas, T. I. Mechanism of Action of Oritavancin and Related Glycopeptide Antibiotics FEMS Microbiol. Rev. 2003, 26, 511-532
28. For references regarding mode of action of chlorobiphenyl vancomycin, see: Goldman, R. C.; Baizman, E. R.; Longley, C. B.; Branstrom, A. A. Chlorobiphenyl-desleucyl-vancomycin Inhibits the Transglycosylation Process Required for Peptidoglycan Synthesis in Bacteria in the Absence of Dipeptide Binding FEMS Microbiol. Lett. 2000, 183, 209-214
29. Kerns, R.; Dong, S. D.; Fukuzawa, S.; Carbeck, J.; Kohler, J.; Silver, L.; Kahne, D. The Role of Hydrophobic Substituents in the Biological Activity of Glycopeptide Antibiotics J. Am. Chem. Soc. 2000, 122, 12608-12609
30. Kim, S. J.; Matsuoka, S.; Patti, G. J.; Schaefer, J. Vancomycin Derivative with Damaged d -Ala- d -Ala Binding Cleft Binds to Cross-Linked Peptidoglycan in the Cell Wall of Staphylococcus aureus Biochemistry 2008, 47, 3822-3831
31. McComas, C. C.; Crowley, B. M.; Hwang, I.; Boger, D. L. Synthesis and Evaluation of Methyl Ether Derivatives of Vancomycin, Teicoplanin, and Ristocetin Aglycon Methyl Ethers Bioorg. Med. Chem. Lett. 2003, 13, 2933-2936
32. McAtee, J. J.; Castle, S. L.; Jin, Q.; Boger, D. L. Synthesis and Evaluation of Vancomycin and Vancomycin Aglycon Analogues that Bear Modifications in the Residue 3 Asparagine Bioorg. Med. Chem. Lett. 2002, 12, 1319-1322
33. Residue 1 modifications, see: Cristofaro, M. F.; Beauregard, D. A.; Yan, H.; Osborn, N. J.; Williams, D. H. Cooperativity Between Nonpolar and Ionic Forces in the Binding of Bacterial Cell Wall Analogues by Vancomycin in Aqueous Solution J. Antibiot. 1995, 48, 805-810
34. Kahne, D.; Walker, S.; Silva, D. J. Desleucyl Glycopeptide Antibiotics and Methods of Making Same. Patent WO 2000/59528 (US 2004110665), 2000.
35. Crane, C. M.; Boger, D. L. Synthesis and Evaluation of Vancomycin Aglycon Analogues That Bear Modifications in the N-Terminal d -Leucyl Amino Acid J. Med. Chem. 2009, 52, 1471-1476
36. Residue 3 modifications of teicoplanin, see: Malabarba, A.; Ciabatti, R.; Kettenring, J.; Ferrari, P.; Vékey, K.; Bellasio, E.; Denaro, M. Structural Modifications of the Active Site in Teicoplanin and Related Glycopeptides. 1. Reductive Hydrolysis of the 1,2- and 2,3-Peptide Bonds J. Org. Chem. 1996, 61, 2137-2150
37. Malabarba, A.; Ciabatti, R.; Gerli, E.; Ripamonti, F.; Ferrari, P.; Colombo, L.; Olsufyeva, E. N.; Pavlov, A. Y.; Reznikova, M. I.; Lazhko, E. I.; Preobrazhenskaya, M. N. Substitution of Amino Acids 1 and 3 in Teicoplanin Aglycon: Synthesis and Antibacterial Activity of Three First Non-natural Dalbaheptides J. Antibiot. 1997, 50, 70-81
38. Leung, S. S. F.; Tirado-Rives, J.; Jorgensen, W. L. Vancomycin Analogs: Seeking to Improve Binding of d -Ala- d -Ala and d -Ala- d -Lac Peptides by Side-Chain and Backbone Modifications Bioorg. Med. Chem. 2009, 17, 5874-5886
39. Leung, S. S. F.; Tirado-Rives, J.; Jorgensen, W. L. Vancomycin Resistance: Modeling Backbone Variants with d -Ala- d -Ala and d -Ala- d -Lac Peptides Bioorg. Med. Chem. Lett. 2009, 19, 1236-1239
40. For references regarding the activity of oritavancin against the present strains of vancomycin sensitive S. aureus ATCC 25923 see: Seral, C.; Van Bambeke, F.; Tulkens, P. M. Quantitative Analysis of Gentamycin, Azithromycin, Telithromycin, Ciprofloxacin, Moxifloxacin, and Oritavancin (LY333328) Activities Against Staphylococcus aureus in Mouse J774 Macrophages Antimicrob. Agents Chemother. 2003, 47, 2283-2292
41. Barcia-Macay, M.; Seral, C.; Mingeot-Leclercq, M.-P.; Tulkens, P. M.; Van Bambeke, F. Pharmacodynamic Evaluation of the Intracellular Activities of Antibiotics against Staphylococcus aureus in a Model of THP-1 Macrophages Antimicrob. Agents Chemother. 2006, 50, 841-851
42. For the activity of oritavancin against vancomycin resistant E. faecalis VanB strain ATCC 51299, see: McKay, G. A.; Beaulieu, S.; Arhin, F. F.; Belley, A.; Sarmiento, I.; Parr, T.; Moeck, G. Time-kill Kinetics of Oritavancin and Comparator Agents against Staphylococcus aureus, Enterococcus faecalis and Enterococcus faecium J. Antimicrob. Chemother. 2009, 63, 1191-1199
43. For the activity of oritavancin against vancomycin and teicoplanin resistance VanA strain, see: Arthur, M.; Depardieu, F.; Reynolds, P.; Courvalin, P. Moderate-Level Resistance to Glycopeptide LY333328 Mediated by Genes of the vanA and vanB Clusters in Enterococci Antimicrob. Agents Chemother. 1999, 43, 1875-1880
44. Sharman, G. J.; Try, A. C.; Dancer, R. J.; Cho, Y. R.; Staroske, T.; Bardsley, B.; Maguire, A. J.; Cooper, M. A.; O'Brien, D. P.; Williams, D. H. The Roles of Dimerization and Membrane Anchoring in Activity of Glycopeptide Antibiotics Against Vancomycin-Resistant Bacteria J. Am. Chem. Soc. 1997, 119, 12041-12047
45. For a review, see: Williams, D. H.; Searle, M. S.; Westwell, M. S.; Mackay, J. P.; Groves, P.; Beauregard, D. A. The Role of Weak Interactions, Dimerization, and Cooperativity in Antibiotic Action and Biological Signaling Chemtracts: Org. Chem. 1994, 7, 133-159
46. Ge, M.; Chen, Z.; Onishi, H. R.; Kohler, J.; Silver, L. L.; Kerns, R.; Fukuzawa, S.; Thompson, C.; Kahne, D. Vancomycin Derivatives that Inhibit Peptidoglycan Biosynthesis Without Binding d -Ala- d -Ala Science 1999, 284, 507-511
47. Chen, L.; Walker, D.; Sun, B.; Hu, Y.; Walker, S.; Kahne, D. Vancomycin Analogs Active Against VanA-Resistant Strains Inhibit Bacterial Transglycosylase Without Binding Substrate Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 5658-5663
48. For the TFA-mediated deglycosylation of vancomycin, see: Boger, D. L.; Miyazaki, S.; Loiseleur, O.; Beresis, R. T.; Castle, S. L.; Wu, J. H.; Jin, Q. Thermal Atropisomerism of Aglucovancomycin Derivatives: Preparation of (M, M, M)- and (P, P, P)-Aglucovancomycins J. Am. Chem. Soc. 1998, 120, 8920-8926
49. Wanner, J.; Tang, D.; McComas, C. C.; Crowley, B. M.; Jiang, W.; Moss, J.; Boger, D. L. A New and Improved Method for Deglycosylation of Glycopeptide Antibiotics Exemplified with Vancomycin, Ristocetin, and Ramoplanin Bioorg. Med. Chem. Lett. 2003, 13, 1169-1173
50. UV-difference titration assays were run as previously described: Nieto, M.; Perkins, H. R. The Specificity of Combination between Ristocetins and Peptides Related to Bacterial Cell Wall Mucopeptide Precursors Biochem. J. 1971, 124, 845-852
51. Nieto, M.; Perkins, H. R. Physiochemical Properties of Vancomycin and Iodovancomycin and their Complexes with Diacetyl- l -lysyl- d -alanyl- d -alanine Biochem. J. 1971, 123, 773-787
52. Perkins, H. R. Specificity of Combination between Mucopeptide Precursors and Vancomycin or Ristocetin Biochem. J. 1969, 111, 195-205
53. For lead reference see: Koteva, K.; Hong, H.-J.; Wang, X. D.; Nazi, I.; Hughes, D.; Naldrett, M. J.; Buttner, M. J.; Wright, G. D. A Vancomycin Photoprobe Identifies the Histidine Kinase VanSsc as a Vancomycin Receptor Nature Chem. Biol. 2010, 6, 327-329
54. For lead reference see: Hong, H.-J.; Hutchings, M. I.; Buttner, M. J. Vancomycin Resistance VanS/VanR Two-Component Systems Adv. Exp. Med. Biol. 2008, 631, 200-213