Discovery of a novel series of semisynthetic vancomycin derivatives effective against vancomycin-resistant bacteria

Journal of Medicinal Chemistry

Volumn 53, Issue 6, 2010, Pages 2528-2533

  Nakama, Yuki ^a   Yoshida, Osamu ^b   Yoda, Masanori ^a   Araki, Keisuke ^a   Sawada, Yuri ^b   Nakamura, Jun ^a   Xu, Shu ^a   Miura, Kenji ^b   Maki, Hideki ^b   Arimoto, Hirokazu ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b SHIONOGI AND CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

10 DECHLORO 10 (2 METHOXYPHENYL); 10 DECHLORO 10 (TRANS 2 PHENYLVINYL); 10 DECHLORO 10 (TRANS 5 PHENYLPENT 1 EN 1 YL); 10 DECHLORO 10 (TRANS OCT 1 EN 1 YL); 10 DECHLORO 10 [TRANS 2 (4 METHOXYPHENYL)VINYL]; 10 DECHLORO 10 [TRANS 2 [4 (TRIFLUOROMETHYL)PHENYL]VINYL]; 10 DECHLORO 10 TRANS [2 (BIPHENYL 4 YL)VINYL]; 10,19 DIDECHLORO 10 (TRANS PROP 1 EN 1 YL) 19 (TRANS OCT 1 EN 1 YL); 10,19 DIDECHLORO 10,19 DI (5 PHENYLPENT 1 EN 1 YL); 10,19 DIDECHLORO 10,19 DI (TRANS OCT 1 EN 1 YL); 10,19 DIDECHLORO 10,19 DI (TRANS PROP 1 EN 1 YL); AMINO ACID; CARBON; CHLORIDE; NAPROXEN; UNCLASSIFIED DRUG; VANCOMYCIN; VANCOMYCIN DERIVATIVE;

ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; ANTIBIOTIC SENSITIVITY; ARTICLE; BACTERIAL STRAIN; CONTROLLED STUDY; CROSS COUPLING REACTION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; STAPHYLOCOCCUS AUREUS; VANCOMYCIN RESISTANT ENTEROCOCCUS;

ANTI-BACTERIAL AGENTS; BACTERIA; DRUG DISCOVERY; MICROBIAL SENSITIVITY TESTS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; STAPHYLOCOCCUS AUREUS; VANCOMYCIN; VANCOMYCIN RESISTANCE;

EID: 77949856353     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm9017543     Document Type: Article

References (27)

1. Miller, D.; Urdaneta, V.; Weltman, A.; Park, S.; Cdc. Vancomycinresistant Staphylococcus aureus. Pennsylvania, 2002. JAMA, J. Am. Med. Assoc. 2002, 288, 2116
2. (Reprinted from Morbidity Mortality Wkly. Rep. 2002, 51, 902).
3. Tiwari, H. K.; Sen, M R. Emergence of vancomycin resistant Staphylococcus aureus (VRSA) from a tertiary care hospital from northern part of India. BMC Infect. Dis. 2006, 5, Article 156.
4. Aligholi, M.; Emaneini, M.; Jabalameli, F.; Shahsavan, S.; Dabiri, H.; Sedaght, H. Emergence of high-level vancomycin-resistant Staphylococcus aureus in the Imam Khomeini hospital in Tehran. Med. Principles Pract. 2008, 17, 432-434.
5. Nicolaou, K. C.; Boddy, C. N. C.; Brase, S.; Winssinger, N. Chemistry, biology, and medicine of the glycopeptide antibiotics. Angew. Chem., Int. Ed. 1999, 38, 2097-2152.
6. Kahne, D.; Leimkuhler, C.; Wei, L.; Walsh, C. Glycopeptide and lipoglycopeptide antibiotics. Chem. Rev. 2005, 105, 425-448.
7. Arimoto, H.; Nishimura, K.; Kinumi, T.; Hayakawa, I.; Uemura, D. Multi-valent polymer of vancomycin: enhanced antibacterial activity against VRE. Chem. Commun. 1999, 1361-1362.
8. Lu, J.; Yoshida, O.; Hayashi, S.; Arimoto, H. Synthesis of rigidlylinked vancomycin dimers and their in vivo efficacy against resistant bacteria. Chem. Commun. 2007, 251-253.
9. King, A.; Phillips, I.; Kaniga, K. Comparative in vitro activity of telavancin (TD-6424), a rapidly bactericidal, concentrationdependent anti-infective with multiple mechanisms of action against Gram-positive bacteria. J. Antimicrob. Chemother. 2004, 53, 797-803.
10. Higgins, D. L.; Chang, R.; Debabov, D. V.; Leung, J.; Wu, T.; Krause, K. M.; Sandvik, E.; Hubbard, J. M.; Kaniga, K.; Schmidt, D. E., Jr.; Gao, Q.; Cass, R. T.; Karr, D. E.; Benton, B. M.; Humphrey, P. P. Telavancin, a multifunctional lipoglycopeptide, disrupts both cell wall synthesis and cell membrane integrity in methicillin-resistant Staphylococcus aureus. Antimicrob. Agents Chemother. 2005, 49, 1127-1134.
11. Belley, A.; Neesham-Grenon, E.; McKay, G.; Arhin, F. F.; Harris, R.; Beveridge, T.; Parr, T. R.; Moeck, G. Oritavancin kills stationary-phase and biofilm Staphylococcus aureus cells in vitro. Antimicrob. Agents Chemother. 2009, 53, 918-925.
12. Lunde, C. S.; Hartouni, S. R.; Jane, J. W.; Mammen, M.; Humphrey, P. P.; Benton, B. M. Telavancin disrupts the functional integrity of the bacterial membrane through targeted interaction with the cell wall precursor lipid II. Antimicrob. Agents Chemother. 2009, 53, 3375-3383.
13. Cooper, R. D. G.; Snyder, N. J.; Zweifel, M. J.; Staszak, M. A.; Wilkie, S. C.; Nicas, T. I.; Mullen, D. L.; Butler, T. F.; Rodriguez, M. J.; Huff, B. E.; Thompson, R. C. Reductive alkylation of glycopeptide antibiotics: synthesis and antibacterial activity. J. Antibiot. 1996, 49, 575-581.
14. Pavlov, A. Y.; Lazhko, E. I.; Preobrazhenskaya, M. N. A new type of chemical modification of glycopeptides antibiotics: aminomethylated derivatives of eremomycin and their antibacterial activity. J. Antibiot. 1997, 50, 509-513.
15. Booth, P. M.; Stone, D. J. M.; Williams, D. H. The Edman degradation of vancomycin: preparation of vancomycin hexapeptide. J. Chem. Soc., Chem. Commun. 1987, 1694-1695.
16. 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.
17. 2NH Tpg(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. Bedford, R. B.; Cazin, C. S. J.; Holder, D. The development of palladium catalysts for C-C and C-heteroatom bond forming reactions of aryl chloride substrates. Coord. Chem. Rev. 2004, 248, 2283-2321.
19. Anderson, K. W.; Buchwald, S. L. General catalysts for the Suzuki-Miyaura and Sonogashira coupling reactions of aryl chlorides and for the coupling of challenging substrate combinations in water. Angew. Chem., Int. Ed. 2005, 44, 6173-6177.
20. Harris, C. M.; Kannan, R.; Kopecka, H.; Harris, T. M. The role of the chlorine substituents in the antibiotic vancomycin: preparation and characterization of mono- and didechlorovancomycin. J. Am. Chem. Soc. 1985, 107, 6652-6658.
21. Barder, T.; Walker, S.; Martinelli, J.; Buchwald, S. Catalysts for Suzuki-Miyaura coupling processes: scope and studies of the effect of ligand structure. J. Am. Cem. Soc. 2005, 127, 4685-4696.
22. Thimmaiah, M.; Zhang, X.; Fang, S. Palladium-catalyzed crosscoupling of aryl chlorides with alkenylboronic acids with low E/Z isomerization. Tetrahedron Lett. 2008, 49, 5605-5607.
23. 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-DAla. Science 1999, 284, 507-511.
24. Chen, L.; Walker, D.; Sun, B.; Hu, Y.; Walker, S.; Kahne, D. Vancomycin analogues active against vanA-resistant strains inhibit bacterial transglycosylase without binding substrate. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 5658-5663
25. Maki, H.; Miura, K.; Yamano, Y. Katanosin B and plusbacin A(3), inhibitors of peptidoglycan synthesis in methidllin-resistant Staphylococcus aureus. Antimicrob. Agents Chemother. 2001, 45, 1823-1827
26. Miura, K.; Yamashiro, H.; Uotani, K.; Kojima, S.; Yutsudo, T.; Lu, J.; Yoshida, O.; Yamano, Y.; Maki, H.; Arimoto, H. Mode of action of Van-M-02, a novel glycopeptide inhibitor of peptidoglycan synthesis, in vancomycin-resistant bacteria. Antimicrob. Agents Chemother. 2010, 54, 960-962.
27. Nitanai, Y.; Kikuchi, T.; Kakoi, K.; Hanamaki, S.; Fujisawa, I.; Aoki, K. Crystal structures of the complexes between vancomycin and cell-wall precursor analogs. J. Mol. Biol. 2009, 385, 1422-1432.