Membrane active vancomycin analogues: A strategy to combat bacterial resistance

Journal of Medicinal Chemistry

Volumn 57, Issue 11, 2014, Pages 4558-4568

  Yarlagadda, Venkateswarlu ^a   Akkapeddi, Padma ^a   Manjunath, Goutham B ^a   Haldar, Jayanta ^a  

^a JAWAHARLAL NEHRU CENTRE FOR ADVANCED SCIENTIFIC RESEARCH   (India)

Author keywords

[No Author keywords available]

Indexed keywords

DALBAVANCIN; TELAVANCIN; VANCOMYCIN DERIVATIVE;

ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; ANTIBIOTIC THERAPY; ARTICLE; BACTERIAL INFECTION; CONTROLLED STUDY; DRUG EFFICACY; DRUG SYNTHESIS; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; NONHUMAN; VANCOMYCIN RESISTANT ENTEROCOCCUS;

ANIMALS; BACTEREMIA; CELL MEMBRANE PERMEABILITY; DRUG RESISTANCE, BACTERIAL; ENTEROCOCCUS; FEMALE; HELA CELLS; HEMOLYSIS; HUMANS; MICE; MICROBIAL SENSITIVITY TESTS; NEUTROPENIA; QUATERNARY AMMONIUM COMPOUNDS; STAPHYLOCOCCAL INFECTIONS; STAPHYLOCOCCUS; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZOLES; VANCOMYCIN;

EID: 84902491232     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm500270w     Document Type: Article

References (48)

1. Kahne, D.; Leimkuhler, C.; Lu, W.; Walsh, C. T. Glycopeptide and lipopeptide antibiotics Chem. Rev. 2005, 105, 425-448
2. Naber, C. K. Staphylococcus aureus bacteremia: epidemiology, pathophysiology, and management strategies Clin. Infect. Dis. 2009, 48, S231-S237
3. Woodford, N.; Livermore, D. M. Infections caused by Gram-positive bacteria: a review of the global challenge J. Infect. 2009, 59, S4-S16
4. Taubes, G. The bacteria fight back Science 2008, 321, 356-361
5. Wenzel, R. P.; Edmond, M. B. Managing antibiotic resistance N. Engl. J. Med. 2000, 343, 1961-1963 (Pubitemid 32064792)
6. Levy, S. B.; Marshall, B. Antibacterial resistance worldwide: causes, challenges and responses Nature Med. 2004, 10, S122-S129
7. Walsh, C. T.; Fisher, S. L.; Park, I. S.; Prahalad, M.; Wu, Z. Bacterial resistance to vancomycin: five genes and one missing hydrogen bond tell the story Chem. Biol. 1996, 3, 21-28 (Pubitemid 126682705)
8. 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 (Pubitemid 36936049)
9. Pootoolal, J.; Neu, J.; Wright, G. D. Glycopeptide antibiotic resistance Annu. Rev. Pharmacol. Toxicol. 2002, 42, 381-408 (Pubitemid 34160531)
10. Rao, J.; Lahiri, J.; Isaacs, L.; Weis, R. M.; Whitesides, G. M. A trivalent system from vancomycin. D-ala·D-Ala with higher affinity than avidin·biotin Science 1998, 280, 708-711 (Pubitemid 28243338)
11. Fu, X.; Albermann, C.; Jiang, J.; Liao, J.; Zhang, C.; Thorson, J. S. Antibiotic optimization via in vitro glycorandomization Nature Biotechnol. 2003, 21, 1467-1469 (Pubitemid 37522706)
12. Xing, B.; Yu, C. W.; Ho, P. L.; Chow, K. H.; Cheung, T.; Gu, H.; Cai, Z.; Xu, B. Multivalent antibiotics via metal complexes: potent divalent vancomycins against vancomycin-resistant Enterococci J. Med. Chem. 2003, 46, 4904-4909 (Pubitemid 37352030)
13. Griffin, J. H.; Linsell, M. S.; Nodwell, M. B.; Chen, Q.; Pace, J. L.; Quast, K. L.; Krause, K. M.; Farrington, L.; Wu, T. X.; Higgins, D. L.; Jenkins, T. E.; Christensen, B. G.; Judice, K. Multivalent drug design. Synthesis and in vitro analysis of an array of vancomycin dimers J. Am. Chem. Soc. 2003, 125, 6517-6531 (Pubitemid 36605420)
14. Yao, N. H.; Liu, G.; He, W. Y.; Niu, C.; Carlson, J. R.; Lam, K. S. Solid-phase synthesis and antibacterial evaluations of N -demethylvancomycin derivatives Bioorg. Med. Chem. Lett. 2005, 15, 2325-2329 (Pubitemid 40523095)
15. Haldar, J.; Yarlagadda, V.; Akkapeddi, P. Cationic antibacterial composition. WO Patent 072838, 2013.
16. Griffith, B. R.; Krepel, C.; Fu, X.; Blanchard, S.; Ahmed, A.; Edmiston, C. E.; Thorson, J. S. Model for antibiotic optimization via neoglycosylation: synthesis of liponeoglycopeptides active against VRE J. Am. Chem. Soc. 2007, 129, 8150-8155 (Pubitemid 47039083)
17. 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
18. Nakama, Y.; Yoshida, O.; Yoda, M.; Araki, K.; Sawada, Y.; Nakamura, J.; Xu, S.; Miura, K.; Maki, H.; Arimato, H. Discovery of a novel series of semisynthetic vancomycin derivatives effective against vancomycin-resistant bacteria J. Med. Chem. 2010, 53, 2528-2533
19. Ashford, P. A.; Bew, S. P. Recent advances in the synthesis of new glycopeptide antibiotics Chem. Soc. Rev. 2012, 41, 957-978
20. Pavlov, A. Y.; Lazhko, E. I.; Preobrazhenskaya, M. N. A new type of chemical modification of glycopeptide antibiotics: aminomethylated derivatives of eremomycin and their antibacterial activity J. Antibiot. 1997, 50, 509-513 (Pubitemid 27326739)
21. Pavlov, A. Y.; Berdnikova, T. F.; Olsufyeva, E. N.; Lazhko, E. I.; Malkova, I. V.; Preobrazhenskaya, M. N. Synthesis and biological activity of derivatives of glycopeptide antibiotics eremomycin and vancomycin nitrosated, acylated or carbamoylated at the N-terminal J. Antibiot. 1993, 46, 1731-1739 (Pubitemid 23355460)
22. Maffioli, S. I.; Ciabatti, R.; Romano, G.; Marzorati, E.; Preobrazhenskaya, M.; Pavlov, A. Synthesis and antibacterial activity of alkyl derivatives of the glycopeptide antibiotic A40926 and their amides Bioorg. Med. Chem. Lett. 2005, 15, 3801-3805 (Pubitemid 41038982)
23. Pavlov, A. Y.; Miroshnikova, O. V.; Printsevskaya, S. S.; Olsufyeva, E. N.; Preobrazhenskaya, M. N. Synthesis of hydrophobic N ′-mono and N ′, N ″-double alkylated eremomycins inhibiting the transglycosylation stage of bacterial cell wall biosynthesis J. Antibiot. 2001, 54, 455-459 (Pubitemid 32515109)
24. Zhanel, G. G.; Calic, D.; Schweizer, F.; Zelenitsky, S.; Adam, H.; Lagace-Wiens, P. R. S.; Rubinstein, E.; Gin, A. S.; Hoban, D. J.; Karlowsky, J. A. New lipoglycopeptides: a comparitive review of dalbavancin, oritavancin and telavancin Drugs 2010, 70, 859-886
25. 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 biosynthesis and cell membrane integrity in methicillin-resistant Staphylococcus aureus Antimicrob. Agents Chemother. 2005, 49, 1127-1134 (Pubitemid 40327734)
26. Domenech, O.; Francius, G.; Tulkens, P. M.; Van Bambeke, F.; Dufrene, Y.; Mingeot-Leclercq, M. P. Interactions of oritavancin, a new lipoglycopeptide derived from vancomyicn, with phospholipid bilayers: effect on membrane permeability and nanoscale lipid membrane organization Biochim. Biophys. Acta 2009, 1788, 1832-1840
27. Xie, J.; Okano, A.; Pierce, J. G.; James, R. C.; Stamm, S.; Crane, C. M.; Boger, D. L. Total synthesis of [Ψ[C(=S)NH]Tpg4]vancomycin aglycon, [Ψ[C(=NH)NH]Tpg4]vancomycin aglycon, and related key compounds: reengineering vancomycin for dual d -Ala- d -Ala and d -Ala- d -Lac binding J. Am. Chem. Soc. 2012, 134, 1284-1297
28. Xie, J.; Pierce, J. G.; James, R. C.; Okano, A.; Boger, D. L. A redesigned vancomycin engineered for dual d -Ala- d -Ala and d -Ala- d -Lac binding exhibits potent antimicrobial activity against vancomycin-resistant bacteria J. Am. Chem. Soc. 2011, 133, 13946-13949
29. Zasloff, M. Antimicrobial peptides of multicellular organisms Nature 2010, 415, 389-395
30. Nederberg, F.; Zhang, Y.; Tan, J. P. K.; Xu, K. J.; Wang, H. Y.; Yang, C.; Gao, S. J.; Guo, X. D.; Fukushima, K.; Li, L. J.; Hedrick, J. L.; Yang, Y. Y. Biodegradable nanostructures with selective lysis of microbial membranes Nature Chem. 2011, 3, 409-414
31. Draghi, D. C.; Benton, B. M.; Krause, K. M.; Thornsberry, C.; Pillar, C.; Sahm, D. F. In vitro activity of telavancin against recent Gram-positive clinical isolates: results of the 2004-05 Prospective European Surveillance Initiative J. Antimicrob. Chemother. 2008, 62, 116-121 (Pubitemid 351865882)
32. Streit, J. M.; Fritsche, T. R.; Sader, H. S.; Jones, R. N. Worldwide assessment of dalbavancin activity and spectrum against over 6000 clinical isolates Diagn. Microbiol. Infect. Dis. 2004, 48, 137-143 (Pubitemid 38221510)
33. Tambe, S. M.; Sampath, L.; Modak, S. M. In vitro evaluation of the risk of developing bacterial resistance to antiseptics and antibiotics used in medical devices J. Antimicrob. Chemother. 2001, 47, 589-598 (Pubitemid 32447645)
34. Zhang, L.; Dhillon, P.; Yan, H.; Farmer, S.; Hancock, R. E. W. Interactions of bacterial cationic peptide antibiotics with outer and cytoplasmic membranes of Pseudomonas aeruginosa Antimicrob. Agents Chemother. 2000, 44, 3317-3321 (Pubitemid 33014325)
35. Boulos, L.; Prevost, M.; Barbeau, B.; Coallier, J.; Desjardins, R. LIVE/DEAD BacLight: application of a new rapid staining method for direct enumeration of viable and total bacteria in drinking water J. Microbiol. Methods 1999, 37, 77-86 (Pubitemid 29248770)
36. Herranz, C.; Cintas, L. M.; Hernandez, P. E.; Moll, G. N.; Driessen, A. J. M. Enterocin P causes potassium ion efflux from Enterococcus faecium T136 cells Antimicrob. Agents Chemother. 2001, 45, 901-904 (Pubitemid 32182042)
37. Andes, D.; Van Ogtrop, M. L.; Peng, J.; Craig, W. A. In vivo pharmacodynamics of a new oxazolidinone (linezolid) Antimicrob. Agents Chemother. 2002, 46, 3484-3489 (Pubitemid 35192915)
38. Sundram, U. N.; Griffin, J. H. General and efficient method for the solution and solid phase synthesis of vancomycin carboxamide derivatives J. Org. Chem. 1995, 60, 1102-1103
39. Wiegand, I.; Hilpert, K.; Hancock, R. E. W. Agar and broth dilution methods to determine the minimal inhibitory concentration (MIC) of antimicrobial substances Nature Protoc. 2008, 3, 163-175 (Pubitemid 351266501)
40. Chin, J. N.; Rybak, M. J.; Cheung, C. M.; Savage, P. B. Antimicrobial activities of ceragenins against clinical isolates of resistant Staphylococcus aureus Antimicrob. Agents Chemother. 2007, 51, 1268-1273 (Pubitemid 46586804)
41. Rotem, S.; Radzishevsky, I. S.; Bourdetsky, D.; Navon-Vanezia, S.; Carmeli, Y.; Mor, A. Analogous oligo-acyl-lysines with distinct antibacterial mechanisms FASEB J. 2008, 22, 2652-2661
42. Pollard, J. E.; Snarr, J.; Chaudhary, V.; Jennings, J. D.; Shaw, H.; Christiansen, B.; Wright, J.; Jia, W.; Bishop, R. E.; Savage, P. B. In vitro evaluation of the potential for resistant development to ceragenin CSA-13 J. Antimicrob. Chemother. 2012, 67, 2665-2672
43. Uppu, D. S. S. M.; Akkapeddi, P.; Manjunath, G. B.; Yarlagadda, V.; Hoque, J.; Haldar, J. Polymers with tunable side chain amphiphilicity as non-hemolytic antibacterial Agents Chem. Commun. 2013, 49, 9389-9391
44. Anantharaman, A.; Sahal, D. Reverse engineering truncations of an antimicrobial peptide dimer to identify the origins of potency and broad spectrum of action J. Med. Chem. 2010, 53, 6079-6088
45. Song, A.; Walker, S. G.; Parker, K. A.; Sampson, N. S. Antibacterial studies of cationic polymers with alternating, random and uniform backbones ACS Chem. Biol. 2011, 6, 590-599
46. Ghosh, C.; Manjunath, G. B.; Akkapeddi, P.; Yarlagadda, V.; Uppu, D. S. S. M.; Hoque, J.; Konai, M. M.; Haldar, J. Small molecular antibacterial peptoid mimics: the simpler the better! J. Med. Chem. 2014, 57, 1428-1436
47. Hoque, J.; Akkapeddi, P.; Yarlagadda, V.; Uppu, D. S. S. M.; Kumar, P.; Haldar, J. Cleavable cationic antibacterial amphiphiles: synthesis, mechanism of action, and cytotoxicities Langmuir 2012, 28, 12225-122234
48. Hegde, S. S.; Reyes, N.; Wiens, T.; Vanasse, N.; Skinner, R.; McCullough, J.; Kaniga, K.; Pace, J.; Thomas, R.; Shaw, J. P.; Obedencio, G.; Judice, J. K. Pharmacodynamics of Telavancin (TD-6424), a novel bactericidal agent against Gram-positive bacteria Antimicrob. Agents Chemother. 2004, 8, 3043-3050 (Pubitemid 38989173)