Marinopyrrole derivatives as potential antibiotic agents against methicillin-resistant Staphylococcus aureus (I)

Marine Drugs

Volumn 10, Issue 4, 2012, Pages 953-962

  Liu, Yan ^a   Haste, Nina M ^b   Thienphrapa, Wdee ^c   Nizet, Victor ^b,c   Hensler, Mary ^c   Li, Rongshi ^a  

^a H LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

^c UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

Author keywords

Antibiotics; Asymmetrical marinopyrroles; Marinopyrrole; MRSA; SAR

Indexed keywords

(3 CHLORO 2 HYDROXYPHENYL)(4,4',5,5' TETRACHLORO 2' (HYDROXYBENZOYL) 1' H 1,3' BIPYRROL 2 YL) METHANONE; (4 CHLORO 2 HYDROXYPHENYL)(4,4',5,5' TETRACHLORO 2' (HYDROXYBENZOYL) 1' H 1,3' BIPYRROL 2 YL) METHANONE; (4 CHLORO 2 METHOXYPHENYL)(4,4',5,5' TETRACHLORO 2' (2 METHOXYBENZOYL) 1'H [1,3'BIPYRROLE] 2 YL) METHANONE; (5 CHLORO 2 HYDROXYPHENYL)(4,4',5,5' TETRACHLORO 2' (HYDROXYBENZOYL) 1' H 1,3' BIPYRROL 2 YL) METHANONE; ANTIBIOTIC AGENT; LINEZOLID; MARINOPYRROLE A; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG; VANCOMYCIN;

ANTIMICROBIAL ACTIVITY; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; SERUM; STRUCTURE ACTIVITY RELATION;

METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; POSIBACTERIA;

EID: 84860604664     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md10040953     Document Type: Article

References (21)

1. Hughes, C.C.; Prieto-Davo, A.; Jensen, P.R.; Fenical, W. The marinopyrroles, antibiotics of an unprecedented structure class from a marine Streptomyces sp. Org. Lett. 2008, 10, 629-631.
2. Nicolaou, K.C.; Simmons, N.L.; Chen, J.S.; Haste, N.M.; Nizet, V. Total synthesis and biological evaluation of marinopyrrole A and analogues. Tetrahedron Lett. 2011, 52, 2041-2043.
3. Hughes, C.C.; Yang, Y.L.; Liu, W.T.; Dorrestein, P.C.; la Clair, J.J.; Fenical, W. Marinopyrrole A target elucidation by acyl dye transfer. J. Am. Chem. Soc. 2009, 131, 12094-12096.
4. Hughes, C.C.; Kauffman, C.A.; Jensen, P.R.; Fenical, W. Structures, reactivities, and antibiotic properties of the marinopyrroles A-F. J. Org. Chem. 2010, 75, 3240-3250.
5. Kanakis, A.A.; Sarli, V. Total synthesis of (±)-marinopyrrole A via copper-mediated N-arylation. Org. Lett. 2010, 12, 4872-4875.
6. Cheng, C.; Pan, L.; Chen, Y.; Song, H.; Qin, Y.; Li, R. Total synthesis of (±)-marinopyrrole a and its library as potential antibiotic and anticancer agents. J. Comb. Chem. 2010, 12, 541-547.
7. Grundmann, H.; Aires-de-Sousa, M.; Boyce, J.; Tiemersma, E. Emergence and resurgence of meticillin-resistant Staphylococcus aureus as a public-health threat. Lancet 2006, 368, 874-885. (Pubitemid 44308640)
8. Como-Sabetti, K.; Harriman, K.H.; Buck, J.M.; Glennen, A.; Boxrud, D.J.; Lynfield, R. Community-associated methicillin-resistant Staphylococcus aureus: Trends in case and isolate characteristics from six years of prospective surveillance. Public Health Rep. 2009, 124, 427-435.
9. Chambers, H.F.; Deleo, F.R. Waves of resistance: Staphylococcus aureus in the antibiotic era. Nat. Rev. Microbiol. 2009, 7, 629-641.
10. Deleo, F.R.; Otto, M.; Kreiswirth, B.N.; Chambers, H.F. Community-associated meticillin-resistant Staphylococcus aureus. Lancet 2010, 375, 1557-1568.
11. Lowy, F.D. Antimicrobial resistance: The example of Staphylococcus aureus. J. Clin. Invest. 2003, 111, 1265-1273. (Pubitemid 36554694)
12. Zhao, K.; Reiner, J.; Xie, W. FDA new drug approvals in 2000. Front. Biotechnol. Pharm. 2001, 2, 329-349.
13. Eisenstein, B.I. Lipopeptides, focusing on daptomycin, for the treatment of Gram-positive infections. Expert. Opin. Investig. Drugs 2004, 13, 1159-1169. (Pubitemid 39242739)
14. FDA Approves Teflaro for Bacterial Infections. FDA News Events 29 October 2010. Available online: http://www.fda.gov/NewsEvents/Newsroom/ PressAnnouncements/ucm231594.htm (accessed on 1 March 2012).
15. Butler, M.S.; Buss, A.D. Natural products - The future scaffolds for novel antibiotics? Biochem. Pharmacol. 2006, 71, 919-929.
16. Haste, N.M.; Hughes, C.C.; Tran, D.N.; Fenical, W.; Jensen, P.R.; Nizet, V.; Hensler, M.E. Pharmacological properties of the marine natural product marinopyrrole A against methicillin-resistant Staphylococcus aureus. Antimicrob. Agents Chemother. 2011, 55, 3305-3312.
17. Furneaux, R.H.; Tyler, P.C. Improved Syntheses of 3H,5H-Pyrrolo[3,2-d] pyrimidines. J. Org. Chem. 1999, 64, 8411-8412. (Pubitemid 29529260)
18. Rochais, C.; Lisowski, V.; Dallemagne, P.; Rault, S. Synthesis and biological evaluation of novel pyrrolopyrrolizinones as anticancer agents. Bioorg. Med. Chem. 2006, 14, 8162-8175. (Pubitemid 44667566)
19. 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)
20. Credito, K.; Lin, G.; Appelbaum, P.C. Activity of daptomycin alone and in combination with rifampin and gentamicin against Staphylococcus aureus assessed by time-kill methodology. Antimicrob. Agents Chemother. 2007, 51, 1504-1507. (Pubitemid 46586838)
21. Ueda, Y.; Kanazawa, K.; Eguchi, K.; Takemoto, K.; Eriguchi, Y.; Sunagawa, M. In vitro and in vivo antibacterial activities of SM-216601, a new broad-spectrum parenteral carbapenem. Antimicrob. Agents Chemother. 2005, 49, 4185-4196. (Pubitemid 41400963)