Chemical conjugation of 2-hexadecynoic acid to C5-curcumin enhances its antibacterial activity against multi-drug resistant bacteria

Bioorganic and Medicinal Chemistry Letters

Volumn 25, Issue 22, 2015, Pages 5067-5071

  Sanabria Ríos, David J ^a   Rivera Torres, Yaritza ^a   Rosario, Joshua ^a   Gutierrez, Ricardo ^a   Torres García, Yeireliz ^a   Montano, Nashbly ^b   Ortíz Soto, Gabriela ^c   Ríos Olivares, Eddy ^c   Rodríguez, José W ^c   Carballeira, Néstor M ^b  

^a INTER AMERICAN UNIVERSITY OF PUERTO RICO   (Puerto Rico)

^b UNIVERSITY OF PUERTO RICO   (Puerto Rico)

^c Universidad Central del Caribe School of Medicine   (Puerto Rico)

Author keywords

Antagonism; Antibacterial agents; C5 curcuminoids synthesis; DNA gyrase; MRSA

Indexed keywords

1,5 BIS(4 HYDROXY 3 METHOXYPHENYL)PENTA 1,4 DIEN 3 ONE; 2 HEXADECYNOIC ACID; ANTIINFECTIVE AGENT; CURCUMIN; FATTY ACID; UNCLASSIFIED DRUG; 2-HEXADECYNOIC ACID; ALKYNE; C5-CURCUMIN-2-HEXADECYNOIC ACID; DNA SUPERCOILING; DNA TOPOISOMERASE (ATP HYDROLYSING); GYRASE INHIBITOR; UNSATURATED FATTY ACID;

ALPHA HEMOLYTIC STREPTOCOCCUS; ANTIBACTERIAL ACTIVITY; ARTICLE; CARBOXYLATION; CELL FUNCTION; CONFORMATIONAL TRANSITION; CONJUGATION; CONTROLLED STUDY; CYTOTOXICITY; DNA REPLICATION; DRUG HALF LIFE; EFFECTIVE CONCENTRATION; ESCHERICHIA COLI; GRAM NEGATIVE BACTERIUM; HYDROLYSIS; KLEBSIELLA PNEUMONIAE; LIPOPHILICITY; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; NONHUMAN; PROTEUS; PROTEUS MIRALEILIS; STRUCTURE ACTIVITY RELATION; ANALOGS AND DERIVATIVES; ANIMAL; CHEMISTRY; CHLOROCEBUS AETHIOPS; CYTOLOGY; DNA SUPERCOILING; DRUG EFFECTS; ENZYMOLOGY; HUMAN; ISOLATION AND PURIFICATION; MONONUCLEAR CELL; PHARMACOLOGY; STAPHYLOCOCCUS AUREUS; SYNTHESIS; VERO CELL LINE;

ALKYNES; ANIMALS; ANTI-BACTERIAL AGENTS; CERCOPITHECUS AETHIOPS; CURCUMIN; DNA GYRASE; DNA, SUPERHELICAL; ESCHERICHIA COLI; FATTY ACIDS, UNSATURATED; HUMANS; LEUKOCYTES, MONONUCLEAR; METHICILLIN-RESISTANT STAPHYLOCOCCUS AUREUS; STAPHYLOCOCCUS AUREUS; TOPOISOMERASE II INHIBITORS; VERO CELLS;

EID: 84945916712     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2015.10.022     Document Type: Article

References (36)

1. CDC: Antibiotic resistance threat in the United States. Technical Report 2013, 77-78.
2. Y. Wang, Z. Lu, H. Wu, and F. Lv Int. J. Food Microbiol. 136 2009 71
3. S. Kaur, N.H. Modi, D. Panda, and N. Roy Eur. J. Med. Chem. 45 2010 4209
4. T. Haukvik, E. Bruzell, S. Kristensen, and H.H. Tonnesen Pharmazie 66 2011 69
5. B.B. Aggarwal, A. Kumar, and A.C. Bharti Anticancer Res. 23 2003 363
6. B.B. Aggarwal Cancer Biol. Ther. 7 2008 1436
7. R.K. Maheshwari, A.K. Singh, J. Gaddipati, and R.C. Srimal Life Sci. 78 2006 2081
8. R.A. Sharma, W.P. Steward, and A.J. Gescher Adv. Exp. Med. Biol. 595 2007 453
9. P. Anand, A.B. Kunnumakkara, R.A. Newman, and B.B. Aggarwal Mol. Pharmacol. 4 2007 807
10. A.P. Zambre, V.M. Kulkarni, S. Padhye, S.K. Sandur, and B.B. Aggarwal Bioorg. Med. Chem. 14 2006 7196
11. L. Lin, Q. Shi, A.K. Nyarko, K.F. Bastow, C.C. Wu, C.Y. Su, C.C. Shih, and K.H. Lee J. Med. Chem. 49 2006 3963
12. N. Handler, W. Jaeger, H. Puschacher, K. Leisser, and T. Erker Chem. Pharm. Bull. 55 2007 64
13. S. Kumar, U. Narain, S. Tripathi, and K. Misra Bioconjugate Chem. 12 2001 464
14. R.K. Singh, D. Rai, D. Yadav, A. Bhargava, J. Balzarini, and E. De Clercq Eur. J. Med. Chem. 45 2010 1078
15. L. Li, F.S. Braiteh, and R. Kurzrock Cancer 104 2005 1322
16. G. Liang, S. Yang, L. Jiang, Y. Zhao, L. Shao, J. Xiao, F. Ye, Y. Li, and X. Li Chem. Pharm. Bull. 56 2008 162
17. G. Liang, L. Shao, Y. Wang, C. Zhao, Y. Chu, J. Xiao, Y. Zhao, X. Li, and S. Yang Bioorg. Med. Chem. 17 2009 2623
18. H. Yamakoshi, H. Ohori, C. Kudo, A. Sato, N. Kanoh, C. Ishioka, H. Shibata, and Y. Iwabuchi Bioorg. Med. Chem. 18 2010 1083
19. D.J. Sanabria-Rios, Y. Rivera-Torres, G. Maldonado-Dominguez, I. Dominguez, C. Rios, D. Diaz, J.W. Rodriguez, J.S. Altieri-Rivera, E. Rios-Olivares, G. Cintron, N. Montano, and N.M. Carballeira Chem. Phys. Lipids 178 2014 84
20. M.R. Klevens, M.A. Morrison, J. Nadle, S. Petit, K. Gershman, S. Ray, L.H. Harrison, R. Lynfield, G. Dumyati, J.M. Townes, A.S. Graig, E.R. Zell, G.E. Fosheim, L.K. McDougal, R.B. Carey, and S.K. Fridkin JAMA 298 2007 1763
21. C.A. Higgins, Z. Delbederi, K. McGarel, T. Mills, O. McGrath, S. Feutren-Burton, W. Watters, P. Armstrong, P.G. Johnston, D. Waugh, and H. van den Berg Bioconjugate Chem. 20 2009 1737
22. D.J. Sanabria-Rios, Y. Rivera-Torres, J. Rosario, C. Rios, R. Gutierrez, N.M. Carballeira, C. Velez, B. Zayas, F. Alvarez-Colon, G. Ortiz-Soto, V. Serrano, J. Altieri-Rivera, E. Rios-Olivares, and J.W. Rodriguez Bioorg. Med. Chem. Lett. 25 2015 2174
23. J.B. Lambert, H.F. Shurvell, D.A. Lightner, and R. Graham Cooks Organic Structural Spectroscopy 1998 Prentice Hall New Jersey
24. T.C. Chou Pharmacol. Rev. 58 2006 621
25. N.M. Carballeira, M. Cartagena, D. Sanabria, D. Tasdemir, C.F. Prada, R.M. Reguera, and R. Balana-Fouce Bioorg. Med. Chem. Lett. 22 2012 6185
26. H.R. Morbidoni, C. Vilchèze, L. Kremer, R. Bittman, J.C. Sacchettini, and W.R. Jacobs Chem. Biol. 13 2006 297
27. G.N. Roth, A. Chandra, and M.G. Nair J. Nat. Prod. 61 1998 542
28. A.C. Ketron, O.N. Gordon, C. Schneider, and N. Osheroff Biochemistry 52 2013 221
29. A. Kumar, and U. Bora Interdisciplinary Sciences 2014
30. K. Suzuki, F. Shono, H. Kai, T. Uno, and M. Uyeda J. Enzyme Inhib. 15 2000 357
31. B.C. Giovanella, J.S. Stehlin, M.E. Wall, M.C. Wani, A.W. Nicholas, L.F. Liu, R. Silber, and M. Potmesil Science 246 1989 1046
32. C. Sheng, Z. Miao, and W. Zhang Curr. Med. Chem. 18 2011 4389
33. Y.C. Tse-Dinh Infect. Disord. Drug Targets 7 2007 3
34. B.J. Bradbury, and M.J. Pucci Curr. Opin. Pharm. 8 2008 574
35. Y. Pommier, E. Leo, H.L. Zhang, and C. Marchand Chem. Biol. 17 2010 421
36. Y. Pommier, E. Leo, H.L. Zhang, and C. Marchand Chem. Biol. 17 2010 421