Antibacterial activity of 2-alkynoic fatty acids against multidrug-resistant bacteria

Chemistry and Physics of Lipids

Volumn 178, Issue , 2014, Pages 84-91

  Sanabria Ríos, David J ^a   Rivera Torres, Yaritza ^a   Maldonado Domínguez, Gamalier ^a   Domínguez, Idializ ^a   Ríos, Camille ^a   Díaz, Damarith ^a   Rodríguez, José W ^b   Altieri Rivera, Joanne S ^b   Ríos Olivares, Eddy ^b   Cintrón, Gabriel ^c   Montano, Nashbly ^c   Carballeira, Néstor M ^c  

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

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

^c UNIVERSITY OF PUERTO RICO   (Puerto Rico)

Author keywords

2 Alkynoic fatty acids; Antibacterial agents; Micelles; MRSA; Nosocomial infections; Synthesis

Indexed keywords

2 (2 HEXADECYNYLOXY)TETRAHYDRO 2H PYRAN; 2 (2 OCTADECYNYLOXY)TETRAHYDRO 2H PYRAN; 2 HEXADECYN 1 OL; 2 HEXADECYNOIC ACID; 2 ICOSANOIC ACID; 2 OCTADECYN 1 OL; 2 OCTADECYNOIC ACID; 2,6 HEXADECYNOIC ACID; 2,9 HEXADECYNOIC ACID; ANTIBIOTIC AGENT; ARACHIDIC ACID; CIPROFLOXACIN; FATTY ACID DERIVATIVE; METICILLIN; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACILLUS CEREUS; BACTERIUM ISOLATE; CONTROLLED STUDY; CRITICAL MICELLE CONCENTRATION; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; KLEBSIELLA PNEUMONIAE; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PRIORITY JOURNAL; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS SAPROPHYTICUS;

BACILLUS CEREUS; KLEBSIELLA PNEUMONIAE; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; NEGIBACTERIA; POSIBACTERIA; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS; STAPHYLOCOCCUS SAPROPHYTICUS;

2-ALKYNOIC FATTY ACIDS; ANTIBACTERIAL AGENTS; MICELLES; MRSA; NOSOCOMIAL INFECTIONS; SYNTHESIS;

ANTI-BACTERIAL AGENTS; DRUG RESISTANCE, MULTIPLE; FATTY ACIDS, UNSATURATED; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIA; HUMANS; LEUKOCYTES, MONONUCLEAR; METHICILLIN-RESISTANT STAPHYLOCOCCUS AUREUS; MICROBIAL SENSITIVITY TESTS;

EID: 84893795817     PISSN: 00093084     EISSN: 18732941     Source Type: Journal    
DOI: 10.1016/j.chemphyslip.2013.12.006     Document Type: Article

References (38)

1. P.S. Brachman, B.B. Dan, R.W. Haley, T.M. Hooton, J.S. Garner, and J.R. Allen Nosocomial surgical infections: incidence and cost Surg. Clin. North Am. 60 1980 15 25 (Pubitemid 10049640)
2. B.J. Bradbury, and M.J. Pucci Recent advances in antibacterial topoisomerase inhibitors Curr. Opin. Pharmacol. 8 2008 574 581
3. E.B. Cahoon, J.A. Schnurr, E.A. Huffman, and R.E. Minto Fungal responsive fatty acid acetylenases occur widely in evolutionarily distant plant families Plant J. 34 2003 671 683 (Pubitemid 36720201)
4. N.M. Carballeira New advances in fatty acids as antimalarial, antimycobateial and antifungal agents Prog. Lipid Res. 47 2008 50 61 (Pubitemid 350216622)
5. N.M. Carballeira, J.E. Betancourt, E.A. Orellano, and F.A. González Total synthesis and biological evaluation of (5Z, 9Z)-5,9-hexadecadienoic acid, an inhibitor of human topoisomeras I J. Nat. Prod. 65 2002 1715 1718 (Pubitemid 35386816)
6. N.M. Carballeira, M. Cartagena, D. Sanabria, D. Tasdemir, C.F. Prada, R.M. Reguera, and R. Balana-Fouce 2-Alkynoic fatty acids inhibit topoisomerase IB from Leishmania donovani Bioorg. Med. Chem. Lett. 22 2012 6185 6189
7. N.M. Carballeira, A. Emiliano, N. Hernandez-Alonso, and F.A. Gonzalez Facile total synthesis and antimicrobial activity of the marine fatty acids (Z)-2-methoxy-5-hexadecenoic acid and (Z)-2-methoxy-6-hexadecenoic acid J. Nat. Prod. 61 1998 1543 1546 (Pubitemid 29024436)
8. N.M. Carballeira, D. Sanabria, C. Cruz, K. Parang, B. Wan, and S. Franzblau 2,6-Hexadecadiynoic acid and 2,6-nonadecadiynoic acid: Novel synthesized acetylenic fatty acids as potent antifungal agents Lipids 41 2006 507 511 (Pubitemid 44204873)
9. N.M. Carballeira, D. Sanabria, and K. Parang Total synthesis and further scrutiny of the in vitro antifungal activity of 6-nonadecynoic acid Arch. Pharm. Chem. Life Sci. 338 2005 441 443 (Pubitemid 41367855)
10. CDC Antibiotic resistance threat in the United States Technical Report 2013 77 78
11. CLSI 7th ed. Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically, M7-A7 vol. 26 2006 Clinical and Laboratory Standards Institute (Formerly NCCLS) Wayne, PA
12. CLSI Performance Standards for Antimicrobial Disk Susceptibility Tests, M02-A11 vol. 32 2012 Clinical and Laboratory Standards Institute (Formerly, NCCLS) Wayne, PA
13. H.S. Courtney, W.A. Simpson, and E.H. Beachey Relationship of critical micelle concentrations of bacterial lipoteichoic acids to biological activities Infect. Immun. 51 1986 414 418 (Pubitemid 16212114)
14. M.O. Fatope, O.A. Adoum, and Y. Takeda C(18) acetylenic fatty acids of Ximenia americana with potential pesticidal activity J. Agric. Food Chem. 48 2000 1872 1874 (Pubitemid 30331537)
15. A. Freitag, H. Rapp, L. Heide, and S.M. Li Metabolic engineering of aminocoumarins: inactivation of the methyltransferase gene cloP and generation of new clorobiocin derivatives in a heterologous host ChemBioChem 6 2005 1411 1418 (Pubitemid 41133905)
16. H. Gershon, and L. Shanks Antifungal properties of 2-alkynoic acids and their methyl esters Can. J. Microbiol. 24 1978 593 597 (Pubitemid 8355697)
17. L. Heide Genetic engineering of antibiotic biosynthesis for the generation of new aminocoumarins Biotechnol. Adv. 27 2009 1006 1014
18. K. Inweregbu, J. Dave, and A. Pittard Nosocomial infections. Counting education in anaesthesia Crit. Care Pain 5 2005 14 17
19. S.C. Kampranis, N.A. Gormley, R. Tranter, G. Orphanides, and A. Maxwell Probing the binding of coumarins and cyclothialidines to DNA gyrase Biochemistry 38 1999 1967 1976
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 Invasive methicillin-resistant Staphylococcus aureus infections in the United States JAMA 298 2007 1763 1771 (Pubitemid 47598444)
21. R.M. Klevens, J.R. Edwards, C.L. Richards, T.C. Horan, R.P. Gaynes, P.A. Pollock, and D.M. Cardo Estimating health care-associated infections and deaths in U.S. hospitals, 2002 Public Health Rep. 122 2007 160 166
22. W. Konthikamee, J.R. Gilbertson, H. Langkamp, and H. Gershon Effect of 2-alkynoic acids on in vitro growth of bacterial and mammalian cells Antimicrob. Agents Chemother. 22 1982 805 809 (Pubitemid 13210058)
23. X.-C. Li, M.R. Jacob, H.N. ElSohly, D.G. Nagle, T.J. Smillie, L.A. Walker, and A.M. Clark Acetylenic acids inhibiting azole-resistant Candida albicans from Pentagonia gigantifolia J. Nat. Prod. 66 2003 1132 1135 (Pubitemid 37034056)
24. X.C. Li, M.R. Jacob, S.I. Khan, M.K. Ashfaq, K.S. Babu, A.K. Agarwal, H.N. Elsohly, S.P. Manly, and A.M. Clark Potent in vitro antifungal activities of naturally occurring acetylenic acids Antimicrob. Agents Chemother. 52 2008 2442 2448 (Pubitemid 351915674)
25. H.R. Morbidoni, C. Vilchèze, L. Kremer, R. Bittman, J.C. Sacchettini, and W.R. Jacobs Dual Inhibition of mycobacterial fatty acid biosynthesis and degradation by 2-alkynoic acids Chem. Biol 13 2006 297 307
26. E.A. Orellano, M.M. Cartagena, K. Rosado, and N.M. Carballeira Synthesis of the novel (±)-2-methoxy-6-icosynoic acid - a fatty acid that induces death of neuroblastoma cells Chem. Phys. Lipids 172-173 2013 14 19
27. D. Pittet, D. Tarara, and R.P. Wenzel Nosocomial bloodstream infection in critically ill patients. Excess length of stay, extra costs, and attributable mortality JAMA 271 1994 1598 1601
28. J. Rudolph, H. Theis, R. Hanke, R. Endermann, L. Johannsen, and F. Geschke seco-Cyclothialidines: new concise synthesis, inhibitory activity toward bacterial and human DNA topoisomerases, and antibacterial properties J. Med. Chem. 44 2001 619 626 (Pubitemid 32156103)
29. C.M. Smith, G.C. Williams, W. Krivit, J.G. White, and R.F. Hanson Micellar properties of 3 alpha, 7 alpha, 12 alpha-trihydroxy-5 beta-cholestan-26-oyl taurine and relationship to in vitro red cell disruption J. Lab. Clin. Med. 94 1979 624 632 (Pubitemid 10210893)
30. P.W. Stone, E. Larson, and L.N. Kawar A systematic audit of economic evidence linking nosocomial infections and infection control interventions: 1990-2000 Am. J. Infect. Control 30 2002 145 152 (Pubitemid 34521457)
31. D. Tasdemir, D. Sanabria, I.L. Lauinger, A. Tarun, R. Herman, R. Perozzo, M. Zloh, S.H. Kappe, R. Brun, and N.M. Carballeira 2-Hexadecynoic acid inhibits plasmodial FAS-II enzymes and arrests erythrocytic and liver stage Plasmodium infections Bioorg. Med. Chem. 18 2010 7475 7485
32. G.C. Upreti, M. Matocha, and R. Wood Effect of 2-hexadecynoic acid on cultured 7288C hepatoma cells Lipids 16 1981 315 322 (Pubitemid 11039079)
33. WHO Prevention of Hospital-Acquired Infections: A Practical Guide 2nd ed. 2002 WHO Geneva 4 6
34. A.J. Wicken, J.D. Evans, and K.W. Knox Critical micelle concentrations of lipoteichoic acids J. Bacteriol. 166 1986 72 77 (Pubitemid 16043282)
35. R. Wood, and T. Lee Metabolism of 2-hexadecynoate and inhibition of fatty acid elongation J. Biol. Chem. 256 1981 12379 12386 (Pubitemid 12141505)
36. T. Xu, S.K. Tripathi, Q. Feng, M.C. Lorenz, M.A. Wright, M.R. Jacob, M.M. Mask, S.R. Baerson, X.C. Li, A.M. Clark, and A.K. Agarwal A potent plant-derived antifungal acetylenic acid mediates its activity by interfering with fatty acid homeostasis Antimicrob. Agents Chemother. 56 2012 2894 2907
37. C. Zhan, and M.R. Miller Excess length of stay, charges, and mortality attributable to medical injuries during hospitalization JAMA 290 2003 1868 1874 (Pubitemid 37430603)
38. C.J. Zheng, J. Yoo, T. Lee, H. Cho, Y. Kim, and W. Kim Fatty acid synthesis is a target for antibacterial activity of unsaturated fatty acids FEBS Lett. 579 2005 5157 5162 (Pubitemid 41318085)