2,6-Hexadecadiynoic acid and 2,6-nonadecadiynoic acid: Novel synthesized acetylenic fatty acids as potent antifungal agents

Lipids

Volumn 41, Issue 5, 2006, Pages 507-511

  Carballeira, Néstor M ^a   Sanabria, David ^a   Cruz, Clarisa ^a   Parang, Keykavous ^b   Wan, Baojie ^c   Franzblau, Scott ^c  

^a UNIVERSITY OF PUERTO RICO   (Puerto Rico)

^b UNIVERSITY OF RHODE ISLAND   (United States)

^c UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COMPOSITION; DISEASES; ENZYME INHIBITION; INITIATORS (CHEMICAL); SYNTHESIS (CHEMICAL);

ANTIFUNGAL AGENTS; CRYPTOCOCCUS; CYTOTOXICITY; HEXADECADIYNOIC;

FATTY ACIDS;

1,5 HEXADIYNE; 1,8 NONADIYNE; 2 HEXADECYNOIC ACID; 2,6 HEXADECADIYNOIC ACID; 2,6 NONADECADIYNOIC ACID; 2,9 HEXADECADIYNOIC ACID; 5 HEXADECYNOIC ACID; 6 NONADECYNOIC ACID; 9 HEXADECYNOIC ACID; ANTIFUNGAL AGENT; FATTY ACID DERIVATIVE; FLUCONAZOLE; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ARTICLE; CANDIDA ALBICANS; CRYPTOCOCCUS NEOFORMANS; CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; FATTY ACID SYNTHESIS; FUNGAL STRAIN; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM TUBERCULOSIS;

ANTIFUNGAL AGENTS; CANDIDA ALBICANS; FATTY ACIDS; FATTY ACIDS, UNSATURATED; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

CANDIDA ALBICANS; FILOBASIDIELLA NEOFORMANS; MYCOBACTERIUM TUBERCULOSIS;

EID: 33746985016     PISSN: 00244201     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11745-006-5124-4     Document Type: Article

References (17)

1. Gershon, H., and Shanks, L. (1978) Antifungal Properties of 2-Alkynoic Acids and Their Methyl Esters, Can. J. Microbiol. 24, 593-597.
2. Gershon, H., and Shanks, L. (1978) Antifungal Activity of Fatty Acids and Derivatives: Structure Activity Relationships, in The Pharmacological Effect of Lipids (J.J. Kabara, ed.), pp. 51-62, American Oil Chemists' Society, Champaign, Illinois.
3. Konthikamee, W., Gilbertson, J.R., Langkamp, H., and Gershon, H. (1982) Effect of 2-Alkynoic Acids on in vitro Growth of Bacterial and Mammalian Cells, Antimicrob. Agents Chemother. 22, 805-809.
4. Wood, R., and Lee, T. (1981) Metabolism of 2-Hexadecynoate and Inhibition of Fatty Acid Elongation, J. Biol. Chem. 256, 12379-12386.
5. Upreti, G.G., Matocha, M., and Wood, R. (1981) Effect 2-Hexadecynoic Acid on Cultured 7288C Hepatoma Cells, Lipids 16, 315-322.
6. Rudnik, D.A., Lu, T., Jackson-Machelski, E., Hernandez, J.C., Li, Q., Gokel, G.W., and Gordon, J.I. (1992) Analogs of Palmitoyl-CoA That Are Substrates for Myristoyl-CoA: Protein N-Myristoyltransferase, Proc. Natl. Acad. Sci. USA 89, 10507-10511.
7. Li, X.-C., Jacob, M.R., ElSohly, H.N., Nagle, D.G., Smillie, T.J., Walker, L.A., and Clark, A.M. (2003) Acetylenic Acids Inhibiting Azole-Resistant Candida albicans from Pentagonia gigantifolia, J. Nat. Prod. 66, 1132-1135.
8. Carballeira N.M., Sanabria, D., and Parang, K. (2005) Total Synthesis and Further Scrutiny of the in vitro Antifungal Activity of 6-Nonadecynoic Acid, Arch. Pharm. 338, 441-443.
9. Wille, J.J., and Kydonieus, A. (2003) Palmitoleic Acid Isomer (C16:1 delta6) in Human Skin Sebum Is Effective Against Gram-Positive Bacteria, Skin Pharmacol. Appl. Skin Physiol. 16, 176-187.
10. Lie Ken Jie, M.S.F., and Lam, C.H. (1978) Fatty Acids. Part XVI. The Synthesis of All Isomeric C18 Furan-Containing Fatty Acids, Chem. Phys. Lipids 21, 275-287.
11. Lam, C.H., and Lie Ken Jie, M.S.F. (1975) Fatty Acids. IV. Synthesis of All the Dimethylene-Interrupted Methyl Octadecadiynoates and a Study of Their Gas-Liquid Chromatographic Properties, J. Chromatogr. 115, 559-570.
12. Galgiani, J.N. (1993) Susceptibility Testing of Fungi: Current Status of the Standardization Process, Antimicrob. Agents Chemother. 37, 2517-2521.
13. Carballeira, N.M., Ortiz, D., Parang, K., and Sardari, S. (2004) Total Synthesis and in vitro Antifungal Activity of (+/-)-2-Methoxytetradecanoic Acid, Arch. Pharm. (Weinheim) 337, 152-155.
14. Nam, N.H., Sardari, S., Selecky, M., and Parang, K. (2004) Carboxylic Acid and Phosphate Ester Derivatives of Fluconazole: Synthesis and Antifungal Activities, Biorg. Med. Chem. 12, 6255-6269.
15. Ames, D.E., and Covell, A.N. (1963) Synthesis of Long-Chain Acids. III. Synthesis of Acetylenic Acids, J. Chem. Soc., 775-778.
16. Carballeira, N.M., Cruz, H., Kwong, C.D., Wan, B., and Franzblau, S. (2004) 2-Methoxylated Fatty Acids in Marine Sponges: Defense Mechanism Against Mycobacteria?, Lipids 39, 675-680.
17. Morbidoni, H.R., Vilcheze, C., Kremer, L., Bittman, R., Sacchettini, J.C., and Jacobs, W.R., Jr. (2006) Dual Inhibition of Mycobacterial Fatty Acid Biosynthesis and Degradation by 2-Alkynoic Acids, Chem. Biol. 13, 297-307.