Antimicrobial activity of long-chain, water-soluble, dendritic tricarboxylato amphiphiles

Journal of Antimicrobial Chemotherapy

Volumn 59, Issue 3, 2007, Pages 451-458

  Williams, André A ^a   Sugandhi, Eko W ^a   Macri, Richard V ^a   Falkinham III, Joseph O ^a   Gandour, Richard D ^a  

^a VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

Author keywords

Fatty acids; Mycobacteria; Solubility; Synthetic lipids

Indexed keywords

AMPHOPHILE; ANTIINFECTIVE AGENT; LONG CHAIN DENDRITIC TRICARBOXYLATO AMPHOPHILE; LONG CHAIN FATTY ACID; SATURATED FATTY ACID; UNCLASSIFIED DRUG; FATTY ACID;

ANTIBIOTIC SENSITIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; ASPERGILLUS NIGER; CANDIDA ALBICANS; CONTROLLED STUDY; CRYPTOCOCCUS NEOFORMANS; DILUTION; DRUG DESIGN; DRUG SOLUBILITY; DRUG STRUCTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; KLEBSIELLA PNEUMONIAE; LACTOBACILLUS PLANTARUM; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; MICROCOCCUS LUTEUS; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM SMEGMATIS; NONHUMAN; SACCHAROMYCES CEREVISIAE; STAPHYLOCOCCUS AUREUS; STRUCTURE ACTIVITY RELATION; BACTERIUM; DRUG EFFECT; FUNGUS; MICROBIOLOGICAL EXAMINATION; SOLUBILITY; SYNTHESIS;

ANTI-INFECTIVE AGENTS; BACTERIA; FATTY ACIDS; FUNGI; MICROBIAL SENSITIVITY TESTS; SOLUBILITY; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 34247377171     PISSN: 03057453     EISSN: 14602091     Source Type: Journal    
DOI: 10.1093/jac/dkl503     Document Type: Article

References (34)

1. Nieman C. Influence of trace amounts of fatty acids on the growth of microorganisms. Bacteriol Rev 1954; 18: 147-63.
2. Walker JE. The germicidal properties of chemically pure soaps. J Infect Dis 1924; 35: 557-66.
3. Kabara JJ Swieczkowski DM, Conley AJ et al. Fatty acids and derivatives as antimicrobial agents. Antimicrob Agents Chemother 1972; 2: 23-8.
4. Kondo E, Kanai K. Lethal effect of long-chain fatty acids on mycobacteria. Jpn J Med Sci Biol 1972; 25: 1-13.
5. Kondo E, Kanai K. Further studies on lethal effect of long-chain fatty acids on mycobacteria. Jpn J Med Sci Biol 1976; 29: 25-37.
6. Kondo E, Kanai K. Relationship between chemical structure of fatty acids and their mycobactericidal activity. Jpn J Med Sci Biol 1977; 30: 171-8.
7. Kabara JJ, Vrable R, Liekenjie MSF. Antimicrobial lipids - natural and synthetic fatty acids and monoglycerides. Lipids 1977; 12: 753-9.
8. Kabara JJ. Structure-function relationships of surfactants as antimicrobial agents. J Soc Cosmet Chem 1978; 29: 733-41.
9. Kabara JJ. Lipids as host-resistance factors of human milk. Nutr Rev 1980; 38: 65-73.
10. Saito H, Tomioka H, Yoneyama T. Growth of group IV mycobacteria on medium containing various saturated and unsaturated fatty acids. Antimicrob Agents Chemother 1984; 26: 164-9.
11. Jossifava LT, Manolov I, Golovinsky EV. Antibacterial action of some saturated and unsaturated long-chain carboxylic acids and their bis(2-chloroethyl)aminoethyl esters in vitro. Pharmazie 1989; 44: 854-6.
12. Bergsson G, Amfinnsson J, Steingrimsson O et al. In vitro killing of Candida albicans by fatty acids and monoglycerides. Antimicrob Agents Chemother 2001; 45: 3209-12.
13. Kitahara T, Koyama N, Matsuda J et al. Antimicrobial activity of saturated fatty acids and fatty amines against methicillin-resistant Staphylococcus aureus. Biol Pharm Bull 2004; 27: 1321-6.
14. 18 fatty acids. Folia Microbiol 2003; 48: 731-5.
15. Vorum H, Brodersen R, Kragh-Hansen U et al. Solubility of long-chain fatty acids in phosphate buffer at pH 7.4. Biochim Biophys Acta 1992; 1126: 135-42.
16. Balgavý P, Devínsky F. Cut-off effects in biological activities of surfactants. Adv Colloid Interface Sci 1996; 66: 23-63.
17. Hansch C, Clayton JM. Lipophilic character and biological activity of drugs. II. Parabolic case. J Pharm Sci 1973; 62: 1-21.
18. Gruber HJ. Interaction of amphiphiles with integral membrane proteins. 2. A simple, minimal model for the nonspecific interaction of amphiphiles with the anion exchanger of the erythrocyte membrane. Biochim Biophys Acta 1988; 944: 425-36.
19. Gaur RK, Chauhan VS. Fatty-acid derivatives of acidic amino acids as potential antibiotics. Indian J Chem, Sect B 1988; 27: 405-8.
20. Sivasamy A, Krishnaveni M, Rao PG. Preparation, characterization, and surface and biological properties of N-stearoyl amino acids. J Am Oil Chem Soc 2001; 78: 897-902.
21. Williams AA, Day BS, Kite BL et al. Homologous, long-chain alkyl dendrons form homologous thin films on silver oxide surfaces. Chem Commun 2005: 5053-5.
22. Newkome GR, Weis CD, Moorefield CN et al. Isocyanate-based dendritic building blocks: Combinatorial tier construction and macromolecular-property modification. Angew Chem, Int Edit 1998; 37: 307-10.
23. Newkome GR, Behera RK, Moorefield CN et al. Chemistry of micelles. 18. Cascade polymers: Syntheses and characterization of one-directional arborols based on adamantane. J Org Chem 1991; 56: 7162-7.
24. Cain CC, Henry AT, Waldo RH et al. Identification and characteristics of a novel Burkholderia strain with broad-spectrum antimicrobial activity. Appl Environ Microbiol 2000; 66: 4139-41.
25. Schwetlick K, Noack R, Stebner F. 3 Fundamental mechanisms of base-catalyzed reactions of isocyanates with hydrogen-acidic compounds. J Chem Soc, Perk 2 1994: 599-608.
26. Kaneko D, Olsson U, Sakamoto K. Self-assembly in some N lauroyl-L-giutamate/water systems. Langmuir 2002; 18: 4699-703.
27. Falbe J. Surfactants in Consumer Products. Berlin: Springer-Vedag, 1986.
28. Bates RG, Allen GF. Acid dissociation constant and related thermodynamic quantities for triethanolammonium ion in water from O° to 50°. J Research Natl Bur Standards 1960; 64A: 343-6.
29. Bashura AG, Klimenko OI, Nurimbetov KN et al. Colloidal-micellar properties of some new surfactants. Farmatsevt Zh (Kiev) 1989: 57-8.
30. Sheu CW, Freese E. Lipopolysaccharide layer protection of Gram-negative bacteria against inhibition by long-chain fatty acids. J Bacteriol 1973; 115: 869-75.
31. van Saene HKF, Weir WI, de la Cal MA et al. MRSA-time for a more pragmatic approach? J Hosp Infect 2004; 56: 170-4.
32. Goldstein AL, McCusker JH. Development of Saccharomyces cerevisae as a model pathogen: A system for the genetic identification of gene products required for survival in the mammalian host environment. Genetics 2001; 159: 499-513.
33. Van Oss CJ, Gillman CF, Neumann AW, Phagocytic Engulfment and Cell Adhesiveness as Cellular Surface Phenomena. New York, NY: Marcel Dekker, Inc., 1975.
34. Brennan PJ, Nikaido H. The envelope of mycobacteria. Annu Rev Biochem 1995; 64: 29-63.