Relationship between structure and antibacterial activity of lipophilic N-acyldiamines

Biomedicine and Pharmacotherapy

Volumn 64, Issue 4, 2010, Pages 287-290

  de Almeida, Camila G ^a   Garbois, Gabriela D ^a   Amaral, Lorena M ^a   Diniz, Cláudio C ^a   Le Hyaric, Mireille ^a  

^a FEDERAL UNIVERSITY OF JUIZ DE FORA   (Brazil)

Author keywords

Lipophilicity; MIC; N acyl diamines

Indexed keywords

ETHYLENEDIAMINE DERIVATIVE; PUTRESCINE DERIVATIVE;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERICIDAL ACTIVITY; CITROBACTER FREUNDII; CONTROLLED STUDY; ENTEROBACTER AEROGENES; ENTEROBACTER CLOACAE; ENTEROCOCCUS FAECALIS; ESCHERICHIA COLI; KLEBSIELLA PNEUMONIAE; LIPOPHILICITY; MICROCOCCUS; MICROCOCCUS LENTUS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PRIORITY JOURNAL; PROTEUS MIRABILIS; PROVIDENCIA STUARTII; PSEUDOMONAS AERUGINOSA; SALMONELLA TYPHI; SERRATIA MARCESCENS; SHIGELLA SONNEI; STAPHYLOCOCCUS AUREUS; STAPHYLOCOCCUS EPIDERMIDIS; STRUCTURE ACTIVITY RELATION;

ANTI-BACTERIAL AGENTS; DIAMINES; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIA; MICROBIAL SENSITIVITY TESTS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77952322249     PISSN: 07533322     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.biopha.2009.09.013     Document Type: Article

References (36)

1. Neu H.C. The crisis in antibiotic resistance. Science 1992, 257:1064-1073.
2. World Health Organization. WHO Global Strategy for Containment of Antimicrobial Resistance. Geneva: World Health Organization; 2001. , accessed in 10/28/2008. http://www.who.int/csr/resources/publications/drugresist/en.
3. Lee do K., Hwang J.U., Baek E.H., Lee K.O., Kim K.J., Ha N.J. New antimicrobial drug resistance and epidemiological typing patterns of Staphylococci from clinical isolates and raw meats. Arch Pharm Res 2008, 31:1016-1022.
4. Freese E., Shew C.W., Galiers E. Function of lipophilic acids as antimicrobial food additives. Nature 1973, 241:321-325.
5. Zheng C.J., Yoo J.-S., Lee T.-G., Cho H.-Y., Kim Y.-H., Kim W.-G. Fatty acid synthesis is a target for antibacterial activity of unsaturated fatty acids. FEBS Letters 2005, 579:5157-5162.
6. Kabara J.J., Conley A.J., Truant J.P. Relationship of chemical structure and antimicrobial activity of alkyl amides and amines. Antimicrob Agents Chemother 1972, 2:492-498.
7. Carballeira N.M., Reyes E.D., Sostre A., Rodríguez A.D., Rodríguez J.L., González F.A. Identification of the novel antimicrobial fatty acid (5Z,9Z)-14-methyl-5,9-pentadecadienoic acid in Eunicea succinea. J Nat Prod 1997, 60:502-504.
8. + ATPase from the red marine algaptilota Filicina J Agardh. Tet Lett 1988, 29:1505-1506.
9. Brady S.F., Clardy J. Palmitoylputrescine, an antibiotic isolated from the heterologous expression of DNA extracted from bromeliad tank water. J Nat Prod 2004, 67:1283-1286.
10. Rosenmund KW. Manufacture of mono-acylated ethylene-diamine and its derivatives. 1933, US Patent 1926015.
11. Klimpel R.R., Hansen R.D. Collectors for the froth flotation of mineral values. Eur Pat Appl 1986, EP174886.
12. Hill A.J, Aspinall S.R. The preparation and cyclization of monoacylethylenediamines. J Am Chem Soc 1939, 61:3195.
13. Takeshita T., Meada S. N-lauroyl-ethylenediamine chelates: preparation and evaluation of surface tension and dispersant properties. J Am Oil Chem Soc 1969, 46:344-347.
14. Takase S. Derivatives of fatty acids. Synthesis of acylethylenediamines and their surface-active properties'. Nippon Kagaku Zasshi 1948, 69:154-157.
15. Ueda M., Murata Y., Mori E. The antibacterial activities of N-acylpolymethylenediamines against oral microorganisms. Yakuzaigaku 1989, 49:133-140.
16. Devinsky F., Lacko I., Mlynarcik D., Krasnec L. Amine oxides.VIII Preparation, infrared spectra, and antimicrobial activity of some N-oxides of N,N-dialkylaminoalkyl esters and N′-N′-dimethylaminoalkylamides of dodecanoic acid. Chemicke Zvesti 1983, 37:263-271.
17. Miyamoto E., Murata Y., Kawashima S., Ueda M. Haemolytic action of N-alkylpolymethylenediamines. J Pharm Pharmacol 1992, 44:269-271.
18. Murata Y., Miyamato E., Ueda M. Antimicrobial activity of N-alkylpolymethylenediamines against some dental plaque bacteria. Caries Res 1990, 24:33-35.
19. Reis R.C., Oda S.C., Almeida M.V., Lourenço M.C.S., Viente F.R.C., Barbosa N.R., et al. Synthesis and antimicrobial activity of amphiphilic carbohydrate derivatives. J Braz Chem Soc 2008, 19:1065-1072.
20. [1H] NMR spectra of compounds 4a-d and 5a-d showed signals referring to the alkyl portion of the molecule and to the diamine moiety. 13C NMR spectra showed a signal referring to amide carbonyl, as well as signals corresponding to diamine moiety and to alkyl chains.
21. CLSI. Performance standards for antimicrobial susceptibility testing, 17th Informational Supplement. CLSI Document M100-S16, 26 Wayne PA: CLSI, 2007.
22. Alviano W.S., Alviano D.S., Diniz C.G., Antoniolli A.R., Alviano C.S., Farias L.M., et al. In vitro antioxidant potential of medicinal plant extracts and their activities against oral bacteria based on Brazilian folk medicine. Arch Oral Biol 2008, 53:545-552.
23. Denyer S.P., Stewart G.S.A.B. Mechanisms of action of disinfectants. Int Biodeter Biodegr 1998, 41:261-268.
24. Glover R.E., Smith R.R., Jones M.V., Jackson S.K., Rowlands C.C. An EPR investigation of surfactant action on bacterial membranes. FEMS Microbiol Lett 1999, 177:57-62.
25. Moore S.L., Denyer S.P., Hanlon G.W., Olliff C.J., Lansley A.B., Rabone K., et al. Alcohol ethoxylates mediate their bacteriostatic effect by altering the cell membrane of Escherichia coli NCTC 8196. Int J Antmicrob Agents 2006, 28:503-513.
26. Baker Z., Harrison R.W., Miller B.F. The bactericidal action of synthetic detergents. J Exp Med 1941, 74:611-620.
27. Elworthy PH, Florence AT, MacFarlane CB. Solubilization. In: Solubilization by surface-active agents and its applications in chemistry and the biological sciences. London, UK: Chapman and Hall; 1968:61-116.
28. Salton MRJ. The action of lytic agents on the surface structures of the bacterial cell. In: Schulman JH, editor. Proc. of the Second International Congress on Surface Activity Butterworth, London 1957;11:245-53.
29. Hancock R.E.W. The bacterial outer membrane as a drug barrier. Trends Microbiol 1997, 5:37-42.
30. Helander I.M., Alakomi H.-L., Latva-Kala K., Mattila-Sandholm T., Pol I., Smid E.J., et al. Characterization of the action of selected essential oil components on Gram-negative bacteria. J Agric Food Chem 1998, 46:3590-3595.
31. Chopra I., Ball P. Transport of antibiotics into bacteria. Adv Microb Physiol 1982, 23:183-240.
32. Ohnishi M., Sagitani H. The effect of nonionic surfactant structure on hemolysis. J Am Oil Chem Soc 1993, 70:679-684.
33. Zaslavsky B.Y., Ossipov N.N., Rogozhin S.V., Sebyakin Y.L., Volkova L.V., Evstigneeva R.P. Action of surface-active substances on biological membranes. IV. Hemolytic and membrane-perturbing action of homologous series of α-d-glucopiranosyl-1-alkylphosphates. Biochim Biophys Acta 1979, 556:314-321.
34. Lein E.J., Hansch C., Anderson S.M. Structure-activity correlations for antibacterial agents on Gram-positive and Gram-negative cells. J Med Chem 1968, 11:430-441.
35. Terada H. Determination of Log Poct by high-performance liquid chromatography, and its application in the study of quantitative structure-activity relationships. Quant Struct Act Relat 1986, 5:81-88.
36. Log(P) values were calculated using ACD/LogP DB software. Free sofware available from http://www.acdlabs.com/.