Flow microcalorimetric studies of phenol and its chlorinated derivatives and a theoretical evaluation of their possible inhibition mode on Chromobacterium violaceum respiration

International Journal of Pharmaceutics

Volumn 282, Issue 1-2, 2004, Pages 163-171

  Basheer, Muftah M ^a   Volpe, Pedro L O ^a   Airoldi, Claudio ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

Chemometric analysis; Chromobacterium violaceum respiration; Flow microcalorimetry; Inhibition effect; Phenol, anisole and their chlorinated derivatives; SAR; Theoretical method

Indexed keywords

ANISOLE; OCTANOL; PHENOL; PHENOL DERIVATIVE; PROTON; SOLVENT; WATER;

AB INITIO CALCULATION; ACIDITY; ARTICLE; CALCULATION; CHEMOMETRICS; CHLORINATION; CHROMOBACTERIUM; CHROMOBACTERIUM VIOLACEUM; CLUSTER ANALYSIS; CONTROLLED STUDY; CORRELATION ANALYSIS; DENSITY FUNCTIONAL THEORY; DISSOCIATION CONSTANT; DRUG ACTIVITY; ENERGY; ENTHALPY; IONIZATION; MELTING POINT; MICROBIAL ACTIVITY; MICROCALORIMETRY; MOLECULAR MODEL; NONHUMAN; PHYSICAL CHEMISTRY; PRINCIPAL COMPONENT ANALYSIS; PRIORITY JOURNAL; SOLVATION;

ANISOLES; CALORIMETRY; CHEMISTRY, PHYSICAL; CHLOROPHENOLS; CHROMOBACTERIUM; CLUSTER ANALYSIS; PHENOLS; PRINCIPAL COMPONENT ANALYSIS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 4444247463     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2004.06.014     Document Type: Article

References (30)

1. K.R. Beebe, R.J. Pell, and M.B. Seasholtz Chemometrics: A Practical Guide 1998 Wiley New York
2. A.E. Beezer Biological Microcalorimetry 1980 Academic Press London
3. A.E. Beezer, P.L.O. Volpe, R.J. Miles, and W.H. Hunter Microcalorimetric measurement of the enthalpies of transfer of a series of m-alkoxyphenols from isotonic aqueous solution to E. coli cells J. Chem. Soc., Faraday Trans. I 82 1986 2929 2932
4. A.E. Beezer, P.L.O. Volpe, C.A. Gooch, and W.H. Hunter Microcalorimetric bioassay and the development of a group additivity scheme for biological response Anal. Proc. 23 1986 399 400
5. A.E. Beezer, P.L.O. Volpe, C.A. Gooch, W.H. Hunter, and R.J. Miles Quantitative structure-activity relationships: microcalorimetric determination of a group additivity scheme for biological response Int. J. Pharm. 29 1986 237 242
6. A. Ben-Naim, and Y. Marcus Solvation thermodynamics of nonionic solutes J. Chem. Phys. 81 1984 2016 2027
7. L.R. Caldas Photochemistry and photobiology in a virgin land Photochem. Photobiol. 26 1977 1 2
8. S.A.M. Critter, S.S. Freitas, and C.A. Airoldi Comparison of microbial activity in some Brazilian soils by microcalorimetric and respirometric methods Thermochim. Acta 410 2004 35 46
9. M.T.D. Cronin, and T.W. Schultz Validation of Vibrio fisheri acute toxicity data: mechanism of action-based QSARs for non-polar narcotics and polar narcotic phenols Sci. Total Environ. 204 1997 75 88
10. A.O. de Souza, J.B. Alderete, F. Schimidt, D.N. Sato, and N. Duran Structure-activity relationship analysis of 4′-bromo-[1,1′-diphenyl] -4-yl 4-X phenyl methanone Arzneim-Forsch. Drug Res. 49 1999 1025 1029
11. J. Devillers, and P. Chambon Acute toxicity and QSAR of chlorophenols on Daphnia magna Bull. Environ. Contam. Toxicol. 37 1986 599 605
12. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery, R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P.M.W. Gill, B.G. Johnson, W. Chen, M.W. Wong, J.L. Andres, M. Head-Gordon, E.S. Replogle, and J.A. Pople Gaussian 98 (Revision A.7) 1998 Gaussian Inc. Pittsburgh, PA
13. J.F. Gonzalez, and W. Hu Effect of glutamate on the degradation of pentachlorophenol by Flavobacterium SP Appl. Microbiol. Biotechnol. 35 1991 100 104
14. E.F.G. Herrington Recommended reference materials for the realization of physicochemical properties Pure Appl. Chem. 40 1974 393
15. International Programme on Chemical Safety (IPCS) Environmental Health Criteria 93: Chlorophenols Other than Pentachlorophenol 1989 World Health Organization Geneva
16. S.C. Kaufman, D. Ceraso, and A. Schugurensky First case reported from Argentina of fatal septicemia caused by Chromobacterium violaceum J. Clin. Microbiol. 23 1986 956 958
17. B.E. Kirsop, and J.J. Snell Maintenance of Microorganisms 1984 Academic Press New York
18. A. Klamt, and V. Jonas Treatment of the outlying charge in continuum solvation models J. Chem. Phys. 105 1996 9972 9981
19. M.J. Koenigbauer Pharmaceutical applications of microcalorimetry Pharm. Res. 11 1994 777 783
20. Mulller, F., Poulenc, R., Pont-de-Claix, L., 1986. Ullman's Encyclopedia of Industrial Chemistry: Chlorophenols to Copper Compounds, fifth ed., vol. A7. France (pp. 1-8).
21. M.A.A. O'Neill, A.E. Beezer, G.J. Vine, R.B. Kemp, D. Olomolaiye, P.L.O. Volpe, and D.A. Oliveira Practical and theoretical consideration of flow-through microcalorimetry: determination of "thermal volume" and its flow rate dependence Thermochim. Acta 413 2004 193 199
22. R. Ponte, and S.G. Jenkins Fatal Chromobacterium violaceum infections associated with exposure to stagnant waters Pediatr. Infect. Dis. J. 11 1992 583 586
23. M. Rutgers, S. Van Bommel, A. Breure, J. Van Andel, and W. Buetz Effect of pH on the toxicity and biodegradation of pentachlorophenol by Sphingomonas sp. strain P5 in Nutristat culture Environ. Toxicol. Chem. 17 1998 792 797
24. H. Saito, M. Sudo, T. Shigeoka, and F. Yamauchi In vitro cytotoxicity of chlorophenols to goldfish GF-scale (GFS) cells and quantitative structure-activity relationships Environ. Toxicol. Chem. 10 1991 235 241
25. 2O in the gas phase and in aqueous solution J. Chem. Phys. 109 1998 9523 9528
26. M.A. Sharaf, D.L. Illman, and B. Kowalski Chemometrics 1986 Wiley New York
27. P.H.A. Sneath N.R. Krieg J.G. Holt Bergey's Manual of Systematic Bacteriology vol. 1 1984 Williams & Williams Baltimore (pp. 580-582)
28. W.J. Stevens, H. Basch, and M. Krauss Compact effective potentials and efficient shared-exponent basis sets for the first- and second-row atoms J. Chem. Phys. 81 1984 6026 6033
29. P.L.O. Volpe Flow microcalorimetric measurements of the antibacterial activity of the homologous series of m-alkoxyphenols and p-hydroxybenzoates on Escherichia coli J. Braz. Chem. Soc. 8 1997 1 6
30. S. Wold, K. Esbensen, and P. Gelati Principal component analysis Chemom. Intell. Lab. Syst. 2 1987 37 52