Quantitative structure-metabolism relationships for substituted benzoic acids in the rabbit: prediction of urinary excretion of glycine and glucuronide conjugates

References

• Anderson E., Veith G. D., Weininger D. SMILES: a line entry notation and computerised interpreter for chemical structures. USEPA Environmental Research Brief. 1987
   Google Scholar
• Bartlett M. The use of transformations. Biometrics 1947; 87: 39–52
   Google Scholar
• Bray H. G., Clowes R. C., Thorpe W. V., White K., Wood P. B. The fate of certain organic acids and amides in the rabbit. 13. Chloro- and fluoro-benzoic acids and amides. Biochemical Journal 1951a; 50: 583–587
   Google Scholar
• Bray H. G., Humphris B. G., Thorpe W. V., White K., Wood P. B. Kinetic studies on metabolism of foreign organic compounds. 6. Reactions of some nuclear substituted benzoic acids, benzamides and toluenes in the rabbit. Biochemical Journal 1955; 59: 162–167
   PubMedGoogle Scholar
• Bray H. G., Hybs Z., Thorpe W. V. Metabolism of derivatives of toluene. 6. Toluonitriles, benzonitrile and some related compounds. Biochemical Journal 1951b; 48: 192–199
   Google Scholar
• Bray H. G., Lake H. J., Neale F. C., Thorpe W. V., Wood P. B. The fate of certain organic acids and amides in the rabbit. 4. The aminobenzoic acids and their amides. Biochemical Journal 1948a; 42: 434–443
   Google Scholar
• Bray H. G., Neale F. C., Thorpe W. V. The fate of certain organic acids and amides in the rabbit. 1. Benzoic and phenylacetic acids and their amides. Biochemical Journal 1946; 40: 134–139
   Web of Science ®Google Scholar
• Bray H. G., Ryman B. E., Thorpe W. V. The fate of certain organic acids and amides in the rabbit. 2. p-Hydroxybenzoic acid and its amide. Biochemical Journal 1947; 41: 212–218
   Web of Science ®Google Scholar
• Bray H. G., Ryman B. E., Thorpe W. V. The fate of certain organic acids and amides in the rabbit. 5. o- and m-Hydroxybenzoic acids and amides. Biochemical Journal 1948b; 43: 561–567
   PubMed Web of Science ®Google Scholar
• Bray H. G., Thorpe W. V., White K. Kinetic studies of the metabolism of foreign compounds. 1. The formation of benzoic acid from benzamide toluene, benzyl alcohol and benzaldehyde and its conjugation with glycine and glucuronic acid in the rabbit. Biochemical Journal 1950a; 48: 88–96
   Google Scholar
• Bray H. G., Thorpe W. V., White K. The fate of certain organic acids and amides in the rabbit. 10. The application of paper chromatography to metabolic studies of hydroxybenzoic acids and amides. Biochemical Journal 1950b; 46: 271–278
   PubMed Web of Science ®Google Scholar
• Bray H. G., Thorpe W. V., Wood P. B. The fate of certain organic acids and amides in the rabbit. 6. Nitrobenzoic acids and amides. Biochemical Journal 1948c; 44: 39–45
   Google Scholar
• Bray H. G., Thorpe W. V., Wood P. B. The fate of certain organic acids and amides in the rabbit. 8. Toluic acids and amides. Biochemical Journal 1949; 45: 39–45
   Google Scholar
• Cammarata A. Some electronic factors in drug-receptor interactions. Journal of Medicinal Chemistry 1968; 11: 1111–1115
   PubMed Web of Science ®Google Scholar
• Cammarata A. An analysis of biological linear free-energy relationships. Journal of Medicinal Chemistry 1969; 12: 314–317
   Google Scholar
• Cammarata A. Electronic representation of the linear lipophilic parameter π. Journal of Medicinal Chemistry 1971; 14: 269–274
   PubMed Web of Science ®Google Scholar
• Chatfield C., Collins A. J. Introduction to Multivariate Analysis. Chapman & Hall, London 1986
   Google Scholar
• Cheney V., Duchamp D. J., Christofferson R. E. Structure-activity correlations for a series of antiallergic agents. 2. Geometric and electronic characterisation of some oxamic and dioxamic acids. Journal of Medicinal Chemistry 1983; 26: 719–725
   Google Scholar
• Darvas F. Predicting metabolic pathways by logic programming. Journal of Molecular Graphics 1988; 6: 80
   Google Scholar
• Edward J. T. Molecular volumes and the Stokes-Einstein equation. Journal of Chemical Education 1970; 47: 261–270
   Web of Science ®Google Scholar
• Ehmann W. D., Janghorbani M. Radiochemical methods of analysis. Instrumental Analysis, 2nd edn, G. D. Christian, S. E. O'Reilly. Allyn & Bacon, London 1986; 594–638
   Google Scholar
• Fournel S., Gregoire B., Magdalou J., Carre M. -C., Lafaurie C., Siest G., Caubere P. Inhibition of bilirubin UDP-glucuronosyltransferase activity by triphenylacetic acid and related compounds. Biochemica et Biophysica Acta 1986; 883: 190–196
   PubMed Web of Science ®Google Scholar
• Geladi P., Kowalski B. R. Partial least-squares regression: a tutorial. Analytica Chimica Acta 1986; 185: 1–17
   Web of Science ®Google Scholar
• Ghauri F. Y. K., Blackledge C. A., Glen R. C., Lindon J. C., Beddell C. R., Wilson I. D., Nicholson J. K. Quantitative structure metabolism relationships for substituted benzoic acids in the rat: computational chemistry, NMR spectroscopy, and pattern recognition studies. Biochemical Pharmacology 1992; 44: 1935–1946
   PubMed Web of Science ®Google Scholar
• Glen R. C., Rose V. S. A computer programme suite for the calculation storage and manipulation of molecular property and activity descriptors. Journal of Molecular Graphics 1987; 5: 79–86
   Google Scholar
• Goldblum A. Structure-activity relationships of cholinesterase inhibitors. Molecular Pharmacology 1983; 24: 436–442
   Google Scholar
• Hammett L. P. Physical Organic Chemistry. McGraw-Hill, New York 1940
   Google Scholar
• Kasuya F., Igarashi K., Fukui M. Clycine conjugation of the substituted benzoic acids in vitro: structure-metabolism relationship study. Journal of Pharmacobiological Dynamics 1990; 13: 432–440
   PubMedGoogle Scholar
• Lewis D. F. V. MO-QSARs: a review of molecular orbital generated quantitative structure-activity relationships. Progress in Drug Metabolism 1994; 12: 205–255
   Google Scholar
• Lide D. R. CRC Handbook of Chemistry and Physics, 71st edn. CRC Press, Boston 1991
   Google Scholar
• Massey H. S. W., Kestleman H. Ancillary Mathematics, 2nd edn. Pitman, London 1964, p Kalc 3.0 for Windows 1.0, Compudrug Chemistry Ltd, Budapest H-1136, Hungary
   Google Scholar
• Pearlman R. S. SAREA, QCPE, 413, Quantum Chemical Program Exchange. University of Indiana, Bloomington 1989
   Google Scholar
• Rietjens I. M. C. M., Soffers A. E. M. F., Veeger C., Vervoot J. Regioselectivity of cytochrome P-450 catalysed hydroxylation of fluorobenzenes predicted by calculated frontier orbital substrate characteristics. Biochemistry 1992; 32: 4801–4812
   Google Scholar
• Ringo J. L. Memory decays at the same rate in macques with and without brain lesions when expressed in d' or arcsine terms. Behavioural Brain Research 1991; 42: 123–134
   PubMed Web of Science ®Google Scholar
• Siest G., Fournel-Gigleux S., Magdalou J., Bagrel D. Cellular and molecular aspects of UDP-glucuronosyl transferases. Drug Metabolism Reviews 1989; 20: 721–731
   PubMed Web of Science ®Google Scholar
• Sharaf M. A., Illman D. L., Kowalski B. R. Exploratory data analysis. Chemometrics. Wiley, Chichester 1989; 179–295
   Google Scholar
• Spahn-Langguth H., Benet L. Z. Acyl glucuronides revisited: is the glucuronidation process a toxification as well as a detoxification mechanism. Drug Metabolism Reviews 1992; 24: 5–48
   PubMed Web of Science ®Google Scholar
• Taft R. W. Steric Effects in Organic Chemistry. Wiley, New York 1956
   Google Scholar
• Williams R. T. The metabolism of aromatic acids. Detoxification Mechanisms; the Metabolism and Detoxification of Drugs, Toxic Substances and Other Organic Compounds. Chapman & Hall, London 1959; 348–389
   Google Scholar