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Volumn 18, Issue 1, 1999, Pages 43-51

Quantitative structure-activity and structure-toxicity relationships of 4-aminodiphenyl sulphone derivatives with antiinflammatory activity

Author keywords

2'4' Substituted 4 aminodiphenyl sulphones; Activity; Antiinflammatory; Cell adhesion; Cell burst; Diffusion into erythrocytes; Methaemoglobin formation; PC and multiple regression analysis

Indexed keywords

BLOOD; CELL ADHESION; CELL DEATH; PRINCIPAL COMPONENT ANALYSIS; REGRESSION ANALYSIS;

EID: 0345059436     PISSN: 09318771     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3838(199901)18:1<43::aid-qsar43>3.0.co;2-%23     Document Type: Article
Times cited : (20)

References (36)
  • 1
    • 0345541910 scopus 로고
    • Application of QSAR in the development of model biological test systems. Diphenylsulphones versus cell-free and whole cell systems
    • J.C. Dearden ed., Elsevier, Amsterdam
    • Seydel, J.K., Coats, A.E., Cordes, H-P., Richter, M., Wiese, M., and Kulkarni, V.M., Application of QSAR in the development of model biological test systems. Diphenylsulphones versus cell-free and whole cell systems, in: Quantitative Approaches in Drug Design, J.C. Dearden ed., Elsevier, Amsterdam, 1983, pp. 253-258.
    • (1983) Quantitative Approaches in Drug Design , pp. 253-258
    • Seydel, J.K.1    Coats, A.E.2    Cordes, H.-P.3    Richter, M.4    Wiese, M.5    Kulkarni, V.M.6
  • 2
    • 0022416802 scopus 로고
    • Multiple regression and principal component analysis of antibacterial activities of sulfones and sulfonamides in whole cell and cell-free systems of various DDS sensitive and resistant strains
    • Coats, A.E., Cordes, H.-P., Kulkarni, V.M., Richter, M., Schaper, K.-J., Wiese, M., and Seydel, J.K., Multiple regression and principal component analysis of antibacterial activities of sulfones and sulfonamides in whole cell and cell-free systems of various DDS sensitive and resistant strains. Quant. Struct.-Act. Relat. 4, 99-109 (1985).
    • (1985) Quant. Struct.-Act. Relat. , vol.4 , pp. 99-109
    • Coats, A.E.1    Cordes, H.-P.2    Kulkarni, V.M.3    Richter, M.4    Schaper, K.-J.5    Wiese, M.6    Seydel, J.K.7
  • 3
    • 0023501974 scopus 로고
    • Multiple regression analysis of sulfones of antimalarial activities in cell-free systems and principal component analysis to compare with antibacterial activities
    • Wiese, M., Seydel, J.K., Pieper, H., Krüger, G., Noll, K.R., and Keck, J., Multiple regression analysis of sulfones of antimalarial activities in cell-free systems and principal component analysis to compare with antibacterial activities. Quant.Struct.-Act. Relat. 6, 164-172 (1987).
    • (1987) Quant.Struct.-Act. Relat. , vol.6 , pp. 164-172
    • Wiese, M.1    Seydel, J.K.2    Pieper, H.3    Krüger, G.4    Noll, K.R.5    Keck, J.6
  • 4
    • 0025055471 scopus 로고
    • In vitro and in vivo experiments with the new inhibitor of Mycobacterium leprae, Brodimoprim, alone and in combination with dapsone
    • Seydel, J.K., Wempe, E.G., Rosenfeld, M., Jaganathan, R., Mahadevan, P.R., Dhople, A.M. In vitro and in vivo experiments with the new inhibitor of Mycobacterium leprae, Brodimoprim, alone and in combination with dapsone. Arzneim-Forsch. 40, 69-75 (1990).
    • (1990) Arzneim-Forsch. , vol.40 , pp. 69-75
    • Seydel, J.K.1    Wempe, E.G.2    Rosenfeld, M.3    Jaganathan, R.4    Mahadevan, P.R.5    Dhople, A.M.6
  • 5
    • 0001912491 scopus 로고
    • Dermatitis herpetiformis
    • Zone, J.J., Dermatitis herpetiformis. Curr. Probl. Derm. 3, 4-42 (1991).
    • (1991) Curr. Probl. Derm. , vol.3 , pp. 4-42
    • Zone, J.J.1
  • 6
    • 0026645711 scopus 로고
    • The role of leukocyte-generated reactive metabolites in the pathogenesis of idiosyncratic drug reactions
    • Uetrecht, J.P., The role of leukocyte-generated reactive metabolites in the pathogenesis of idiosyncratic drug reactions. Drug Metab. Rev. 24, 299-366 (1992).
    • (1992) Drug Metab. Rev. , vol.24 , pp. 299-366
    • Uetrecht, J.P.1
  • 7
    • 0026079216 scopus 로고
    • Mechanism of the inhibition of myeloperoxidase by anti-inflammatory drugs
    • Kettle, A.J., Winterboume, C.C., Mechanism of the inhibition of myeloperoxidase by anti-inflammatory drugs. Biochem. Pharmacol. 41, 1485-1492 (1991).
    • (1991) Biochem. Pharmacol. , vol.41 , pp. 1485-1492
    • Kettle, A.J.1    Winterboume, C.C.2
  • 10
    • 0027407134 scopus 로고
    • Inhibition of neutrophil adherence to antibody by dapsone: A possible therapeutic mechanism of dapsone in the treatment of IgA dermatoses
    • Thuong-Nguyen, V., Kadunce, D.P., Hendrix, J.D., Gammon, W.R., Zone, J.J., Inhibition of neutrophil adherence to antibody by dapsone: a possible therapeutic mechanism of dapsone in the treatment of IgA dermatoses. J. Invest. Pharmacol. 100, 349-355 (1993).
    • (1993) J. Invest. Pharmacol. , vol.100 , pp. 349-355
    • Thuong-Nguyen, V.1    Kadunce, D.P.2    Hendrix, J.D.3    Gammon, W.R.4    Zone, J.J.5
  • 11
    • 0029059090 scopus 로고
    • Dapsone inhibits generation of 5-lipoxygenase products in human polymorphonuclear leukocytes
    • Wozel, G., Lehmann, B., Dapsone inhibits generation of 5-lipoxygenase products in human polymorphonuclear leukocytes. Skin Pharmacol. 8, 196-202 (1995).
    • (1995) Skin Pharmacol. , vol.8 , pp. 196-202
    • Wozel, G.1    Lehmann, B.2
  • 12
    • 0024466393 scopus 로고
    • Bioactivation of dapsone to a cytotoxic metabolite by human hepatic microsomal enzymes
    • Coleman, M.D., Breckenridge, A.M., Park, B.K., Bioactivation of dapsone to a cytotoxic metabolite by human hepatic microsomal enzymes. Br. J. Clin. Pharmacol. 28, 389-395 (1989).
    • (1989) Br. J. Clin. Pharmacol. , vol.28 , pp. 389-395
    • Coleman, M.D.1    Breckenridge, A.M.2    Park, B.K.3
  • 13
    • 0025038855 scopus 로고
    • The use of cimetidine as a selective inhibitor of dapsone N-hydroxylation in man
    • Coleman, M.D., Scott, A.K., Breckenridge, A.M., Park, B.K., The use of cimetidine as a selective inhibitor of dapsone N-hydroxylation in man. Br. J. Clin. Pharmacol. 30, 761-767 (1990)
    • (1990) Br. J. Clin. Pharmacol. , vol.30 , pp. 761-767
    • Coleman, M.D.1    Scott, A.K.2    Breckenridge, A.M.3    Park, B.K.4
  • 14
    • 0026794121 scopus 로고
    • The use of cimetidine to reduce dapsone-dependent methaemoglobinaemia in dermatitis herpetiformis patients
    • Coleman, M.D., Rhodes, L.A., Scott, A.K., Breckenridge, A.M., Park, B.K., The use of cimetidine to reduce dapsone-dependent methaemoglobinaemia in dermatitis herpetiformis patients. Br. J. Clin. Pharmacol. 34, 244-249 (1992).
    • (1992) Br. J. Clin. Pharmacol. , vol.34 , pp. 244-249
    • Coleman, M.D.1    Rhodes, L.A.2    Scott, A.K.3    Breckenridge, A.M.4    Park, B.K.5
  • 15
    • 0018581446 scopus 로고
    • Studies on dapsone-induced haemolytic anaemia: Methaemoglobin production and glucose-6-phosphate activity in correlation with dapsone dosage
    • Manfredi, G., De Paufilis, G., Zampetti, M., Allegra, F., Studies on dapsone-induced haemolytic anaemia: methaemoglobin production and glucose-6-phosphate activity in correlation with dapsone dosage. Br. J. Dermatol. 100, 427-432 (1979).
    • (1979) Br. J. Dermatol. , vol.100 , pp. 427-432
    • Manfredi, G.1    De Paufilis, G.2    Zampetti, M.3    Allegra, F.4
  • 16
    • 0024450737 scopus 로고
    • Preparation and biological activity of new substituted antimalarial diaminodiphenylsulfones
    • Pieper, H., Seydel, J.K., Krüger, G., Noll, K., Keck, J., Wiese, M., Preparation and biological activity of new substituted antimalarial diaminodiphenylsulfones. Arzneim.-Forsch. 39, 1073-1080 (1989).
    • (1989) Arzneim.-Forsch. , vol.39 , pp. 1073-1080
    • Pieper, H.1    Seydel, J.K.2    Krüger, G.3    Noll, K.4    Keck, J.5    Wiese, M.6
  • 17
    • 0020678028 scopus 로고
    • Inhibitory activity and mode of action of DDS in cell-free folate synthesizing systems prepared from M. lufu and M. leprae - A comparison
    • Kulkarni, V.M., Seydel, J.K., Inhibitory activity and mode of action of DDS in cell-free folate synthesizing systems prepared from M. lufu and M. leprae - A comparison, Chemotherapy 29, 58-67 (1983).
    • (1983) Chemotherapy , vol.29 , pp. 58-67
    • Kulkarni, V.M.1    Seydel, J.K.2
  • 19
    • 0029958064 scopus 로고    scopus 로고
    • Studies on the toxicity of novel analogues of dapsone in-vitro using rat, human and heterologously expressed metabolizing systems
    • Coleman, M.D., Smith, St., Kelly, D.E., Kelly, St.L., and Seydel, J.K., Studies on the toxicity of novel analogues of dapsone in-vitro using rat, human and heterologously expressed metabolizing systems. J. Pharm. Pharmacol. 48, 945-950 (1996).
    • (1996) J. Pharm. Pharmacol. , vol.48 , pp. 945-950
    • Coleman, M.D.1    Smith, S.2    Kelly, D.E.3    Kelly, S.L.4    Seydel, J.K.5
  • 20
    • 0031027351 scopus 로고    scopus 로고
    • Studies on the inhibitory effects of analogues of dapsone on neutrophil function in-vitro
    • Coleman, M.D., Smith, J.K., Perris, A.D., Buck, N.S., and Seydel, J.K., Studies on the inhibitory effects of analogues of dapsone on neutrophil function in-vitro. J. Pharm. Pharmacol. 23, 53-57 (1997).
    • (1997) J. Pharm. Pharmacol. , vol.23 , pp. 53-57
    • Coleman, M.D.1    Smith, J.K.2    Perris, A.D.3    Buck, N.S.4    Seydel, J.K.5
  • 21
    • 0006753279 scopus 로고
    • Die bestimmung von methaemoglobin im blut mit dem lichtelektrischen kolorimeter
    • Havemann, R., Jung, R., v. Issekutz, B., Die Bestimmung von Methaemoglobin im Blut mit dem lichtelektrischen Kolorimeter. Biochem. Z. 301, 116-124 (1939).
    • (1939) Biochem. Z. , vol.301 , pp. 116-124
    • Havemann, R.1    Jung, R.2    Issekutz, B.V.3
  • 22
    • 0023236937 scopus 로고
    • The metabolism of 17αethinyloestradiol by human liver microsomes: Formation of catechol and chemically reactive metabolites
    • Purba, H.S., Maggs, J.L., Orme, M.L.E., Back, D.J., and Park, B.K., The metabolism of 17αethinyloestradiol by human liver microsomes: formation of catechol and chemically reactive metabolites. Br. J. Clin. Pharmacol. 23, 447-453 (1987).
    • (1987) Br. J. Clin. Pharmacol. , vol.23 , pp. 447-453
    • Purba, H.S.1    Maggs, J.L.2    Orme, M.L.E.3    Back, D.J.4    Park, B.K.5
  • 23
    • 0025611212 scopus 로고
    • Investigation into the role of metabolism in dapsone-induced methaemoglobinaemia using a two-compartment in-vitro test system
    • Tingle, M.D., Coleman, M.D., and Park, B.K., Investigation into the role of metabolism in dapsone-induced methaemoglobinaemia using a two-compartment in-vitro test system. J. Clin. Pharmacol. 30, 829-838 (1990).
    • (1990) J. Clin. Pharmacol. , vol.30 , pp. 829-838
    • Tingle, M.D.1    Coleman, M.D.2    Park, B.K.3
  • 24
    • 0025995577 scopus 로고
    • An investigation into the haematological toxicity of structural analogues of dapsone in-vitro and in-vivo
    • Coleman, M.D., Tingle, M.D., Hussain, F., Storr, R.C., Park, B.K., An investigation into the haematological toxicity of structural analogues of dapsone in-vitro and in-vivo. Br. J. Clin.Pharmacol. 43, 779-784 (1991).
    • (1991) Br. J. Clin.pharmacol. , vol.43 , pp. 779-784
    • Coleman, M.D.1    Tingle, M.D.2    Hussain, F.3    Storr, R.C.4    Park, B.K.5
  • 25
    • 0019209334 scopus 로고
    • QSAR studies of potential antimalarial sulfonamide partitioning into erythrocytes and binding to erythrocytes
    • Saxena, A.K., and Seydel, J.K., QSAR studies of potential antimalarial sulfonamide partitioning into erythrocytes and binding to erythrocytes. Eur. J. Med. Chem. 15, 241-246 (1980).
    • (1980) Eur. J. Med. Chem. , vol.15 , pp. 241-246
    • Saxena, A.K.1    Seydel, J.K.2
  • 26
    • 0026800839 scopus 로고
    • The induction by human interleukin-6 of apoptosis in the promonocytix cell line U937 and human neutrophils
    • Afford, S.C., Pongracz, J., Stockley, R.A., Croker, J., Burnett, D., The induction by human interleukin-6 of apoptosis in the promonocytix cell line U937 and human neutrophils. J. Biol. Chem. 267, 21612-21616 (1992).
    • (1992) J. Biol. Chem. , vol.267 , pp. 21612-21616
    • Afford, S.C.1    Pongracz, J.2    Stockley, R.A.3    Croker, J.4    Burnett, D.5
  • 27
    • 0027464956 scopus 로고
    • Improved rapid photometric assay for quantitative measurement of PMN migration
    • Junger, W.G., Cardoza, T.A., Liu, F.C., Hoyt, D.B., Goodwin, R., Improved rapid photometric assay for quantitative measurement of PMN migration. J. Immunol. Methods 160, 73-79 (1993).
    • (1993) J. Immunol. Methods , vol.160 , pp. 73-79
    • Junger, W.G.1    Cardoza, T.A.2    Liu, F.C.3    Hoyt, D.B.4    Goodwin, R.5
  • 28
    • 0019544354 scopus 로고
    • Down with multiple 't' tests
    • Elashoff, J.D., Down with multiple 't' tests. Gastroenterology 80, 615-619 (1981).
    • (1981) Gastroenterology , vol.80 , pp. 615-619
    • Elashoff, J.D.1
  • 31
    • 0344248220 scopus 로고
    • Kinetik der haemoglobinbildung. IV. Mitteilung. Die haemoglobinbildung durch phenylhydroxylamin und nitrobenzol in roten zellen in vitro
    • Kiese, M., Reinwein, D., Waller, H.D., Kinetik der Haemoglobinbildung. IV. Mitteilung. Die Haemoglobinbildung durch Phenylhydroxylamin und Nitrobenzol in roten Zellen in vitro. Naunyn-Schmiedebergs Archiv. Ex. Path. Pharm. 210, 393-398 (1950).
    • (1950) Naunyn-schmiedebergs Archiv. Ex. Path. Pharm. , vol.210 , pp. 393-398
    • Kiese, M.1    Reinwein, D.2    Waller, H.D.3
  • 32
    • 0015793793 scopus 로고
    • Liver metabolic reactions: Tertiary amine N-dealkylation, tertiary amine N-oxidation, N-oxide reduction, and N-oxide N-dealkylation, II. N,N-Dimethylaniline
    • Willi, P., Bickel, M.H., Liver metabolic reactions: Tertiary amine N-dealkylation, tertiary amine N-oxidation, N-oxide reduction, and N-oxide N-dealkylation, II. N,N-Dimethylaniline. Arch. Biochem. Biophys. 156, 772-779 (1973).
    • (1973) Arch. Biochem. Biophys. , vol.156 , pp. 772-779
    • Willi, P.1    Bickel, M.H.2
  • 33
    • 0345110567 scopus 로고
    • N-demethylation and N-oxidation of N-dimethylaniline by rat liver microsomes
    • Gorrod J.W., Damani L.A., eds. Chapt. 8, Verlag Chemie, Weinheim
    • Houdi, A.A., Damani, L.A., N-demethylation and N-oxidation of N-dimethylaniline by rat liver microsomes. in: Gorrod J.W., Damani L.A., eds. Biological Oxydation of Nitrogen in Organic Molecules, Chapt. 8, pp. 96-100, Verlag Chemie, Weinheim 1985.
    • (1985) Biological Oxydation of Nitrogen in Organic Molecules , pp. 96-100
    • Houdi, A.A.1    Damani, L.A.2
  • 34
    • 84982317749 scopus 로고
    • The quantitative treatment of the ortho-effect
    • Charton, M., The quantitative treatment of the ortho-effect. Prog. Phys. Org. Chem. 8, 235-317 (1971).
    • (1971) Prog. Phys. Org. Chem. , vol.8 , pp. 235-317
    • Charton, M.1
  • 35
    • 5344247073 scopus 로고
    • Field and resonance components of substituent effects
    • Swain, C.G., and Lupton, E.C., Field and resonance components of substituent effects. J. Am. Chem. Soc. 90, 4328-4337 (1968).
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 4328-4337
    • Swain, C.G.1    Lupton, E.C.2
  • 36


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