메뉴 건너뛰기




Volumn 36, Issue 4, 2008, Pages 721-730

Metabolite generation via microbial biotransformations with actinomycetes: Rapid screening for active strains and biosynthesis of important human metabolites of two development-stage compounds, 5-[(5S,9R)-9-(4-cyanophenyl)-3- (3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]non7-yl-methyl] -3-thiophenecarboxylic acid (BMS-587101) and dasatinib

Author keywords

[No Author keywords available]

Indexed keywords

5 [(9 (4 CYANOPHENYL) 3 (3,5 DICHLOROPHENYL) 1 METHYL 2,4 DIOXO 1,3,7 TRIAZASPIRO[4.4]NON8 EN 7 YL)METHYL]THIOPHENE 3 CARBOXYLIC ACID; 5 [9 (4 CYANOPHENYL) 3 (3,5 DICHLOROPHENYL) 1 METHYL 2,4 DIOXO 1,3,7 TRIAZASPIRO[4.4]NON7 YL METHYL] 3 THIOPHENECARBOXYLIC ACID; BMS 587101; CARBOXYLIC ACID DERIVATIVE; CYTOCHROME P450; DASATINIB; DICLOFENAC; DRUG METABOLITE; SPIRO COMPOUND; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 41549109840     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.107.019570     Document Type: Article
Times cited : (22)

References (34)
  • 1
    • 0032895172 scopus 로고    scopus 로고
    • Microbial models of mammalian metabolism of xenobiotics: An updated review
    • Abourashed EA, Clark AM, and Hufford CD (1999) Microbial models of mammalian metabolism of xenobiotics: an updated review. Curr Med Chem 6:359-374.
    • (1999) Curr Med Chem , vol.6 , pp. 359-374
    • Abourashed, E.A.1    Clark, A.M.2    Hufford, C.D.3
  • 2
    • 0032608923 scopus 로고    scopus 로고
    • Microbial models for drug metabolism
    • Azerad R (1999) Microbial models for drug metabolism. Adv Biochem Eng Biotechnol 63:169-218.
    • (1999) Adv Biochem Eng Biotechnol , vol.63 , pp. 169-218
    • Azerad, R.1
  • 4
    • 33846417686 scopus 로고    scopus 로고
    • Cloning and expression of a cytochrome P450 hydroxylase gene from Amycolatopsis orientalis: Hydroxylation of epothilone B for the production of epothilone F
    • Basch J and Chiang SJ (2007) Cloning and expression of a cytochrome P450 hydroxylase gene from Amycolatopsis orientalis: hydroxylation of epothilone B for the production of epothilone F. J Ind Microbiol Biotechnol 34:171-176.
    • (2007) J Ind Microbiol Biotechnol , vol.34 , pp. 171-176
    • Basch, J.1    Chiang, S.J.2
  • 6
    • 0026604758 scopus 로고
    • Microbial transformation of immunosuppressive compounds. I. Desmethylation of FK506 and immunomycin (FR 900520) by Actinoplanes sp. ATCC 53771
    • Chen TS, Arison BH, Wicker LS, Inamine ES, and Monaghan RL (1992) Microbial transformation of immunosuppressive compounds. I. Desmethylation of FK506 and immunomycin (FR 900520) by Actinoplanes sp. ATCC 53771. J Antibiot 45:118-123.
    • (1992) J Antibiot , vol.45 , pp. 118-123
    • Chen, T.S.1    Arison, B.H.2    Wicker, L.S.3    Inamine, E.S.4    Monaghan, R.L.5
  • 7
    • 33750989362 scopus 로고    scopus 로고
    • C2-Aminothiazole as a novel kinase inhibitor template. Structure-activity relationship studies toward the discovery of N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1- piperazinyl)]-2-methyl-4-pyrimidinyl]amino)]-1,3-thiazole-5-carboxamide (dasatinib, BMS-354825) as a potent pan-Src kinase inhibitor
    • Das J, Chen P, Norris D, Padmanabha R, Lin J, Moquin RV, Shen Z, Cook LS, Doweyko AM, Pitt S, et al. (2006) C2-Aminothiazole as a novel kinase inhibitor template. Structure-activity relationship studies toward the discovery of N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1- piperazinyl)]-2-methyl-4-pyrimidinyl]amino)]-1,3-thiazole-5-carboxamide (dasatinib, BMS-354825) as a potent pan-Src kinase inhibitor. J Med Chem 49:6819-68326.
    • (2006) J Med Chem , vol.49 , pp. 6819-68326
    • Das, J.1    Chen, P.2    Norris, D.3    Padmanabha, R.4    Lin, J.5    Moquin, R.V.6    Shen, Z.7    Cook, L.S.8    Doweyko, A.M.9    Pitt, S.10
  • 8
    • 33845734598 scopus 로고    scopus 로고
    • A regulatory perspective on issues and approaches in characterizing human metabolites
    • Davis-Bruno KL and Atrakchi A (2006) A regulatory perspective on issues and approaches in characterizing human metabolites. Chem Res Toxicol 19:1561-1563.
    • (2006) Chem Res Toxicol , vol.19 , pp. 1561-1563
    • Davis-Bruno, K.L.1    Atrakchi, A.2
  • 9
    • 0035101279 scopus 로고    scopus 로고
    • Effectiveness of orbital shaking for the aeration of suspended bacterial cultures in square-deepwell microtiter plates
    • Duetz WA and Witholt BW (2001) Effectiveness of orbital shaking for the aeration of suspended bacterial cultures in square-deepwell microtiter plates. Biochem Eng J 7:113-115.
    • (2001) Biochem Eng J , vol.7 , pp. 113-115
    • Duetz, W.A.1    Witholt, B.W.2
  • 10
    • 0024994530 scopus 로고
    • Microbiologic oxidation of estratrienes and estratetraenes by Streptomyces roseochromogenes ATCC 13400
    • Ferrer JC, Calzada V, and Bonet JJ (1990) Microbiologic oxidation of estratrienes and estratetraenes by Streptomyces roseochromogenes ATCC 13400. Steroids 55:390-394.
    • (1990) Steroids , vol.55 , pp. 390-394
    • Ferrer, J.C.1    Calzada, V.2    Bonet, J.J.3
  • 11
    • 33845792941 scopus 로고    scopus 로고
    • Safety assessment of stable drug metabolites
    • Guengerich FP (2006) Safety assessment of stable drug metabolites. Chem Res Toxicol 19:1559-1560.
    • (2006) Chem Res Toxicol , vol.19 , pp. 1559-1560
    • Guengerich, F.P.1
  • 12
    • 33845769325 scopus 로고    scopus 로고
    • Safety assessment of drug metabolites: Characterization of chemically stable metabolites
    • Humphreys WG and Unger SE (2006) Safety assessment of drug metabolites: characterization of chemically stable metabolites. Chem Res Toxicol 19:1564-1569.
    • (2006) Chem Res Toxicol , vol.19 , pp. 1564-1569
    • Humphreys, W.G.1    Unger, S.E.2
  • 13
    • 0032824448 scopus 로고    scopus 로고
    • Biotransformation of doxepin by Cunninghamella elegans
    • Joanna DM, James PF, and Carl EC (1999) Biotransformation of doxepin by Cunninghamella elegans. Drug Metab Dispos 27:1157-1164.
    • (1999) Drug Metab Dispos , vol.27 , pp. 1157-1164
    • Joanna, D.M.1    James, P.F.2    Carl, E.C.3
  • 15
    • 41549150597 scopus 로고    scopus 로고
    • Microbial transformation method for the preparation of an epothilone
    • U.S. patent 6,780,620 B1. 2004 Aug 24
    • Li W, Matson JA, Xiaohua H, Lam KS, and McClure GA (2004) Microbial transformation method for the preparation of an epothilone. U.S. patent 6,780,620 B1. 2004 Aug 24.
    • (2004)
    • Li, W.1    Matson, J.A.2    Xiaohua, H.3    Lam, K.S.4    McClure, G.A.5
  • 16
    • 41549136798 scopus 로고    scopus 로고
    • Metabolite generation and characterization via microbial biotransformation with actinomycetes
    • 23-27 Oct, Maui, Hawaii. Abstract 351
    • Li W, Josephs JL, and Humphreys WG (2005) Metabolite generation and characterization via microbial biotransformation with actinomycetes. 13th North American ISSX Meeting; 23-27 Oct 2005; Maui, Hawaii. Abstract 351.
    • (2005) 13th North American ISSX Meeting
    • Li, W.1    Josephs, J.L.2    Humphreys, W.G.3
  • 17
    • 0035434257 scopus 로고    scopus 로고
    • Effects of amino acids on the amidation of polyaromatic carboxylic acids by Bacillus cereus
    • Maruyama R, Kawata A, Ono S, Nishizawa M, Ito S, and Inoue M (2001) Effects of amino acids on the amidation of polyaromatic carboxylic acids by Bacillus cereus. Biosci Biotechnol Biochem 65:1761-1765.
    • (2001) Biosci Biotechnol Biochem , vol.65 , pp. 1761-1765
    • Maruyama, R.1    Kawata, A.2    Ono, S.3    Nishizawa, M.4    Ito, S.5    Inoue, M.6
  • 18
    • 0032824448 scopus 로고    scopus 로고
    • Biotransformation of doxepin by Cunninghamella elegans
    • Moody JD, Freeman JP, and Cerniglia CE (1999) Biotransformation of doxepin by Cunninghamella elegans. Drug Metab Dispos 27:1157-1164.
    • (1999) Drug Metab Dispos , vol.27 , pp. 1157-1164
    • Moody, J.D.1    Freeman, J.P.2    Cerniglia, C.E.3
  • 20
    • 0021029529 scopus 로고
    • Taxonomy of actinomycetes capable of hydroxylation of ML-236B (compactin)
    • Okazaki T, Serizawa N, Enokita R, Torikata A, and Terahara A (1983) Taxonomy of actinomycetes capable of hydroxylation of ML-236B (compactin). J Antibiot 36:1176-1183.
    • (1983) J Antibiot , vol.36 , pp. 1176-1183
    • Okazaki, T.1    Serizawa, N.2    Enokita, R.3    Torikata, A.4    Terahara, A.5
  • 22
    • 33845364193 scopus 로고    scopus 로고
    • Discovery and development of 5-[(5S,9R)-9-(4-cyanophenyl)-3-(3,5-dichlorophenyl)-1-methyl-2,4- dioxo-1,3,7-triazaspiro[4.4]non-7-ylmethyl]-3-thiophenecarboxylic acid (BMS-587101)-a small molecule antagonist leukocyte function associated antigen-1
    • Potin D, Launa M, Monatlik F, Malabre P, Fabreguettes M, Fouquet A, Maillet M, Nicolai E, Dorgeret L, Chevallier F, et al. (2006) Discovery and development of 5-[(5S,9R)-9-(4-cyanophenyl)-3-(3,5-dichlorophenyl)-1-methyl-2,4- dioxo-1,3,7-triazaspiro[4.4]non-7-ylmethyl]-3-thiophenecarboxylic acid (BMS-587101)-a small molecule antagonist leukocyte function associated antigen-1. J Med Chem 49:6946-6949.
    • (2006) J Med Chem , vol.49 , pp. 6946-6949
    • Potin, D.1    Launa, M.2    Monatlik, F.3    Malabre, P.4    Fabreguettes, M.5    Fouquet, A.6    Maillet, M.7    Nicolai, E.8    Dorgeret, L.9    Chevallier, F.10
  • 23
    • 0001876763 scopus 로고
    • Actinomycete cytochromes P-450 involved in oxidative metabolism: Biochemistry and molecular biology
    • Sariaslani FS and Omer A (1992) Actinomycete cytochromes P-450 involved in oxidative metabolism: biochemistry and molecular biology. Crit Rev Plant Sci 11:1-16.
    • (1992) Crit Rev Plant Sci , vol.11 , pp. 1-16
    • Sariaslani, F.S.1    Omer, A.2
  • 24
    • 0016250297 scopus 로고
    • Microbial models of mammalian metabolism. Aromatic hydroxylation
    • Smith RV and Rosazza JP (1974) Microbial models of mammalian metabolism. Aromatic hydroxylation. Arch Biochem Biophys 161:551-558.
    • (1974) Arch Biochem Biophys , vol.161 , pp. 551-558
    • Smith, R.V.1    Rosazza, J.P.2
  • 25
    • 0020587033 scopus 로고
    • Microbial transformations of pergolide to pergolide sulfoxide and pergolide sulfone
    • Smith RV, Davis PJ, and Kerr KM (1983) Microbial transformations of pergolide to pergolide sulfoxide and pergolide sulfone. J Pharm Sci 72:733-736.
    • (1983) J Pharm Sci , vol.72 , pp. 733-736
    • Smith, R.V.1    Davis, P.J.2    Kerr, K.M.3
  • 26
    • 33845748169 scopus 로고    scopus 로고
    • Metabolites and safety: What are the concerns, and how should we address them?
    • Smith DA and Obach RS (2006) Metabolites and safety: what are the concerns, and how should we address them? Chem Res Toxicol 19:1570-1579.
    • (2006) Chem Res Toxicol , vol.19 , pp. 1570-1579
    • Smith, D.A.1    Obach, R.S.2
  • 27
    • 0034647555 scopus 로고    scopus 로고
    • Cloning, overexpression, and purification of novobiocic acid synthetase from Streptomyces spheroides NCIMB 11891
    • Steffensky M, Li S-M, and Heide L (2000) Cloning, overexpression, and purification of novobiocic acid synthetase from Streptomyces spheroides NCIMB 11891. J Biol Chem 275:21754-21760.
    • (2000) J Biol Chem , vol.275 , pp. 21754-21760
    • Steffensky, M.1    Li, S.-M.2    Heide, L.3
  • 28
    • 0018635186 scopus 로고
    • Biotransformation of diclofenac sodium (Voltaren) in animals and in man. I. Identification and isolation of principal metabolites
    • Stierlin H, Faigle JW, Sallmann A, Küng W, Richter WJ, Kriemler HP, Alt KO, and Winkler T (1979) Biotransformation of diclofenac sodium (Voltaren) in animals and in man. I. Identification and isolation of principal metabolites. Xenobiotica 9:601-610.
    • (1979) Xenobiotica , vol.9 , pp. 601-610
    • Stierlin, H.1    Faigle, J.W.2    Sallmann, A.3    Küng, W.4    Richter, W.J.5    Kriemler, H.P.6    Alt, K.O.7    Winkler, T.8
  • 30
    • 0026726458 scopus 로고
    • Cloning, nucleotide sequence determination and expression of the genes encoding cytochrome P-450soy (soyC) and ferredoxinsoy (soyB) from Streptomyces griseus
    • Trower MK, Lenstra R, Omer C, Buchholz SE, and Sariaslani FS (1992) Cloning, nucleotide sequence determination and expression of the genes encoding cytochrome P-450soy (soyC) and ferredoxinsoy (soyB) from Streptomyces griseus. Mol Microbiol 6:2125-2134.
    • (1992) Mol Microbiol , vol.6 , pp. 2125-2134
    • Trower, M.K.1    Lenstra, R.2    Omer, C.3    Buchholz, S.E.4    Sariaslani, F.S.5
  • 32
    • 22944438036 scopus 로고    scopus 로고
    • Biotransformation of pantoprazole by the fungus Cunninghamella blakesleeana
    • Xie ZY, Huang HH, and Zhong DF (2005) Biotransformation of pantoprazole by the fungus Cunninghamella blakesleeana. Xenobiotica 35:467-477.
    • (2005) Xenobiotica , vol.35 , pp. 467-477
    • Xie, Z.Y.1    Huang, H.H.2    Zhong, D.F.3
  • 33
    • 31344457289 scopus 로고    scopus 로고
    • Structural elucidation of human oxidative metabolites of muraglitazar: Use of microbial bioreactors in the biosynthesis of metabolite standards
    • Zhang D, Zhang H, Aranibar N, Hanson R, Huang Y, Cheng PT, Wu S, Bonacorsi S, Zhu M, Swaminathan A, et al. (2006) Structural elucidation of human oxidative metabolites of muraglitazar: use of microbial bioreactors in the biosynthesis of metabolite standards. Drug Metab Dispos 34:267-280.
    • (2006) Drug Metab Dispos , vol.34 , pp. 267-280
    • Zhang, D.1    Zhang, H.2    Aranibar, N.3    Hanson, R.4    Huang, Y.5    Cheng, P.T.6    Wu, S.7    Bonacorsi, S.8    Zhu, M.9    Swaminathan, A.10
  • 34
    • 33646787431 scopus 로고    scopus 로고
    • Application of biocatalysis to drug metabolism: Preparation of mammalian metabolites of a biaryl-bis-sulfonamide AMPA (α-amino-3-hydroxy- 5-methylisoxazole-4-propionic acid) receptor potentiator using Actinoplanes missouriensis
    • Zmijewski M, Gillespie TA, Jackson DA, Schmidt DF, Yi P, and Kulanthaivel P (2006) Application of biocatalysis to drug metabolism: preparation of mammalian metabolites of a biaryl-bis-sulfonamide AMPA (α-amino-3-hydroxy- 5-methylisoxazole-4-propionic acid) receptor potentiator using Actinoplanes missouriensis. Drug Metab Dispos 34:925-931.
    • (2006) Drug Metab Dispos , vol.34 , pp. 925-931
    • Zmijewski, M.1    Gillespie, T.A.2    Jackson, D.A.3    Schmidt, D.F.4    Yi, P.5    Kulanthaivel, P.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.