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Volumn 43, Issue 5, 2012, Pages 2073-2085

Effect of structural modification on the gastrointestinal stability and hepatic metabolism of α-aminoxy peptides

Author keywords

Aminoxy peptide; Cytochrome P450 enzyme; Gastrointestinal stability; Hepatic metabolism; Structural modification

Indexed keywords

ALPHA AMINOXY PEPTIDE 1; ALPHA AMINOXY PEPTIDE 2; ALPHA AMINOXY PEPTIDE 3; ALPHA AMINOXY PEPTIDE 4; ALPHA AMINOXY PEPTIDE 5; CHLORIDE CHANNEL; CYTOCHROME P450 3A4; DRUG METABOLITE; PEPTIDE; UNCLASSIFIED DRUG;

EID: 84868152929     PISSN: 09394451     EISSN: 14382199     Source Type: Journal    
DOI: 10.1007/s00726-012-1291-1     Document Type: Article
Times cited : (11)

References (32)
  • 1
    • 0033890792 scopus 로고    scopus 로고
    • Participation of CYP2A in cocaine-induced hepatotoxicity in female mice
    • Aoki K, Takimoto M, Ota H, Yoshida T (2000) Participation of CYP2A in cocaine-induced hepatotoxicity in female mice. Pharmacol Toxicol 87(1):26-32 (Pubitemid 30644596)
    • (2000) Pharmacology and Toxicology , vol.87 , Issue.1 , pp. 26-32
    • Aoki, K.1    Takimoto, M.2    Ota, H.3    Yoshida, T.4
  • 2
    • 0026758261 scopus 로고
    • Structural specificity of mucosal-cell transport and metabolism of peptide drugs: Implication for oral peptide drug delivery
    • Bai JP, Amidon GL (1992) Structural specificity of mucosal-cell transport and metabolism of peptide drugs: implication for oral peptide drug delivery. Pharm Res 9(8):969-978
    • (1992) Pharm Res , vol.9 , Issue.8 , pp. 969-978
    • Bai, J.P.1    Amidon, G.L.2
  • 4
    • 84862768277 scopus 로고    scopus 로고
    • Extraordinary metabolic stability of peptides containing alpha-aminoxy acids
    • doi:10.1007/s00726-011-1095-8
    • Chen F, Ma B, Yang ZC, Lin G, Yang D (2011) Extraordinary metabolic stability of peptides containing alpha-aminoxy acids. Amino Acids. doi:10.1007/s00726-011-1095-8
    • (2011) Amino Acids
    • Chen, F.1    Ma, B.2    Yang, Z.C.3    Lin, G.4    Yang, D.5
  • 5
    • 0036787071 scopus 로고    scopus 로고
    • The contribution of cytochrome P-450 isoenzymes to the metabolism of phenothi-azine neuroleptics
    • Daniel WA, Syrek M, Haduch A (2002) The contribution of cytochrome P-450 isoenzymes to the metabolism of phenothi-azine neuroleptics. Eur Neuropsychopharmacol 12(5):371-377
    • (2002) Eur Neuropsychopharmacol , vol.12 , Issue.5 , pp. 371-377
    • Daniel, W.A.1    Syrek, M.2    Haduch, A.3
  • 6
    • 0035382627 scopus 로고    scopus 로고
    • The outstanding biological stability of β- and γ-peptides toward proteolytic enzymes: An in vitro investigation with fifteen peptidases
    • Frackenpohl J, Arvidsson PI, Schreiber JV, Seebach D (2001) The outstanding biological stability of beta-and gamma-peptides toward proteolytic enzymes: an in vitro investigation with fifteen peptidases. ChemBioChem 2(6):445-455. doi:10.1002/1439-7633(20010601)2:6\445 (Pubitemid 33723576)
    • (2001) ChemBioChem , vol.2 , Issue.6 , pp. 445-455
    • Frackenpohl, J.1    Arvidsson, P.I.2    Schreiber, J.V.3    Seebach, D.4
  • 7
    • 34247362490 scopus 로고    scopus 로고
    • Foldamers as versatile frameworks for the design and evolution of function
    • DOI 10.1038/nchembio876, PII NCHEMBIO876
    • Goodman CM, Choi S, Shandler S, DeGrado WF (2007) Foldamers as versatile frameworks for the design and evolution of function. Nat Chem Biol 3(5):252-262. doi:10.1038/nchembio876 (Pubitemid 46628637)
    • (2007) Nature Chemical Biology , vol.3 , Issue.5 , pp. 252-262
    • Goodman, C.M.1    Choi, S.2    Shandler, S.3    DeGrado, W.F.4
  • 9
    • 0019950970 scopus 로고
    • Distribution of pepstatin and statine following oral and intravenous administration in rats. Tissue localisation by whole body autoradiography
    • DOI 10.1016/0006-2952(82)90120-4
    • Grant DA, Ford TF, McCulloch RJ (1982) Distribution of pepstatin and statine following oral and intravenous administration in rats. Tissue localisation by whole body autoradiography. Biochem Pharmacol 31(13):2302-2305 (Pubitemid 12085299)
    • (1982) Biochemical Pharmacology , vol.31 , Issue.13 , pp. 2302-2305
    • Grant, D.A.W.1    Ford, T.F.2    McCulloch, R.J.3
  • 11
    • 19544372954 scopus 로고    scopus 로고
    • Effect of CYP3A1(23) induction on clarithromycin pharmacokinetics in rats with diabetes mellitus
    • DOI 10.1128/AAC.49.6.2528-2532.2005
    • Kim YC, Lee JH, Kim SH, Lee MG (2005) Effect of CYP3A1(23) induction on clarithromycin pharmacokinetics in rats with diabetes mellitus. Antimicrob Agents Chemother 49(6):2528-2532. doi:10.1128/AAC.49.6.2528-2532.2005 (Pubitemid 40734497)
    • (2005) Antimicrobial Agents and Chemotherapy , vol.49 , Issue.6 , pp. 2528-2532
    • Kim, Y.C.1    Lee, J.H.2    Kim, S.H.3    Lee, M.G.4
  • 12
    • 55949134723 scopus 로고    scopus 로고
    • Strain differences in hepatic cytochrome P450 1A and 3A expression between Sprague-Dawley and Wistar rats
    • Kishida T, Muto S, Hayashi M, Tsutsui M, Tanaka S, Murakami M, Kuroda J (2008) Strain differences in hepatic cytochrome P450 1A and 3A expression between Sprague-Dawley and Wistar rats. J Toxicol Sci 33(4):447-457
    • (2008) J Toxicol Sci , vol.33 , Issue.4 , pp. 447-457
    • Kishida, T.1    Muto, S.2    Hayashi, M.3    Tsutsui, M.4    Tanaka, S.5    Murakami, M.6    Kuroda, J.7
  • 13
    • 0034600005 scopus 로고    scopus 로고
    • Structural characteristics of human P450s involved in drug metabolism: QSARs and lipophilicity profiles
    • DOI 10.1016/S0300-483X(99)00207-3, PII S0300483X99002073
    • Lewis DF (2000) Structural characteristics of human P450s involved in drug metabolism: QSARs and lipophilicity profiles. Toxicology 144(1-3):197-203 (Pubitemid 30201637)
    • (2000) Toxicology , vol.144 , Issue.1-3 , pp. 197-203
    • Lewis, D.F.V.1
  • 14
    • 33746888291 scopus 로고    scopus 로고
    • Peptides of aminoxy acids as foldamers
    • DOI 10.1039/b602230h
    • Li X, Yang D (2006) Peptides of aminoxy acids as foldamers. Chem Commun (Cambridge) 32:3367-3379 (Pubitemid 44200344)
    • (2006) Chemical Communications , Issue.32 , pp. 3367-3379
    • Li, X.1    Yang, D.2
  • 15
    • 34250837547 scopus 로고    scopus 로고
    • A small synthetic molecule forms chloride channels to mediate chloride transport across cell membranes
    • DOI 10.1021/ja071961h
    • Li X, Shen B, Yao XQ, Yang D (2007) A small synthetic molecule forms chloride channels to mediate chloride transport across cell membranes. J Am Chem Soc 129(23):7264-7265. doi:10.1021/ja071961h (Pubitemid 46980799)
    • (2007) Journal of the American Chemical Society , vol.129 , Issue.23 , pp. 7264-7265
    • Li, X.1    Shen, B.2    Yao, X.-Q.3    Yang, D.4
  • 16
    • 57349199922 scopus 로고    scopus 로고
    • Alpha-aminoxy acids: New possibilities from foldamers to anion receptors and channels
    • doi:10.1021/ar8001393
    • Li X, Wu YD, Yang D (2008) Alpha-aminoxy acids: new possibilities from foldamers to anion receptors and channels. Acc Chem Res 41(10):1428-1438. doi:10.1021/ar8001393
    • (2008) Acc Chem Res , vol.41 , Issue.10 , pp. 1428-1438
    • Li, X.1    Wu, Y.D.2    Yang, D.3
  • 17
    • 70349739273 scopus 로고    scopus 로고
    • Synthetic chloride channel regulates cell membrane potentials and voltage-gated calcium channels
    • doi:10.1021/ja902352g
    • Li X, Shen B, Yao XQ, Yang D (2009) Synthetic chloride channel regulates cell membrane potentials and voltage-gated calcium channels. J Am Chem Soc 131(38):13676-13680. doi:10.1021/ja902352g
    • (2009) J Am Chem Soc , vol.131 , Issue.38 , pp. 13676-13680
    • Li, X.1    Shen, B.2    Yao, X.Q.3    Yang, D.4
  • 18
    • 34047168722 scopus 로고    scopus 로고
    • Deacetylclivorine: A gender-selective metabolite of clivorine formed in female Sprague-Dawley rat liver microsomes
    • DOI 10.1124/dmd.106.014100
    • Lin G, Tang J, Liu XQ, Jiang Y, Zheng J (2007) Deacetylclivorine: a gender-selective metabolite of clivorine formed in female Sprague-Dawley rat liver microsomes. Drug Metab Dispos 35(4):607-613. doi:10.1124/dmd.106.014100 (Pubitemid 46513264)
    • (2007) Drug Metabolism and Disposition , vol.35 , Issue.4 , pp. 607-613
    • Lin, G.1    Tang, J.2    Xiao, Q.L.3    Jiang, Y.4    Zheng, J.5
  • 19
    • 0142057081 scopus 로고    scopus 로고
    • Quantitative structure-activity relationships for predicting metabolism and modeling cytochrome P450 enzyme activities
    • DOI 10.1897/01-480
    • Long A, Walker JD (2003) Quantitative structure-activity relationships for predicting metabolism and modeling cytochrome p450 enzyme activities. Environ Toxicol Chem 22(8):1894-1899 (Pubitemid 37337313)
    • (2003) Environmental Toxicology and Chemistry , vol.22 , Issue.8 , pp. 1894-1899
    • Long, A.1    Walker, J.D.2
  • 20
    • 79961056417 scopus 로고    scopus 로고
    • Effect of structural modification of alpha-aminoxy peptides on their intestinal absorption and transport mechanism
    • Ma B, Zha H, Li N, Yang D, Lin G (2011) Effect of structural modification of alpha-aminoxy peptides on their intestinal absorption and transport mechanism. Mol Pharm 8(4):1073-1082
    • (2011) Mol Pharm , vol.8 , Issue.4 , pp. 1073-1082
    • Ma, B.1    Zha, H.2    Li, N.3    Yang, D.4    Lin, G.5
  • 22
    • 33845473315 scopus 로고    scopus 로고
    • Species differences between mouse, rat, dog, monkey and human CYP-mediated drug metabolism, inhibition and induction
    • DOI 10.1517/17425255.2.6.875
    • Martignoni M, Groothuis GM, de Kanter R (2006) Species differences between mouse, rat, dog, monkey and human CYP-mediated drug metabolism, inhibition and induction. Expert Opin Drug Metab Toxicol 2(6):875-894 (Pubitemid 44911538)
    • (2006) Expert Opinion on Drug Metabolism and Toxicology , vol.2 , Issue.6 , pp. 875-894
    • Martignoni, M.1    Groothuis, G.M.M.2    De Kanter, R.3
  • 23
    • 37849031379 scopus 로고    scopus 로고
    • Measurements of rat and mouse gastrointestinal p H, fluid and lymphoid tissue, and implications for in vivo experiments
    • McConnell EL, Basit AW, Murdan S (2008) Measurements of rat and mouse gastrointestinal p H, fluid and lymphoid tissue, and implications for in vivo experiments. J Pharm Pharmacol 60(1):63-70
    • (2008) J Pharm Pharmacol , vol.60 , Issue.1 , pp. 63-70
    • McConnell, E.L.1    Basit, A.W.2    Murdan, S.3
  • 24
    • 33746757103 scopus 로고    scopus 로고
    • Metabolites of hirsuteine and hirsutine, the major indole alkaloids of Uncaria rhynchophylla, in rats
    • DOI 10.1248/bpb.29.1671
    • Nakazawa T, Banba K, Hata K, Nihei Y, Hoshikawa A, Ohsawa K (2006) Metabolites of hirsuteine and hirsutine, the major indole alkaloids of Uncaria rhynchophylla, in rats. Biol Pharm Bull 29(8):1671-1677 (Pubitemid 44166371)
    • (2006) Biological and Pharmaceutical Bulletin , vol.29 , Issue.8 , pp. 1671-1677
    • Nakazawa, T.1    Banba, K.-I.2    Hata, K.3    Nihei, Y.4    Hoshikawa, A.5    Ohsawa, K.6
  • 25
    • 9644278194 scopus 로고    scopus 로고
    • Improving the decision-making process in the structural modification of drug candidates: Enhancing metabolic stability
    • DOI 10.1016/S1359-6446(04)03280-5, PII S1359644604032805
    • Nassar AE, Kamel AM, Clarimont C (2004) Improving the decision-making process in the structural modification of drug candidates: enhancing metabolic stability. Drug Discov Today 9(23):1020-1028. doi:10.1016/S1359-6446(04)03280-5 (Pubitemid 39574558)
    • (2004) Drug Discovery Today , vol.9 , Issue.23 , pp. 1020-1028
    • Nassar, A.-E.F.1    Kamel, A.M.2    Clarimont, C.3
  • 26
    • 78651165715 scopus 로고
    • The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature
    • Omura T, Sato R (1964) The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature. J Biol Chem 239:2370-2378
    • (1964) J Biol Chem , vol.239 , pp. 2370-2378
    • Omura, T.1    Sato, R.2
  • 28
    • 21644447392 scopus 로고    scopus 로고
    • In vitro confirmation of selegiline N-oxidation by flavin-containing monooxygenase in rat microsome using LC-ESI MS
    • DOI 10.1248/bpb.27.1572
    • Tsutsumi H, Katagi M, Nishikawa M, Tsuchihashi H, Kasuya F, Igarashi K (2004) In vitro confirmation of selegiline N-oxidation by flavin-containing monooxygenase in rat microsome using LC-ESI MS. Biol Pharm Bull 27(10):1572-1575 (Pubitemid 41701641)
    • (2004) Biological and Pharmaceutical Bulletin , vol.27 , Issue.10 , pp. 1572-1575
    • Tsutsumi, H.1    Katagi, M.2    Nishikawa, M.3    Tsuchihashi, H.4    Kasuya, F.5    Igarashi, K.6
  • 29
    • 33745107170 scopus 로고    scopus 로고
    • Strategies to improve plasma half life time of peptide and protein drugs
    • DOI 10.1007/s00726-005-0289-3
    • Werle M, Bernkop-Schnurch A (2006) Strategies to improve plasma half life time of peptide and protein drugs. Amino Acids 30(4):351-367 (Pubitemid 43886897)
    • (2006) Amino Acids , vol.30 , Issue.4 , pp. 351-367
    • Werle, M.1    Bernkop-Schnurch, A.2
  • 32
    • 45249121177 scopus 로고    scopus 로고
    • Drugs behave as substrates, inhibitors and inducers of human cytochrome P450 3A4
    • Zhou SF (2008) Drugs behave as substrates, inhibitors and inducers of human cytochrome P450 3A4. Curr Drug Metab 9(4):310-322
    • (2008) Curr Drug Metab , vol.9 , Issue.4 , pp. 310-322
    • Zhou, S.F.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.