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Volumn 52, Issue 10, 2009, Pages 3205-3211

Design, synthesis, and pharmacological effects of a cyclization-activated steroid prodrug for colon targeting in inflammatory bowel disease

Author keywords

[No Author keywords available]

Indexed keywords

5 [2 {2 (2 (11,17 DIHYDROXY 10,13 DIMETHYL 3 OXO 6,7,8,9,10,11,12,13,14,15,16,17 DODECAHYDRO 3H CYCLOPENTA[R]PHENANTHREN 17 YL) 2 OXOETHOXYCARBONYL)ETHYL}PHENYLAZO] 2 HYDROXYBENZOIC ACID TERT BUTYL ESTER; 5 [2 {2 (2 (11,17 DIHYDROXY 10,13 DIMETHYL 3 OXO 6,7,8,9,10,11,12,13,14,15,16,17 DODECAHYDRO 3H CYCLOPENTA[R]PHENANTHREN 17 YL) 2 OXOETHOXYCARBONYL)METHYL}PHENYLAZO] 2 HYDROXYBENZOIC ACID; 5 [2 {2 (2 (11,17 DIHYDROXY 10,13 DIMETHYL 3 OXO 6,7,8,9,10,11,2,13,14,15,16,17 DODECAHYDRO 3H CYCLOPENTA[R]PHENANTHREN 17 YL) 2-OXOETHOXYCARBONYL)ETHYL}PHENYLAZO] 2 HYDROXYBENZOIC ACID; 5[2 {2 (2 (11,17 DIHYDROXY 10,13 DIMETHYL 3 OXO 6,7,8,9,10,11,12,13,14,15,16,17 DODECAHYDRO 3H CYCLOPENTA[R]PHENANTHREN 17 YL) 2 OXOETHOXYCARBONYL)METHYL}PHENYLAZO] 2 HYDROXYBENZOIC ACID TERT BUTYL ESTER; CORTICOSTEROID; CYCLODEXTRIN; ESTER; PREDNISOLONE; PRODRUG; STEROID; UNCLASSIFIED DRUG;

EID: 66249102258     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm8016317     Document Type: Article
Times cited : (31)

References (29)
  • 3
    • 0029559317 scopus 로고
    • Targeting of peptide and protein drugs to specific sites in the oral route
    • Bai, J. P.; Chsang, L. L.; Guo, J. H. Targeting of peptide and protein drugs to specific sites in the oral route. Crit. Rev. Ther. Drug Carrier Syst. 1995, 12, 339-371.
    • (1995) Crit. Rev. Ther. Drug Carrier Syst. , vol.12 , pp. 339-371
    • Bai, J.P.1    Chsang, L.L.2    Guo, J.H.3
  • 5
    • 0034956847 scopus 로고    scopus 로고
    • Colonic drug delivery: Prodrug approach
    • Sinha, V. R.; Kumria, R. Colonic drug delivery: prodrug approach. Pharm. Res. 2001, 18 (5), 557-564.
    • (2001) Pharm. Res. , vol.18 , Issue.5 , pp. 557-564
    • Sinha, V.R.1    Kumria, R.2
  • 6
    • 0033956273 scopus 로고    scopus 로고
    • Oral colon-specific drug delivery using amylose-based film coatings
    • Basit, A. W. Oral colon-specific drug delivery using amylose-based film coatings. Pharm. Technol. Eur. 2000, 12, 30-36.
    • (2000) Pharm. Technol. Eur. , vol.12 , pp. 30-36
    • Basit, A.W.1
  • 7
    • 0032484163 scopus 로고    scopus 로고
    • New preparation method of intestinal pressure-controlled colon delivery capsules by coating machine and evaluation in beagle dogs
    • DOI 10.1016/S0168-3659(98)00090-X, PII S016836599800090X
    • Hu, Z.; Kimura, G.; Mawatari, S.; Shimokawa, T.; Yoshikawa, Y.; Takada, K. New preparation method of intestinal pressure-controlled colon delivery capsules coating machine and evaluation in beagle dogs. J. Controlled Release 1998, 56, 293-302. (Pubitemid 28511149)
    • (1998) Journal of Controlled Release , vol.56 , Issue.1-3 , pp. 293-302
    • Hu, Z.1    Kimura, G.2    Mawatari, S.-S.3    Shimokawa, T.4    Yoshikawa, Y.5    Takada, K.6
  • 8
    • 0042526078 scopus 로고    scopus 로고
    • Prednisolone 21-sulfate sodium: A colon-specific pro-drug of prednisolone
    • Jung, Y. J.; Doh, M. J.; Kim, I. H.; Kong, H. S.; Lee, J. S.; Kim, Y. M. Prednisolone 21-sulfate sodium: a colon-specific pro-drug of prednisolone. J. Pharm. Pharmacol. 2003, 55, 1075-1082.
    • (2003) J. Pharm. Pharmacol. , vol.55 , pp. 1075-1082
    • Jung, Y.J.1    Doh, M.J.2    Kim, I.H.3    Kong, H.S.4    Lee, J.S.5    Kim, Y.M.6
  • 9
    • 0027449074 scopus 로고
    • In vitro evaluation of dexamethasone-beta-D-glucuronide for colon-specific drug delivery
    • Haeberlin, B.; Rubas, W.; Nolen, H. W.; Friend, D. R. In vitro evaluation of dexamethasone-beta-D-glucuronide for colon-specific drug delivery. Pharm. Res. 1993, 11, 1553-1562.
    • (1993) Pharm. Res. , vol.11 , pp. 1553-1562
    • Haeberlin, B.1    Rubas, W.2    Nolen, H.W.3    Friend, D.R.4
  • 10
    • 0029555330 scopus 로고
    • In vivo pharmacokinetic study for the assessment of poly(L-aspartic acid) as a drug carrier for colon-specific drug delivery
    • Leopold, C. S.; Friend, D. R. In vivo pharmacokinetic study for the assessment of poly(L-aspartic acid) as a drug carrier for colon-specific drug delivery. J. Pharmacokinet. Biopharm. 1995, 23, 397-406.
    • (1995) J. Pharmacokinet. Biopharm. , vol.23 , pp. 397-406
    • Leopold, C.S.1    Friend, D.R.2
  • 11
    • 0037133114 scopus 로고    scopus 로고
    • Colon-specific delivery of prednisolone-appended α-cyclodextrin conjugate: Alleviation of systemic side effect after oral administration
    • DOI 10.1016/S0168-3659(01)00532-6, PII S0168365901005326
    • Yano, H.; Hirayama, F.; Kamada, M.; Arima, H.; Uekama, K. Colon-specific delivery of prednisolone-appended alfa-cyclodextrin conjugate: alleviation of systemic side effect after oral administration. J. Controlled Release 2002, 79, 103-112. (Pubitemid 34164164)
    • (2002) Journal of Controlled Release , vol.79 , Issue.1-3 , pp. 103-112
    • Yano, H.1    Hirayama, F.2    Kamada, M.3    Arima, H.4    Uekama, K.5
  • 12
    • 0028096152 scopus 로고
    • A glucocorticoid prodrug facilitates normal mucosal function in rat colitis without adrenal suppression
    • McLeod, A. D.; Fedorak, R. N.; Friend, D. R.; Tozer, T. N.; Cui, N. A glucocorticoid prodrug facilitates normal mucosal function in rat colitis without adrenal suppression. Gastroenterology 1994, 106, 405-413. (Pubitemid 24041218)
    • (1994) Gastroenterology , vol.106 , Issue.2 , pp. 405-413
    • McLeod, A.D.1    Fedorak, R.N.2    Friend, D.R.3    Tozer, T.N.4    Cui, N.5
  • 14
    • 0035974705 scopus 로고    scopus 로고
    • Novel azo derivatives as prodrugs of 5-aminosalicylic acid and amino derivatives with potent platelet activating factor antagonist activity
    • Carceller, E.; Salas, J.; Merlos, M.; Giral, M.; Ferrando, R.; Escamilla, I.; Ramis, J.; García-Rafanell, J.; Forn, J. Novel azo derivatives as prodrugs of 5-aminosalicylic acid and amino derivatives with potent platelet activating factor antagonist activity. J. Med. Chem. 2001, 44, 3001-3013.
    • (2001) J. Med. Chem. , vol.44 , pp. 3001-3013
    • Carceller, E.1    Salas, J.2    Merlos, M.3    Giral, M.4    Ferrando, R.5    Escamilla, I.6    Ramis, J.7    García-Rafanell, J.8    Forn, J.9
  • 15
    • 0035839271 scopus 로고    scopus 로고
    • Biorecognizable HPMA copolymer-drug conjugates for colon-specific delivery of 9-aminocamptothecin
    • DOI 10.1016/S0168-3659(01)00405-9, PII S0168365901004059
    • Sakuma, S.; Lu, Z. R.; Kopecková, P.; Kopecek, J. Biorecognizable HPMA copolymer-drug conjugates for colon-specific delivery of 9-aminocamptothecin. J. Controlled Release 2001, 75, 365-379. (Pubitemid 32727266)
    • (2001) Journal of Controlled Release , vol.75 , Issue.3 , pp. 365-379
    • Sakuma, S.1    Lu, Z.-R.2    Kopeckova, P.3    Kopecek, J.4
  • 16
    • 0027988024 scopus 로고
    • The relation between swelling properties and enzymatic degradation of azo polymers designed for colon-specific drug delivery
    • Van den Mooter, G.; Samyn, C.; Kinget, R. The relation between swelling properties and enzymatic degradation of azo polymers designed for colon-specific drug delivery. Pharm. Res. 1994, 11, 1737-1741.
    • (1994) Pharm. Res. , vol.11 , pp. 1737-1741
    • Van Den Mooter, G.1    Samyn, C.2    Kinget, R.3
  • 17
    • 0022975260 scopus 로고
    • Oral absorption of 21-corticosteroid esters: A function of aqueous stability and intestinal enzyme activity and distribution
    • Fleisher, D.; Johnson, K. C.; Stewart, B. H.; Amidon, G. L. Oral absorption of 21-corticosteroid esters: a function of aqueous stability and intestinal enzyme activity and distribution. J. Pharm. Sci. 1986, 75, 934-939.
    • (1986) J. Pharm. Sci. , vol.75 , pp. 934-939
    • Fleisher, D.1    Johnson, K.C.2    Stewart, B.H.3    Amidon, G.L.4
  • 18
    • 33846597467 scopus 로고    scopus 로고
    • Design and synthesis of furoxan-based nitric oxide-releasing glucocorticoid derivatives with potent anti-inflammatory activity and improved safety
    • Fang, L.; Zhang, Y.; Lehmann, J.; Wang, Y.; Ji, H.; Ding, D. Design and synthesis of furoxan-based nitric oxide-releasing glucocorticoid derivatives with potent anti-inflammatory activity and improved safety. Bioorg. Med. Chem. Lett. 2007, 17, 1062-1066.
    • (2007) Bioorg. Med. Chem. Lett. , vol.17 , pp. 1062-1066
    • Fang, L.1    Zhang, Y.2    Lehmann, J.3    Wang, Y.4    Ji, H.5    Ding, D.6
  • 19
    • 37049112474 scopus 로고
    • Anilide formation from an aliphatic ester. the mechanism of cyclisation of methyl 3-(2-aminophenyl)propionate
    • Kirby, A. J.; Mujahid, T. G. Anilide formation from an aliphatic ester. The mechanism of cyclisation of methyl 3-(2-aminophenyl)propionate. J. Chem. Soc., Perkin Trans. 2 1979, 1610-1616.
    • (1979) J. Chem. Soc., Perkin Trans. 2 , pp. 1610-1616
    • Kirby, A.J.1    Mujahid, T.G.2
  • 20
    • 0002590924 scopus 로고
    • Intramolecular aminolysis of esters. Cyclization of esters of (o-aminophenyl)acetic acid
    • Fife, T. H.; Duddy, N. W. Intramolecular aminolysis of esters. Cyclization of esters of (o-aminophenyl)acetic acid. J. Am. Chem. Soc. 1983, 105, 74-79.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 74-79
    • Fife, T.H.1    Duddy, N.W.2
  • 21
    • 4644250429 scopus 로고    scopus 로고
    • Identification of budesonide and prednisone as substrates of the intestinal drug efflux pump p-glycoprotein
    • DOI 10.1097/00054725-200409000-00012
    • Dilger, K.; Schwab, M.; Fromm, M. Identification of budesodine and prednisone as substrates of the intestinal drug efflux pump Pglycoprotein. Inflammatory Bowel Dis. 2006, 10, 578-583. (Pubitemid 39276465)
    • (2004) Inflammatory Bowel Diseases , vol.10 , Issue.5 , pp. 578-583
    • Dilger, K.1    Schwab, M.2    Fromm, M.F.3
  • 23
    • 0025181580 scopus 로고
    • A novel method in the induction of reliable experimental acute and chronic ulcerative colitis in mice
    • Okayasu, I.; Hatakeyama, S.; Yamada, M.; Ohkusa, T.; Inagaki, Y.; Nakaya, R. A novel method in the induction of reliable experimental acute and chronic ulcerative colitis in mice. Gastroenterology 1990, 98, 694-702. (Pubitemid 20069706)
    • (1990) Gastroenterology , vol.98 , Issue.3 , pp. 694-702
    • Okayasu, I.1    Hatakeyama, S.2    Yamada, M.3    Ohkusa, T.4    Inagaki, Y.5    Nakaya, R.6
  • 27
    • 50249143507 scopus 로고    scopus 로고
    • Effects of Lactobacillus salivarius 433118 on intestinal inflammation, immunity status and in vitro colon function in two mouse models of inflammatory bowel disease
    • Feighery, L. M.; Smith, P.; O'Mahony, L.; Fallon, P. G.; Brayden, D. J. Effects of Lactobacillus salivarius 433118 on intestinal inflammation, immunity status and in vitro colon function in two mouse models of inflammatory bowel disease. Dig. Dis. Sci. 2008, 53, 2495-2506.
    • (2008) Dig. Dis. Sci. , vol.53 , pp. 2495-2506
    • Feighery, L.M.1    Smith, P.2    O'Mahony, L.3    Fallon, P.G.4    Brayden, D.J.5
  • 28
    • 0037133114 scopus 로고    scopus 로고
    • Colon-specific delivery of prednisolone-appended α-cyclodextrin conjugate: Alleviation of systemic side effect after oral administration
    • DOI 10.1016/S0168-3659(01)00532-6, PII S0168365901005326
    • Yano, H.; Hirayama, F.; Kamada, M.; Arima, H.; Uekama, K. Colon-specific delivery of prednisolone-appended alpha-cyclodextrin conjugate: alleviation of systemic side effect after oral administration. J. Controlled Release 2002, 79, 103-112. (Pubitemid 34164164)
    • (2002) Journal of Controlled Release , vol.79 , Issue.1-3 , pp. 103-112
    • Yano, H.1    Hirayama, F.2    Kamada, M.3    Arima, H.4    Uekama, K.5
  • 29
    • 36849072605 scopus 로고    scopus 로고
    • Cyclization-activated prodrugs
    • Gomes, P.; Vale, N.; Moreira, R. Cyclization-activated prodrugs. Molecules 2007, 12, 2484-2506.
    • (2007) Molecules , vol.12 , pp. 2484-2506
    • Gomes, P.1    Vale, N.2    Moreira, R.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.