메뉴 건너뛰기




Volumn 10, Issue 2, 2013, Pages 532-537

Design, synthesis, and evaluation of novel cyclic phosphates of 5-aminosalicylic acid as cytochrome P450-activated prodrugs

Author keywords

5 aminosalicylic acid; bioactivation bioconversion; cyclic phosphate; cytochrome P450 enzyme; prodrug

Indexed keywords

5 AMINO 2 ((2 OXIDO 4 PHENYL 1,3,2 DIOXAPHOSPHINAN 2 YL)OXY)BENZOIC ACID; 5 AMINO 2 ((4 (2 CHLOROPHENYL) 2 OXIDO 1,3,2 DIOXAPHOSPHINAN 2 YL)OXY)BENZOIC ACID; 5 AMINO 2 ((4 (3 CHLOROPHENYL) 2 OXIDO 1,3,2 DIOXAPHOSPHINAN 2 YL)OXY)BENZOIC ACID; 5 AMINO 2 ((4 (4 CHLOROPHENYL) 2 OXIDO 1,3,2 DIOXAPHOSPHINAN 2 YL)OXY)BENZOIC ACID; AMINOSALICYLIC ACID; CYTOCHROME P450; PRODRUG; UNCLASSIFIED DRUG;

EID: 84873326782     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp300330v     Document Type: Article
Times cited : (11)

References (28)
  • 1
    • 84859913096 scopus 로고    scopus 로고
    • The pharmacological profile and clinical use of mesalazine (5-aminosalicylic acid)
    • Klotz, U. The pharmacological profile and clinical use of mesalazine (5-aminosalicylic acid) Arzneim. Forsch. 2012, 62 (2) 53-8
    • (2012) Arzneim. Forsch. , vol.62 , Issue.2 , pp. 53-58
    • Klotz, U.1
  • 2
    • 0015374469 scopus 로고
    • Absorption, metabolism, and excretion of salicylazosulfapyridine in man
    • Schroder, H.; Campbell, D. E. Absorption, metabolism, and excretion of salicylazosulfapyridine in man Clin. Pharmacol. Ther. 1972, 13 (4) 539-51
    • (1972) Clin. Pharmacol. Ther. , vol.13 , Issue.4 , pp. 539-551
    • Schroder, H.1    Campbell, D.E.2
  • 4
    • 0035155157 scopus 로고    scopus 로고
    • Colon-specific prodrugs of 5-aminosalicylic acid: Synthesis and in vitro/in vivo properties of acidic amino acid derivatives of 5-aminosalicylic acid
    • DOI 10.1002/jps.1126
    • Jung, Y. J.; Lee, J. S.; Kim, Y. M. Colon-specific prodrugs of 5-aminosalicylic acid: synthesis and in vitro / in vivo properties of acidic amino acid derivatives of 5-aminosalicylic acid J. Pharm. Sci. 2001, 90 (11) 1767-75 (Pubitemid 33062597)
    • (2001) Journal of Pharmaceutical Sciences , vol.90 , Issue.11 , pp. 1767-1775
    • Jung, Y.J.1    Lee Soo, J.2    Kim, Y.M.3
  • 5
    • 0032996689 scopus 로고    scopus 로고
    • Release of 5-amino salicylic acid from acrylic type polymeric prodrugs designed for colon-specific drug delivery
    • DOI 10.1016/S0168-3659(98)00167-9, PII S0168365998001679
    • Davaran, S.; Hanaee, J.; Khosravi, A. Release of 5-amino salicylic acid from acrylic type polymeric prodrugs designed for colon-specific drug delivery J. Controlled Release 1999, 58 (3) 279-87 (Pubitemid 29142452)
    • (1999) Journal of Controlled Release , vol.58 , Issue.3 , pp. 279-287
    • Davaran, S.1    Hanaee, J.2    Khosravi, A.3
  • 6
    • 0037436032 scopus 로고    scopus 로고
    • Dendrimers conjugates for colonic delivery of 5-aminosalicylic acid
    • DOI 10.1016/S0168-3659(02)00461-3
    • Wiwattanapatapee, R.; Lomlim, L.; Saramunee, K. Dendrimers conjugates for colonic delivery of 5-aminosalicylic acid J. Controlled Release 2003, 88 (1) 1-9 (Pubitemid 36173949)
    • (2003) Journal of Controlled Release , vol.88 , Issue.1 , pp. 1-9
    • Wiwattanapatapee, R.1    Lomlim, L.2    Saramunee, K.3
  • 7
    • 33750014292 scopus 로고    scopus 로고
    • Dextran and 5-aminosalicylic acid (5-ASA) conjugates: synthesis, characterisation and enzymic hydrolysis
    • DOI 10.1016/j.carres.2006.08.015, PII S0008621506003958
    • Ahmad, S.; Tester, R. F.; Corbett, A.; Karkalas, J. Dextran and 5-aminosalicylic acid (5-ASA) conjugates: synthesis, characterization and enzymic hydrolysis Carbohydr. Res. 2006, 341 (16) 2694-2701 (Pubitemid 44572199)
    • (2006) Carbohydrate Research , vol.341 , Issue.16 , pp. 2694-2701
    • Ahmad, S.1    Tester, R.F.2    Corbett, A.3    Karkalas, J.4
  • 8
    • 9644302324 scopus 로고    scopus 로고
    • Synthesis and properties of polysaccharide prodrugs of 5-aminosalicylic acid as potential colon-specific delivery systems
    • DOI 10.1016/j.ejpb.2004.06.004, PII S0939641104001717
    • Zou, M.; Okamoto, H.; Cheng, G.; Hao, X.; Sun, J.; Cui, F.; Danjo, K. Synthesis and properties of polysaccharide prodrugs of 5-aminosalicylic acid as potential colon-specific delivery systems Eur. J. Pharm. Biopharm. 2005, 59 (1) 155-60 (Pubitemid 39573448)
    • (2005) European Journal of Pharmaceutics and Biopharmaceutics , vol.59 , Issue.1 , pp. 155-160
    • Zou, M.1    Okamoto, H.2    Cheng, G.3    Hao, X.4    Sun, J.5    Cui, F.6    Danjo, K.7
  • 9
    • 23844468191 scopus 로고    scopus 로고
    • Liposomal formulations of inflammatory bowel disease drugs: Local versus systemic drug delivery in a rat model
    • DOI 10.1007/s11095-005-5376-3
    • Kesisoglou, F.; Zhou Simon, Y.; Niemiec, S.; Lee Jordan, W.; Zimmermann Ellen, M.; Fleisher, D. Liposomal formulations of inflammatory bowel disease drugs: local versus systemic drug delivery in a rat model Pharm. Res. 2005, 22 (8) 1320-30 (Pubitemid 41176036)
    • (2005) Pharmaceutical Research , vol.22 , Issue.8 , pp. 1320-1330
    • Kesisoglou, F.1    Zhou, S.Y.2    Niemiec, S.3    Lee, J.W.4    Zimmermann, E.M.5    Fleisher, D.6
  • 11
    • 79651473955 scopus 로고    scopus 로고
    • Design, synthesis, and sustained-release property of 1,3-cyclic propanyl phosphate ester of 18(beta)-glycyrrhetinic acid
    • Sun, W.; Peng, W.; Li, G.; Jiang, T. Design, synthesis, and sustained-release property of 1,3-cyclic propanyl phosphate ester of 18(beta)-glycyrrhetinic acid Chem. Biol. Drug Des. 2011, 77 (3) 206-211
    • (2011) Chem. Biol. Drug Des. , vol.77 , Issue.3 , pp. 206-211
    • Sun, W.1    Peng, W.2    Li, G.3    Jiang, T.4
  • 12
    • 43049135625 scopus 로고    scopus 로고
    • Prodrugs for Liver-targeted Drug Delivery
    • 1 st ed. Stella, V. J. Borchardt, R. T. Hageman, M. J. Oliyai, R. Maag, H. Tilley, J. W. Springer Science + Business Media: New York
    • Erion, M. D. Prodrugs for Liver-targeted Drug Delivery. In Prodrugs: Challenges and Rewards, Part 1, 1 st ed.; Stella, V. J.; Borchardt, R. T.; Hageman, M. J.; Oliyai, R.; Maag, H.; Tilley, J. W., Eds.; Springer Science + Business Media: New York, 2007; pp 541-72.
    • (2007) Prodrugs: Challenges and Rewards, Part 1 , pp. 541-572
    • Erion, M.D.1
  • 13
    • 0035254244 scopus 로고    scopus 로고
    • Design, synthesis, and biological evaluation of a series of lavendustin A analogues that inhibit EGFR and Syk tyrosine kinases, as well as tubulin polymerization
    • DOI 10.1021/jm000387g
    • Mu, F.; Coffing, S. L.; Riese, D. J., 2nd; Geahlen, R. L.; Verdier-Pinard, P.; Hamel, T. E.; Johnson, J.; Cushman, M. Design, synthesis, and biological evaluation of a series of lavendustin A analogues that inhibit EGFR and Syk tyrosine kinases, as well as tubulin polymerization J. Med. Chem. 2001, 44 (3) 441-52 (Pubitemid 32113589)
    • (2001) Journal of Medicinal Chemistry , vol.44 , Issue.3 , pp. 441-452
    • Mu, F.1    Coffing, S.L.2    Riese II, D.J.3    Geahlen, R.L.4    Verdier-Pinard, P.5    Hamel, E.6    Johnson, J.7    Cushman, M.8
  • 15
    • 33845953970 scopus 로고    scopus 로고
    • Synthesis and characterization of a novel liver-targeted prodrug of cytosine-1-β-D-arabinofuranoside monophosphate for the treatment of hepatocellular carcinoma
    • DOI 10.1021/jm0607449
    • Boyer, S. H.; Sun, Z.; Jiang, H.; Esterbrook, J.; Gomez-Galeno, J. E.; Craigo, W.; Reddy, K. R.; Ugarkar, B. G.; MacKenna, D. A.; Erion, M. D. Synthesis and characterization of a novel liver-targeted prodrug of cytosine-1-beta-D-arabinofuranoside monophosphate for the treatment of hepatocellular carcinoma J. Med. Chem. 2006, 49 (26) 7711-20 (Pubitemid 46033662)
    • (2006) Journal of Medicinal Chemistry , vol.49 , Issue.26 , pp. 7711-7720
    • Boyer, S.H.1    Sun, Z.2    Jiang, H.3    Esterbrook, J.4    Gomez-Galeno, J.E.5    Craigo, W.6    Reddy, K.R.7    Ugarkar, B.G.8    MacKenna, D.A.9    Erion, M.D.10
  • 17
    • 32844455838 scopus 로고    scopus 로고
    • Phosphoramidate and phosphate prodrugs of (-)-β-D-(2R,4R)-dioxolane- thymine: Synthesis, anti-HIV activity and stability studies
    • DOI 10.1016/j.bmc.2005.11.008, PII S0968089605010692
    • Liang, Y.; Narayanasamy, J.; Schinazi, R. F.; Chu, C. K. Phosphoramidate and phosphate prodrugs of (-)-beta-D-(2R,4R)-dioxolane-thymine: synthesis, anti-HIV activity and stability studies Bioorg. Med. Chem. 2006, 14 (7) 2178-89 (Pubitemid 43254732)
    • (2006) Bioorganic and Medicinal Chemistry , vol.14 , Issue.7 , pp. 2178-2189
    • Liang, Y.1    Narayanasamy, J.2    Schinazi, R.F.3    Chu, C.K.4
  • 18
    • 77953579329 scopus 로고    scopus 로고
    • Reduction of aromatic and aliphatic keto esters using sodium borohydride/MeOH at room temperature: A thorough investigation
    • Kim, J.; De Castro, K. A.; Lim, M.; Rhee, H. Reduction of aromatic and aliphatic keto esters using sodium borohydride/MeOH at room temperature: a thorough investigation Tetrahedron 2010, 66 (23) 3995-4001
    • (2010) Tetrahedron , vol.66 , Issue.23 , pp. 3995-4001
    • Kim, J.1    De Castro, K.A.2    Lim, M.3    Rhee, H.4
  • 19
    • 0344938358 scopus 로고    scopus 로고
    • Inhibition and induction of human cytochrome P450 (CYP) enzymes
    • DOI 10.1080/004982598238886
    • Pelkonen, O.; Maenpaa, J.; Taavitsainen, P.; Rautio, A.; Raunio, H. Inhibition and induction of human cytochrome P450 (CYP) enzymes Xenobiotica 1998, 28 (12) 1203-1253 (Pubitemid 29017141)
    • (1998) Xenobiotica , vol.28 , Issue.12 , pp. 1203-1253
    • Pelkonen, O.1    Maenpaaj, J.2    Taavitsainen, P.3    Rautio, A.4    Raunio, H.5
  • 20
    • 27744539745 scopus 로고    scopus 로고
    • Distribution of cytochrome P450 2C, 2E1, 3A4, and 3A5 in human colon mucosa
    • Bergheim, I.; Bode, C.; Parlesak, A. Distribution of cytochrome P450 2C, 2E1, 3A4, and 3A5 in human colon mucosa BMC Clin. Pharmacol. 2005, 5, 4
    • (2005) BMC Clin. Pharmacol. , vol.5 , pp. 4
    • Bergheim, I.1    Bode, C.2    Parlesak, A.3
  • 23
    • 54149089672 scopus 로고    scopus 로고
    • Drug Metabolism
    • Brunton, L. L. Lazo, J. S. Parker, K. L. The McGraw-Hill Companies, Inc. New York
    • Gonzalez, F. J.; Tukey, R. H. Drug Metabolism. In Goodman and Gilman's The Pharmacological Basis of Therapeutics; Brunton, L. L.; Lazo, J. S.; Parker, K. L., Eds.; The McGraw-Hill Companies, Inc.: New York, 2006; pp 71-91.
    • (2006) Goodman and Gilman's the Pharmacological Basis of Therapeutics , pp. 71-91
    • Gonzalez, F.J.1    Tukey, R.H.2
  • 24
    • 33847092271 scopus 로고    scopus 로고
    • The biochemistry of drug metabolism - An introduction part 2. Redox reactions and their enzymes
    • DOI 10.1002/cbdv.200790032
    • Testa, B.; Kramer, S. D. The biochemistry of drug metabolism - an introduction: Part 2. Redox reactions and their enzymes Chem. Biodiversity 2007, 4 (3) 257-405 (Pubitemid 46937873)
    • (2007) Chemistry and Biodiversity , vol.4 , Issue.3 , pp. 257-405
    • Testa, B.1    Kramer, S.D.2
  • 25
    • 79959216005 scopus 로고    scopus 로고
    • Genetics and pathogenesis of inflammatory bowel disease
    • Khor, B.; Gardet, A.; Xavier, R. J. Genetics and pathogenesis of inflammatory bowel disease Nature 2011, 474 (7351) 307-17
    • (2011) Nature , vol.474 , Issue.7351 , pp. 307-317
    • Khor, B.1    Gardet, A.2    Xavier, R.J.3
  • 27
    • 49849099622 scopus 로고    scopus 로고
    • Development and validation of a HPLC-ESI-MS/MS method for the determination of 5-aminosalicylic acid and its major metabolite N-acetyl-5-aminosalicylic acid in human plasma
    • Pastorini, E.; Locatelli, M.; Simoni, P.; Roda, G.; Roda, E.; Roda, A. Development and validation of a HPLC-ESI-MS/MS method for the determination of 5-aminosalicylic acid and its major metabolite N-acetyl-5-aminosalicylic acid in human plasma J. Chromatogr., B: Anal. Technol. Biomed. Life Sci. 2008, 872 (1-2) 99-106
    • (2008) J. Chromatogr., B: Anal. Technol. Biomed. Life Sci. , vol.872 , Issue.12 , pp. 99-106
    • Pastorini, E.1    Locatelli, M.2    Simoni, P.3    Roda, G.4    Roda, E.5    Roda, A.6
  • 28
    • 0343844454 scopus 로고    scopus 로고
    • Prodrugs of phosphates, phosphonates, and phosphinates
    • DOI 10.1016/0169-409X(95)00111-J
    • Krise, J. P.; Stella, V. J. Prodrugs of phosphates, phosphonates, and phosphinates Adv. Drug Delivery Rev. 1996, 19 (2) 287-310 (Pubitemid 26192967)
    • (1996) Advanced Drug Delivery Reviews , vol.19 , Issue.2 , pp. 287-310
    • Krise, J.P.1    Stella, V.J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.