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Volumn 23, Issue 4-5, 2004, Pages 337-345

N 4-alkyloxycarbonyl derivatives of cytosine: Physicochemical characterisation, and cytosine regeneration rates and release from alginic acid gels

Author keywords

Cytosine; Helicobacter pylori; Hydrolysis; Lipophilicity; N alkyloxycarbonyl derivatives; Prodrug; Release; Solubility; Ulcus

Indexed keywords

ALGINIC ACID; CYTOSINE DERIVATIVE; N 4 ADAMANTYLOXYCARBONYLCYTOSINE; N 4 BENZYLOXYCARBONYLCYTOSINE; N 4 BUTYLOXYCARBONYLCYTOSINE; N 4 ETHYLOXYCARBONYLCYTOSINE; N 4 HEXYLOXYCARBONYLCYTOSINE; N 4 ISOBUTYLOXYCARBONYLCYTOSINE; N 4 METHYLCARBONYLCYTOSINE; N 4 NEOPENTYLOXYCARBONYLCYTOSINE; N 4 OCTYLOXYCARBONYLCYTOSINE; PEPSIN A; UNCLASSIFIED DRUG; URACIL; CYTOSINE; DRUG DERIVATIVE; GLUCURONIC ACID; HEXURONIC ACID;

EID: 9644270221     PISSN: 09280987     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejps.2004.08.007     Document Type: Article
Times cited : (3)

References (34)
  • 1
    • 85012738381 scopus 로고
    • The estimation of pepsin, trypsin, papain, and cathepsin with hemoglobin
    • M.L. Anson The estimation of pepsin, trypsin, papain, and cathepsin with hemoglobin J. Gen. Physiol. 22 1938 79 89
    • (1938) J. Gen. Physiol. , vol.22 , pp. 79-89
    • Anson, M.L.1
  • 2
    • 0035962381 scopus 로고    scopus 로고
    • Improvement in the mucoadhesive properties of alginate by the covalent attachment of cysteine
    • A. Bernkop-Schnurch, C.E. Kast, and M.F. Richter Improvement in the mucoadhesive properties of alginate by the covalent attachment of cysteine J. Control. Release 71 2001 277 285
    • (2001) J. Control. Release , vol.71 , pp. 277-285
    • Bernkop-Schnurch, A.1    Kast, C.E.2    Richter, M.F.3
  • 3
    • 0025857380 scopus 로고
    • Prodrugs of cimetidine with increased lipophilicity: N-acyloxymethyl and N-alkoxycarbonyl derivatives
    • A. Buur, and H. Bundgaard Prodrugs of cimetidine with increased lipophilicity: N-acyloxymethyl and N-alkoxycarbonyl derivatives Acta Pharm. Nord. 3 1991 51 56
    • (1991) Acta Pharm. Nord. , vol.3 , pp. 51-56
    • Buur, A.1    Bundgaard, H.2
  • 6
    • 0015374607 scopus 로고
    • Solvolyses of cytosine and cytidine
    • E.R. Garrett, and J. Tsau Solvolyses of cytosine and cytidine J. Pharm. Sci. 61 1972 1052 1061
    • (1972) J. Pharm. Sci. , vol.61 , pp. 1052-1061
    • Garrett, E.R.1    Tsau, J.2
  • 7
    • 0001597080 scopus 로고
    • Synthesis and properties of some 6-substituted purines
    • A. Giner-Sorolla, and A. Bendich Synthesis and properties of some 6-substituted purines J. Amer. Chem. Soc. 80 1958 3932 3937
    • (1958) J. Amer. Chem. Soc. , vol.80 , pp. 3932-3937
    • Giner-Sorolla, A.1    Bendich, A.2
  • 8
    • 0032478330 scopus 로고    scopus 로고
    • Inhibition of translation and bacterial growth by peptide nucleic acid targeted to ribosomal RNA
    • L. Good, and P.E. Nielsen Inhibition of translation and bacterial growth by peptide nucleic acid targeted to ribosomal RNA Proc. Natl. Acad. Sci. USA 95 1998 2073 2076
    • (1998) Proc. Natl. Acad. Sci. USA , vol.95 , pp. 2073-2076
    • Good, L.1    Nielsen, P.E.2
  • 10
    • 0029911619 scopus 로고    scopus 로고
    • Relationship between Helicobacter pylori eradication and reduced dudenal and gastric ulcer recurrence: A review
    • R.J. Hopkins, L.S. Girardi, and E.A. Turney Relationship between Helicobacter pylori eradication and reduced dudenal and gastric ulcer recurrence: a review Gastroenterology 110 1996 1244 1252
    • (1996) Gastroenterology , vol.110 , pp. 1244-1252
    • Hopkins, R.J.1    Girardi, L.S.2    Turney, E.A.3
  • 11
    • 0026387906 scopus 로고
    • Current progress on nucleoside antibiotics
    • K. Isono Current progress on nucleoside antibiotics Pharmacol. Ther. 52 1991 269 286
    • (1991) Pharmacol. Ther. , vol.52 , pp. 269-286
    • Isono, K.1
  • 12
    • 0025756596 scopus 로고
    • N-Acyl derivatives as prodrug forms for amides: Chemical stability and enzymatic hydrolysis of various N-acyl and N-alkoxycarbonyl amide derivatives
    • A.H. Kahns, and H. Bundgaard N-Acyl derivatives as prodrug forms for amides: chemical stability and enzymatic hydrolysis of various N-acyl and N-alkoxycarbonyl amide derivatives Int. J. Pharm. 71 1991 31 43
    • (1991) Int. J. Pharm. , vol.71 , pp. 31-43
    • Kahns, A.H.1    Bundgaard, H.2
  • 14
    • 0028182206 scopus 로고
    • 4-(dialkylamino)methylene derivatives of 2′- deoxycytidine and arabinocytidine: Physicochemical studies for potential prodrug applications
    • 4-(dialkylamino)methylene derivatives of 2′-deoxycytidine and arabinocytidine: physicochemical studies for potential prodrug applications J. Pharm. Sci. 83 1994 582 586
    • (1994) J. Pharm. Sci. , vol.83 , pp. 582-586
    • Kerr, S.G.1    Kalman, T.I.2
  • 16
    • 0023607319 scopus 로고
    • N-Mannich-base prodrugs of 5-iodo-2′-deoxycytidine as topical delivery enhancers
    • S.A. Koch, and K.B. Sloan N-Mannich-base prodrugs of 5-iodo-2′- deoxycytidine as topical delivery enhancers Pharm. Res. 4 1987 317 320
    • (1987) Pharm. Res. , vol.4 , pp. 317-320
    • Koch, S.A.1    Sloan, K.B.2
  • 17
    • 0006089244 scopus 로고
    • Kinetics and mechanisms of hydrolytic reactions of methylated cytidines under acidic and neutral conditions
    • J. Kusmierek, R. Käppi, K. Neuvonen, D. Shugar, and H. Lönnberg Kinetics and mechanisms of hydrolytic reactions of methylated cytidines under acidic and neutral conditions Acta Chem. Scand. 43 1989 196 202
    • (1989) Acta Chem. Scand. , vol.43 , pp. 196-202
    • Kusmierek, J.1    Käppi, R.2    Neuvonen, K.3    Shugar, D.4    Lönnberg, H.5
  • 18
    • 0033867779 scopus 로고    scopus 로고
    • Assessment of rate of drug release from oil vehicle using a rotating dialysis cell
    • D.H. Larsen, K. Fredholt, and C. Larsen Assessment of rate of drug release from oil vehicle using a rotating dialysis cell Eur. J. Pharm. Sci. 11 2000 223 229
    • (2000) Eur. J. Pharm. Sci. , vol.11 , pp. 223-229
    • Larsen, D.H.1    Fredholt, K.2    Larsen, C.3
  • 19
    • 0003887404 scopus 로고
    • Influence of solvent, nucleophile, leaving group, and substrate structure
    • Harper & Row New York
    • T.H. Lowry, and K.S. Richardson Influence of solvent, nucleophile, leaving group, and substrate structure Mechanism and Theory in Organic Chemistry 1987 Harper & Row New York
    • (1987) Mechanism and Theory in Organic Chemistry
    • Lowry, T.H.1    Richardson, K.S.2
  • 21
    • 0027242340 scopus 로고
    • Fluorinated probes to measure carboxylesterase activities using 19F NMR spectroscopy: Application to erythrocytes and Helicobacter pylori
    • G.L. Mendz, T.N. Lim, and S.L. Hazell Fluorinated probes to measure carboxylesterase activities using 19F NMR spectroscopy: application to erythrocytes and Helicobacter pylori Arch. Biochem. Biophys. 305 1993 252 260
    • (1993) Arch. Biochem. Biophys. , vol.305 , pp. 252-260
    • Mendz, G.L.1    Lim, T.N.2    Hazell, S.L.3
  • 22
    • 0025325008 scopus 로고
    • Comparative studies on the antitumor and immunosuppressive effects of the new fluorouracil derivative N(4)-trimethoxybenzoyl-5′-deoxy-5- fluorocytidine and its parent drug 5′-deoxy-5-fluorouridine
    • M. Miwa, T. Ishikawa, H. Eda, M. Ryu, K. Fujimoto, Y. Ninomiya, I. Umeda, K. Yokose, and H. Ishitsuka Comparative studies on the antitumor and immunosuppressive effects of the new fluorouracil derivative N(4)-trimethoxybenzoyl-5′-deoxy-5-fluorocytidine and its parent drug 5′-deoxy-5-fluorouridine Chem. Pharm. Bull. 38 1990 998 1003
    • (1990) Chem. Pharm. Bull. , vol.38 , pp. 998-1003
    • Miwa, M.1    Ishikawa, T.2    Eda, H.3    Ryu, M.4    Fujimoto, K.5    Ninomiya, Y.6    Umeda, I.7    Yokose, K.8    Ishitsuka, H.9
  • 23
    • 0032127244 scopus 로고    scopus 로고
    • Design of a novel oral fluoropyrimidine carbamate, capecitabine, which generates 5-fluorouracil selectively in tumours by enzymes concentrated in human liver and cancer tissue
    • M. Miwa, M. Ura, M. Nishida, N. Sawada, T. Ishikawa, K. Mori, N. Shimma, I. Umeda, and H. Ishitsuka Design of a novel oral fluoropyrimidine carbamate, capecitabine, which generates 5-fluorouracil selectively in tumours by enzymes concentrated in human liver and cancer tissue Eur. J. Cancer. 34 1998 1274 1281
    • (1998) Eur. J. Cancer. , vol.34 , pp. 1274-1281
    • Miwa, M.1    Ura, M.2    Nishida, M.3    Sawada, N.4    Ishikawa, T.5    Mori, K.6    Shimma, N.7    Umeda, I.8    Ishitsuka, H.9
  • 24
    • 0021797832 scopus 로고
    • Enhanced delivery of mitomycin C prodrugs through the skin
    • E. Mukai, K. Arase, M. Hashida, and H. Sezaki Enhanced delivery of mitomycin C prodrugs through the skin Int. J. Pharm. 25 1985 95 103
    • (1985) Int. J. Pharm. , vol.25 , pp. 95-103
    • Mukai, E.1    Arase, K.2    Hashida, M.3    Sezaki, H.4
  • 25
    • 0014454162 scopus 로고
    • Acylation of cytosine by ethyl N-hydroxycarbamate and its acyl derivatives and the binding of these agents to nucleic acids and proteins
    • Nery, R., 1969. Acylation of cytosine by ethyl N-hydroxycarbamate and its acyl derivatives and the binding of these agents to nucleic acids and proteins. J. Chem. Soc. (C), pp. 1860-1865.
    • (1969) J. Chem. Soc. , Issue.C , pp. 1860-1865
    • Nery, R.1
  • 26
    • 0028084811 scopus 로고
    • N-alkoxycarbonyl prodrugs of mebendazole with increased water solubility
    • L.S. Nielsen, F. Slok, and H. Bundgaard N-alkoxycarbonyl prodrugs of mebendazole with increased water solubility Int. J. Pharm. 102 1994 231 239
    • (1994) Int. J. Pharm. , vol.102 , pp. 231-239
    • Nielsen, L.S.1    Slok, F.2    Bundgaard, H.3
  • 27
    • 0142026037 scopus 로고    scopus 로고
    • Treatment of Helicobacter pylori infection
    • F. Perri, A. Qasim, L. Marras, and C. O'Morain Treatment of Helicobacter pylori infection Helicobacter 8 Suppl. 1 2003 53 60
    • (2003) Helicobacter , vol.8 , Issue.1 , pp. 53-60
    • Perri, F.1    Qasim, A.2    Marras, L.3    O'Morain, C.4
  • 28
  • 30
    • 0001515698 scopus 로고
    • Spectrophotometric studies op nucleic acid derivatives and related compounds as a function of pH
    • D. Shugar, and J.J. Fox Spectrophotometric studies op nucleic acid derivatives and related compounds as a function of pH Biochimica et Biophysica Acta 9 1952 199 218
    • (1952) Biochimica et Biophysica Acta , vol.9 , pp. 199-218
    • Shugar, D.1    Fox, J.J.2
  • 32
    • 0015928956 scopus 로고
    • Reaction of diethyl pyrocarbonate with nucleic acid compounds: Bases and nucleosides derived from guanine, cytosine, and uracil
    • A. Vincze, R.E.L. Henderson, J.J. McDonald, and N.J. Leonard Reaction of diethyl pyrocarbonate with nucleic acid compounds: bases and nucleosides derived from guanine, cytosine, and uracil J. Amer. Chem. Soc. 95 1973 2677 2682
    • (1973) J. Amer. Chem. Soc. , vol.95 , pp. 2677-2682
    • Vincze, A.1    Henderson, R.E.L.2    McDonald, J.J.3    Leonard, N.J.4
  • 33


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.