INHIBITION OF CYTIDINE DEAMINASE BY DERIVATIVES OF 1-(BETA-D-RIBOFURANOSYL)-DIHYDROPYRIMIDIN-2-ONE (ZEBULARINE)

被引：16

作者：

BARCHI, JJ ^{[1
]}

HACES, A ^{[1
]}

MARQUEZ, VE ^{[1
]}

MCCORMACK, JJ ^{[1
]}

机构：

[1] UNIV VERMONT,BURLINGTON,VT 05405

来源：

NUCLEOSIDES & NUCLEOTIDES | 1992年 / 11卷 / 10期

关键词：

D O I：

10.1080/07328319208017823

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The 2'-deoxy and ara derivatives of 1-beta-(D-ribofuranosyl)-1,2-dihydropyrimidin-2-one (zebularine) were synthesized by improved routes and tested for their inhibitory properties against cytidine deaminase. It was shown that the K(i)'s of both compounds were comparable to that of the parent zebularine in inhibition studies with purified enzyme. In contrast to zebularine, 2'-deoxy and ara zebularine showed only nominal cytotoxicity against MOLT-4 and L1210 cells in vitro. A model compound for the inhibition of deoxycytidylate deaminase, 2'-deoxyzebularine 5'-monophosphate (6), was also prepared.

引用

页码：1781 / 1793

页数：13

共 23 条

[1] ANTI-RETROVIRUS ACTIVITY OF 3'-FLUORO-SUBSTITUTED AND 3'-AZIDO-SUBSTITUTED PYRIMIDINE 2',3'-DIDEOXYNUCLEOSIDE ANALOGS
BALZARINI, J
BABA, M
PAUWELS, R
HERDEWIJN, P
DECLERCO, E
[J]. BIOCHEMICAL PHARMACOLOGY, 1988, 37 (14) : 2847 - 2856
[2] THE DECOMPOSITION OF 1-(BETA-D-RIBOFURANOSYL)-1,2-DIHYDROPYRIMIDIN-2-ONE (ZEBULARINE) IN ALKALI - MECHANISM AND PRODUCTS
BARCHI, JJ
MUSSER, S
MARQUEZ, VE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (02) : 536 - 541
[3] TRIS(TRIMETHYLSILYL)SILANE - A NEW REDUCING AGENT
CHATGILIALOGLU, C
GRILLER, D
LESAGE, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (15) : 3641 - 3642
[4] ANTITUMOR PROPERTIES OF 2(1H)-PYRIMIDINONE RIBOSIDE (ZEBULARINE) AND ITS FLUORINATED ANALOGS
DRISCOLL, JS
MARQUEZ, VE
PLOWMAN, J
LIU, PS
KELLEY, JA
BARCHI, JJ
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (11) : 3280 - 3284
[5] FRICK L, 1989, BIOCHEMISTRY-US, V28, P943
[6] SYNTHESIS OF NUCLEOSIDES FLUORINATED IN THE SUGAR MOIETY - THE APPLICATION OF DIETHYLAMINOSULFUR TRIFLUORIDE TO THE SYNTHESIS OF FLUORINATED NUCLEOSIDES
HERDEWIJN, P
VANAERSCHOT, A
KERREMANS, L
[J]. NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 1989, 8 (01) : 65 - 96
[7] HO DHW, 1973, CANCER RES, V33, P2816
[8] SILYLATION-MEDIATED OXIDATION OF DIHYDROPYRIMIDINE BASES AND NUCLEOSIDES
KELLEY, JA
ABBASI, MM
BEISLER, JA
[J]. ANALYTICAL BIOCHEMISTRY, 1980, 103 (02) : 203 - 213
[9] SYNTHESIS OF PYRIMIDIN-2-ONE NUCLEOSIDES AS ACID-STABLE INHIBITORS OF CYTIDINE DEAMINASE
KIM, CH
MARQUEZ, VE
MAO, DT
HAINES, DR
MCCORMACK, JJ
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (08) : 1374 - 1380
[10] STRUCTURAL REQUIREMENTS FOR ENZYMATIC DEAMINATION OF CYTOSINE NUCLEOSIDES
KREIS, W
WATANABE, KA
FOX, JJ
[J]. HELVETICA CHIMICA ACTA, 1978, 61 (03) : 1011 - 1016

← 1 2 3 →