Xylylated dimers of putrescine and polyamines: influence of the polyamine backbone on spermidine transport inhibition

被引:11
作者
Covassin, L
Desjardins, M
Soulet, D
Charest-Gaudreault, R
Audette, M
Poulin, R [1 ]
机构
[1] Univ Laval, Fac Med, Dept Physiol, St Foy, PQ G1K 7P4, Canada
[2] Univ Laval, Fac Med, Fac Pharm, St Foy, PQ G1K 7P4, Canada
[3] Univ Laval, Fac Med, Dept Pharmacol, St Foy, PQ G1K 7P4, Canada
[4] Univ Laval, Fac Med, Dept Med Biol, St Foy, PQ G1K 7P4, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
D O I
10.1016/S0960-894X(03)00668-1
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Dimeric norspermidine and spermidine derivatives are strong competitive inhibitors of polyamine transport. A xylyl tether was used for the dimerization of various triamines and spermine via a secondary amino group, and of putrescine via an ether or an amino group. Dimerization of putrescine moieties potentiates their ability to compete against spermidine transport to a much greater extent than for triamine dimers. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3267 / 3271
页数:5
相关论文
共 35 条
[1]   INCREASED SURVIVAL OF L1210 LEUKEMIC MICE BY PREVENTION OF THE UTILIZATION OF EXTRACELLULAR POLYAMINES - STUDIES USING A POLYAMINE-UPTAKE MUTANT, ANTIBIOTICS AND A POLYAMINE-DEFICIENT DIET [J].
ASK, A ;
PERSSON, L ;
HEBY, O .
CANCER LETTERS, 1992, 66 (01) :29-34
[2]  
AZIZ SM, 1995, J PHARMACOL EXP THER, V274, P181
[3]   Proteoglycan involvement in polyamine uptake [J].
Belting, M ;
Persson, S ;
Fransson, LÅ .
BIOCHEMICAL JOURNAL, 1999, 338 :317-323
[4]   Tumor attenuation by combined heparan sulfate and polyamine depletion [J].
Belting, M ;
Borsig, L ;
Fuster, MM ;
Brown, JR ;
Persson, L ;
Fransson, LÅ ;
Esko, JD .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2002, 99 (01) :371-376
[5]   HEXAHYDROPYRIMIDINES AS MASKED SPERMIDINE VECTORS IN DRUG DELIVERY [J].
BERGERON, RJ ;
SELIGSOHN, HW .
BIOORGANIC CHEMISTRY, 1986, 14 (04) :345-355
[6]  
BERGERON RJ, 1981, SYNTHESIS-STUTTGART, P732
[7]   A comparison of structure-activity relationships between spermidine and spermine analogue antineoplastics [J].
Bergeron, RJ ;
Feng, Y ;
Weimar, WR ;
McManis, JS ;
Dimova, H ;
Porter, C ;
Raisler, B ;
Phanstiel, O .
JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (10) :1475-1494
[8]   Amino acid/spermine conjugates: Polyamine amides as potent spermidine uptake inhibitors [J].
Burns, MR ;
Carlson, CL ;
Vanderwerf, SM ;
Ziemer, JR ;
Weeks, RS ;
Cai, F ;
Webb, HK ;
Graminski, GF .
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (22) :3632-3644
[9]   PROPERTIES AND PHYSIOLOGICAL-FUNCTION OF THE POLYAMINE TRANSPORT-SYSTEM [J].
BYERS, TL ;
PEGG, AE .
AMERICAN JOURNAL OF PHYSIOLOGY, 1989, 257 (03) :C545-C553
[10]  
Cohen S.S., 1998, GUIDE POLYAMINES