Solid phase synthesis of polyamine conjugates for the study of trypanothione reductase

被引:35
作者
Marsh, IR [1 ]
Bradley, M [1 ]
机构
[1] UNIV SOUTHAMPTON,DEPT CHEM,SOUTHAMPTON SO17 1BJ,HANTS,ENGLAND
基金
英国工程与自然科学研究理事会;
关键词
D O I
10.1016/S0040-4020(97)10156-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A number of polyamine scaffolds were synthesised, enabling the facile preparation of a variety of polyamine conjugates using both Boc and Fmoc protecting group strategies. Products were released from the solid support by treatment with either triflic acid/trifluoroacetic acid or trifluoroacetic acid. The trypanosomal metabolite N-1, N-8-bis(glutathionyl)spermidine [trypanothione], and a range of related analogues were prepared for biological evaluation as previously communicated. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:17317 / 17334
页数:18
相关论文
共 26 条
[1]   PREPARATION AND APPLICATION OF THE 5-(4-(9-FLUORENYLMETHYLOXYCARBONYL)AMINOMETHYL-3,5-DIMETHOXYPHENOXY)VALERIC ACID (PAL) HANDLE FOR THE SOLID-PHASE SYNTHESIS OF C-TERMINAL PEPTIDE AMIDES UNDER MILD CONDITIONS [J].
ALBERICIO, F ;
KNEIBCORDONIER, N ;
BIANCALANA, S ;
GERA, L ;
MASADA, RI ;
HUDSON, D ;
BARANY, G .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (12) :3730-3743
[2]   PEPTIDE-SYNTHESIS .2. PROCEDURES FOR SOLID-PHASE SYNTHESIS USING N-ALPHA-FLUORENYLMETHOXYCARBONYLAMINO-ACIDS ON POLYAMIDE SUPPORTS - SYNTHESIS OF SUBSTANCE-P AND OF ACYL CARRIER PROTEIN 65-74 DECAPEPTIDE [J].
ATHERTON, E ;
LOGAN, CJ ;
SHEPPARD, RC .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (02) :538-546
[3]   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
[4]   Practical, convergent total synthesis of polyamine amide spider toxin NSTX-3 [J].
Blagbrough, IS ;
Moya, E ;
Walford, SP .
TETRAHEDRON LETTERS, 1996, 37 (04) :551-554
[5]   SYNTHESIS OF THE SPIDER TOXINS NEPHILATOXIN-9 AND NEPHILATOXIN-11 BY A NOVEL SOLID-PHASE STRATEGY [J].
BYCROFT, BW ;
CHAN, WC ;
HONE, ND ;
MILLINGTON, S ;
NASH, IA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (16) :7415-7416
[6]   SYNTHESIS AND ASSAY OF HYBRID ANALOGS OF ARGIOTOXIN-636 AND PHILANTHOTOXIN-433 - GLUTAMATE-RECEPTOR ANTAGONISTS [J].
CHOI, SK ;
NAKANISHI, K ;
USHERWOOD, PNR .
TETRAHEDRON, 1993, 49 (26) :5777-5790
[7]   TARGETING OF CYTOTOXIC AGENTS BY POLYAMINES - SYNTHESIS OF A CHLORAMBUCIL SPERMIDINE CONJUGATE [J].
COHEN, GM ;
CULLIS, PM ;
HARTLEY, JA ;
MATHER, A ;
SYMONS, MCR ;
WHEELHOUSE, RT .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (04) :298-300
[8]  
FAIRLAMB AH, 1992, ANNU REV MICROBIOL, V46, P695, DOI 10.1146/annurev.micro.46.1.695
[9]   TRYPANOTHIONE - A NOVEL BIS(GLUTATHIONYL)SPERMIDINE COFACTOR FOR GLUTATHIONE-REDUCTASE IN TRYPANOSOMATIDS [J].
FAIRLAMB, AH ;
BLACKBURN, P ;
ULRICH, P ;
CHAIT, BT ;
CERAMI, A .
SCIENCE, 1985, 227 (4693) :1485-1487
[10]  
FURAGAWA S, 1980, TETRAHEDRON LETT, V21, P1355