Thioglycosylated cationic porphyrins - convenient synthesis and photodynamic activity in vitro

被引：34

作者：

Ahmed, S ^{[1
]}

Davoust, E ^{[1
]}

Savoie, H ^{[1
]}

Boa, AN ^{[1
]}

Boyle, RW ^{[1
]}

机构：

[1] Univ Hull, Dept Chem, Kingston Upon Hull HU6 7RX, Yorks, England

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 31期

基金：

英国惠康基金; 英国生物技术与生命科学研究理事会;

关键词：

porphyrins; photobiology;

D O I：

10.1016/j.tetlet.2004.06.021

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient and flexible synthesis of meso-tetraaryl porphyrins substituted with three thioglycosyl units, and also bearing one pyridyl substituent is reported. Quaternisation of the pyridine nitrogen with alkyl iodides gives access to a range of water soluble glycosyl cationic porphyrins. Screening for photodynamic activity against human colorectal adenocarcinoma cells (HT-29) indicates that all the glycosyl cationic porphyrins made in this way are active photosensitisers, but direct comparison with a cationic porphyrin bearing no sugar residues indicates an important role for these groups in reducing generalised 'dark' toxicity. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：6045 / 6047

页数：3

共 11 条

[1] PHOTOSENSITIZERS OF THE PORPHYRIN AND PHTHALOCYANINE SERIES FOR PHOTODYNAMIC THERAPY [J].

BONNETT, R .

CHEMICAL SOCIETY REVIEWS, 1995, 24 (01) :19-33

[2] Structure and biodistribution relationships of photodynamic sensitizers [J].

Boyle, RW ;

Dolphin, D .

PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1996, 64 (03) :469-485

[3] GLYCOSYLATED CATIONIC PORPHYRINS AS POTENTIAL AGENTS IN CANCER PHOTOTHERAPY [J].

DRIAF, K ;

KRAUSZ, P ;

VERNEUIL, B ;

SPIRO, M ;

BLAIS, JC ;

BOLBACH, G .

TETRAHEDRON LETTERS, 1993, 34 (06) :1027-1030

[4] Synthesis of new glycosylated neutral and cationic porphyrin dimers [J].

Kaldapa, C ;

Blais, JC ;

Carré, V ;

Granet, R ;

Sol, V ;

Guilloton, M ;

Spiro, M ;

Krausz, P .

TETRAHEDRON LETTERS, 2000, 41 (03) :331-335

[5] Basic principles of photodynamic therapy [J].

MacDonald, IJ ;

Dougherty, TJ .

JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, 2001, 5 (02) :105-129

[6] RAPID COLORIMETRIC ASSAY FOR CELLULAR GROWTH AND SURVIVAL - APPLICATION TO PROLIFERATION AND CYTO-TOXICITY ASSAYS [J].

MOSMANN, T .

JOURNAL OF IMMUNOLOGICAL METHODS, 1983, 65 (1-2) :55-63

[7] Synthesis of hydrolytically stable porphyrin C- and S-glycoconjugates in high yields [J].

Pasetto, P ;

Chen, X ;

Drain, CM ;

Franck, RW .

CHEMICAL COMMUNICATIONS, 2001, (01) :81-82

[8] Regioselective synthesis of multifunctionalised porphyrins - Coupling of mono-(pentafluorophenyl)porphyrins to electrophiles [J].

Shaw, SJ ;

Edwards, C ;

Boyle, RW .

TETRAHEDRON LETTERS, 1999, 40 (42) :7585-7586

[9] Mono-(pentafluorophenyl)porphyrins - Useful intermediates in the regioselective synthesis of multifunctionalised porphyrins [J].

Shaw, SJ ;

Elgie, KJ ;

Edwards, C ;

Boyle, RW .

TETRAHEDRON LETTERS, 1999, 40 (08) :1595-1596

[10] Porphyrin-based photosensitizers for use in photodynamic therapy [J].

Sternberg, ED ;

Dolphin, D ;

Brückner, C .

TETRAHEDRON, 1998, 54 (17) :4151-4202

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