The first example of anomeric glycoconjugation to phthalocyanines

被引:70
作者
Alvarez-Mico, X [1 ]
Calvete, MJF [1 ]
Hanack, M [1 ]
Ziegler, T [1 ]
机构
[1] Univ Tubingen, Inst Organ Chem 2, D-72076 Tubingen, Germany
关键词
carbohydrates; phthalocyanines; anomeric link;
D O I
10.1016/j.tetlet.2006.03.029
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Preparation and characterization of peripherally glucose substituted zinc(II) phthalocyanine 6, linked via the anomerie carbon through a novel glycosidation method is reported for the first time, for which classical Pc template chemistry with the unprotected phthalonitrile 4 could be used. Phthalocyanine 6 was formed in high yield and is displaying a high solubility in water as a primary condition for a potential biological application. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3283 / 3286
页数:4
相关论文
共 20 条
[1]   Metal complexes as photo- and radiosensitizers [J].
Ali, H ;
van Lier, JE .
CHEMICAL REVIEWS, 1999, 99 (09) :2379-2450
[2]   Expression and localization of GLUT1 and GLUT12 in prostate carcinoma [J].
Chandler, JD ;
Williams, ED ;
Slavin, JL ;
Best, JD ;
Rogers, S .
CANCER, 2003, 97 (08) :2035-2042
[3]   Efficient synthesis and photodynamic activity of porphyrin-saccharide conjugates: Targeting and incapacitating cancer cells [J].
Chen, X ;
Hui, L ;
Foster, DA ;
Drain, CM .
BIOCHEMISTRY, 2004, 43 (34) :10918-10929
[4]  
Chen X., 2004, DRUG DESIGN REV ONLI, V1, P215
[5]   Saccharide-directed cell recognition and molecular delivery using macrocyclic saccharide clusters: Masking of hydrophobicity to enhance the saccharide specificity [J].
Fujimoto, K ;
Miyata, T ;
Aoyama, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (14) :3558-3559
[6]   Synthesis of 5-fluoro N-acetylglucosamine glycosides and pyrophosphates via epoxide fluoridolysis:: Versatile reagents for the study of glycoconjugate biochemistry [J].
Hartman, MCT ;
Coward, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (34) :10036-10053
[7]  
Kumamoto K, 2001, CANCER RES, V61, P4620
[8]   Synthesis and in vitro photodynamic activity of novel galactose-containing phthalocyanines [J].
Lee, PPS ;
Lo, PC ;
Chan, EYM ;
Fong, WP ;
Ko, WH ;
Ng, DKP .
TETRAHEDRON LETTERS, 2005, 46 (09) :1551-1554
[9]   Functionalization of OEP-based benzochlorins to develop carbohydrate-conjugated photosensitizers.: Attempt to target β-galactoside-recognized proteins [J].
Li, GL ;
Pandey, SK ;
Graham, A ;
Dobhal, MP ;
Mehta, R ;
Chen, YH ;
Gryshuk, A ;
Rittenhouse-Olson, K ;
Oseroff, A ;
Pandey, RK .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (01) :158-172
[10]   Basic principles of photodynamic therapy [J].
MacDonald, IJ ;
Dougherty, TJ .
JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, 2001, 5 (02) :105-129