Synthesis and post-synthetic derivatization of a cyanine-based amino acid.: Application to the preparation of a novel water-soluble NIR dye

被引：30

作者：

Chipon, Bertrand

Clave, Guillaume

Bouteiller, Cedric

Massonneau, Marc

Renard, Pierre-Yves ^{[1
]}

Romieu, Anthony

机构：

[1] INSA Rouen, UMR 6014, CNRS, IRCOF,LHO,Equipe Chim Bioorgan, F-76131 Mont St Aignan, France

[2] Univ Rouen, F-76131 Mont St Aignan, France

[3] ESIGELEC, QUIDD, F-76801 St Etienne, France

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 47期

关键词：

cyanine dye; fluorescent amino acid; sulfonation;

D O I：

10.1016/j.tetlet.2006.09.100

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthesis of a new fluorescent amino acid derived from a pentamethylene cyanine dye is described. Selective derivatization of its amino group with an original trisulfonated linker has led to a novel water-soluble NIR dye suitable for covalent labeling of biomolecules. (c) 2006 Elsevier Ltd. All rights reserved.

引用

收藏

页码：8279 / 8284

页数：6

相关论文

共 37 条

[1]

ALMEIDA P, 1999, QUIMICA, V73, P9

[2] Fluorescein-based amino acids for solid phase synthesis of fluorogenic protease substrates [J].

Burchak, ON ;

Mugherli, L ;

Chatelain, F ;

Balakirev, MY .

BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (08) :2559-2568

[3] Latent fluorophores based on a Mannich cyclisation trigger [J].

Clave, Guillaume ;

Bernardin, Aude ;

Massonneau, Marc ;

Renard, Pierre-Yves ;

Romieu, Anthony .

TETRAHEDRON LETTERS, 2006, 47 (35) :6229-6233

[4] Tautomerism studies of 3-(ω-sulphoalkylamino)benzoic acids.: Substituent effects [J].

de Jesús, MN ;

Hioka, N ;

da Costa, WF ;

Maionchi, F .

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2002, 15 (09) :617-622

[5] Functionalized tricarbocyanine dyes as near-infrared fluorescent probes for biomolecules [J].

Flanagan, JH ;

Khan, SH ;

Menchen, S ;

Soper, SA ;

Hammer, RP .

BIOCONJUGATE CHEMISTRY, 1997, 8 (05) :751-756

[6] Long-wavelength fluorophores:: new trends in their analytical use [J].

Gómez-Hens, A ;

Aguilar-Caballos, MP .

TRAC-TRENDS IN ANALYTICAL CHEMISTRY, 2004, 23 (02) :127-136

[7] Preparation of thiol-reactive Cy5 derivatives from commercial Cy5 succinimidyl ester [J].

Gruber, HJ ;

Kada, G ;

Pragl, B ;

Riener, C ;

Hahn, CD ;

Harms, GS ;

Ahrer, W ;

Dax, TG ;

Hohenthanner, K ;

Knaus, HG .

BIOCONJUGATE CHEMISTRY, 2000, 11 (02) :161-166

[8] Monofunctional near-infrared fluorochromes for imaging applications [J].

Hilderbrand, SA ;

Kelly, KA ;

Weissleder, R ;

Tung, CH .

BIOCONJUGATE CHEMISTRY, 2005, 16 (05) :1275-1281

[9] Synthesis and reactivities of 3-indocyanine-green-acyl-1,3-thiazolidine-2-thione (ICG-ATT) as a new near-infrared fluorescent-labeling reagent [J].

Hirata, T ;

Kogiso, H ;

Morimoto, K ;

Miyamoto, S ;

Taue, H ;

Sano, S ;

Muguruma, N ;

Ito, S ;

Nagao, Y .

BIOORGANIC & MEDICINAL CHEMISTRY, 1998, 6 (11) :2179-2184

[10] Development of water-soluble far-red fluorogenic dyes for enzyme sensing [J].

Ho, NH ;

Weissleder, R ;

Tung, CS .

TETRAHEDRON, 2006, 62 (04) :578-585

← 1 2 3 4 →