Synthesis and utility of chlorinated fluoresceins for labeling of proteins

ORGN 108

Min Tian1, Xiang-Long Wu1, Yin-Juan Bai2, Bing-Qin Yang3, and Zhen Shi1. (1) Department of Chemistry, Northwest University, 229 Taibai Road, Xi'an, 710069, China, (2) Department of Chemistry and College of Life Science, Northwest University, 229 Taibai Road, Xi'an, 710069, China, (3) Department of Chemistry and Shaanxi Key Laboratory of Physical-Inorgaric Chemistry, Northwest University, 229 Taibai Road, Xi'an, 710069, China

Selective substitution of xanthene molecules (such as fluoresceins) by chlorine has been proven to be an effective method for developing a fluorescent probe that has narrower emission spectra. The fluorescent probes of narrower emission are a valuable tool for multi-color imaging application such as the high content analysis of live cells.

Three novel chlorinated fluoresceins tetrachloro-6-(5-carboxypentyl)fluorescein (a, b) and hexachloro-6- (5-carboxypentyl) fluorescein (c) were synthesized as fluorescent probes for labeling proteins. These fluoresceins contain 6-aminohexanoic acid linker to minimize the fluorescence quenching of the fluorescein molecules by the proteins to be labeled. These novel fluoresceins demonstrate strong fluorescence, high photostability and good biocompatibility. 

 

a: R1= H, R2 = Cl   b: R1= Cl, R2 = H  c: R1= Cl, R2 = Cl

 

Physical Organic Chemistry, Combinatorial and Process Chemistry, New Reactions and Methodology, Peptides, Proteins and Amino Acids
8:00 PM-10:00 PM, Sunday, April 6, 2008 Morial Convention Center -- Hall A, Poster

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008