The first fluorescent diboronic acid sensor specific for hepatocellular carcinoma cells expressing sialyl Lewis X.

Abstract

Carbohydrate antigens with subterminal fucosylation have been implicated in the development and progression of several cancers, including hepatocellular carcinoma (HCC). Fluorescent sensors targeting fucosylated carbohydrate antigens could potentially be used for diagnostic and other applications. We have designed and synthesized a series of 26 diboronic acid compounds as potential fluorescent sensors for such carbohydrates. Among these compounds, 7q was able to fluorescently label cells expressing high levels of sLex (HEPG2) within a concentration range of 0.5 to 10 microM. This compound (7q) did not label cells expressing Lewis Y (HEP3B), nor cells without fucosylated antigens (COS7). This represents the first example of a fluorescent compound labeling cells based on cell surface carbohydrate structures.

• Authors: Wenqian Yang, Haiying Fan, Xingming Gao, Shouhai Gao, Vishnu Vardhan Reddy Karnati, Weijuan Ni, W Borden Hooks, John Carson, Brent Weston, Binghe Wang
• Journal: Chemistry & biology (Chem Biol) Vol. 11 Issue 4 Pg. 439-48 (Apr 2004) ISSN: 1074-5521 [Print] United States
• PMID: 15123238 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't, Research Support, U.S. Gov't, P.H.S.)

Chemical References

• Boronic Acids
• Oligosaccharides
• Sialyl Lewis X Antigen

Topics

• Animals
• Boronic Acids (chemical synthesis, chemistry)
• Carcinoma, Hepatocellular (genetics, immunology, metabolism)
• Cell Line
• Fluorescence
• Gene Expression Regulation, Neoplastic
• Humans
• Liver Neoplasms (genetics, immunology, metabolism)
• Molecular Structure
• Oligosaccharides (analysis, chemistry, genetics)
• Sialyl Lewis X Antigen