ORGN 567 |
Search for novel fluorescent zinc sensors
| James W. Canary and Maksim Royzen. Department of Chemistry, New York University, 100 Washington Square East, New York, NY 10003 |
Zinc imaging is a valuable tool for brain research. It has allowed linkage of several devastating cerebral disorders, such as Alzheimer’s disease, Parkinson’s disease and Amyotrophic lateral sclerosis (ALS) to abnormally high vesicular Zn2+ concentration. Imaging techniques rely on fluorescent Zn2+ sensors, the most prominent of which is N-(6-Methoxy-8-quinolinyl)-4-methylbenzenesulfonamide or TSQ. Development of better Zn2+ sensors may prove to be a valuable contribution to this field. One of the properties that needs improvement is sensitivity. We address this question by designing ligands based on 8-hydroxyquinaldine, a well established analytical tool for zinc chelation. It forms a 2:1 ligand- Zn2+ complex with binding affinity of logb2=16.76 (logK1=8.66, logK2=8.1). Incorporation of two 8-hydroxyquinaldine moieties in one ligand, as shown below, provides a possibility for combining binding affinities of two chelating groups thereby achieving a 1:1 ligand-metal complex with dramatically large logK1. Several ligands were synthesized utilizing ether and thioether linkers of various lengths. A direct correlation was found between the length of the linker and the sensor’s zinc sensitivity. |
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Bioorganic, Molecular Recognition, Asymmetric Reactions and Syntheses
11:00 AM-1:00 PM, Wednesday, September 10, 2003 Javits Convention Center -- Hall 1B/1C, Poster
Division of Organic Chemistry
The 226th ACS National Meeting, New York, NY, September 7-11, 2003
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