Fluorescence probe with a pH-sensitive trigger

Bioconjugate Chemistry
Amit K GalandeChing-Hsuan Tung

Abstract

Acid-catalyzed hydrolysis was used as the mechanism to design a new type of environmentally sensitive fluorescence probe. A mild and selective periodate oxidation of the 2-amino alcohol of serine in the presence of a disulfide bond was developed to prepare dialdehyde peptides. Two identical fluorochrome hydrazide derivatives were then linked to the dialdehyde peptide forming an acid-labile hydrazone linkage. This self-quenched probe is weakly fluorescent at a physiological pH of 7.4 but shows more than 3-fold fluorescence enhancement at pH 4.5.

References

Dec 4, 2002·Nature Reviews. Molecular Cell Biology·Jin ZhangRoger Y Tsien
Feb 4, 2003·Nature Reviews. Drug Discovery·Markus Rudin, Ralph Weissleder
Sep 12, 2003·Organic Letters·Amit K Galande, Arno F Spatola
Mar 15, 2005·Journal of Combinatorial Chemistry·Amit K GalandeChing-Hsuan Tung
Jan 13, 2006·Nature Chemical Biology·Daisuke KatoMatthew Bogyo

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Citations

Dec 25, 2007·Journal of Fluorescence·Feng-Yan Ge, Li-Gong Chen
May 9, 2012·The Review of Scientific Instruments·Han YanGultekin Gulsen
Apr 13, 2013·Bioconjugate Chemistry·Ouafâa El-Mahdi, Oleg Melnyk
May 10, 2007·Journal of Bone and Mineral Research : the Official Journal of the American Society for Bone and Mineral Research·Kenneth M KozloffUmar Mahmood
Sep 4, 2015·Bioconjugate Chemistry·Kasey J ClearBradley D Smith
Sep 1, 2006·ChemMedChem·Jesus RazkinIsabelle Texier
Jan 17, 2020·Chemistry : a European Journal·Alejandro Méndez-ArdoyJavier Montenegro
Dec 20, 2007·Journal of the American Chemical Society·Adah AlmutairiJean M J Fréchet

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