TY - DATA T1 - Fluorescence Probe with a pH-Sensitive Trigger PY - 2006/03/15 AU - Amit K. Galande AU - Ralph Weissleder AU - Ching-Hsuan Tung UR - https://acs.figshare.com/articles/journal_contribution/Fluorescence_Probe_with_a_pH_Sensitive_Trigger/3233239 DO - 10.1021/bc050330e.s001 L4 - https://ndownloader.figshare.com/files/5067304 KW - periodate oxidation KW - presence KW - Trigger KW - 7.4 KW - pH KW - hydrazone KW - mechanism KW - disulfide bond KW - type KW - serine KW - dialdehyde peptides KW - linkage KW - fluorochrome hydrazide derivatives KW - hydrolysis KW - 4.5. KW - Fluorescence Probe KW - dialdehyde peptide KW - fluorescence enhancement KW - fluorescence probe N2 - 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. ER -