bc050330e_si_001.pdf (293.54 kB)
Fluorescence Probe with a pH-Sensitive Trigger
journal contribution
posted on 2006-03-15, 00:00 authored by Amit K. Galande, Ralph Weissleder, Ching-Hsuan TungAcid-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.