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A Naphthalimide‐Based Cd 2+ Fluorescent Probe with Carbamoylmethyl Groups Working as Chelators and PET‐Promoters under Neutral Conditions
Author(s) -
Tsukamoto Koji,
Shimabukuro Shota,
Mabuchi Miyuki,
Maeda Hatsuo
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201600556
Subject(s) - fluorescence , promoter , chemistry , biophysics , biochemistry , biology , physics , gene , optics , gene expression
We have developed a novel naphthalimide‐based Cd 2+ fluorescent probe ( 1 ), featuring almost no background response, high sensitivity and selectivity toward Cd 2+ through its high association constant [ K =(2.10±0.423)×10 6 ], and a practical working pH range. Membrane‐permeability was conferred on 1 by replacing the imide and amide substituents with n ‐butyl groups, and hence the derivative ( 4 ) has found practical utility on fluorescent imaging of Cd 2+ in HeLa cells. Comparison of fluorescent properties between various compounds derived from 1 has demonstrated that the carbamoylmethyl groups in 1 function not only as Cd 2+ chelators but also as promoters for photoinduced electron transfer (PET) by lowering the basicity of the two tertiary amino groups. As a result, 1 and 4 exhibited highly practical performance as Cd 2+ probes under neutral conditions.