title: A Naphthalimide-Based Cd(2+) Fluorescent Probe with Carbamoylmethyl Groups Working as Chelators and PET-Promoters under Neutral Conditions.
abstract: 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.
authors.affiliation: School of Pharmacy, Hyogo University of Health Sciences, 1-3-6 Minatojima, Chuo-ku, Kobe, Hyogo, 650-8530, Japan. kotukamoto@huhs.ac.jp.
authors.forename: Koji
authors.initials: K
authors.lastname: Tsukamoto
authors.affiliation: School of Pharmacy, Hyogo University of Health Sciences, 1-3-6 Minatojima, Chuo-ku, Kobe, Hyogo, 650-8530, Japan.
authors.forename: Shota
authors.initials: S
authors.lastname: Shimabukuro
authors.affiliation: School of Pharmacy, Hyogo University of Health Sciences, 1-3-6 Minatojima, Chuo-ku, Kobe, Hyogo, 650-8530, Japan.
authors.forename: Miyuki
authors.initials: M
authors.lastname: Mabuchi
authors.affiliation: School of Pharmacy, Hyogo University of Health Sciences, 1-3-6 Minatojima, Chuo-ku, Kobe, Hyogo, 650-8530, Japan.
authors.forename: Hatsuo
authors.initials: H
authors.lastname: Maeda
mesh_terms: D002104:Cadmium / Q000737:chemistry*; D002384:Catalysis; D002463:Cell Membrane Permeability / Q000187:drug effects; D004579:Electron Transport; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D006367:HeLa Cells; D006801:Humans; D006863:Hydrogen-Ion Concentration; D007094:Imides / Q000737:chemistry; D008027:Light; D018613:Microscopy, Confocal; D053644:Naphthalimides / Q000737:chemistry*
chemical_list: D005456:Fluorescent Dyes; D007094:Imides; D053644:Naphthalimides; D002104:Cadmium
keywords: cadmium; fluorescence; fluorescent probes; naphthalimide; photoinduced electron transfer