A Sensitive Fluorescent Probe for Cysteine Based on 1,8-Naphthalimide Derivative and Application in Bioimaging†

doi:10.7503/cjcu20160960

Abstract

Abstract:

A turn-on fluorescent probe glyoxal mono(N-hydroxyethyl-1,8-naphthalimide-4-hydrazone)(NAD) was designed and synthesized for the detection of cysteine(Cys). The fluorescent probe shows high selectivity and sensitivity toward Cys over other various amino acids. When Cys was added to the solution of the probe, the CN isomerization process was inhibited by an intramolecular hydrogen bond, resulting in enhanced fluorescence. Furthermore, the probe NAD could effectively detect Cys in living cells.

Key words: Fluorescent probe, Cysteine, Cells imaging, 1,8-Naphthalimide derivative

CLC Number:

O625

TrendMD:

YANG Jingjing, YU Yuewen, WANG Bingxiang, JIANG Yuliang. A Sensitive Fluorescent Probe for Cysteine Based on 1,8-Naphthalimide Derivative and Application in Bioimaging^†[J]. Chem. J. Chinese Universities, 2017, 38(7): 1198.

Figures/Tables 7

Scheme 1 Synthetic routes of probe NAD

Fig.1 UV-Vis spectra of probe NAD upon the gra-dual addition of cysteine

Fig.2 Various fluorescence intensity ratio(F/F0) of the probe NAD(50 μmol/L) in the absence and presence of various individual metal ions(A) and amino acids(B)F0 and F are the fluorescence intensity in the absence and presence of metal ions and amino acids, respectively. c(Metal ions)=c(amino acids)=10 μmol/L. (A) a. Blank; b. Co2+; c. Mn2+; d. Cr3+; e. Pb2+; f. Cu2+; g. Ni2+; h. Cd2+; i. Zn2+; j. Ca2+; k. Na+; l. Ag+; m. Fe3+; n. Mg2+; o. K+. (B) a. Blank; b. Met; c. His; d. Iso; e. Gly; f. Phe. g. Tyr; h. Val; i. Try; j. Leu; k. Ala; l. Thr; m. Cys.

Fig.3 Fluorescence response of NAD(A) and linear relationship of F/F0(B) upon the adition of cysteine from 0 to 47 μmol/L

Scheme 2 Mechanism of the ‘off-on’ detection of Cys

Fig.4 Cytotoxicity of probe NAD by a MTT assay(n=3)

Fig.5 Fluorescence microscope images of HeLa cell with different treatmentBright-field image(A, C) and fluorescence mode(B, D) of HeLa cells treated with probe NAD(10 μmol/L)(A, B) and treated with probe NAD(10 μmol/L) and cysteine(10 μmol/L)(C, D). λex=488 nm.

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