Journal
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
Volume 388, Issue -, Pages -Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jphotochem.2019.112151
Keywords
Perylene diimides; Biothiols; H2S and Cys; NIR probe; Biosensor; Bioimaging
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Funding
- Council of Scientific and Industrial Research (CSIR) [02(0267)/16/EMR-II]
- Science and Education Research Board, Department of Science and Technology (DST-SERB) [EMR/2016/002239]
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DFT Design of ratiometric probes which can differentiate bioactive sulphur species (H2S, Cys and GSH) are in demand. In this work, perylenediimide-7-nitro-2,1,3-benzoxadiazole based near-IR chromofluorescent probe (NBD-PDI) was designed for discriminative detection of H2S and Cysteine. The chemodosimetric reaction of NBD-PDI with H2S induces cleavage of the NBD moiety via thiolysis and thereby affords PDI-OH (lambda(max) 680 nm) and NBD-SH (lambda(max), 550 nm) with diminution of emission intensity at 537 nm. Meanwhile after the reaction of NBD-PDI with cysteine, only absorbance at 680 nm observed while emission at 660 nm decreased and 537 nm increased. The intensities of NBD-PDI showed linearity with increase of H2S and Cys concentrations with detection limits of 3.29 mu M and 13.5 mu M (UV-vis); 1.3 mu M and 3 mu M (fluorescence), respectively. Moreover, applicability of NBD-PDI for the fluorescence imaging of H2S and cysteine in MG-63 cells was investigated. The unique differential response of NBD-PDI towards H2S and Cysteine allowed fabrication of IMP, INH, OR, NOR and TRANSFER logic gates. NBD-PDI coated TLC strips can be used for visualization of H2S/Cysteine and for writing alphabets using H2S/Cysteine as ink. The mechanism of H2S interaction using H-1 NMR titration, DFT and CV studies are also discussed.
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