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An AIE and ICT based NIR florescent probe for cysteine and homocysteine
KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.ORCID iD: 0000-0001-6508-8355
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2017 (English)In: Dyes and pigments, ISSN 0143-7208, E-ISSN 1873-3743, Vol. 136, p. 724-731Article in journal (Refereed) Published
Abstract [en]

A combination of aggregation-induced emission and intramolecular charge transfer was achieved by using a triphenylamine analogue and a dicyanovinyl moiety as the electron donating and accepting units, respectively. Hence, we designed and synthesized a probe with a D-π-A framework as a near-infrared fluorescence turn-on probe for biothiols (cysteine and homocysteine). Owing to the remarkable intramolecular charge transfer effect as well as intramolecular rotations associated with the donor moiety, the probe exhibits extremely weak fluorescence, which becomes a good starting point for developing fluorescence “turn-on” probes. Upon reaction with cysteine or homocysteine utilizing the dicyanovinyl moiety, the intramolecular charge transfer character was weakened, and the reacting products were observed to aggregate in aqueous solutions, resulting in the aggregation-induced emission effect with red fluorescence at 651 and 656 nm, respectively. Hence, the probe could be used as a fluorescence “turn-on” sensor for cysteine and homocysteine, with the sensing time of less than 4 min and the detection limits of 8.4 μM and 5.7 μM towards cysteine and homocysteine, respectively. The probe could distinguish cysteine and homocysteine from glutathione. The sensing mechanism was systematically investigated by employing high resolution mass spectrometry, 1H NMR and density functional theory calculations as well as checking the solvent viscosity dependent fluorescence, and thus the nucleophilic addition products, the intramolecular charge transfer character, and the aggregation-induced emission behaviour were clearly elucidated. It is noteworthy that the low cytotoxicity, the intrinsic aggregation-induced emission nature and near-infrared emissions enable the application of the probe in living cell imaging. © 2016 Elsevier Ltd

Place, publisher, year, edition, pages
2017. Vol. 136, p. 724-731
Keywords [en]
AIE, Biothiols, Cell imaging, Fluorescent probes, ICT, Addition reactions, Amino acids, Charge transfer, Density functional theory, Fluorescence, Infrared devices, Lanthanum compounds, Mass spectrometry, Solutions, Aggregation-induced emissions, High resolution mass spectrometry, Intra-molecular charge transfer, Near-infrared emissions, Near-infrared fluorescence, Probes
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Chemical Sciences
Identifiers
URN: urn:nbn:se:kth:diva-195127DOI: 10.1016/j.dyepig.2016.09.032ISI: 000387837200087Scopus ID: 2-s2.0-84988524950OAI: oai:DiVA.org:kth-195127DiVA, id: diva2:1044843
Note

Funding Details: 91227201, NSFC, National Natural Science Foundation of China. QC 20161107

Available from: 2016-11-07 Created: 2016-11-02 Last updated: 2017-11-29Bibliographically approved

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Li, XinÅgren, Hans

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