New 1,2-Dihydropyridine-Based Fluorophores and Their Applications as Fluorescent Probes

New 1,2-dihydropyridine (1,2-DHP)-based fluorophores 1a–1h were designed and synthesized by a one-pot four-component condensation reaction using dienaminodioate, aldehydes, and an in situ-generated hydrazone mediated by trifluoroacetic acid. The photophysical properties of 1,2-DHPs were studied in d...

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Bibliographic Details
Published in:ACS omega 2018-01, Vol.3 (1), p.856-862
Main Authors: Jamsheena, Vellekkatt, Mishra, Rakesh K, Veena, Kollery S, Sini, Suresh, Jayamurthy, Purushothaman, Lankalapalli, Ravi S
Format: Article
Language:English
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Summary:New 1,2-dihydropyridine (1,2-DHP)-based fluorophores 1a–1h were designed and synthesized by a one-pot four-component condensation reaction using dienaminodioate, aldehydes, and an in situ-generated hydrazone mediated by trifluoroacetic acid. The photophysical properties of 1,2-DHPs were studied in detail, and a few of them exhibited selective mitochondrial staining ability in HeLa cell lines (cervical cancer cells). A detailed photophysical investigation led to the design of 1,2-DHP 1h as an optimal fluorophore suitable for its potential application as a small molecule probe in the aqueous medium. Also, 1,2-DHP 1h exhibited sixfold enhanced emission intensity than its phosphorylated analogue 1h′ in the long wavelength region (λem ≈ 600 nm), which makes 1,2-DHP 1h′ meet the requirement as a bioprobe for protein tyrosine phosphatases, shown in L6 muscle cell lysate.
ISSN:2470-1343
2470-1343
DOI:10.1021/acsomega.7b01835