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

ABSTRACT: 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 (?em ? 600 nm), which makes 1,2-DHP 1h' meet the requirement as a bioprobe for protein tyrosine phosphatases, shown in L6 muscle cell lysate.

SUBMITTER: Jamsheena V

PROVIDER: S-EPMC6045324 | biostudies-literature | 2018 Jan

REPOSITORIES: biostudies-literature

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

Jamsheena Vellekkatt V Mishra Rakesh K RK Veena Kollery S KS Sini Suresh S Jayamurthy Purushothaman P Lankalapalli Ravi S RS

ACS omega 20180124 1

New 1,2-dihydropyridine (1,2-DHP)-based fluorophores <b>1a-1h</b> 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 <b>1h ...[more]

PMID: 30023792

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