A 7-nitrobenz-2-oxa-1,3-diazole based highly sensitive and selective turn-on chemosensor for copper(II) ion with intracellular application without cytotoxicity

Tarun Mistri; Rabiul Alam; Malay Dolai; Sushil Kumar Mandal; Anisur Rahman Khuda-Bukhsh; Mahammad Ali

doi:10.1039/C3OB27405E

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Organic & Biomolecular Chemistry

Issue 9, 2013

The international home of synthetic, physical and biomolecular organic chemistry.

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Paper

A 7-nitrobenz-2-oxa-1,3-diazole based highly sensitive and selective turn-on chemosensor for copper(II) ion with intracellular application without cytotoxicity

Tarun Mistri,^a Rabiul Alam,^a Malay Dolai,^a Sushil Kumar Mandal,^b Anisur Rahman Khuda-Bukhsh^b and Mahammad Ali*^a

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Department of Chemistry, Jadavpur University, Kolkata 700 032, India

Department of Zoology, Kalyani University, Kalyani, India
E-mail: m_ali2062@yahoo.com

Org. Biomol. Chem., 2013,11, 1563-1569

DOI: 10.1039/C3OB27405E
Received 12 Dec 2012, Accepted 08 Jan 2013
First published online 09 Jan 2013

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A 7-nitrobenz-2-oxa-1,3-diazole (NBD) derived turn-on fluorescent probe (1) exhibits a reversible binding to Cu²⁺ ion in presence of other metal ions, giving [similar] 20 fold increase in fluorescence intensity. The apparent association constant (K_a) for Cu²⁺ was found to be 2.62 × 10⁴ M⁻¹. The intracellular Cu²⁺ imaging behaviour of chemosensor 1 on HeLa cells studied by fluorescence microscopy revealed that after incubation with 1 cells exhibited intensive fluorescence when exogenous Cu²⁺ was introduced into the cell. Thus this probe features the ready availability, high sensitivity and selectivity towards Cu²⁺ in MeCN–H₂O (1:1, v/v) with cell imaging possibilities with no or negligible cytotoxicity.