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CHEF-Affected Fluorogenic Nanomolar Detection of Al3+ by an Anthranilic Acid-Naphthalene Hybrid: Cell Imaging and
Arghyadeep Bhattacharyya1, Subhash Chandra Makhal1, Nikhil Guchhait1
1Department of Chemistry, University of Calcutta, 92, A.P.C. Road, Kolkata 700009, India.
Abstract:
We report the synthesis of a novel hydrazine-bridged anthranilic acid-naphthalene conjugate (E)-2-(benzamido)-N'-((2-hydroxynaphthalen-1-yl) methylene) benzohydrazide (BBHAN) and its crystal structure. BBHAN can detect Al3+ by a sharp increment in fluorescence intensity (∼40 times) in aqueous methanolic medium. The limit of detection of BBHAN towards Al3+ is 1.68 × 10-9 M, and the former undergoes a 2:1 binding with Al3+ with a high binding constant of ∼1.15 × 1011 M2-. BBHAN detects Al3+ by the well-known mechanism of chelation-enhanced fluorescence (CHEF), established by fluorescence time-resolved measurement. The mode of interaction between BBHAN and Al3+ has been explored by 1H NMR and electrospray ionization mass spectrometry techniques. Paper strips coated with BBHAN can detect Al3+ under UV light observed through the naked eye. Lastly, BBHAN can detect Al3+ in MDA-MB-468 cells.
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