Hydrazinopyrimidine derived novel Al3+ chemosensor: Molecular logic gate and biological applications

Bhriguram Das, Satyajit Dey, Guru Prasad Maiti, Ankita Bhattacharjee, Anamika Dhara, Atanu Jana

Research output: Contribution to journalArticlepeer-review

73 Scopus citations

Abstract

Cost-effective and highly sensitive biocompatible probes for the detection of Al3+ have tremendously important practical applications. Herein, we report for the first time, the hydrazinopyrimidine based Al3+ chemosensor L (1-[(4,6-dimethyl-pyrimidin-2-yl)-hydrazonomethyl]-naphthalen-2-ol) prepared by the condensation of 2-hydroxy-1-naphthaldehyde and 4,6-dimethyl-2-hydrazino-pyrimidine. Our as-synthesized chemosensor L (Φ = 0.0066) shows ∼15 fold fluorescence enhancement in the presence of Al3+ (Φ = 0.0955, Ka = 1.9 × 104 M-1) via chelation enhanced fluorescence (CHEF), excited state intramolecular proton transfer (ESIPT), and inhibited photo-induced electron transfer (PET) phenomena. The limit of detection (LOD) and limit of quantification (LOQ) were estimated to be 2.78 μM and 9.27 μM, respectively. Furthermore, for the first time, a hydrazino pyrimidine based 'INHIBIT' molecular logic gate for Al3+ was successfully developed using the fluorescence properties of L. The experimental sensing mechanisms of L for Al3+ were corroborated by theoretical calculations. Biocompatibility and good water-solubility properties of a pyrimidine moiety of L inspired us to investigate Al3+ imaging in human embryonic kidney cell lines, HEK293, and the results for practical applications are highly promising.

Original languageEnglish
Pages (from-to)9424-9435
Number of pages12
JournalNew Journal of Chemistry
Volume42
Issue number12
DOIs
StatePublished - 2018

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