Knoevenagel condensation triggered synthesis of dual-channel oxene based chemosensor: Discriminative spectrophotometric recognition of F-, CN- and HSO4- with breast cancer cell imaging, real sample analysis and molecular keypad lock applications

Sourav Bej; Riyanka Das; Amita Mondal; Rima Saha; Kishor Sarkar; Priyabrata Banerjee

doi:10.1016/j.saa.2022.120989

Knoevenagel condensation triggered synthesis of dual-channel oxene based chemosensor: Discriminative spectrophotometric recognition of F^-, CN^- and HSO₄^- with breast cancer cell imaging, real sample analysis and molecular keypad lock applications

Spectrochim Acta A Mol Biomol Spectrosc. 2022 May 15:273:120989. doi: 10.1016/j.saa.2022.120989. Epub 2022 Feb 8.

Authors

Sourav Bej¹, Riyanka Das¹, Amita Mondal², Rima Saha³, Kishor Sarkar³, Priyabrata Banerjee⁴

Affiliations

¹ Surface Engineering & Tribology Group, CSIR-Central Mechanical Engineering Research Institute, Mahatma Gandhi Avenue, Durgapur 713209, India; Academy of Scientific & Innovative Research (AcSIR), AcSIR Headquarters CSIR-HRDC Campus, Postal Staff College Area, Sector 19, Kamla Nehru Nagar, Ghaziabad 201002, Uttar Pradesh, India.
² Surface Engineering & Tribology Group, CSIR-Central Mechanical Engineering Research Institute, Mahatma Gandhi Avenue, Durgapur 713209, India; Department of Chemistry, National Institute of Technology, M.G. Avenue, Durgapur 713209, India.
³ Gene Therapy and Tissue Engineering Lab, Department of Polymer Science and Technology, University of Calcutta, 92, A.P.C. Road, Kolkata 700009, India.
⁴ Surface Engineering & Tribology Group, CSIR-Central Mechanical Engineering Research Institute, Mahatma Gandhi Avenue, Durgapur 713209, India; Academy of Scientific & Innovative Research (AcSIR), AcSIR Headquarters CSIR-HRDC Campus, Postal Staff College Area, Sector 19, Kamla Nehru Nagar, Ghaziabad 201002, Uttar Pradesh, India. Electronic address: pr_banerjee@cmeri.res.in.

PMID: 35183856
DOI: 10.1016/j.saa.2022.120989

Abstract

A novel oxene based unusual sensory receptor (HyMa) has been synthesized via.Knoevenagel condensation triggered carbon-heteroatom (oxygen) intramolecular bond formation reaction at room temperature for discriminative detection of multi-analytes like HSO₄^-, CN^- & F^- by spectro-photometric alterations with profound selectivity with the detection limit of 38 ppb, 18 ppb & 94 ppb respectively. Examination of the sensing mechanism was exhaustively investigated through several spectroscopic means like ¹H NMR, FT-IR, absorption and fluorescence spectra etc. In addition, quantum mechanical calculations like DFT and Loewdin spin population analyses also validated the rationality of the host-guest interaction. Apart from these, the reversible spectroscopic responses of HyMa towards F^- and Al³⁺ can imitate several complex logic functions that in turn help in preparing molecular keypad lock. This molecular keypad lock has the potential to protect the confidential information at the molecular scale. Additionally, the MTT assay of HyMa showed low cytotoxicity and membrane permeability indicating its attractive capability for bio-imaging towards triple negative breast cancer. HyMa-coated test strips could also be employed towards on-site detection of these deadly contaminants via "Dip Stick" approach without help of any instrumentation. In addition, HyMa has also been exploited for quantitative determination of HSO₄^- from various real water samples. In a nutshell, detection of lethal contaminants like CN^-, F^- & HSO₄^- at ppb level with in vitro live cell imaging has been explored with proper photophysical characterisation and theoretical calculations with real field applications.

Keywords: DFT; Knoevenagel condensation; Live cell imaging; Molecular keypad lock; Oxene; Real field water sample analysis; ppb level discriminative multi-anion detection.

MeSH terms

Breast Neoplasms*
Epoxy Compounds
Female
Humans
Spectrometry, Fluorescence
Spectroscopy, Fourier Transform Infrared

Substances

Epoxy Compounds
oxirene