ItemArticle

Fluorogenic selective detection of Zn2+ using a pyrazole-ortho-vanillin conjugate: insights from DFT, molecular docking, bioimaging and anticancer applications

Title
Fluorogenic selective detection of Zn2+ using a pyrazole-ortho-vanillin conjugate: insights from DFT, molecular docking, bioimaging and anticancer applications
Creator
Kumar, Malavika S.; Pakrashy, Sourav; Manna, Sounik; Choudhury, Sujata Maiti; Das, Bhriguram; Ghosh, Abhishek; Seikh, Asiful H.; Dolai, Malay; Das, Avijit Kumar
Description
A fluorescent sensor, (E)-N?-(2-hydroxy-3-methoxybenzylidene)-3,5-dimethyl-1H-pyrazole-1-carbohydrazide (HMPC), was designed and synthesized for the selective fluorescence recognition of Zn2+ in semi-aqueous media. Notably, HMPC exhibited a red-shifted, two-fold fluorescence turn-on enhancement in response to Zn2+ at 490 nm, with a detection limit of 1.68 ?M, which is significantly lower than the WHO guideline (76.0 ?M). The binding constant of HMPC with Zn2+ was calculated to be 5 104 M?1. The fluorescence enhancement of HMPC in the presence of Zn2+ is attributed to the suppression of the PET process and the enhancement of ICT, leading to fluorescence via the CHEF mechanism. The sensing mechanism was demonstrated through UV-vis, fluorescence spectroscopy, Job plots, ESI-MS, and DFT calculations. For biological applications, cytotoxicity and cell imaging studies were performed using MCF-7 cells. Molecular docking studies revealed a high binding energy of HMPC (?G = ?7.1 kcal mol?1) with the 4,5-diaryl isoxazole HSP90 chaperone protein, suggesting its potential as an anticancer agent. Additionally, its binding energy of ?6.5 kcal mol?1 with the HDAC8 protein indicates greater efficacy than suberoylanilide hydroxamic acid (SAHA) in inhibiting HDAC, as it binds more strongly to the HDAC8 protein than SAHA (?7.4 kcal mol?1). Furthermore, due to its favorable ADME profile, HMPC may be suitable for oral administration, enhancing its potential as an anticancer drug. 2025 The Royal Society of Chemistry.
Source
Analytical Methods;Volume;17;Issue;9;pp.2125-2133
Date
01-01-2025
Publisher
Royal Society of Chemistry
Coverage
Kumar M.S., Department of Chemistry, Christ University, Hosur Road, Karnataka, Bangalore, 560029, India; Pakrashy S., Department of Chemistry, Prabhat Kumar College, Vidyasagar University, Purba Medinipur, W. B., 721404, India; Manna S., Biochemistry, Molecular Endocrinology and Reproductive Physiology Laboratory, Department of Human Physiology, Vidyasagar University, W. B., Midnapore, 721102, India; Choudhury S.M., Biochemistry, Molecular Endocrinology and Reproductive Physiology Laboratory, Department of Human Physiology, Vidyasagar University, W. B., Midnapore, 721102, India; Das B., Department of Chemistry, Vidyasagar University, Paschim Medinipur, W. B., 721102, India; Ghosh A., Department of Applied Science, University of Quebec at Chicoutimi, Saguenay, G7H 2B1, QC, Canada; Seikh A.H., Department of Mechanical Engineering, College of Engineering, King Saud University, Riyadh, 11421, Saudi Arabia; Dolai M., Department of Chemistry, Prabhat Kumar College, Vidyasagar University, Purba Medinipur, W. B., 721404, India; Das A.K., Department of Chemistry, Christ University, Hosur Road, Karnataka, Bangalore, 560029, India
Rights
All Open Access; Hybrid Gold Open Access
Relation
ISSN: 17599660;
Format
online
Language
English
Type
Article

Citation

Kumar, Malavika S.; Pakrashy, Sourav; Manna, Sounik; Choudhury, Sujata Maiti; Das, Bhriguram; Ghosh, Abhishek; Seikh, Asiful H.; Dolai, Malay; Das, Avijit Kumar, “Fluorogenic selective detection of Zn2+ using a pyrazole-ortho-vanillin conjugate: insights from DFT, molecular docking, bioimaging and anticancer applications,” CHRIST (Deemed To Be University) Institutional Repository, accessed June 18, 2026, https://archives.christuniversity.in/items/show/22543.

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