A Simple Isoniazid-Based N-Acylhydrazone Derivative as Potential Fluorogenic Probe for Zn 2+ Ions
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ORIGINAL ARTICLE
A Simple Isoniazid-Based N-Acylhydrazone Derivative as Potential Fluorogenic Probe for Zn2+ Ions Daniela Corrêa Santos 1,2 & Paulo José Sousa Maia 1 & Marcos Antonio de Abreu Lopes Jr. 1,3 & Josué Sebastián Bello Forero 3 & Andréa Luzia Ferreira de Souza 1,3 Received: 14 July 2020 / Accepted: 9 November 2020 # Springer Science+Business Media, LLC, part of Springer Nature 2020
Abstract This study evaluated three isoniazid-based N-acylhydrazone derivatives (HL1, HL2, and HL3) varying their substituting groups (-H, -N(CH3)2, and -NO2) as potential chemosensors for Zn2+ ions. To this end, the absorption and emission properties of these derivatives were investigated in the presence of Zn2+ ions. Results point to the derivative HL2 as the best chemosensor for Zn2+ ions because of its comparatively higher sensitivity. The color of this derivative changed from colorless to strong yellow with zinc addition, as indicated by the shift in UV-vis spectrum. Moreover, HL2 was the only derivative to emit fluorescence in the presence of Zn2+ ions, attributable to PET inhibition and bond isomerization promoted by coordination with this metal. LOD, LOQ, and binding constant values for HL2 + Zn2+ were 0.43 μmol.l−1, 0.93 μmol.l−1, and 5.04 × 1012 l.mol−1, respectively. The fluorescence of HL2 with other metal ions (Fe3+, Mg2+, Na+, Cd2+, Cu2+, Co2+, Ni2+, Ca2+, and K+) was also investigated. Zn2+ yielded the best result without Cd2+ interferences. Job’s Plot showed that the stoichiometric ratio of the complex formed by HL2 and Zn2+ ions is 2:1 (ligand:metal). The strip test with adsorbed HL2 indicated fluorescence in the presence of zinc ions under 365 nm UV irradiation. Keywords Zinc(II) . Fluorescence . N-acylhydrazone . Isoniazid . Chemosensor
Introduction Zinc is the second most abundant transition metal in the human body; it is directly involved in many physiological and pathological processes in living organisms [1]. Zn2+ ions are key elements in structural components of numerous proteins and act as catalysts in enzymes central to many cellular processes [2]. Anomalous zinc levels can cause serious problems. Zinc deficiency has been reported to cause chronic liver and kidney diseases while its surplus can cause neurotoxicity and
* Andréa Luzia Ferreira de Souza [email protected] 1
Universidade Federal do Rio de Janeiro, Campus Macaé Professor Aloísio Teixeira, CEP, Macaé, RJ 27930-560, Brazil
2
Instituto de Macromoléculas, Universidade Federal do Rio de Janeiro, Cidade Universitária, CEP, Rio de Janeiro, RJ 21941-598, Brazil
3
Pós-Graduação em Química (PGQu), Instituto de Química, Universidade Federal do Rio de Janeiro, Cidade Universitária, Rio de Janeiro, RJ CEP21941-909, Brazil
dysregulation of calcium homeostasis [3–5]. Furthermore, zinc imbalance is directly related to diseases such as Alzheimer, Parkinson, amyotrophic lateral sclerosis, prostate cancer, diabetes, among others [6]. For this reason, Zn2+ detection has attracted increasing interest in the fields of chemistry and biology.
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