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Synthesis and Investigation of the Analgesic Potential of Enantiomerically Pure Schiff Bases: A Mechanistic Approach

Schiff bases are a class of organic compounds with azomethine moiety, exhibiting a wide range of biological potentials. In this research, six chiral Schiff bases, three ‘S’ series (H1–H3) and three ‘R’ series (H4–H6), were synthesized. The reaction was neat, which means without a solvent, and occurr...

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Autores principales: Afridi, Hamid Hussain, Shoaib, Muhammad, Al-Joufi, Fakhria A., Shah, Syed Wadood Ali, Hussain, Haya, Ullah, Abid, Zahoor, Mohammad, Mughal, Ehsan Ullah
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9416351/
https://www.ncbi.nlm.nih.gov/pubmed/36014445
http://dx.doi.org/10.3390/molecules27165206
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author Afridi, Hamid Hussain
Shoaib, Muhammad
Al-Joufi, Fakhria A.
Shah, Syed Wadood Ali
Hussain, Haya
Ullah, Abid
Zahoor, Mohammad
Mughal, Ehsan Ullah
author_facet Afridi, Hamid Hussain
Shoaib, Muhammad
Al-Joufi, Fakhria A.
Shah, Syed Wadood Ali
Hussain, Haya
Ullah, Abid
Zahoor, Mohammad
Mughal, Ehsan Ullah
author_sort Afridi, Hamid Hussain
collection PubMed
description Schiff bases are a class of organic compounds with azomethine moiety, exhibiting a wide range of biological potentials. In this research, six chiral Schiff bases, three ‘S’ series (H1–H3) and three ‘R’ series (H4–H6), were synthesized. The reaction was neat, which means without a solvent, and occurred at room temperature with a high product yield. The synthesized compounds were evaluated for analgesic potential in vivo at doses of 12.5 and 25 mg/kg using acetic-acid-induced writhing assay, formalin test, tail immersion and hot plate models, followed by investigating the possible involvement of opioid receptors. The compounds H2 and H3 significantly (*** p < 0.001) reduced the writhing frequency, and H3 and H5 significantly (*** p < 0.001) reduced pain in both phases of the formalin test. The compounds H2 and H5 significantly (*** p < 0.001) increased latency at 90 min in tail immersion, while H2 significantly (*** p < 0.001) increased latency at 90 min in the hot plate test. The ‘S’ series Schiff bases, H1–H3, were found more potent than the ‘R’ series compounds, H4–H6. The possible involvement of opioid receptors was also surveyed utilizing naloxone in tail immersion and hot plate models, investigating the involvement of opioid receptors. The synthesized compounds could be used as alternative analgesic agents subjected to further evaluation in other animal models to confirm the observed biological potential.
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spelling pubmed-94163512022-08-27 Synthesis and Investigation of the Analgesic Potential of Enantiomerically Pure Schiff Bases: A Mechanistic Approach Afridi, Hamid Hussain Shoaib, Muhammad Al-Joufi, Fakhria A. Shah, Syed Wadood Ali Hussain, Haya Ullah, Abid Zahoor, Mohammad Mughal, Ehsan Ullah Molecules Article Schiff bases are a class of organic compounds with azomethine moiety, exhibiting a wide range of biological potentials. In this research, six chiral Schiff bases, three ‘S’ series (H1–H3) and three ‘R’ series (H4–H6), were synthesized. The reaction was neat, which means without a solvent, and occurred at room temperature with a high product yield. The synthesized compounds were evaluated for analgesic potential in vivo at doses of 12.5 and 25 mg/kg using acetic-acid-induced writhing assay, formalin test, tail immersion and hot plate models, followed by investigating the possible involvement of opioid receptors. The compounds H2 and H3 significantly (*** p < 0.001) reduced the writhing frequency, and H3 and H5 significantly (*** p < 0.001) reduced pain in both phases of the formalin test. The compounds H2 and H5 significantly (*** p < 0.001) increased latency at 90 min in tail immersion, while H2 significantly (*** p < 0.001) increased latency at 90 min in the hot plate test. The ‘S’ series Schiff bases, H1–H3, were found more potent than the ‘R’ series compounds, H4–H6. The possible involvement of opioid receptors was also surveyed utilizing naloxone in tail immersion and hot plate models, investigating the involvement of opioid receptors. The synthesized compounds could be used as alternative analgesic agents subjected to further evaluation in other animal models to confirm the observed biological potential. MDPI 2022-08-15 /pmc/articles/PMC9416351/ /pubmed/36014445 http://dx.doi.org/10.3390/molecules27165206 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Afridi, Hamid Hussain
Shoaib, Muhammad
Al-Joufi, Fakhria A.
Shah, Syed Wadood Ali
Hussain, Haya
Ullah, Abid
Zahoor, Mohammad
Mughal, Ehsan Ullah
Synthesis and Investigation of the Analgesic Potential of Enantiomerically Pure Schiff Bases: A Mechanistic Approach
title Synthesis and Investigation of the Analgesic Potential of Enantiomerically Pure Schiff Bases: A Mechanistic Approach
title_full Synthesis and Investigation of the Analgesic Potential of Enantiomerically Pure Schiff Bases: A Mechanistic Approach
title_fullStr Synthesis and Investigation of the Analgesic Potential of Enantiomerically Pure Schiff Bases: A Mechanistic Approach
title_full_unstemmed Synthesis and Investigation of the Analgesic Potential of Enantiomerically Pure Schiff Bases: A Mechanistic Approach
title_short Synthesis and Investigation of the Analgesic Potential of Enantiomerically Pure Schiff Bases: A Mechanistic Approach
title_sort synthesis and investigation of the analgesic potential of enantiomerically pure schiff bases: a mechanistic approach
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9416351/
https://www.ncbi.nlm.nih.gov/pubmed/36014445
http://dx.doi.org/10.3390/molecules27165206
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