Synthesis of Bi-heterocyclic Sulfonamides as Tyrosinase Inhibitors: Lineweaver–Burk Plot Evaluation and Computational Ascriptions

The designed bi-heterocyclic sulfonamides were synthesized through a two-step protocol and their structures were ascertained by spectral techniques including IR, 1H NMR and 13C NMR along with CHN analysis. The in vitro inhibitory effects of these sulfonamides were evaluated against tyrosinase and ki...

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Main Authors:	Muhammad Athar Abbasi, Zia Ur Rehman, Aziz Ur Rehman, Sabhat Zahra Siddiqui, Majid Nazir, Mubashir Hassan, Hussain Raza, Syed Adnan Ali Shah, sung-Yum Seo
Format:	Article
Language:	English
Published:	Slovenian Chemical Society 2020-06-01
Series:	Acta Chimica Slovenica
Subjects:	bi-heterocycles 1-phenyl-piperazine sulfonamides tyrosinase chemical kinetics computational study
Online Access:	https://journals.matheo.si/index.php/ACSi/article/view/5283

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spelling	doaj-bf2ec3bb107843a59f213522901baa732020-11-25T02:51:23ZengSlovenian Chemical SocietyActa Chimica Slovenica1318-02071580-31552020-06-0167240341410.17344/acsi.2019.5283826Synthesis of Bi-heterocyclic Sulfonamides as Tyrosinase Inhibitors: Lineweaver–Burk Plot Evaluation and Computational AscriptionsMuhammad Athar Abbasi0Zia Ur Rehman1Aziz Ur Rehman2Sabhat Zahra Siddiqui3Majid Nazir4Mubashir Hassan5Hussain Raza6Syed Adnan Ali Shah7sung-Yum Seo8GC University, LahoreDepartment of Chemistry, Government College University, LahoreDepartment of Chemistry, Government College University, LahoreDepartment of Chemistry, Government College University, LahoreDepartment of Chemistry, Government College University, LahoreCollege of Natural Sciences, Department of Biological Sciences, Kongju National University, Gongju, 32588, South KoreaCollege of Natural Sciences, Department of Biological Sciences, Kongju National University, Gongju, 32588, South KoreaFaculty of Pharmacy and Atta-ur-Rahman Institute for Natural Products Discovery (AuRIns), Level 9, FF3, Universiti Teknologi MARA, Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor Darul Ehsan, MalaysiaCollege of Natural Sciences, Department of Biological Sciences, Kongju National University, Gongju, 32588, South KoreaThe designed bi-heterocyclic sulfonamides were synthesized through a two-step protocol and their structures were ascertained by spectral techniques including IR, 1H NMR and 13C NMR along with CHN analysis. The in vitro inhibitory effects of these sulfonamides were evaluated against tyrosinase and kinetics mechanism was analyzed by Lineweaver–Burk plots. The binding modes of these molecules were ascribed through molecular docking studies. These synthesized bi-heterocyclic molecules were identified as potent inhibitors relative to the standard (kojic acid) and compound 5 inhibited the tyrosinase non-competitively by forming an enzyme-inhibitor complex. The inhibition constant Ki (0.09 µM) for compound 5 was calculated from Dixon plots. Computational results also displayed that all compounds possessed good binding profile against tyrosinase and interacted with core residues of target protein.https://journals.matheo.si/index.php/ACSi/article/view/5283bi-heterocycles1-phenyl-piperazinesulfonamidestyrosinasechemical kineticscomputational study
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Muhammad Athar Abbasi Zia Ur Rehman Aziz Ur Rehman Sabhat Zahra Siddiqui Majid Nazir Mubashir Hassan Hussain Raza Syed Adnan Ali Shah sung-Yum Seo
spellingShingle	Muhammad Athar Abbasi Zia Ur Rehman Aziz Ur Rehman Sabhat Zahra Siddiqui Majid Nazir Mubashir Hassan Hussain Raza Syed Adnan Ali Shah sung-Yum Seo Synthesis of Bi-heterocyclic Sulfonamides as Tyrosinase Inhibitors: Lineweaver–Burk Plot Evaluation and Computational Ascriptions Acta Chimica Slovenica bi-heterocycles 1-phenyl-piperazine sulfonamides tyrosinase chemical kinetics computational study
author_facet	Muhammad Athar Abbasi Zia Ur Rehman Aziz Ur Rehman Sabhat Zahra Siddiqui Majid Nazir Mubashir Hassan Hussain Raza Syed Adnan Ali Shah sung-Yum Seo
author_sort	Muhammad Athar Abbasi
title	Synthesis of Bi-heterocyclic Sulfonamides as Tyrosinase Inhibitors: Lineweaver–Burk Plot Evaluation and Computational Ascriptions
title_short	Synthesis of Bi-heterocyclic Sulfonamides as Tyrosinase Inhibitors: Lineweaver–Burk Plot Evaluation and Computational Ascriptions
title_full	Synthesis of Bi-heterocyclic Sulfonamides as Tyrosinase Inhibitors: Lineweaver–Burk Plot Evaluation and Computational Ascriptions
title_fullStr	Synthesis of Bi-heterocyclic Sulfonamides as Tyrosinase Inhibitors: Lineweaver–Burk Plot Evaluation and Computational Ascriptions
title_full_unstemmed	Synthesis of Bi-heterocyclic Sulfonamides as Tyrosinase Inhibitors: Lineweaver–Burk Plot Evaluation and Computational Ascriptions
title_sort	synthesis of bi-heterocyclic sulfonamides as tyrosinase inhibitors: lineweaver–burk plot evaluation and computational ascriptions
publisher	Slovenian Chemical Society
series	Acta Chimica Slovenica
issn	1318-0207 1580-3155
publishDate	2020-06-01
description	The designed bi-heterocyclic sulfonamides were synthesized through a two-step protocol and their structures were ascertained by spectral techniques including IR, 1H NMR and 13C NMR along with CHN analysis. The in vitro inhibitory effects of these sulfonamides were evaluated against tyrosinase and kinetics mechanism was analyzed by Lineweaver–Burk plots. The binding modes of these molecules were ascribed through molecular docking studies. These synthesized bi-heterocyclic molecules were identified as potent inhibitors relative to the standard (kojic acid) and compound 5 inhibited the tyrosinase non-competitively by forming an enzyme-inhibitor complex. The inhibition constant Ki (0.09 µM) for compound 5 was calculated from Dixon plots. Computational results also displayed that all compounds possessed good binding profile against tyrosinase and interacted with core residues of target protein.
topic	bi-heterocycles 1-phenyl-piperazine sulfonamides tyrosinase chemical kinetics computational study
url	https://journals.matheo.si/index.php/ACSi/article/view/5283
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Synthesis of Bi-heterocyclic Sulfonamides as Tyrosinase Inhibitors: Lineweaver–Burk Plot Evaluation and Computational Ascriptions

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