4,4-Nitrophenoxyaniline derived Azo ester: Structural elucidation, DFT simulation, and DNA interactional studies via wet and in silico methods

Samina Qamar; Fouzia Perveen; Zareen Akhter; Sammer Yousuf; Muhammd Sultan; Sule Erten Ela; Naimat Ullah; Kalsoom Fatima; Sehrish kanwal

doi:10.1016/j.molstruc.2021.131695

4,4-Nitrophenoxyaniline derived Azo ester: Structural elucidation, DFT simulation, and DNA interactional studies via wet and in silico methods

Samina Qamar, Fouzia Perveen, Zareen Akhter^*, Sammer Yousuf, Muhammd Sultan, Sule Erten Ela, Naimat Ullah, Kalsoom Fatima, Sehrish kanwal

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

Abstract

A new ester namely,1-((4-(4-nitrophenoxy)phenyl)diazenyl)biphenyl benzoate, has been synthesized by esterification reaction between reported nitro terminated azo alcohol and benzoyl chloride. Complete structural elucidation of the synthesized ester was done by different spectroscopic techniques including (FT-IR), (Proton and Carbon-13 NMR), (UV/VIS) spectroscopy, and single-crystal XRD analysis and cyclic voltammetry. XRD structural elucidation revealed the ester 1a to be in Triclinic crystal system with P-1 space groups, showing two-dimensional supramolecular structure, involving only one intermolecular interaction between O4-O9…H9. DFT simulations were also performed to illustrate structural ramification of synthesized ester. Further, Drug DNA interaction was used to determine the biological significance of the produced ester. UV–VIS spectroscopy, hydrodynamic measurement, and molecular docking were used to determine the preferred binding mode of interaction of the synthesized ester with Salmon Sperm (SS) DNA and found that molecule interacts in groove binding fashion with DNA molecule. 2021 Elsevier Ltd. All rights reserved.

Original language	English
Article number	131695
Journal	Journal of Molecular Structure
Volume	1250
DOIs	https://doi.org/10.1016/j.molstruc.2021.131695
State	Published - 15 Feb 2022
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2021 Elsevier B.V.

Keywords

Azo-esters
DFT simulation
DNA binding
Molecular docking
Synthesis
Viscosity

ASJC Scopus subject areas

Analytical Chemistry
Spectroscopy
Organic Chemistry
Inorganic Chemistry

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10.1016/j.molstruc.2021.131695

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@article{81e484d371ec44289e65b8d8df43f27e,

title = "4,4-Nitrophenoxyaniline derived Azo ester: Structural elucidation, DFT simulation, and DNA interactional studies via wet and in silico methods",

abstract = "A new ester namely,1-((4-(4-nitrophenoxy)phenyl)diazenyl)biphenyl benzoate, has been synthesized by esterification reaction between reported nitro terminated azo alcohol and benzoyl chloride. Complete structural elucidation of the synthesized ester was done by different spectroscopic techniques including (FT-IR), (Proton and Carbon-13 NMR), (UV/VIS) spectroscopy, and single-crystal XRD analysis and cyclic voltammetry. XRD structural elucidation revealed the ester 1a to be in Triclinic crystal system with P-1 space groups, showing two-dimensional supramolecular structure, involving only one intermolecular interaction between O4-O9…H9. DFT simulations were also performed to illustrate structural ramification of synthesized ester. Further, Drug DNA interaction was used to determine the biological significance of the produced ester. UV–VIS spectroscopy, hydrodynamic measurement, and molecular docking were used to determine the preferred binding mode of interaction of the synthesized ester with Salmon Sperm (SS) DNA and found that molecule interacts in groove binding fashion with DNA molecule. 2021 Elsevier Ltd. All rights reserved.",

keywords = "Azo-esters, DFT simulation, DNA binding, Molecular docking, Synthesis, Viscosity",

author = "Samina Qamar and Fouzia Perveen and Zareen Akhter and Sammer Yousuf and Muhammd Sultan and \{Erten Ela\}, Sule and Naimat Ullah and Kalsoom Fatima and Sehrish kanwal",

note = "Publisher Copyright: {\textcopyright} 2021 Elsevier B.V.",

year = "2022",

month = feb,

day = "15",

doi = "10.1016/j.molstruc.2021.131695",

language = "English",

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TY - JOUR

T1 - 4,4-Nitrophenoxyaniline derived Azo ester

T2 - Structural elucidation, DFT simulation, and DNA interactional studies via wet and in silico methods

AU - Qamar, Samina

AU - Perveen, Fouzia

AU - Akhter, Zareen

AU - Yousuf, Sammer

AU - Sultan, Muhammd

AU - Erten Ela, Sule

AU - Ullah, Naimat

AU - Fatima, Kalsoom

AU - kanwal, Sehrish

PY - 2022/2/15

Y1 - 2022/2/15

N2 - A new ester namely,1-((4-(4-nitrophenoxy)phenyl)diazenyl)biphenyl benzoate, has been synthesized by esterification reaction between reported nitro terminated azo alcohol and benzoyl chloride. Complete structural elucidation of the synthesized ester was done by different spectroscopic techniques including (FT-IR), (Proton and Carbon-13 NMR), (UV/VIS) spectroscopy, and single-crystal XRD analysis and cyclic voltammetry. XRD structural elucidation revealed the ester 1a to be in Triclinic crystal system with P-1 space groups, showing two-dimensional supramolecular structure, involving only one intermolecular interaction between O4-O9…H9. DFT simulations were also performed to illustrate structural ramification of synthesized ester. Further, Drug DNA interaction was used to determine the biological significance of the produced ester. UV–VIS spectroscopy, hydrodynamic measurement, and molecular docking were used to determine the preferred binding mode of interaction of the synthesized ester with Salmon Sperm (SS) DNA and found that molecule interacts in groove binding fashion with DNA molecule. 2021 Elsevier Ltd. All rights reserved.

AB - A new ester namely,1-((4-(4-nitrophenoxy)phenyl)diazenyl)biphenyl benzoate, has been synthesized by esterification reaction between reported nitro terminated azo alcohol and benzoyl chloride. Complete structural elucidation of the synthesized ester was done by different spectroscopic techniques including (FT-IR), (Proton and Carbon-13 NMR), (UV/VIS) spectroscopy, and single-crystal XRD analysis and cyclic voltammetry. XRD structural elucidation revealed the ester 1a to be in Triclinic crystal system with P-1 space groups, showing two-dimensional supramolecular structure, involving only one intermolecular interaction between O4-O9…H9. DFT simulations were also performed to illustrate structural ramification of synthesized ester. Further, Drug DNA interaction was used to determine the biological significance of the produced ester. UV–VIS spectroscopy, hydrodynamic measurement, and molecular docking were used to determine the preferred binding mode of interaction of the synthesized ester with Salmon Sperm (SS) DNA and found that molecule interacts in groove binding fashion with DNA molecule. 2021 Elsevier Ltd. All rights reserved.

KW - Azo-esters

KW - DFT simulation

KW - DNA binding

KW - Molecular docking

KW - Synthesis

KW - Viscosity

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U2 - 10.1016/j.molstruc.2021.131695

DO - 10.1016/j.molstruc.2021.131695

M3 - Article

AN - SCOPUS:85117375026

SN - 0022-2860

VL - 1250

JO - Journal of Molecular Structure

JF - Journal of Molecular Structure

M1 - 131695

ER -

4,4-Nitrophenoxyaniline derived Azo ester: Structural elucidation, DFT simulation, and DNA interactional studies via wet and in silico methods

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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