Privileged Scaffold Chalcone: Synthesis, Characterization and Its Mechanistic Interaction Studies with BSA Employing Spectroscopic and Chemoinformatics Approaches
Identifieur interne : 000074 ( Main/Exploration ); précédent : 000073; suivant : 000075Privileged Scaffold Chalcone: Synthesis, Characterization and Its Mechanistic Interaction Studies with BSA Employing Spectroscopic and Chemoinformatics Approaches
Auteurs : Nidhi Singh [Inde] ; Neeraj Kumar [Inde] ; Garima Rathee [Inde] ; Damini Sood [Inde] ; Aarushi Singh [Inde] ; Vartika Tomar [Inde] ; Sujata K. Dass [Inde] ; Ramesh Chandra [Inde]Source :
- ACS Omega [ 2470-1343 ] ; 2020.
Abstract
Chalcone, a privileged structure, is considered as an effective template in the field of medicinal chemistry for potent drug discovery. In the present study, a privileged template chalcone was designed, synthesized, and characterized by various spectroscopic techniques (NMR, high-resolution mass spectrometry, Fourier transform infrared (FT-IR) spectroscopy, UV spectroscopy, and single-crystal X-ray diffraction). The mechanism of binding of chalcone with bovine serum albumin (BSA) was determined by multispectroscopic techniques and computational methods. Steady-state fluorescence spectroscopy suggests that the intrinsic fluorescence of BSA was quenched upon the addition of chalcone by the combined dynamic and static quenching mechanism. Time-resolved spectroscopy confirms complex formation. FT-IR and circular dichroism spectroscopy suggested the presence of chalcone in the BSA molecule microenvironment and also the possibility of rearrangement of the native structure of BSA. Moreover, molecular docking studies confirm the moderate binding of chalcone with BSA and the molecular dynamics simulation analysis shows the stability of the BSA–drug complex system with minimal deformability fluctuations and potential interaction by the covariance matrix. Moreover, pharmacodynamics and pharmacological analysis show good results through Lipinski rules, with no toxicity profile and high gastrointestinal absorptions by boiled egg permeation assays. This study elucidates the mechanistic profile of the privileged chalcone scaffold to be used in therapeutic applications.
Url:
DOI: 10.1021/acsomega.9b03479
PubMed: 32064388
PubMed Central: 7016911
Affiliations:
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and Its Mechanistic Interaction Studies with BSA Employing Spectroscopic
and Chemoinformatics Approaches</title><author><name sortKey="Singh, Nidhi" sort="Singh, Nidhi" uniqKey="Singh N" first="Nidhi" last="Singh">Nidhi Singh</name><affiliation wicri:level="1"><nlm:aff id="aff1">Department of Chemistry,<institution>University of Delhi</institution>, Delhi 110007,<country>India</country></nlm:aff><country xml:lang="fr">Inde</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Kumar, Neeraj" sort="Kumar, Neeraj" uniqKey="Kumar N" first="Neeraj" last="Kumar">Neeraj Kumar</name><affiliation wicri:level="1"><nlm:aff id="aff1">Department of Chemistry,<institution>University of Delhi</institution>, Delhi 110007,<country>India</country></nlm:aff><country xml:lang="fr">Inde</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Rathee, Garima" sort="Rathee, Garima" uniqKey="Rathee G" first="Garima" last="Rathee">Garima Rathee</name><affiliation wicri:level="1"><nlm:aff id="aff1">Department of Chemistry,<institution>University of Delhi</institution>, Delhi 110007,<country>India</country></nlm:aff><country xml:lang="fr">Inde</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Sood, Damini" sort="Sood, Damini" uniqKey="Sood D" first="Damini" last="Sood">Damini Sood</name><affiliation wicri:level="1"><nlm:aff id="aff1">Department of Chemistry,<institution>University of Delhi</institution>, Delhi 110007,<country>India</country></nlm:aff><country xml:lang="fr">Inde</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Singh, Aarushi" sort="Singh, Aarushi" uniqKey="Singh A" first="Aarushi" last="Singh">Aarushi Singh</name><affiliation wicri:level="1"><nlm:aff id="aff1">Department of Chemistry,<institution>University of Delhi</institution>, Delhi 110007,<country>India</country></nlm:aff><country xml:lang="fr">Inde</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Tomar, Vartika" sort="Tomar, Vartika" uniqKey="Tomar V" first="Vartika" last="Tomar">Vartika Tomar</name><affiliation wicri:level="1"><nlm:aff id="aff1">Department of Chemistry,<institution>University of Delhi</institution>, Delhi 110007,<country>India</country></nlm:aff><country xml:lang="fr">Inde</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Dass, Sujata K" sort="Dass, Sujata K" uniqKey="Dass S" first="Sujata K." last="Dass">Sujata K. Dass</name><affiliation wicri:level="1"><nlm:aff id="aff2"><institution>BLK Super Speciality Hospital</institution>, Pusa Road, Delhi, New Delhi 110005,<country>India</country></nlm:aff><country xml:lang="fr">Inde</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Chandra, Ramesh" sort="Chandra, Ramesh" uniqKey="Chandra R" first="Ramesh" last="Chandra">Ramesh Chandra</name><affiliation wicri:level="1"><nlm:aff id="aff1">Department of Chemistry,<institution>University of Delhi</institution>, Delhi 110007,<country>India</country></nlm:aff><country xml:lang="fr">Inde</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation><affiliation wicri:level="1"><nlm:aff id="aff3">Dr. B. R. Ambedkar Center for Biomedical Research,<institution>University of Delhi</institution>, Delhi 110007,<country>India</country></nlm:aff><country xml:lang="fr">Inde</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author></analytic><series><title level="j">ACS Omega</title><idno type="eISSN">2470-1343</idno><imprint><date when="2020">2020</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p content-type="toc-graphic"><graphic xlink:href="ao9b03479_0009" id="ab-tgr1"></graphic></p><p>Chalcone,
a privileged structure, is considered as an effective
template in the field of medicinal chemistry for potent drug discovery.
In the present study, a privileged template chalcone was designed,
synthesized, and characterized by various spectroscopic techniques
(NMR, high-resolution mass spectrometry, Fourier transform infrared
(FT-IR) spectroscopy, UV spectroscopy, and single-crystal X-ray diffraction).
The mechanism of binding of chalcone with bovine serum albumin (BSA)
was determined by multispectroscopic techniques and computational
methods. Steady-state fluorescence spectroscopy suggests that the
intrinsic fluorescence of BSA was quenched upon the addition of chalcone
by the combined dynamic and static quenching mechanism. Time-resolved
spectroscopy confirms complex formation. FT-IR and circular dichroism
spectroscopy suggested the presence of chalcone in the BSA molecule
microenvironment and also the possibility of rearrangement of the
native structure of BSA. Moreover, molecular docking studies confirm
the moderate binding of chalcone with BSA and the molecular dynamics
simulation analysis shows the stability of the BSA–drug complex
system with minimal deformability fluctuations and potential interaction
by the covariance matrix. Moreover, pharmacodynamics and pharmacological
analysis show good results through Lipinski rules, with no toxicity
profile and high gastrointestinal absorptions by boiled egg permeation
assays. This study elucidates the mechanistic profile of the privileged
chalcone scaffold to be used in therapeutic applications.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="Carter, D C" uniqKey="Carter D">D. C. Carter</name></author><author><name sortKey="Ho, J X0a X" uniqKey="Ho J">J.
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