Rational Design and Synthesis of Naphthalene Diimide Linked Bis-Naphthalimides as DNA Interactive Agents

M. Shaheer Malik; Syed Farooq Adil; Ziad Moussa; Hatem M. Altass; Ismail I. Althagafi; Moataz Morad; Mohammad Azam Ansari; Qazi Mohammad Sajid Jamal; Rami J. Obaid; Abdulrahman A. Al-Warthan; Thokhir B. Shaik; Saleh A. Ahmed

doi:10.3389/fchem.2021.630357

Rational Design and Synthesis of Naphthalene Diimide Linked Bis-Naphthalimides as DNA Interactive Agents

M. Shaheer Malik, Syed Farooq Adil, Ziad Moussa, Hatem M. Altass, Ismail I. Althagafi, Moataz Morad, Mohammad Azam Ansari, Qazi Mohammad Sajid Jamal, Rami J. Obaid, Abdulrahman A. Al-Warthan, Thokhir B. Shaik, Saleh A. Ahmed

Department of Chemistry

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

9 Citations (Scopus)

Abstract

A molecular modeling assisted rational design and synthesis of naphthalene diimide linked bis-naphthalimides as potential DNA interactive agents is described. Chemical templates incorporating naphthalene diimide as a linker in bis-naphthalimide motif were subjected to molecular docking analysis at specific intercalation and telomeric DNA G-quadruplex sites. Excellent results were obtained, which were better than the standards. A short and convenient synthetic route was employed to access these hybrids experimentally, followed by evaluation of their ability to cause thermal denaturation of DNA and cytotoxic properties along with ADME predictions. The obtained results provided useful insights and two potential molecules were identified for further development.

Original language	English
Article number	630357
Journal	Frontiers in Chemistry
Volume	9
DOIs	https://doi.org/10.3389/fchem.2021.630357
Publication status	Published - Mar 10 2021

Keywords

DNA interactive
anticancer agents
bis-naphthalimides
molecular modeling
naphthalene diimide

ASJC Scopus subject areas

Chemistry(all)

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10.3389/fchem.2021.630357

Cite this

Malik, M. S., Farooq Adil, S., Moussa, Z., Altass, H. M., Althagafi, I. I., Morad, M., Ansari, M. A., Sajid Jamal, Q. M., Obaid, R. J., Al-Warthan, A. A., Shaik, T. B., & Ahmed, S. A. (2021). Rational Design and Synthesis of Naphthalene Diimide Linked Bis-Naphthalimides as DNA Interactive Agents. Frontiers in Chemistry, 9, Article 630357. https://doi.org/10.3389/fchem.2021.630357

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title = "Rational Design and Synthesis of Naphthalene Diimide Linked Bis-Naphthalimides as DNA Interactive Agents",

abstract = "A molecular modeling assisted rational design and synthesis of naphthalene diimide linked bis-naphthalimides as potential DNA interactive agents is described. Chemical templates incorporating naphthalene diimide as a linker in bis-naphthalimide motif were subjected to molecular docking analysis at specific intercalation and telomeric DNA G-quadruplex sites. Excellent results were obtained, which were better than the standards. A short and convenient synthetic route was employed to access these hybrids experimentally, followed by evaluation of their ability to cause thermal denaturation of DNA and cytotoxic properties along with ADME predictions. The obtained results provided useful insights and two potential molecules were identified for further development.",

keywords = "DNA interactive, anticancer agents, bis-naphthalimides, molecular modeling, naphthalene diimide",

author = "Malik, {M. Shaheer} and {Farooq Adil}, Syed and Ziad Moussa and Altass, {Hatem M.} and Althagafi, {Ismail I.} and Moataz Morad and Ansari, {Mohammad Azam} and {Sajid Jamal}, {Qazi Mohammad} and Obaid, {Rami J.} and Al-Warthan, {Abdulrahman A.} and Shaik, {Thokhir B.} and Ahmed, {Saleh A.}",

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doi = "10.3389/fchem.2021.630357",

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AU - Altass, Hatem M.

AU - Althagafi, Ismail I.

AU - Morad, Moataz

AU - Ansari, Mohammad Azam

AU - Sajid Jamal, Qazi Mohammad

AU - Obaid, Rami J.

AU - Al-Warthan, Abdulrahman A.

AU - Shaik, Thokhir B.

AU - Ahmed, Saleh A.

N1 - Funding Information: The authors would like to thank the Deanship of Scientific Research at Umm Al-Qura University for supporting this work by grant code 19-SCI-1-01-0019. Publisher Copyright: © Copyright © 2021 Malik, Farooq Adil, Moussa, Altass, Althagafi, Morad, Ansari, Sajid Jamal, Obaid, Al-Warthan, Shaik and Ahmed.

PY - 2021/3/10

Y1 - 2021/3/10

N2 - A molecular modeling assisted rational design and synthesis of naphthalene diimide linked bis-naphthalimides as potential DNA interactive agents is described. Chemical templates incorporating naphthalene diimide as a linker in bis-naphthalimide motif were subjected to molecular docking analysis at specific intercalation and telomeric DNA G-quadruplex sites. Excellent results were obtained, which were better than the standards. A short and convenient synthetic route was employed to access these hybrids experimentally, followed by evaluation of their ability to cause thermal denaturation of DNA and cytotoxic properties along with ADME predictions. The obtained results provided useful insights and two potential molecules were identified for further development.

AB - A molecular modeling assisted rational design and synthesis of naphthalene diimide linked bis-naphthalimides as potential DNA interactive agents is described. Chemical templates incorporating naphthalene diimide as a linker in bis-naphthalimide motif were subjected to molecular docking analysis at specific intercalation and telomeric DNA G-quadruplex sites. Excellent results were obtained, which were better than the standards. A short and convenient synthetic route was employed to access these hybrids experimentally, followed by evaluation of their ability to cause thermal denaturation of DNA and cytotoxic properties along with ADME predictions. The obtained results provided useful insights and two potential molecules were identified for further development.

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Rational Design and Synthesis of Naphthalene Diimide Linked Bis-Naphthalimides as DNA Interactive Agents

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