Literature DB >> 30457873

Electron-Mediated Aminyl and Iminyl Radicals from C5 Azido-Modified Pyrimidine Nucleosides Augment Radiation Damage to Cancer Cells.

Zhiwei Wen1, Jufang Peng1, Paloma R Tuttle1, Yaou Ren1, Carol Garcia1, Dipra Debnath2, Sunny Rishi2, Cameron Hanson2, Samuel Ward2, Anil Kumar2, Yanfeng Liu3, Weixi Zhao3, Peter M Glazer3, Yuan Liu1, Michael D Sevilla2, Amitava Adhikary2, Stanislaw F Wnuk1.   

Abstract

Two classes of azido-modified pyrimidine nucleosides were synthesized as potential radiosensitizers; one class is 5-azidomethyl-2'-deoxyuridine (AmdU) and cytidine (AmdC), while the second class is 5-(1-azidovinyl)-2'-deoxyuridine (AvdU) and cytidine (AvdC). The addition of radiation-produced electrons to C5-azido nucleosides leads to the formation of π-aminyl radicals followed by facile conversion to σ-iminyl radicals either via a bimolecular reaction involving intermediate α-azidoalkyl radicals in AmdU/AmdC or by tautomerization in AvdU/AvdC. AmdU demonstrates effective radiosensitization in EMT6 tumor cells.

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Year:  2018        PMID： 30457873      PMCID： PMC6465127          DOI： 10.1021/acs.orglett.8b03035

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  35 in total

1.  Radiosensitization effect of zidovudine on human malignant glioma cells.

Authors:  Fu-Xiang Zhou; Zheng-Kai Liao; Jing Dai; Jie Xiong; Cong-Hua Xie; Zhi-Guo Luo; Shi-Quan Liu; Yun-Feng Zhou
Journal:  Biochem Biophys Res Commun       Date:  2007-01-02       Impact factor: 3.575

2.  Pyrimidine Nucleobase Radical Reactivity in DNA and RNA.

Authors:  Marc M Greenberg
Journal:  Radiat Phys Chem Oxf Engl 1993       Date:  2016-06-07       Impact factor: 2.858

3.  Prehydrated One-Electron Attachment to Azido-Modified Pentofuranoses: Aminyl Radical Formation, Rapid H-Atom Transfer, and Subsequent Ring Opening.

Authors:  Mukesh Mudgal; Sunny Rishi; Daniel A Lumpuy; Keaton A Curran; Kathryn Lynn Verley; Adam J Sobczak; Thao P Dang; Natasha Sulimoff; Anil Kumar; Michael D Sevilla; Stanislaw F Wnuk; Amitava Adhikary
Journal:  J Phys Chem B       Date:  2017-05-03       Impact factor: 2.991

4.  Polyfunctional radiosensitizers IV. The effect of contact time and temperature on sensitization of hypoxic Chinese hamster cells in vitro by bifunctional nitroxyl compounds.

Authors:  B C Millar; E M Fielden; C E Smithen
Journal:  Br J Cancer Suppl       Date:  1978-06

5.  Independent Photochemical Generation and Reactivity of Nitrogen-Centered Purine Nucleoside Radicals from Hydrazines.

Authors:  Liwei Zheng; Lu Lin; Ke Qu; Amitava Adhikary; Michael D Sevilla; Marc M Greenberg
Journal:  Org Lett       Date:  2017-11-10       Impact factor: 6.005

6.  Oxygen independent DNA interstrand cross-link formation by a nucleotide radical.

Authors:  In Seok Hong; Hui Ding; Marc M Greenberg
Journal:  J Am Chem Soc       Date:  2006-01-18       Impact factor: 15.419

Review 7.  Radiotherapy for patients with the human immunodeficiency virus: are special precautions necessary?

Authors:  Nadine Housri; Robert Yarchoan; Aradhana Kaushal
Journal:  Cancer       Date:  2010-01-15       Impact factor: 6.860

8.  5-Substituted 2'-deoxyuridines: correlation between inhibition of tumor cell growth and inhibition of thymidine kinase and thymidylate synthetase.

Authors:  J Balzarini; E De Clercq; M P Mertes; D Shugar; P F Torrence
Journal:  Biochem Pharmacol       Date:  1982-11-15       Impact factor: 5.858

9.  The toxicity of azidothymidine (AZT) on human and animal cells in culture at concentrations used for antiviral therapy.

Authors:  D T Chiu; P H Duesberg
Journal:  Genetica       Date:  1995       Impact factor: 1.082

10.  2'-Azido RNA, a versatile tool for chemical biology: synthesis, X-ray structure, siRNA applications, click labeling.

Authors:  Katja Fauster; Markus Hartl; Tobias Santner; Michaela Aigner; Christoph Kreutz; Klaus Bister; Eric Ennifar; Ronald Micura
Journal:  ACS Chem Biol       Date:  2012-01-24       Impact factor: 5.100
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  5 in total

1.  Fluorescent 5-Pyrimidine and 8-Purine Nucleosides Modified with an N-Unsubstituted 1,2,3-Triazol-4-yl Moiety.

Authors:  Zhiwei Wen; Paloma R Tuttle; A Hasan Howlader; Anna Vasilyeva; Laura Gonzalez; Antonija Tangar; Ruipeng Lei; Eduardo E Laverde; Yuan Liu; Jaroslava Miksovska; Stanislaw F Wnuk
Journal:  J Org Chem       Date:  2019-03-06       Impact factor: 4.354

2.  Quasi-Free Electron-Mediated Radiation Sensitization by C5-Halopyrimidines.

Authors:  Jun Ma; Teseer Bahry; Sergey A Denisov; Amitava Adhikary; Mehran Mostafavi
Journal:  J Phys Chem A       Date:  2021-09-02       Impact factor: 2.944

3.  Site of Azido Substitution in the Sugar Moiety of Azidopyrimidine Nucleosides Influences the Reactivity of Aminyl Radicals Formed by Dissociative Electron Attachment.

Authors:  Mukesh Mudgal; Thao P Dang; Adam J Sobczak; Daniel A Lumpuy; Priya Dutta; Samuel Ward; Katherine Ward; Moaadh Alahmadi; Anil Kumar; Michael D Sevilla; Stanislaw F Wnuk; Amitava Adhikary
Journal:  J Phys Chem B       Date:  2020-12-03       Impact factor: 2.991

Review 4.  Reaction of Electrons with DNA: Radiation Damage to Radiosensitization.

Authors:  Anil Kumar; David Becker; Amitava Adhikary; Michael D Sevilla
Journal:  Int J Mol Sci       Date:  2019-08-16       Impact factor: 5.923

5.  5-Nitro-2,4-Dichloropyrimidine as an Universal Model for Low-Energy Electron Processes Relevant for Radiosensitization.

Authors:  Thomas F M Luxford; Stanislav A Pshenichnyuk; Nail L Asfandiarov; Tomáš Perečko; Martin Falk; Jaroslav Kočišek
Journal:  Int J Mol Sci       Date:  2020-10-31       Impact factor: 5.923
  5 in total

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