Theoretical insights into the formation, structure, and electronic properties of anticancer oxaliplatin drug and cucurbit[n]urils n = 5 to 8

Ambigapathy Suvitha, Natarajan Sathiyamoorthy Venkataramanan, Hiroshi Mizuseki, Yoshiyuki Kawazoe, Nobiaki Ohuchi

Research output: Contribution to journalReview article

47 Citations (Scopus)

Abstract

Geometries, formation and electronic properties of cucurbit[n]uril-oxaliplatin n = 5-8, host-guest complexes are investigated with DFT calculations. The formation of inclusion complexes of CB[n]-oxaliplatin are facile in CB[n] n = 6-8. In the complex, the cyclohexyl group is found to be deep inside the cavity, with the formation of a hydrogen bonding between the portal oxygen atoms and the amine nitrogen of the oxaliplatin guest. NBO analysis shows the transfer of charge from the metal center to the CB[7] unit and the existence of hydrogen bonding between the oxygen portal and amine nitrogen. The HOMO orbital is localized on the carboxylate group and the LUMO orbital are localized on the cucurbituril unit in CB[7]-oxaliplatin complex. The strength of the interaction determined here reflects the ability of CB[n] to act as a host for suitably oxaliplatin guests, even in aqueous solution.

Original languageEnglish
Pages (from-to)213-218
Number of pages6
JournalJournal of Inclusion Phenomena and Macrocyclic Chemistry
Volume66
Issue number3
DOIs
Publication statusPublished - 2010 Jan 1

Keywords

  • Cancer drugs
  • Cucurbit[n]urils
  • DFT
  • Inclusion complex
  • Oxaliplatin

ASJC Scopus subject areas

  • Food Science
  • Chemistry(all)
  • Condensed Matter Physics

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