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

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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.

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Acknowledgments

Grants-in-aid for Research Project; Promotion of Advanced Medical Technology (H18-Nano-001); Ministry of Health, Labour and Welfare of Japan is gratefully acknowledged. The authors thank the crew of the Center for Computational Materials Science at Institute for Materials Research, Tohoku University, for their continuous support of the HITACHI SR11000 supercomputing facility.

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Authors and Affiliations

  1. Institute for Materials Research (IMR), Tohoku University, 2-1-1, Katahira, Aoba-Ku, Sendai, 980-8577, Japan

    Ambigapathy Suvitha, Natarajan Sathiyamoorthy Venkataramanan, Hiroshi Mizuseki & Yoshiyuki Kawazoe

  2. Department of Surgical Oncology, Tohoku University School of Medicine, Sendai, 980-8579, Japan

    Nobiaki Ohuchi

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  1. Ambigapathy Suvitha
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  2. Natarajan Sathiyamoorthy Venkataramanan
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  3. Hiroshi Mizuseki
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Correspondence to Natarajan Sathiyamoorthy Venkataramanan.

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Suvitha, A., Venkataramanan, N.S., Mizuseki, H. et al. Theoretical insights into the formation, structure, and electronic properties of anticancer oxaliplatin drug and cucurbit[n]urils n = 5 to 8. J Incl Phenom Macrocycl Chem 66, 213–218 (2010). https://doi.org/10.1007/s10847-009-9601-2

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