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Inclusion of capecitabine into cucurbiturils: DFT study for supramolecular encapsulation of anticancer drug

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Abstract

Electronic structure and stability of the encapsulated complexes of capecitabine (CAP, prodrug of 5-fluorouracil) with cucurbit [n = 5 ~ 8]urils (CB[n]) in water were studied by means of DFT computations with dispersion (D3) and geometrical counterpoise (gCP) corrections. Among CB [n = 5 ~ 8] with different inner sizes, CB [n = 6, 7] can form more stable inclusion complexes (CAP@CB[n]) with CAP than CB [n = 5, 8]. DFT computations showed that CAP@CB[7] with the normal CB[7] was the most stable in water, and some inverted CB[7] and CB[6] can also form relatively stable inclusion complexes. Dispersion correction played an important role in calculation of interaction energy between CAP and C [n]. Intermolecular non-covalent interaction and natural bond orbital analysis showed that electron transfer from CB[7] to CAP made CAP@CB[7] stable, when two hydrogen bonds (N–H…O and O–H…O) between CAP and CB[7] played positive role.

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Authors and Affiliations

  1. Faculty of Chemistry, Kim Il Sung University, Pyongyang, Democratic People’s Republic of Korea

    Kye-Ryong Sin, Chol-Jin Kim, Sun-Gyong Ko, Sung-Hui Pak, Mun-Ho Son & Mun-Il Choe

  2. Faculty of Chemistry, Kim Hyong Jik Normal University, Pyongyang, Democratic People’s Republic of Korea

    Chol-Jin Kim

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  1. Kye-Ryong Sin
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  2. Chol-Jin Kim
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  3. Sun-Gyong Ko
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  4. Sung-Hui Pak
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  5. Mun-Ho Son
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Sin, KR., Kim, CJ., Ko, SG. et al. Inclusion of capecitabine into cucurbiturils: DFT study for supramolecular encapsulation of anticancer drug. Monatsh Chem 152, 209–216 (2021). https://doi.org/10.1007/s00706-020-02724-0

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  • DOI: https://doi.org/10.1007/s00706-020-02724-0

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