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Deciphering the nature of interactions in nandrolone/testosterone encapsulated cucurbituril complexes: a computational study

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Abstract

The intention of the study is to find the nature of interactions that exist in inclusion complexes formed between the steroids, nandrolone, and testosterone with cucurbit[n]urnils (n = 7 and 8) host, using density functional theory incorporated with empirical dispersion correction. Upon encapsulation, nandrolone caused a larger geometrical distortion in cucurbit[8]uril geometry, while testosterone inclusion complex is formed with a larger number of intermolecular hydrogen bonds. The molecular electrostatic potential examination shows that the positive potential observed on the eight-membered ring in CB7 got reduced upon encapsulation, while on the nandrolone the negative potential on carbonyl unit has increased. AIM analysis shows that in inclusion complexes, the observed electron density are higher for the interactions between the oxygen atoms of carbonyl fringe of cucurbituril molecule and the steroid molecules. The NCI isosurface of nandrolone@CB7 has green patches in between the nandrolone and cucurbituril molecule, evenly distributed. In the testosterone@CB7, along with the green patches, red patches, due to the steric crowding between the testosterone and cucurbit[7]uril, were observed. The energy decomposition analysis parameters show that Pauli’s repulsive term was highest for nandrolone@CB7. When testosterone is the guest, repulsive energy was found to be larger than nandrolone guest. From the above interference, it can be confirmed that the steric hindrance that arises during the interaction of testosterone with CB7 reduces the stability of the complex, and the nandrolone best fit inside the CB7 cavity with the combination of hydrogen bonding and weak van der Waals bonding as intermolecular interactions.

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Funding

Funding was provided by Science and Engineering Research Board (Grant No: EMR-II-SB/S1/PC-047/2013).

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Authors and Affiliations

  1. Department of Chemistry, School of Chemical and Biotechnology (SCBT), SASTRA Deemed University, Thanjavur, 613 401, India

    A. Suvitha & N. S. Venkataramanan

  2. Research Center for Structural Materials, NIMS, 1-2-1 Sengen, Tsukuba, Ibaraki, 305-0047, Japan

    M. Souissi & R. Sahara

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  1. A. Suvitha
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  2. M. Souissi
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  3. R. Sahara
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  4. N. S. Venkataramanan
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Correspondence to N. S. Venkataramanan.

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Suvitha, A., Souissi, M., Sahara, R. et al. Deciphering the nature of interactions in nandrolone/testosterone encapsulated cucurbituril complexes: a computational study. J Incl Phenom Macrocycl Chem 93, 183–192 (2019). https://doi.org/10.1007/s10847-018-0869-y

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