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p-Sulfonatocalixarene versus p-thiasulfonatocalixarene: encapsulation of tenofovir disoproxil fumarate and implications to ESI-MS, HPLC, NMR, DFT and anti-MRSA activities

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Abstract

The inclusion complexes of tenofovir disoproxil fumarate (TDF) with p-sulfonato-calix[4]arene (SCX4) and p-sulfanatothiacalix[4]arene (TSCX4) macrocycles are characterized through an array of experiments including 1H NMR, NOESY, HPLC, HRMS, FT-IR and PXRD in conjunction with the density functional theory. An encapsulation of TDF within SCX4 and TSCX4 macrocycles conduce 1:1 complexes those prevail over 1:2 or 1:3 Stoichiometries which exhibis distinct structural features. A loss of crystallinity accompanying the complexation ascertains the inclusion of the guest within the macrocycle. A comparison of the measured 13C NMR spectra of the complexes with individual hosts ascertains the cone conformation of SCX4 in such complexes as in its free state. It has been demonstrated that the TDF guest penetrates deeply within the cavity of SCX4 facilitating the hydrogen bonding interactions between adenine protons and the hydroxyl as well as methylene protons of the macrocycle. The measured 1H NMR spectra thus reveal large upfield signals (δ 8.35, 8.48 ppm) for adenine protons of the SCX4 complex. On the other hand, the partial encapsulation of TDF in TSCX4 reflects in the deshielding of hydroxyl protons in the measured 1H NMR spectra. The characteristic C=N and SO stretching vibrations in the infrared spectra engender’frequency shifts’ in the opposite directions compared to the individual host or guest. A simple reverse phase high performance liquid chromatography method is presented. The adenine encapsulation further has been qualitatively correlated with MRSA activities.

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Acknowledgements

One of the authors, S.V.P. acknowledges supports Women Scientist (WOS-A) from the research project (SR/WOS-A/CS-87/2018 (G) DST) from the Department of Science and Technology, India. Authors thank the Central Instrumental Facility, Savitribai Phule Pune University for the instrumentation facilities. V.S.N. thanks to Savitribai Phule Pune University, Post-Doctoral Fellowship for financial support. S.P.G acknowledges support from the research projects (37(2)/14/11/2015-BRNS) from the Board of Research in Nuclear Sciences (BRNS) and University Grants Commission, New Delhi (F. No. 42-289/2013) and the National Param Supercomputing Facility at the Centre for Development of Advanced Computing (CDAC), Pune, India where the molecular modelling studies were carried out.

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  1. Department of Chemistry, Savitribai Phule Pune University, Pune, Maharashtra, 411007, India

    Asmita B. Jarange, Sanhita V. Patil, Dipalee D. Malkhede, Shreya M. Deodhar, Vinod S. Nandre, Sulakshana V. Athare, Kisan M. Kodam & Shridhar P. Gejji

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Jarange, A.B., Patil, S.V., Malkhede, D.D. et al. p-Sulfonatocalixarene versus p-thiasulfonatocalixarene: encapsulation of tenofovir disoproxil fumarate and implications to ESI-MS, HPLC, NMR, DFT and anti-MRSA activities. J Incl Phenom Macrocycl Chem 99, 43–59 (2021). https://doi.org/10.1007/s10847-020-01022-w

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  • DOI: https://doi.org/10.1007/s10847-020-01022-w

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