p-Sulfonatocalixarene versus p-thiasulfonatocalixarene: encapsulation of tenofovir disoproxil fumarate and implications to ESI-MS, HPLC, NMR, DFT and anti-MRSA activities
Asmita B. Jarange, Sanhita V. Patil, Dipalee D. Malkhede, Shreya M. Deodhar, Vinod S. Nandre, Sulakshana V. Athare, Kisan M. Kodam, Shridhar P. Gejji
{"title":"p-Sulfonatocalixarene versus p-thiasulfonatocalixarene: encapsulation of tenofovir disoproxil fumarate and implications to ESI-MS, HPLC, NMR, DFT and anti-MRSA activities","authors":"Asmita B. Jarange, Sanhita V. Patil, Dipalee D. Malkhede, Shreya M. Deodhar, Vinod S. Nandre, Sulakshana V. Athare, Kisan M. Kodam, Shridhar P. Gejji","doi":"10.1007/s10847-020-01022-w","DOIUrl":null,"url":null,"abstract":"<p>The inclusion complexes of tenofovir disoproxil fumarate (TDF) with <i>p</i>-sulfonato-calix[4]arene (SCX4) and <i>p</i>-sulfanatothiacalix[4]arene (TSCX4) macrocycles are characterized through an array of experiments including <sup>1</sup>H 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 <sup>13</sup>C 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 <sup>1</sup>H 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 <sup>1</sup>H 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.</p>","PeriodicalId":54324,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":1.7000,"publicationDate":"2021-01-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/s10847-020-01022-w","citationCount":"5","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s10847-020-01022-w","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 5
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.
期刊介绍:
The Journal of Inclusion Phenomena and Macrocyclic Chemistry is the premier interdisciplinary publication reporting on original research into all aspects of host-guest systems. Examples of specific areas of interest are: the preparation and characterization of new hosts and new host-guest systems, especially those involving macrocyclic ligands; crystallographic, spectroscopic, thermodynamic and theoretical studies; applications in chromatography and inclusion polymerization; enzyme modelling; molecular recognition and catalysis by inclusion compounds; intercalates in biological and non-biological systems, cyclodextrin complexes and their applications in the agriculture, flavoring, food and pharmaceutical industries; synthesis, characterization and applications of zeolites.
The journal publishes primarily reports of original research and preliminary communications, provided the latter represent a significant advance in the understanding of inclusion science. Critical reviews dealing with recent advances in the field are a periodic feature of the journal.