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

IF 1.7 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Journal of Inclusion Phenomena and Macrocyclic Chemistry Pub Date : 2021-01-14 DOI:10.1007/s10847-020-01022-w
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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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.

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对磺酰基杯芳烃与对巯基杯芳烃:富马酸替诺福韦二氧吡酯的包封及其对ESI-MS、HPLC、NMR、DFT和抗mrsa活性的影响
结合密度泛函理论,通过1H NMR、noesi、HPLC、HRMS、FT-IR和PXRD等一系列实验表征了富马酸替诺福韦二氧吡酯(TDF)与对磺酰基杯[4]芳烃(SCX4)和对磺酰基杯[4]芳烃(TSCX4)大环的包合物。将TDF包封在SCX4和TSCX4大环内可形成1:1的配合物,这些配合物优于1:2或1:3的化学计量学,具有明显的结构特征。结晶度的损失伴随着络合确定了客体在大环内的包含。通过与单个宿主的13C核磁共振谱的比较,确定了SCX4在这些配合物中如在其自由状态下的锥形构象。研究表明,TDF客体深入SCX4的腔内,促进了腺嘌呤质子与大环的羟基和亚甲基质子之间的氢键相互作用。因此,测量的1H NMR谱揭示了SCX4配合物的腺嘌呤质子的大上场信号(δ 8.35, 8.48?ppm)。另一方面,TDF在TSCX4中的部分包封反映在1H NMR谱中羟基质子的去屏蔽。红外光谱中的特征C=N和SO伸展振动产生与单个主客体相反方向的“频移”。提出了一种简单的反相高效液相色谱法。腺嘌呤包封进一步与MRSA活性定性相关。
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来源期刊
Journal of Inclusion Phenomena and Macrocyclic Chemistry
Journal of Inclusion Phenomena and Macrocyclic Chemistry Agricultural and Biological Sciences-Food Science
CiteScore
4.10
自引率
8.70%
发文量
54
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.
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