دورية أكاديمية
Time- and concentration-dependent reactivity of Cys, Hcy, and GSH on the Diels-Alder-grafted 1,3,5-tris conjugate of calix[6]arene to bring selectivity for Cys: spectroscopy, microscopy, and its reactivity in cells.
| العنوان: | Time- and concentration-dependent reactivity of Cys, Hcy, and GSH on the Diels-Alder-grafted 1,3,5-tris conjugate of calix[6]arene to bring selectivity for Cys: spectroscopy, microscopy, and its reactivity in cells. |
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| المؤلفون: | Mummidivarapu VV; Bioinorganic Laboratory, Department of Chemistry, Indian Institute of Technology Bombay , Powai, Mumbai 400 076, India., Yarramala DS, Kondaveeti KK, Rao CP |
| المصدر: | The Journal of organic chemistry [J Org Chem] 2014 Nov 07; Vol. 79 (21), pp. 10477-86. Date of Electronic Publication: 2014 Oct 22. |
| نوع المنشور: | Journal Article; Research Support, Non-U.S. Gov't |
| اللغة: | English |
| بيانات الدورية: | Publisher: American Chemical Society Country of Publication: United States NLM ID: 2985193R Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1520-6904 (Electronic) Linking ISSN: 00223263 NLM ISO Abbreviation: J Org Chem Subsets: MEDLINE |
| أسماء مطبوعة: | Publication: Columbus Oh : American Chemical Society Original Publication: Easton, Pa. [etc.] |
| مواضيع طبية MeSH: | Calixarenes/*chemical synthesis , Calixarenes/*chemistry , Cysteine/*chemistry , Glutathione/*chemistry , Homocysteine/*chemistry , Norbornanes/*chemical synthesis , Norbornanes/*chemistry , Phenols/*chemical synthesis , Phenols/*chemistry, Cycloaddition Reaction ; HeLa Cells ; Humans ; Magnetic Resonance Spectroscopy ; Microscopy/methods ; Microscopy, Fluorescence/methods |
| مستخلص: | Herein we report the synthesis and characterization of 7-oxanorbornadiene (OND)-appended 1,3,5-tris conjugate of calix[6]arene (L2). L2 has been shown to exhibit selective reactivity toward cysteine (Cys) over homocysteine (Hcy) and glutathione (GSH) under stoichiometric conditions. The selectivity of L2 is attributed to the steric crowding of three Diels-Alder centers possessing OND units present on the calix[6]arene platform, while a control molecular system possessing only one such unit without the calix[6]arene platform (L1) does not show any selectivity toward Cys. While L2 exhibited spherical particles, its reactivity with Cys resulted in flowerlike morphological features, as revealed by scanning electron microscopy. However, the reaction with GSH did not result in any such morphological features, a result that is in agreement with that observed from fluorescence studies in solution. L2 has been shown to react with Cys present in HeLa and Jurkat E6 cells by fluorescence microscopy. |
| المشرفين على المادة: | 0 (7-oxanorbornadiene) 0 (Norbornanes) 0 (Phenols) 0 (calix(6)arene) 0LVT1QZ0BA (Homocysteine) 130036-26-9 (Calixarenes) GAN16C9B8O (Glutathione) K848JZ4886 (Cysteine) |
| تواريخ الأحداث: | Date Created: 20141014 Date Completed: 20150930 Latest Revision: 20150105 |
| رمز التحديث: | 20240628 |
| DOI: | 10.1021/jo5021213 |
| PMID: | 25310270 |
| قاعدة البيانات: | MEDLINE |
Find this issue from the American Chemical Society | تدمد: | 1520-6904 |
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| DOI: | 10.1021/jo5021213 |