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

Herein we report the synthesis and characterization of 7-oxanorbornadiene (OND)-appended 1,3,5-tris conjugate of calix[6]arene (L 2 ). L 2 has been shown to exhibit selective reactivity toward cysteine (Cys) over homocysteine (Hcy) and glutathione (GSH) under stoichiometric conditions. The selectivi...

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Bibliographic Details
Published in:Journal of organic chemistry 2014-11, Vol.79 (21), p.10477-10486
Main Authors: Mummidivarapu, V. V. Sreenivasu, Yarramala, Deepthi S, Kondaveeti, Karuna Kumar, Rao, Chebrolu P
Format: Article
Language:English
Subjects:
Calixarenes - chemical synthesis
Calixarenes - chemistry
Cycloaddition Reaction
Cysteine - chemistry
Glutathione - chemistry
HeLa Cells
Homocysteine - chemistry
Humans
Magnetic Resonance Spectroscopy
Microscopy - methods
Microscopy, Fluorescence - methods
Norbornanes - chemical synthesis
Norbornanes - chemistry
Phenols - chemical synthesis
Phenols - chemistry
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Summary:Herein we report the synthesis and characterization of 7-oxanorbornadiene (OND)-appended 1,3,5-tris conjugate of calix[6]arene (L 2 ). L 2 has been shown to exhibit selective reactivity toward cysteine (Cys) over homocysteine (Hcy) and glutathione (GSH) under stoichiometric conditions. The selectivity of L 2 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 (L 1 ) does not show any selectivity toward Cys. While L 2 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. L 2 has been shown to react with Cys present in HeLa and Jurkat E6 cells by fluorescence microscopy.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo5021213