Harnessing Pillar[5]arene Host–Guest Complexation To Improve pH Stability and Affect Enzymatic Degradation of the Anticancer Prodrug Capecitabine: A 19F NMR Study

Author:

Horin Inbar1,Slovak Sarit1,Cohen Yoram12ORCID

Affiliation:

1. School of Chemistry, Sackler Faculty of Exact Sciences Tel Aviv University Ramat Aviv 6977801 Tel Aviv Israel

2. Sagol School of Neurosciences Tel Aviv University Ramat Aviv 6977801 Tel Aviv Israel

Abstract

AbstractCancer is a global health problem, and supramolecular chemotherapy is emerging as a novel strategy to battle the disease. Here, we first evaluated the thermodynamic and kinetic stability of the complexes formed between several water‐soluble per‐substituted pillar[5]arene derivatives and capecitabine (1), a widely used oral chemotherapeutic prodrug. The exchange rate was studied, for the first time in pillararene chemistry, by the 19F guest exchange saturation transfer (GEST) NMR technique. Importantly, when we evaluated the effect of complexation on the characteristics of 1, we found that the complexation of 1 with such pillar[5]arene hosts increased capecitabine stability at acidic pH very significantly and slowed its enzymatic degradation by the carboxylesterase enzyme in a manner that depended on the host. These interesting findings could have implications on the clinical use of this heavily used prodrug and might affect the management of cancer patients.

Funder

Israel Science Foundation

Publisher

Wiley

Subject

General Chemistry,Catalysis,Organic Chemistry

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