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Medicinal Hypervalent Tellurium Prodrugs Bearing Different Ligands: A Comparative Study of the Chemical Profiles of AS101 and Its Halido Replaced Analogues
- Source :
- International Journal of Molecular Sciences; Volume 23; Issue 14; Pages: 7505
- Publication Year :
- 2022
-
Abstract
- Ammonium trichloro (dioxoethylene-O,O′) tellurate (AS101) is a potent immunomodulator prodrug that, in recent years, entered various clinical trials and was tested for a variety of potential therapeutic applications. It has been demonstrated that AS101 quickly activates in aqueous milieu, producing TeOCl3−, which likely represents the pharmacologically active species. Here we report on the study of the activation process of AS101 and of two its analogues. After the synthesis and characterization of AS101 and its derivatives, we have carried out a comparative study through a combined experimental and computational analysis. Based on the obtained results, we describe here, for the first time, the detailed reaction that AS101 and its bromido- and iodido-replaced analogues undergo in presence of water, allowing the conversion of the original molecule to the likely true pharmacophore. Interestingly, moving down in the halogens’ group we observed a higher tendency to react, attributable to the ligands’ effect. The chemical and mechanistic implications of these meaningful differences are discussed.
- Subjects :
- clinical trials
metalloids
AS101
bioinorganic chemistry
coordination chemistry
inorganic drugs
prodrugs
tellurium
Adjuvants, Immunologic
Ethylenes
Ligands
Tellurium
Prodrugs
Organic Chemistry
General Medicine
Catalysis
Computer Science Applications
Inorganic Chemistry
Immunologic
Adjuvants
Physical and Theoretical Chemistry
Molecular Biology
Spectroscopy
Subjects
Details
- Language :
- English
- Database :
- OpenAIRE
- Journal :
- International Journal of Molecular Sciences; Volume 23; Issue 14; Pages: 7505
- Accession number :
- edsair.doi.dedup.....7fe4a48bcd37385585948ce239e66340