Unconventional amino acids in medicinal chemistry: First report on taurine merged within carbonic anhydrase inhibitors

[Display omitted] •New taurinamido-containing compounds were reported as inhibitors of the hCAs.•Inhibitors 2, 3 and 12 showed promising SIs and potencies against the hCA IX.•New potential theragnostic tools for the management of hypoxic tumors may be developed fro the ma. This study reports the des...

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Bibliographic Details
Published in:Bioorganic chemistry 2020-10, Vol.103, p.104236-104236, Article 104236
Main Authors: Akgül, Özlem, Angeli, Andrea, Vullo, Daniela, Carta, Fabrizio, Supuran, Claudiu T.
Format: Article
Language:English
Subjects:
Benzenesulfonamide
Carbonic Anhydrase Inhibitors (CAIs)
Carbonic Anhydrase Inhibitors - chemical synthesis
Carbonic Anhydrase Inhibitors - chemistry
Carbonic Anhydrases - chemistry
Drug Design
Enzyme Assays
Humans
Isoenzymes - chemistry
Kinetics
Molecular Structure
Structure-Activity Relationship
Structure-Activity Relationship (SAR)
Sulfonamides - chemical synthesis
Sulfonamides - chemistry
Taurine
Taurine - analogs & derivatives
Taurine - chemical synthesis
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Summary:[Display omitted] •New taurinamido-containing compounds were reported as inhibitors of the hCAs.•Inhibitors 2, 3 and 12 showed promising SIs and potencies against the hCA IX.•New potential theragnostic tools for the management of hypoxic tumors may be developed fro the ma. This study reports the design, synthesis of a series of taurine containing benzenesulfonamide derivatives which were all screened in vitro against the physiological relevant human (h) expressed Carbonic Anhydrase (CA; EC 4.2.1.1) I, II, IX, XII isozymes. Compound 2, 5, 11–16 displayed superior inhibitory activities against the tumor associated hCA IX over the reference drug Acetazolamide (AAZ). Both hCA IX and XII isoforms were selectively inhibited only by compound 3, whereas the chloro-containing compound 12 was showed as the most selective and effective inhibitor profile for the CA IX isoforms. To the best of our knowledge the data reported herein are the first of this kind and introduce in the literature new compounds worth for future development within the Medicinal Chemistry field.
ISSN:0045-2068
1090-2120
DOI:10.1016/j.bioorg.2020.104236