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  • Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids.

Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids.

Bioorganic & medicinal chemistry (2010-02-27)
Alessio Innocenti, S Beyza Oztürk Sarikaya, Ilhami Gülçin, Claudiu T Supuran
RESUMEN

A series of phenolic acids and phenol natural products, such as p-hydroxybenzoic acid, p-coumaric acid, caffeic acid, ferulic acid, gallic acid, syringic acid, quercetin, and ellagic acid, were investigated for their inhibitory effects against the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1). All mammalian isozymes of human (h) or murine (m) origin hCA I-hCA XII, mCA XIII and hCA XIV were inhibited in the low micromolar or submicromolar range by these (poly)phenols (K(I)s in the range of 0.87-7.79 microM). p-Hydroxybenzoic acid was the best inhibitor of all isozymes (K(I)s of 0.87-35.4 microM) and the different isozymes showed very variable inhibition profiles with these derivatives. Phenols like the ones investigated here possess a CA inhibition mechanism distinct of that of the sulfonamides/sulfamates used clinically or the coumarins. Unlike the sulfonamides, which bind to the catalytic zinc ion, phenols are anchored at the Zn(II)-coordinated water molecule and bind more externally within the active site cavity, making contacts with various amino acid residues. As this is the region with the highest variability between the many CA isozymes found in mammals, this class of compounds may lead to isoform-selective inhibitors targeting just one or few of the medicinally relevant CAs.

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Sigma-Aldrich
Gallic acid, 97.5-102.5% (titration)
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Phenol solution, BioReagent, Equilibrated with 10 mM Tris HCl, pH 8.0, 1 mM EDTA, for molecular biology
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Caffeic acid, ≥98.0% (HPLC)
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Phenol, puriss. p.a., ACS reagent, reag. Ph. Eur., 99.0-100.5%
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p-Coumaric acid, ≥98.0% (HPLC)
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Phenol, for molecular biology
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Liquified Phenol, ≥89.0%
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Phenol, BioXtra, ≥99.5% (GC)
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Phenol solution, Saturated with 0.1 M citrate buffer, pH 4.3 ± 0.2, BioReagent, for molecular biology
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trans-Ferulic acid, 99%
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1,2-Dihydroxybenzene, ReagentPlus®, ≥99%
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Phenol, ≥99%
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Ellagic acid, ≥95% (HPLC), powder, from tree bark
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4-Hydroxybenzoic acid, ReagentPlus®, ≥99%
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4-Hydroxybenzoic acid, ReagentPlus®, 99%
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Gallic acid monohydrate, ACS reagent, ≥98.0%
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Pyrocatechol, ≥99%
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Phenol, contains hypophosphorous as stabilizer, loose crystals, ACS reagent, ≥99.0%
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Syringic acid, ≥95% (HPLC)
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Gallic acid monohydrate, ≥99% (HPLC)
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Phenol, unstabilized, ReagentPlus®, ≥99%
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Phenol, puriss., meets analytical specification of Ph. Eur., BP, USP, 99.5-100.5% (GC)
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Phenol solution, certified reference material, 500 μg/mL in methanol
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Phenol, BioUltra, for molecular biology, TE-saturated, ~73% (T)
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Phenol, PESTANAL®, analytical standard
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Phenol, puriss., ≥99.5% (GC), meets analytical specification of Ph. Eur., BP, USP, crystalline (detached)
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trans-Ferulic acid, ≥99%
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Phenol solution, 5000 μg/mL in methanol, certified reference material
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Phenol, unstabilized, purified by redistillation, ≥99%
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Caffeic acid, matrix substance for MALDI-MS, ≥99.0% (HPLC)