Phenols and Polyphenols as Carbonic Anhydrase Inhibitors

Karioti, Anastasia; Carta, Fabrizio; Supuran, Claudiu T.

doi:10.3390/molecules21121649

Cited by 80 publications

(48 citation statements)

References 82 publications

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“…Some examples (acetazolamide, brinzolamide and dorzolamide) are shown in Figure 2 . Compounds that anchor to the-zinc coordinated water molecule/hydroxide ion, such as phenols and polyamines [ 3 , 24 , 26 ]. Compounds occluding the entrance of the active site (coumarins and their isosters) [ 3 , 24 , 27 ].…”

Section: Carbonic Anhydrase Inhibitors (Cais)mentioning

confidence: 99%

Amino Acids as Building Blocks for Carbonic Anhydrase Inhibitors

et al. 2018

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Carbonic anhydrases (CAs) are a superfamily of metalloenzymes widespread in all life, classified into seven genetically different families (α–θ). These enzymes catalyse the reversible hydration of carbonic anhydride (CO2), generating bicarbonate (HCO3−) and protons (H+). Fifteen isoforms of human CA (hCA I–XV) have been isolated, their presence being fundamental for the regulation of many physiological processes. In addition, overexpression of some isoforms has been associated with the outbreak or progression of several diseases. For this reason, for a long time CA inhibitors (CAIs) have been used in the control of glaucoma and as diuretics. Furthermore, the search for new potential CAIs for other pharmacological applications is a very active field. Amino acids constitute the smallest fundamental monomers of protein and, due to their useful bivalent chemical properties, are widely used in organic chemistry. Both proteinogenic and non-proteinogenic amino acids have been extensively used to synthesize CAIs. This article provides an overview of the different strategies that have been used to design new CAIs containing amino acids, and how these bivalent molecules influence the properties of the inhibitors.

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Section: Carbonic Anhydrase Inhibitors (Cais)mentioning

confidence: 99%

Amino Acids as Building Blocks for Carbonic Anhydrase Inhibitors

et al. 2018

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“…Ferulic acid was also described as an inhibitor of carbonic anhydrase II, although its experimental IC 50 value was at least 10-fold higher compared to acetazolamide, the reference enzyme inhibitor drug [58]. Despite there still being no specific studies, the putative interactions between carbonic anhydrase II and the other studied phenolic compounds, especially those characterized by a favorable pharmacokinetic profile, suggest further enzyme inhibition effects [59], that could explain, at least in part, the traditional use of A. aspera decoctions as diuretic agents, as well [4].…”

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Qualitative Phytochemical Fingerprint and Network Pharmacology Investigation of Achyranthes aspera Linn. Extracts

et al. 2020

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Achyranthes aspera Linn. (Amaranthaceae), commonly known as the Prickly Chaff flower, is used as herbal medicine in the Ivorian’s culture, Africa. Nonetheless, there is currently a paucity of scientific information on A. aspera from the Ivory Coast. Herein, the antioxidant activity of A. aspera extracts (methanol, dichloromethane, ethyl acetate and infusion) as well as the enzymatic inhibitory potentials towards key enzymes in human diseases, namely Alzheimer’s disease, (cholinesterases: AchE and BChE), type 2 diabetes (α-glucosidase and α-amylase) and hyperpigmentation (tyrosinase) were assessed. The total phenolic (TPC) and flavonoid (TFC) content was determined using colorimetric methods and the individual compounds were characterized using ultra-high performance liquid chromatography coupled with hybrid quadrupole-Orbitrap high resolution mass spectrometry (UHPLC-HRMS). Furthermore, a network pharmacology analysis was conducted to predict putative targets of identified phenolic compounds. The highest TPC was observed in the infused extract (28.86 ± 0.12 mg GAE/g), while the dichloromethane extract (38.48 ± 1.48 mg RE/g) showed the highest level of TFC. UHPLC-HRMS analysis has revealed an abundance of fatty acids, flavonoids, phenols and acylquinic acids. Among tested extracts, the infused extract displayed the highest free radical quenching, reducing and metal-chelating ability. The extracts (except infusion) were effective as enzyme inhibitors against AChE, while only methanolic and infused extracts showed noteworthy anti-BChE effects. The methanolic extract showed a remarkable antityrosinase effect (56.24 ± 5.05 mg KAE/g), as well. Modest to moderate inhibitory activity was observed against α-amylase (all extracts) and α-glucosidase (only dichloromethane extract). Finally, the network pharmacology analysis suggested the carbonic anhydrase II enzyme as a putative target for explaining, at least in part, the traditional use of A. aspera preparations as diuretic and blood clotting agent. Data amassed herein tend to validate the use of A. aspera in traditional medicine, as well as act as a stepping stone for further studies in the quest for novel phytopharmaceuticals. In this context, it is desirable that this study will contribute to the validation of the traditional uses of this plant in the African herbal medicine, and to the valorization of the whole chain production of A. aspera, as a local and sustainable botanical resource.

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“…Several small compounds, such as p-aminophenol, were classified as carbonic anhydrase binders. (Karioti et al, 2016) (218) were previously not known. With trepidation, we show in Figure 9 thirty of these "new" associations.…”

Section: Figmentioning

confidence: 99%

Compound Collections at KU 1947-2017: Cheminformatic Analysis and Computational Protein Target Prediction

Pearson¹,

Singh²,

Bošković

2020

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<div> <div> <div> <p>We report the comparison of two small-molecule collections synthesized at KU at two different eras. We used a machine learning tool to classify the compounds in these collections by their predicted protein targets. The analyses shine light on the evolution of medicinal chemistry research at the University of Kansas, and reveal several new associations between compounds and protein targets. </p> </div> </div> </div>

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Phenols and Polyphenols as Carbonic Anhydrase Inhibitors

Cited by 80 publications

References 82 publications

Amino Acids as Building Blocks for Carbonic Anhydrase Inhibitors

Amino Acids as Building Blocks for Carbonic Anhydrase Inhibitors

Qualitative Phytochemical Fingerprint and Network Pharmacology Investigation of Achyranthes aspera Linn. Extracts

Compound Collections at KU 1947-2017: Cheminformatic Analysis and Computational Protein Target Prediction

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