Ninhydrins inhibit carbonic anhydrases directly binding to the metal ion

Bouzina, Abdeslem; Berredjem, Malika; Nocentini, Alessio; Bua, Silvia; Bouaziz, Zouhair; Jose, Joachim; Borgne, Marc Le; Marminon, Christelle; Gratteri, Paola; Supuran, Claudiu T.

doi:10.1016/j.ejmech.2020.112875

Cited by 18 publications

(13 citation statements)

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Section: Other Chemotypes With Ca Inhibitory Powermentioning

confidence: 99%

“…An overview of the main new chemotypes acting as CAIs discovered up until now is shown in Figure 6, in which the "fresh" discovery of the ninhydrins is also mentioned 126 . Indeed, ninhydrins, such as compound 10, possess a gem-diol stable functionality which has been shown by means of kinetic and computational techniques to coordinate to the metal ion from the enzyme active site 126 . Furthermore, Figure 7 shows the X-ray crystal structures of some of the new chemotypes detected in the last period, such as the selenol 11 95 (Figure 7(A)), unsubstituted ninhydrin 10 126 (Figure 7(B)) and a catechol derivative 12 127 (Figure 7(C)) which has been recently reported to bind to hCA II by a new inhibition mechanism.…”

Section: Other Chemotypes With Ca Inhibitory Powermentioning

confidence: 99%

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Reconsidering anion inhibitors in the general context of drug design studies of modulators of activity of the classical enzyme carbonic anhydrase

Nocentini

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Winum

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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Inorganic anions inhibit the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1) generally by coordinating to the active site metal ion. Cyanate was reported as a non-coordinating CA inhibitor but those erroneous results were subsequently corrected by another group. We review the anion CA inhibitors (CAIs) in the more general context of drug design studies and the discovery of a large number of inhibitor classes and inhibition mechanisms, including zinc binders (sulphonamides and isosteres, dithiocabamates and isosteres, thiols, selenols, benzoxaboroles, ninhydrins, etc.); inhibitors anchoring to the zinc-coordinated water molecule (phenols, polyamines, sulfocoumarins, thioxocoumarins, catechols); CAIs occluding the entrance to the active site (coumarins and derivatives, lacosamide), as well as compounds that bind outside the active site. All these new chemotypes integrated with a general procedure for obtaining isoform-selective compounds (the tail approach) has resulted, through the guidance of rigorous X-ray crystallography experiments, in the development of highly selective CAIs for all human CA isoforms with many pharmacological applications.

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Section: Other Chemotypes With Ca Inhibitory Powermentioning

confidence: 99%

Section: Other Chemotypes With Ca Inhibitory Powermentioning

confidence: 99%

Reconsidering anion inhibitors in the general context of drug design studies of modulators of activity of the classical enzyme carbonic anhydrase

Nocentini

Carta

Winum

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…Enzyme concentrations in the assay system were in the range of 3.8–9.5 nM. Enzymes used here were recombinant ones, prepared and purified as described earlier [ 63 , 64 , 65 ]. The known CA inhibitor, acetazolamide, was employed as control.…”

Section: Methodsmentioning

confidence: 99%

The Glitazone Class of Drugs as Carbonic Anhydrase Inhibitors—A Spin-Off Discovery from Fragment Screening

et al. 2021

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The approved drugs that target carbonic anhydrases (CA, EC 4.2.1.1), a family of zinc metalloenzymes, comprise almost exclusively of primary sulfonamides (R-SO2NH2) as the zinc binding chemotype. New clinical applications for CA inhibitors, particularly for hard-to-treat cancers, has driven a growing interest in the development of novel CA inhibitors. We recently discovered that the thiazolidinedione heterocycle, where the ring nitrogen carries no substituent, is a new zinc binding group and an alternate CA inhibitor chemotype. This heterocycle is curiously also a substructure of the glitazone class of drugs used in the treatment options for type 2 diabetes. Herein, we investigate and characterise three glitazone drugs (troglitazone 11, rosiglitazone 12 and pioglitazone 13) for binding to CA using native mass spectrometry, protein X-ray crystallography and hydrogen–deuterium exchange (HDX) mass spectrometry, followed by CA enzyme inhibition studies. The glitazone drugs all displayed appreciable binding to and inhibition of CA isozymes. Given that thiazolidinediones are not credited as a zinc binding group nor known as CA inhibitors, our findings indicate that CA may be an off-target of these compounds when used clinically. Furthermore, thiazolidinediones may represent a new opportunity for the development of novel CA inhibitors as future drugs.

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“…Moreover, the fingerprints need to be dealt with distinctively. Therefore, it is critical to select the fingerprint visualizing powders [14]. In connection to that, literature shows that previously non-toxic plant materials, food powders [15], cosmetics [9a], food colors [9a], and food items [16] have been used to detect fingerprints.…”

Section: Introductionmentioning

confidence: 99%

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2023

J. Med. Chem. Sci.

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The current study aimed to present a simple, non-toxic, inexpensive, and easyto-use fingerprint powder extracted from nail henna leaf to identify latent fingerprints on porous and non-porous surfaces. The powder dusting technique was applied in the current study by using nail henna leaves with a particle size of 60 to 200 mesh. Moreover, the current study used 101 fingerprint samples derived on ethnicity, gender, and blood type to determine fingerprint patterns. The results of the development of nail henna powder from sizes 100 and 200 mesh revealed the clear visualization of fingerprint patterns with prominent brown contrast on non-porous surfaces. Besides, the loop fingerprint patterns reflected the highest percentage based on ethnicity, gender, and blood group.

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Ninhydrins inhibit carbonic anhydrases directly binding to the metal ion

Cited by 18 publications

References 50 publications

Reconsidering anion inhibitors in the general context of drug design studies of modulators of activity of the classical enzyme carbonic anhydrase

Reconsidering anion inhibitors in the general context of drug design studies of modulators of activity of the classical enzyme carbonic anhydrase

The Glitazone Class of Drugs as Carbonic Anhydrase Inhibitors—A Spin-Off Discovery from Fragment Screening

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