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Synthesis of novel acridine bis-sulfonamides with effective inhibitory activity against the carbonic anhydrase isoforms I, II, IX and XII.

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TLDR
By using a multi component reaction system (MCR), nitro acridine sulfonamides were obtained from cyclic-1,3-diketones, 4-aminobenzene sulfonamide and aromatic aldehydes and showed low micromolar inhibition against the medically relevant isoforms hCA I, II, IX, and XII.
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This article is published in Bioorganic & Medicinal Chemistry.The article was published on 2015-10-15 and is currently open access. It has received 25 citations till now. The article focuses on the topics: Carbonic anhydrase II & Carbonic Anhydrase I.

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Citations
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Journal ArticleDOI

Recent developments in the synthesis and biological activity of acridine/acridone analogues

TL;DR: This survey describes acridine and acridone derivatives reported since 2013, methods of their synthesis and their potential clinical applications, as well as investigating their clinical application in Alzheimer's disease and other diseases.
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Functionalized Multi-Walled Carbon Nanotubes (f-MWCNT) as Highly Efficient and Reusable Heterogeneous Catalysts for the Synthesis of Acridinedione Derivatives

TL;DR: In this article, carboxylic acid groups were immobilized onto carbon nanotubes and their catalytic properties were examined for the first time for the synthesis of acridinedione derivatives, opening new paths in the investigation of catalysis and their comparison with carbon-based materials.
Journal ArticleDOI

Anion inhibition profiles of the complete domain of the η-carbonic anhydrase from Plasmodium falciparum.

TL;DR: Cloned, purified and investigated the catalytic activity and anion inhibition profiles of a full catalytic domain (358 amino acid residues) carbonic anhydrase from Plasmodium falciparum, PfCAdom, an enzyme belonging to the η-CA class and identified in the genome of the malaria-producing protozoa.
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Evaluation of sodium acetate trihydrate–urea DES as a benign reaction media for the Biginelli reaction. Unexpected synthesis of methylenebis(3-hydroxy-5,5-dimethylcyclohex-2-enones), hexahydroxanthene-1,8-diones and hexahydroacridine-1,8-diones

TL;DR: In this paper, the physical properties of the deep eutectic solvent (DES) such as viscosity, electrical conductivity, density, pH and refractive index were measured and analyzed as a function of temperature.
Journal ArticleDOI

Synthesis of N-alkyl (aril)-tetra pyrimidine thiones and investigation of their human carbonic anhydrase I and II inhibitory effects.

TL;DR: Tetrahydropyrimidine thiones, which are cyclic thiocarbamides derivatives, were synthesised from thiourea, β-diketones and substituted benzaldehydes, and tested for inhibition of the cytosolic human isoforms I and II.
References
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Journal ArticleDOI

Deciphering the mechanism of carbonic anhydrase inhibition with coumarins and thiocoumarins.

TL;DR: A new series of variously substituted coumarins and a thiocoumarin for their interaction with 13 mammalian CA isoforms, detecting low nanomolar and isoform selective inhibitors, afford isoform-selective CAIs with various biomedical applications, which render these classes of compounds superior to the clinically used sulfonamides.
Journal ArticleDOI

An overview of the alpha-, beta- and gamma-carbonic anhydrases from Bacteria: can bacterial carbonic anhydrases shed new light on evolution of bacteria?

TL;DR: It is proposed that bacterial CAs can be used as markers for understanding the evolution and genetic variability of the Gram-positive and Gram-negative bacteria.
Journal ArticleDOI

Carbonic anhydrases: from biomedical applications of the inhibitors and activators to biotechnological use for CO(2) capture.

TL;DR: Novel drug design strategies have been reported principally based on the tail approach for obtaining all these types of CAIs, which exploit more external binding regions within the enzyme active site (in addition to coordination to the metal ion), leading thus to isoformselective compounds.
Journal ArticleDOI

Carbonic anhydrase inhibitors and activators for novel therapeutic applications

TL;DR: Inhibition of mammalian α-CAs is exploited by some diuretics, whereas antiglaucoma, anticonvulsant, anti-obesity, altitude sickness and anti-tumor drugs/diagnostic agents target various of the 15 isoforms described so far in these organisms.
Journal ArticleDOI

Antiobesity carbonic anhydrase inhibitors: a literature and patent review.

TL;DR: This review deals with the scientific and patent literature regarding obesity or obesity-related pathologies, being particularly focused on the use of carbonic anhydrase inhibitors (CAI) such as TPM and ZNS which inhibit the de novo lipogenesis.
Related Papers (5)
Frequently Asked Questions (19)
Q1. What have the authors contributed in "Synthesis of novel acridine bis-sulfonamides with effective inhibitory activity against the carbonic anhydrase isoforms i, ii, ix and xii" ?

In this paper, a multi component reaction system ( MCRS ) was used to synthesize acridine sulfonamides from cyclic-1,3-diketones, 4-aminobenzene sulfonamide and aromatic aldehydes. 

In vivo experiments showed that silencing of hCA IX reduces xenograft tumors to 40% of the volume along with up-regulation response of the gene encoding for hCA XII. 

For the compounds 6b, 6e, 6h and 6k singlet peaks were observed in between 2.18 and 2.52 ppm belong to protons of the methyl group. 

The prepared compounds containing both acridine ring and sulfonamide group are thought to be of interest because sulfonamides are used in the treatment of many diseases, possessing antimicrobial, antimalarial, antiglaucoma, and anticancer properties. 

The small range of inhibitory power of these compounds against the two transmembrane isoforms may be due to the fact that the variations in the structure are at rather distant parts of the tail from the primary sulfonamide, and the authors hypothesize that these parts of the molecules lay outside the active site, affording thus for less specific interactions with amino acid residues crucial for the binding of inhibitors. 

12,13 Furthermore, many acridine sulfonamides are known as strong carbonic anhydrase (CA, EC 4.2.1.1) inhibitors (CAIs), potentially useful for the treatment glaucoma9,10 or other conditions, which the activity of the CA isoforms are deregulated. 

The large use of CAIs for pharmaceutical applications relies on the wide distribution of the 15 human (h) CA isoforms within different tissues as well as on their implication in many physiological/pathological conditions. 

For the dominant cytosolic isoform hCA II, as for isoform CA I, it was observed that the new derivatives were rather ineffective inhibitors, showing a limited range of inhibitory power, with a variation of KI between 0.10 and 0.96 lM. 

The main drawback associated to the use of CAIs is represented by the lack of selectivity in inhibiting various isoforms by many of the first and second generation CAIs, thus resulting in a plethora of side effects. 

20–22 Moreover novel CAIs classes such as the polyamines,23 phenols,24 dithiocarbamates,25 xanthates,26 coumarins, thiocoumarins, 2-thioxo-coumarins and coumarin oximes16,27–29were identified and their inhibition mechanisms of many of these compounds were determined by means of X-ray crystallography CA II adducts. 

It should be stressed that currently a sulfonamide CA IX inhibitor (SLC0111) entered in Phase The authorclinical studies for the treatment of hypoxic, advanced stage metastatic solid tumors. 

Well-known drugs containing the acridine moiety include Amsacrine, Asulacrine, Acronycine, Acridine carboxamide (DACA), Proflavine and Ascididemin (Chart 1), and they have been used as anti-cancer or anti-bacterial agents. 

It was observed that increasing of the bulkiness of the tails for the compound series 4a, 4b, and 6a–f (Chart 2) resulted with slight increasing of KI values, that is, decreasing on inhibitory effect, in the range of 0.69–6.92 lM. 

It is suggested that due to the fact hCA II has a wide entrance to active site, probably the hydrophobic and hydrophilic interactions of these tails with the active site were not highly effective, and leading in fact to the flat SAR mentioned above also for isoform hCA I. 

It is thus probable that the bulky scaffold of these sulfonamides does not make a lot of favorable contacts with the enzyme active site, whereas the secondary sulfonamide moiety is too far away for assuring the right interactions with the residues at the entrance of the cavity, which would lead to isoform-selective CAIs (Charts 4 and 5). 

The structure–activity relationships (SAR) for the inhibition of these isoforms with the acridine bis-sulfonamides are also discussed. 

The compounds were characterized by physicochemical methods and tested for their in vitro inhibition activity against the CA isoforms I, II, IX and XII. 

Also the signals of the CH protons were observed at 4.90 and 4.98 ppm and the signals for the aromatic protons were observed between 6.30 and 8.36 ppm. 

The transmembrane isoform hCA IX was inhibited better than the cytosolic ones, with KIs ranging between 90 nM and 1.12 lM (Table 1).