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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.
Journal ArticleDOI

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.
Journal ArticleDOI

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

A small-molecule drug conjugate for the treatment of carbonic anhydrase IX expressing tumors.

TL;DR: The first small-molecule drug conjugates for the treatment of carbonic anhydrase IX expressing solid tumors are described, demonstrating that such molecules can preferentially accumulate inside antigen-positive lesions, have fast targeting kinetics and good tumor-penetrating properties, and are easily accessible by total synthesis.
Journal ArticleDOI

Glycosyl coumarin carbonic anhydrase IX and XII inhibitors strongly attenuate the growth of primary breast tumors.

TL;DR: A series of 7-substituted coumarins incorporating various glycosyl moieties were synthesized and investigated for the inhibition of the zinc enzyme carbonic anhydrase, constituting interesting candidates for the development of conceptually novel anticancer drugs.
Journal ArticleDOI

Polyamines inhibit carbonic anhydrases by anchoring to the zinc-coordinated water molecule

TL;DR: In this article, the X-ray crystal structure of the CA II-spermine adduct allowed understanding of the inhibition mechanism, and Spermine anchors to the nonprotein zinc ligand through a network of hydrogen bonds.
Journal ArticleDOI

Carbonic anhydrase inhibitors as emerging drugs for the treatment of obesity

TL;DR: The use of topiramate and zonisamide as lead molecules for the design of CA inhibitors targeting isozymes involved in lipogenesis could represent the beginning of a very promising new approach for the treatment of obesity.
Journal ArticleDOI

Structural annotation of human carbonic anhydrases

TL;DR: The favourable properties of hCA II such as fast kinetics, easy expression and purification, high solubility and intermediate heat resistance have made it an attractive candidate for numerous industrial applications.
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).