Carbonic Anhydrases inhibitory effects of new benzenesulfonamides synthesized by using superacid chemistry

Liu, Fei; Martin‐Mingot, Agnès; Lecornué, Frédéric; Jouannetaud, Marie‐Paule; Maresca, Alfonso; Thibaudeau, Sébastien; Supuran, Claudiu T.

doi:10.3109/14756366.2011.638921

Cited by 73 publications

(29 citation statements)

References 36 publications

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“…The inhibition constants were obtained by non-linear least-squares methods using PRISM 3 and the Cheng-Prusoff equation, as reported earlier 2,5 , and represent the mean from at least three different determinations. All CA isoforms were recombinant ones obtained in-house as reported earlier [52][53][54][55][56] .…”

Section: Ca Inhibitionmentioning

confidence: 99%

7-Aryl-triazolyl-substituted sulfocoumarins are potent, selective inhibitors of the tumor-associated carbonic anhydrase IX and XII

Nocentini

Ceruso

Carta

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

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Section: Ca Inhibitionmentioning

confidence: 99%

7-Aryl-triazolyl-substituted sulfocoumarins are potent, selective inhibitors of the tumor-associated carbonic anhydrase IX and XII

Nocentini

Ceruso

Carta

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…For this reason, exploring novel coumarin derivatives as CAIs, or compounds known in the literature but not yet investigated for this activity, is of interest in the design of isoform-selective pharmacological agents of this type. Indeed, CAIs have a range of applications as antiglaucoma, antiobesity, antiepileptic or diuretic agents [12][13][14][15][16][17][18][19][20][21][22][23][24][25][26] . Furthermore, inhibition of CAs from various bacteria or fungi may also lead to the development of antiinfectives based on CAIs 27,28 .…”

Section: Introductionmentioning

confidence: 99%

Novel coumarins and benzocoumarins acting as isoform-selective inhibitors against the tumor-associated carbonic anhydrase IX

Sharma¹,

Tiwari²,

Supuran

2013

Journal of Enzyme Inhibition and Medicinal Chemistry

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A series of coumarins and benzocoumarins incorporating methyl and hydroxyl moieties in the heterocyclic ring were investigated for the inhibition of the zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1). These coumarins were very weak or ineffective as inhibitors of the housekeeping, offtarget isoforms CA I and II, but showed effective, submicromolar inhibition of the transmembrane, tumor-associated isoforms CA IX and to a slightly less extent, CA XII. The nature and position of the groups substituting the coumarin ring influenced CA inhibitory properties. 4-Methyl-5,7-dihydroydroxycoumarin showed K I s 4200 mM against CA I and II, of 0.19 mM against CA IX and of 6.4 mM against CA XII, being thus a selective, efficient inhibitor for the tumor-associated over cytosolic CA isoforms. These compounds are interesting leads for designing isoform-selective enzyme inhibitors.

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“…However, the inhibition mechanism with secondary and tertiary sulfonamides is unknown, as no X-ray crystal structures of such derivatives bound to the CA are available to date. Thus, the sulfonamides reported here incorporate in their molecule the urea fragment found in SLC-0111 and the secondary sulfonamide moiety present in sulfa drugs and several recently investigated CAIs [35][36][37][38][39][40][41][42][43][44][45][46][47][48][49] .…”

Section: Chemistrymentioning

confidence: 99%

“…In addition, a range of secondary and tertiary sulfonamides has been investigated as CAIs recently, some of them showing effective and selective inhibition of several important isoforms [35][36][37][38][39][40][41][42][43][44][45][46][47][48][49] . However, the inhibition mechanism with secondary and tertiary sulfonamides is unknown, as no X-ray crystal structures of such derivatives bound to the CA are available to date.…”

Section: Chemistrymentioning

confidence: 99%

Design, synthesis and biological evaluation ofN-(5-methyl-isoxazol-3-yl/1,3,4-thiadiazol-2-yl)-4-(3-substitutedphenylureido) benzenesulfonamides as human carbonic anhydrase isoenzymes I, II, VII and XII inhibitors

Mishra

Kumari

Angeli

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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A series of N-(5-methyl-isoxazol-3-yl/1,3,4-thiadiazol-2-yl)-4-(3-substitutedphenylureido) benzenesulfonamide derivatives has been designed, synthesized and screened for their in vitro human carbonic anhydrase (hCA; EC 4.2.1.1) inhibition potential. These newly synthesized sulfonamide compounds were assessed against isoforms hCA I, II, VII and XII, with acetazolamide (AAZ) as a reference compound. The majority of these compounds were found quite weak inhibitor against all tested isoforms. Compound 15 showed a modest inhibition potency against hCA I (K i ¼ 73.7 mM) and hCA VII (K i ¼ 85.8 mM). Compounds 19 and 25 exhibited hCA II inhibition with K i values of 96.0 mM and 87.8 mM, respectively. The results of the present study suggest that, although the synthesized derivatives have weak inhibitory potential towards all investigated isoforms, some of them may serve as lead molecules for the further development of selective inhibitors incorporating secondary sulfonamide functionalities, a class of inhibitors for which the inhibition mechanism is poorly understood.

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Carbonic Anhydrases inhibitory effects of new benzenesulfonamides synthesized by using superacid chemistry

Cited by 73 publications

References 36 publications

7-Aryl-triazolyl-substituted sulfocoumarins are potent, selective inhibitors of the tumor-associated carbonic anhydrase IX and XII

7-Aryl-triazolyl-substituted sulfocoumarins are potent, selective inhibitors of the tumor-associated carbonic anhydrase IX and XII

Novel coumarins and benzocoumarins acting as isoform-selective inhibitors against the tumor-associated carbonic anhydrase IX

Design, synthesis and biological evaluation ofN-(5-methyl-isoxazol-3-yl/1,3,4-thiadiazol-2-yl)-4-(3-substitutedphenylureido) benzenesulfonamides as human carbonic anhydrase isoenzymes I, II, VII and XII inhibitors

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