Sulfonamides containing coumarin moieties selectively and potently inhibit carbonic anhydrases II and IX: Design, synthesis, inhibitory activity and 3D-QSAR analysis

Wang, Zhongchang; Qin, Yajuan; Wang, Pengfei; Yang, Yulong; Wen, Qing; Zhang, Xin; Qiu, Han‐Yue; Duan, Yongtao; Wang, Yanting; Sang, Ya-Li; Zhu, Hai‐Liang

doi:10.1016/j.ejmech.2013.04.035

Cited by 56 publications

(33 citation statements)

References 37 publications

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“…The second unfortunate example that I shall present here is from a research group in Shanghai, China [161][162][163][164] . In several papers this group presented interesting scaffolds of aromatic/heterocyclic sulfonamides and their inhibition data mainly against hCA II and IX (as this last isoform is an attractive target due to its involvement in tumorigenesis 1,2,19 ).…”

Section: Fabricated Data and Scientific Misconduct Issues Of The Ca Fmentioning

confidence: 99%

“…In several papers this group presented interesting scaffolds of aromatic/heterocyclic sulfonamides and their inhibition data mainly against hCA II and IX (as this last isoform is an attractive target due to its involvement in tumorigenesis 1,2,19 ). Initially I was rather enthusiastic of these papers [161][162][163][164] as they were mainly based on the tail approach developed by my group in the late 90s 81,82 . However when I read their experimental parts I realized that the enzyme inhibition procedure was basically exactly the one from our papers.…”

Section: Fabricated Data and Scientific Misconduct Issues Of The Ca Fmentioning

confidence: 99%

“…For the next 5 decades, there were only variations on the sulfonamide theme with the sulfamates and sulfamides the most logical class of compounds to be considered as CAIs 161 . Indeed, such an activity has been demonstrated for the simple, inorganic sulfamide and sulfamate 168 , although Maryanoff et al 169 reported that some sugar sulfamates (one of which later became the antiepileptic drug topiramate 10) were devoid of CA inhibitory properties.…”

Section: Fabricated Data and Scientific Misconduct Issues Of The Ca Fmentioning

confidence: 99%

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How many carbonic anhydrase inhibition mechanisms exist?

Supuran

2015

Journal of Enzyme Inhibition and Medicinal Chemistry

626

519

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Six genetic families of the enzyme carbonic anhydrase (CA, EC 4.2.1.1) were described to date. Inhibition of CAs has pharmacologic applications in the field of antiglaucoma, anticonvulsant, anticancer, and anti-infective agents. New classes of CA inhibitors (CAIs) were described in the last decade with enzyme inhibition mechanisms differing considerably from the classical inhibitors of the sulfonamide or anion type. Five different CA inhibition mechanisms are known: (i) the zinc binders coordinate to the catalytically crucial Zn(II) ion from the enzyme active site, with the metal in tetrahedral or trigonal bipyramidal geometries. Sulfonamides and their isosters, most anions, dithiocarbamates and their isosters, carboxylates, and hydroxamates bind in this way; (ii) inhibitors that anchor to the zinc-coordinated water molecule/hydroxide ion (phenols, carboxylates, polyamines, 2-thioxocoumarins, sulfocoumarins); (iii) inhibitors which occlude the entrance to the active site cavity (coumarins and their isosters), this binding site coinciding with that where CA activators bind; (iv) compounds which bind out of the active site cavity (a carboxylic acid derivative was seen to inhibit CA in this manner), and (v) compounds for which the inhibition mechanism is not known, among which the secondary/tertiary sulfonamides as well as imatinib/nilotinib are the most investigated examples. As CAIs are used clinically in many pathologies, with a sulfonamide inhibitor (SLC-0111) in Phase I clinical trials for the management of metastatic solid tumors, this review updates the recent findings in the field which may be useful for a structure-based drug design approach of more selective/potent modulators of the activity of these enzymes. KeywordsAnchoring to zinc-coordinated water, carbonic anhydrase, inhibition mechanism, inhibitors, occlusion of the active site entrance, out of the active site binding, zinc binder History

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Section: Fabricated Data and Scientific Misconduct Issues Of The Ca Fmentioning

confidence: 99%

Section: Fabricated Data and Scientific Misconduct Issues Of The Ca Fmentioning

confidence: 99%

Section: Fabricated Data and Scientific Misconduct Issues Of The Ca Fmentioning

confidence: 99%

See 1 more Smart Citation

How many carbonic anhydrase inhibition mechanisms exist?

Supuran

2015

Journal of Enzyme Inhibition and Medicinal Chemistry

626

519

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“…Recently, several workers (Bochkov et al, 2013;Borah et al, 2012;Dawara and Singh, 2011;Iaroshenko et al, 2012;Ibrahim et al, 2009;Ivano et al, 2013;Kapoor et al, 2012;Kasabe et al, 2010;Li et al, 2012;Milevskii et al, 2013;Mulwad and Hegde, 2009a;Patil et al, 2011;Rehman et al, 2005;Sabetie et al, 2001;Strakova et al, 2003;Wang et al, 2013) …”

Section: Chloroformylationmentioning

confidence: 97%

Recent advances in 4-hydroxycoumarin chemistry. Part 1: Synthesis and reactions

Abdou

El‐Saeed

Bondock

2019

Arabian Journal of Chemistry

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“…12) more strongly inhibited the hCA II (IC 50 = 23 nM) and hCA IX (IC 50 = 24 nM), respectively. The IC 50 values of the latter compounds against B16-F10 and MCF7 cells were ≤ 0.19 µM [85].…”

Section: Coumarins Containing Imine Bond At C-3mentioning

confidence: 99%