Università degli Studi di Firenze, Laboratorio di Chimica Bioinorganica, Rm. 188, Via della Lastruccia 3, I-50019 Sesto Fiorentino (Firenze), Italy.
Istituto di Biochimica delle Proteine - CNR, Via P. Castellino 111, 80131 Napoli, Italy.
Bioorg Med Chem Lett. 2014 Jan 1;24(1):275-9. doi: 10.1016/j.bmcl.2013.11.021. Epub 2013 Nov 20.
The δ-carbonic anhydrase (CA, EC 4.2.1.1) TweCA from the marine diatom Thalassiosira weissflogii has recently been cloned, purified and its activity/inhibition with anions investigated. Here we report the first sulfonamide/sulfamate inhibition study of a δ-class CA. Among the 40 such compounds investigated so far, 3-bromosulfanilamide, acetazolamide, ethoxzolamide, dorzolamide and brinzolamide were the most effective TweCA inhibitors detected, with KIs of 49.6-118nM. Many simple aromatic sulfonamides as well as dichlorophenamide, benzolamide, topiramate, zonisamide, indisulam and valdecoxib were medium potency inhibitors, (KIs of 375-897nM). Saccharin and hydrochlorothiazide were ineffective inhibitors of the δ-class enzyme, with KIs of 4.27-9.20μM. The inhibition profile of the δ-CA is very different from that of α-, β- and γ-CAs from different organisms. Although no X-ray crystal structure of this enzyme is available, we hypothesize that as for other CA classes, the sulfonamides inhibit the enzymatic activity by binding to the Zn(II) ion from the δ-CA active site.
海洋硅藻威氏海链藻中的 δ-碳酸酐酶(CA,EC 4.2.1.1) TweCA 最近被克隆、纯化,并对其与阴离子的活性/抑制作用进行了研究。本文首次报道了 δ 类 CA 的磺酰胺/磺酸盐抑制研究。在迄今为止研究的 40 种此类化合物中,3-溴磺胺、乙酰唑胺、乙氧唑胺、多佐胺和布林佐胺是检测到的最有效的 TweCA 抑制剂,KI 值为 49.6-118nM。许多简单的芳香族磺酰胺以及二氯苯酰胺、苯酰胺、托吡酯、唑尼沙胺、异噁唑并嘧啶和伐地昔布是中等效力的抑制剂,KI 值为 375-897nM。糖精和氢氯噻嗪对 δ 类酶没有抑制作用,KI 值分别为 4.27-9.20μM。δ-CA 的抑制谱与来自不同生物体的 α、β 和 γ-CA 非常不同。尽管该酶的 X 射线晶体结构尚不可用,但我们假设,与其他 CA 类一样,磺酰胺通过与 δ-CA 活性位点中的 Zn(II)离子结合来抑制酶的活性。