Krungkrai Jerapan, Krungkrai Sudaratana R, Supuran Claudiu T
Department of Biochemistry, Faculty of Medicine, Chulalongkorn University, Bangkok, Thailand.
Curr Top Med Chem. 2007;7(9):909-17. doi: 10.2174/156802607780636744.
Plasmodium falciparum is responsible for the majority of life-threatening cases of human malaria. The global emergence of drug-resistant malarial parasites necessitates identification and characterization of novel drug targets. At present, carbonic anhydrase (CA) genes are identified in limited numbers of protozoa and helminthes parasites, however, they are demonstrated in at least 4 Plasmodium species. The CA gene of P. falciparum encodes an alpha-carbonic anhydrase enzyme possessing catalytic properties distinct of that of the human host enzymes. A small library of aromatic sulfonamides, most of which were Schiff's bases derived from sulfanilamide/homosulfanilamide/4-aminoethylbenzenesulfonamide and substituted-aromatic aldehydes, or ureido-substituted sulfonamides are good inhibitors of P. falciparum enzyme. The 4-(3,4-dichlorophenylureido-ethyl)-benzenesulfonamide is the most effective antimalarial activity against growth of P. falciparum in vitro. The nature of the groups substituting the aromatic-ureido- or aromatic-azomethine fragment of the molecule and the length of the parent sulfonamide (i.e., from sulfanilamide to 4-aminoethylbenzenesulfonamide) from which the Schiff's base obtained, are the critical parameters for the CA inhibitory activities of these aromatic sulfonamide derivatives, both against the malarial as well as human enzymes. Thus, the sulfonamide CA inhibitors may have the potential for the development of novel antimalarial drugs.
恶性疟原虫是导致大多数危及生命的人类疟疾病例的病原体。全球耐药疟原虫的出现使得鉴定和表征新型药物靶点成为必要。目前,碳酸酐酶(CA)基因仅在有限数量的原生动物和蠕虫寄生虫中被鉴定出来,不过,至少在4种疟原虫中得到了证实。恶性疟原虫的CA基因编码一种α-碳酸酐酶,其催化特性与人类宿主酶不同。一个小型的芳香族磺酰胺文库,其中大多数是由磺胺/高磺胺/4-氨基乙基苯磺酰胺与取代芳香醛衍生的席夫碱,或脲基取代的磺酰胺,是恶性疟原虫酶的良好抑制剂。4-(3,4-二氯苯基脲基-乙基)-苯磺酰胺对恶性疟原虫体外生长具有最有效的抗疟活性。取代分子芳香脲基或芳香偶氮甲碱片段的基团的性质以及席夫碱所源自的母体磺酰胺(即从磺胺到4-氨基乙基苯磺酰胺)的长度,是这些芳香族磺酰胺衍生物对疟原虫和人类酶的CA抑制活性的关键参数。因此,磺酰胺类CA抑制剂可能具有开发新型抗疟药物的潜力。