Bitonti A J, Byers T L, Bush T L, Casara P J, Bacchi C J, Clarkson A B, McCann P P, Sjoerdsma A
Merrell Dow Research Institute, Cincinnati, Ohio 45215.
Antimicrob Agents Chemother. 1990 Aug;34(8):1485-90. doi: 10.1128/AAC.34.8.1485.
A structural analog, 5'-([(Z)-4-amino-2-butenyl]methylamino)-5'-deoxy adenosine (MDL 73811), of decarboxy S-adenosyl-L-methionine, the product of the reaction catalyzed by S-adenosyl-L-methionine (AdoMet) decarboxylase (DC), was found to inhibit Trypanosoma brucei brucei AdoMet DC. The inhibition was time dependent (tau 50, 0.3 min), exhibited pseudo-first-order kinetics (Ki, 1.5 microM), and was apparently irreversible. The natural substrate of the reaction, AdoMet, protected the enzyme from inactivation, suggesting that MDL 73811 was directed at the enzyme active site and was probably catalytically activated. Administration of MDL 73811 to T. b. brucei-infected rats resulted in rapid inhibition of AdoMet DC activity, a decrease in spermidine, and an increase in putrescine in the trypanosomes isolated from treated rats. Treatment of T. b. brucei-infected mice with MDL 73811 (20 mg/kg of body weight intraperitoneally twice daily for 4 days) resulted in cures of the trypanosome infections. Additionally, drug-resistant T. brucei rhodesiense infections in mice were cured by either a combination of MDL 73811 (50 mg/kg intraperitoneally three times per day for 5 days) and relatively low oral doses of alpha-difluoromethylornithine or MDL 73811 (50 mg/kg per day for 7 days) administered alone in implanted miniosmotic pumps. These data suggest that MDL 73811 and, perhaps, other inhibitors of AdoMet DC have potential for therapeutic use in various forms of African trypanosomiasis.
已发现脱羧S-腺苷-L-甲硫氨酸(由S-腺苷-L-甲硫氨酸(AdoMet)脱羧酶(DC)催化反应的产物)的一种结构类似物5'-([(Z)-4-氨基-2-丁烯基]甲基氨基)-5'-脱氧腺苷(MDL 73811)可抑制布氏布氏锥虫的AdoMet DC。该抑制作用具有时间依赖性(τ50为0.3分钟),呈现伪一级动力学(Ki为1.5微摩尔),且显然是不可逆的。该反应的天然底物AdoMet可保护酶不被灭活,这表明MDL 73811作用于酶的活性位点,且可能被催化激活。给感染布氏布氏锥虫的大鼠施用MDL 73811会导致AdoMet DC活性迅速受到抑制,从经处理的大鼠中分离出的锥虫中的亚精胺减少,腐胺增加。用MDL 73811(20毫克/千克体重,腹腔注射,每日两次,共4天)治疗感染布氏布氏锥虫的小鼠可治愈锥虫感染。此外,小鼠体内的抗药性罗德西亚锥虫感染可通过MDL 73811(50毫克/千克,腹腔注射,每日三次,共5天)与相对低剂量口服α-二氟甲基鸟氨酸联合使用或单独在植入的微型渗透泵中施用MDL 73811(50毫克/千克/天,共7天)来治愈。这些数据表明MDL 73811以及或许其他AdoMet DC抑制剂在治疗各种形式的非洲锥虫病方面具有潜在用途。