Department of Pharmacology and Toxicology, Institute of Pharmacy, University of Regensburg, Regensburg, Germany.
Biochemistry. 2010 Jul 6;49(26):5494-503. doi: 10.1021/bi100684g.
Cyclic adenosine 3',5'-monophosphate (cAMP) and cyclic guanosine 3',5'-monophosphate (cGMP) are second messengers for numerous mammalian cell functions. The natural occurrence and synthesis of a third cyclic nucleotide (cNMP), cyclic cytidine 3',5'-monophosphate (cCMP), is a matter of controversy, and almost nothing is known about cyclic uridine 3',5'-monophosphate (cUMP). Bacillus anthracis and Bordetella pertussis secrete the adenylyl cyclase (AC) toxins edema factor (EF) and CyaA, respectively, weakening immune responses and facilitating bacterial proliferation. A cell-permeable cCMP analogue inhibits human neutrophil superoxide production. Here, we report that EF and CyaA also possess cytidylyl cyclase (CC) and uridylyl cyclase (UC) activity. CC and UC activity was determined by a radiometric assay, using [alpha-(32)P]CTP and [alpha-(32)P]UTP as substrates, respectively, and by a high-performance liquid chromatography method. The identity of cNMPs was confirmed by mass spectrometry. On the basis of available crystal structures, we developed a model illustrating conversion of CTP to cCMP by bacterial toxins. In conclusion, we have shown both EF and CyaA have a rather broad substrate specificity and exhibit cytidylyl and uridylyl cyclase activity. Both cCMP and cUMP may contribute to toxin actions.
环磷酸腺苷 3',5'-单磷酸(cAMP)和环磷酸鸟苷 3',5'-单磷酸(cGMP)是许多哺乳动物细胞功能的第二信使。第三种环核苷酸(cNMP),环胞苷 3',5'-单磷酸(cCMP)的自然发生和合成是一个有争议的问题,而关于环尿苷 3',5'-单磷酸(cUMP)几乎一无所知。炭疽杆菌和百日咳博德特氏菌分别分泌腺苷酸环化酶(AC)毒素水肿因子(EF)和 CyaA,削弱免疫反应并促进细菌增殖。一种细胞通透性的 cCMP 类似物抑制人中性粒细胞超氧化物的产生。在这里,我们报告 EF 和 CyaA 还具有胞苷酰基环化酶(CC)和尿苷酰基环化酶(UC)活性。CC 和 UC 活性通过放射性测定法确定,分别使用 [alpha-(32)P]CTP 和 [alpha-(32)P]UTP 作为底物,并通过高效液相色谱法确定。cNMP 的身份通过质谱法确认。根据现有的晶体结构,我们开发了一个模型,说明细菌毒素将 CTP 转化为 cCMP。总之,我们已经证明 EF 和 CyaA 具有相当广泛的底物特异性,并表现出胞苷酰基和尿苷酰基环化酶活性。cCMP 和 cUMP 都可能有助于毒素作用。