PHOTOADDITION OF CHLORPROMAZINE TO GUANOSINE‐5′‐MONOPHOSPHATE

PHOTOADDITION OF CHLORPROMAZINE TO GUANOSINE‐5′‐MONOPHOSPHATE
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氯丙嗪与 5-单磷酸鸟苷的光加成

DOI:
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发表时间:
1986
影响因子:
3.3
通讯作者:
I. Kochevar
I. Kochevar
中科院分区:
生物学3区
文献类型:
--
作者:
T. Ciulla;G. Epling;I. Kochevar

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摘要-研究了氯丙嗪(CPZ)与鸟苷-5 ′-单磷酸(GMP)的光化学反应,作为CPZ与DNA光加成的模型。照射CPZ与小牛胸腺DNA产生的产品发射在520 nm,而GMP发射在495 nm。[~ 3 H]CPZ与GMP和[~(14)C]GMP与CPZ的光解混合物的HPLC分离表明形成了三种光加合物。加合物之一在500 nm处发荧光,并且似乎是Fujita等人检测到但未分离的产物(Photochem.光生物学1981,34,101-105)。第二个加合物在460 nm处发射,第三个是非荧光的。在500 nm处发射的光加合物通过UV、荧光和NMR表征为鸟嘌呤的C-8位与CPZ的吩噻嗪环的C-2位偶联的加合物。CPZ的阳离子自由基(CPZ +)似乎不是中间体,因为酶促产生的CPZ +形成了一种产物,其洗脱的保留时间接近于光加合物的保留时间,但在520 nm处不发光。
Abstrart—The photochemistry of chlorpromazine (CPZ) with guanosine‐5′‐monophosphate (GMP) was studied as a model for the photoaddition of CPZ to DNA. Irradiation of CPZ with calf thymus DNA produced a product emitting at 520 nm, whereas with GMP emission was at 495 nm. HPLC separation of photolysis mixtures of [3H]CPZ with GMP and [14C]GMP with CPZ indicated that three photoadducts were formed. One of the adducts fluoresced at 500 nm and appeared to be the product detected but not separated by Fujita et al. (Photochem. Photobiol. 1981, 34, 101–105). A second adduct emitted at 460 nm, and the third was nonfluorescent. The photoadduct emitting at 500 nm was characterized by UV, fluorescence, and NMR to be an adduct from coupling of the C‐8 position of guanine to the C‐2 position of the phenothiazine ring of CPZ. The cation radical of CPZ (CPZ +) does not appear to be an intermediate since enzymatically generated CPZ + formed a product that eluted with a retention time close to that of the photoadducts, but did not emit at 520 nm.
DOI: 10.1111/1523-1747.ep12479244
发表时间: 1981-01-01
影响因子: 6.5
作者:
KOCHEVAR, IE
通讯作者: KOCHEVAR, IE
氯丙嗪与 DNA 的光加成。
DOI: 10.1016/0009-2797(84)90153-4
发表时间: 1984
影响因子: 5.1
作者:
Kochevar,IE;Chung,FL;Jeffrey,AM
通讯作者: Jeffrey,AM