溴化乙锭双插入类似物的合成、DNA结合及生物活性
Synthesis, DNA-binding and biological activity of a double intercalating analog of ethidium bromide.
作者信息
Kuhlmann K F, Charbeneau N J, Mosher C W
出版信息
Nucleic Acids Res. 1978 Jul;5(7):2629-41. doi: 10.1093/nar/5.7.2629.
Abstract
A bis-phenanthridinium salt has been synthesized and its DNA-binding studied. Evidence provided by UV and CD spectra, by thermal denaturation profiles and by equilibrium dialysis of the drug-DNA complex lead to the conclusion that both phenanthridine moieties intercalate in the helix. The double intercalator appears to be less potent than ethidium chloride as an inhibitor of nucleic acid synthesis in cultured L1210 cells, though it is more potent than a monomeric analog. The low potency may be due to a low cell influx rate.
摘要
已合成了一种双菲啶盐并对其与DNA的结合进行了研究。紫外光谱、圆二色光谱、热变性曲线以及药物-DNA复合物的平衡透析所提供的证据表明，两个菲啶部分均嵌入螺旋结构中。作为培养的L1210细胞中核酸合成的抑制剂，这种双嵌入剂的效力似乎比氯化乙锭低，不过比单体类似物的效力高。效力低可能是由于细胞内流速率低所致。
相似文献
1
Synthesis, DNA-binding and biological activity of a double intercalating analog of ethidium bromide.溴化乙锭双插入类似物的合成、DNA结合及生物活性
Nucleic Acids Res. 1978 Jul;5(7):2629-41. doi: 10.1093/nar/5.7.2629.
2
Extended ethidium bromide analogue as a triple helix intercalator: synthesis, photophysical properties and nucleic acids binding.作为三链螺旋嵌入剂的溴化乙锭类似物：合成、光物理性质及与核酸的结合
Chem Commun (Camb). 2006 Jul 5(25):2684-6. doi: 10.1039/b604281c. Epub 2006 May 26.
3
New dimeric analogues of ethidium; synthesis, interaction with DNA, and antitumor activity.
J Med Chem. 1981 Nov;24(11):1333-7. doi: 10.1021/jm00143a014.
4
Intercalative interactions of ethidium dyes with triplex structures.溴化乙锭染料与三链结构的嵌入相互作用。
Bioorg Med Chem. 1995 Jun;3(6):701-11. doi: 10.1016/0968-0896(95)00061-k.
5
Molecular determinants for DNA minor groove recognition: design of a bis-guanidinium derivative of ethidium that is highly selective for AT-rich DNA sequences.DNA小沟识别的分子决定因素：一种对富含AT的DNA序列具有高度选择性的乙锭双胍衍生物的设计。
Biochemistry. 2005 Feb 15;44(6):1941-52. doi: 10.1021/bi047983n.
6
Binding of ethidium and bis(methidium)spermine to Z DNA by intercalation.溴化乙锭和双（甲溴化）精胺通过嵌入作用与Z-DNA结合。
Nucleic Acids Res. 1984 Jun 11;12(11):4679-90. doi: 10.1093/nar/12.11.4679.
7
DNA Bifunctional intercalators. 2. Fluorescence properties and DNA binding interaction of an ethidium homodimer and an acridine ethidium heterodimer.DNA双功能嵌入剂。2. 溴化乙锭同二聚体和吖啶溴化乙锭异二聚体的荧光性质及与DNA的结合相互作用。
Biochemistry. 1978 Nov 28;17(24):5078-88. doi: 10.1021/bi00617a002.
8
[DNA-intercalating compounds. Synthesis of several monomers and 1 dimer of phenanthridinium bearing aminoalkoylated chains].[DNA嵌入化合物。几种带有氨基烷基化链的菲啶鎓单体和1种二聚体的合成]
C R Acad Hebd Seances Acad Sci D. 1976 Nov 8;283(11 D):1365-7.
9
Covalent attachment of ethidium to DNA results in enhanced topoisomerase II-mediated DNA cleavage.溴化乙锭与DNA的共价连接导致拓扑异构酶II介导的DNA切割增强。
Biochemistry. 1997 Dec 16;36(50):15884-91. doi: 10.1021/bi971858c.
10
Anticooperative Binding Governs the Mechanics of Ethidium-Complexed DNA.抗合作结合控制着吖啶复合物 DNA 的力学性质。
Biophys J. 2019 Apr 23;116(8):1394-1405. doi: 10.1016/j.bpj.2019.03.005. Epub 2019 Mar 19.
引用本文的文献
1
Contemporary Progress and Opportunities in RNA-Targeted Drug Discovery.RNA靶向药物研发的当代进展与机遇
ACS Med Chem Lett. 2023 Feb 23;14(3):251-259. doi: 10.1021/acsmedchemlett.3c00020. eCollection 2023 Mar 9.
2
Structure-activity relationships for the 9-(pyridin-2'-yl)- aminoacridines.9-（吡啶-2'-基）-氨基吖啶的构效关系。
Molecules. 2004 Feb 28;9(3):102-8. doi: 10.3390/90300102.
3
Viscometric analysis of the interaction of bisphenanthridinium compounds with closed circular supercoiled and linear DNA.双菲啶鎓化合物与闭环超螺旋和线性DNA相互作用的粘度分析。
Nucleic Acids Res. 1982 Jul 10;10(13):4093-106. doi: 10.1093/nar/10.13.4093.
4
1H NMR study of an ethidium dimer poly(dA-dT) complex: evidence of a transition between bis and monointercalation.溴化乙锭二聚体聚（dA-dT）复合物的¹H NMR研究：双插入和单插入之间转变的证据
Nucleic Acids Res. 1983 Jul 11;11(13):4467-82. doi: 10.1093/nar/11.13.4467.
5
Photocleavage of DNA and photofootprinting of E. coli RNA polymerase bound to promoter DNA by azido-9-acridinylamines.叠氮-9-吖啶胺对DNA的光切割及与启动子DNA结合的大肠杆菌RNA聚合酶的光足迹分析
Nucleic Acids Res. 1988 Jul 11;16(13):5755-70. doi: 10.1093/nar/16.13.5755.
本文引用的文献
1
The effects of antimicrobial agents on deoxyribonucleic acid polymerase.抗菌剂对脱氧核糖核酸聚合酶的作用。
Biochem J. 1963 Mar;86(3):562-7. doi: 10.1042/bj0860562.
2
COMPLEX FORMATION WITH DNA AND INHIBITION OF ESCHERICHIA COLI RNA POLYMERASE BY ETHIDIUM BROMIDE.溴化乙锭与DNA的复合物形成及对大肠杆菌RNA聚合酶的抑制作用
Biochim Biophys Acta. 1964 Jun 22;87:358-61. doi: 10.1016/0926-6550(64)90238-5.
3
Statistical thermodynamics of nucleic acid melting transitions with coupled binding equilibria.具有耦合结合平衡的核酸熔解转变的统计热力学
Biopolymers. 1971 Nov;10(11):2147-60. doi: 10.1002/bip.360101110.
4
Binding to deoxyribonucleic acid and inhibition of ribonucleic acid polymerase by analogs of chloroquine.
J Med Chem. 1974 Aug;17(8):856-62. doi: 10.1021/jm00254a015.
5
The PROPHET system and resource sharing.先知系统与资源共享。
Fed Proc. 1974 Dec;33(12):2390-2.
6
Diacridines - double intercalators as chemotherapeutic agents.
Biochem Pharmacol. 1976 Jan 15;25(2):231-6. doi: 10.1016/0006-2952(76)90304-x.
7
Diacridines: bifunctional intercalators. III. Definition of the general site of action.
Biochim Biophys Acta. 1976 Feb 5;418(3):300-14. doi: 10.1016/0005-2787(76)90292-6.
8
Diacridines: bifunctional intercalators. II. The biological effects of putrescine, sperimidine and spermine diacridines on HeLa cells and on the L-1210 and P-388 leukemia cells.
Biochim Biophys Acta. 1976 Feb 5;418(3):290-9. doi: 10.1016/0005-2787(76)90291-4.
9
Diacridines: bifunctional intercalators. I. Chemistry, physical chemistry and growth inhibitory properties.
Biochim Biophys Acta. 1976 Feb 5;418(3):277-89. doi: 10.1016/0005-2787(76)90290-2.
10
Theoretical calculations of the helix-coil transition of DNA in the presence of large, cooperatively binding ligands.在存在大的、协同结合配体的情况下DNA螺旋-卷曲转变的理论计算。
Biopolymers. 1976 Jul;15(7):1345-75. doi: 10.1002/bip.1976.360150710.
Zotero 插件