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修饰多核苷酸。VI. 一种含有抗疱疹剂（E）-5-（2-溴乙烯基）-2'-脱氧尿苷的合成DNA的性质

Modified polynucleotides. VI. Properties of a synthetic DNA containing the anti-herpes agent (E)-5-(2-bromovinyl)-2'-deoxyuridine.

作者信息

Sági J, Czuppon A, Kajtár M, Szabolcs A, Szemzö A, Otvös L

出版信息

Nucleic Acids Res. 1982 Oct 11;10(19):6051-66. doi: 10.1093/nar/10.19.6051.

DOI:10.1093/nar/10.19.6051
PMID:6755397
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC320950/
Abstract

A new modified polydeoxynucleotide, a copolymer of nucleotides of 2'-deoxyadenosine and the very efficacious anti-herpesvirus agent (E)-5-(2-bromovinyl)-2'-deoxyuridine was synthesized with E. coli DNA polymerase I enzyme. It is characterized by its physical (absorption and circular dichroism spectra, thermal transition, sedimentation analysis) and bioorganic (template activity, stability) properties. Compared to poly [d(A-T)], the modified polydeoxynucleotide had a lower thermal stability but exhibited higher stability against DNases and higher template activity for DNA synthesis. Template activity for RNA synthesis of this template was, however, poor and extent of AMP and UMP incorporation was limited as well.

摘要

一种新的修饰多脱氧核苷酸，即2'-脱氧腺苷核苷酸与非常有效的抗疱疹病毒剂（E）-5-（2-溴乙烯基）-2'-脱氧尿苷的共聚物，使用大肠杆菌DNA聚合酶I酶合成。它具有物理性质（吸收光谱和圆二色光谱、热转变、沉降分析）和生物有机性质（模板活性、稳定性）。与聚[d（A-T）]相比，修饰的多脱氧核苷酸热稳定性较低，但对脱氧核糖核酸酶表现出更高的稳定性，并且对DNA合成具有更高的模板活性。然而，该模板的RNA合成模板活性较差，AMP和UMP掺入程度也有限。

相似文献

1
Modified polynucleotides. VI. Properties of a synthetic DNA containing the anti-herpes agent (E)-5-(2-bromovinyl)-2'-deoxyuridine.修饰多核苷酸。VI. 一种含有抗疱疹剂（E）-5-（2-溴乙烯基）-2'-脱氧尿苷的合成DNA的性质
Nucleic Acids Res. 1982 Oct 11;10(19):6051-66. doi: 10.1093/nar/10.19.6051.
2
Incorporation of the carbocyclic analogue of (E)-5-(2-bromovinyl)-2'-deoxyuridine 5'-triphosphate into a synthetic DNA.将（E）-5-（2-溴乙烯基）-2'-脱氧尿苷5'-三磷酸的碳环类似物掺入合成DNA中。
Biochem Biophys Res Commun. 1987 Sep 30;147(3):1105-12. doi: 10.1016/s0006-291x(87)80184-5.
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Modified polynucleotides. VII. Impaired integrity of a synthetic DNA containing the antiherpetic agent 5-isopropyl-2'-deoxyuridine.修饰的多核苷酸。VII. 含有抗疱疹剂5-异丙基-2'-脱氧尿苷的合成DNA的完整性受损。
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(E)-5-(2-bromovinyl)-2'-deoxyuridine-5'-triphosphate as a DNA polymerase substrate.（E）-5-（2-溴乙烯基）-2'-脱氧尿苷-5'-三磷酸作为DNA聚合酶底物
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Preparation and properties of the repeating sequence polymers d(A-I-C)n-d(I-C-T)n and d(A-G-C)n-d(G-C-T)n.重复序列聚合物d(A-I-C)n-d(I-C-T)n和d(A-G-C)n-d(G-C-T)n的制备与性质
Biochemistry. 1976 Jan 13;15(1):168-76. doi: 10.1021/bi00646a026.
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Poly(dG-dC) in the Z-form inhibits E. coli DNA polymerase I and AMV DNA polymerase activity.Z型的聚（dG-dC）抑制大肠杆菌DNA聚合酶I和禽成髓细胞瘤病毒DNA聚合酶的活性。
Biochem Int. 1985 Sep;11(3):281-90.
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Action of DNA polymerase I of Escherichia coli with DNA-RNA hybrids as templates.以DNA-RNA杂交体为模板时大肠杆菌DNA聚合酶I的作用。
Proc Natl Acad Sci U S A. 1972 Feb;69(2):398-402. doi: 10.1073/pnas.69.2.398.

引用本文的文献

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Minimising the secondary structure of DNA targets by incorporation of a modified deoxynucleoside: implications for nucleic acid analysis by hybridisation.通过掺入修饰的脱氧核苷使DNA靶标的二级结构最小化：对杂交核酸分析的影响。
Nucleic Acids Res. 2000 Oct 15;28(20):3904-9. doi: 10.1093/nar/28.20.3904.
2
A comparative study of the thermal stability of oligodeoxyribonucleotides containing 5-substituted 2'-deoxyuridines.含5-取代2'-脱氧尿苷的寡脱氧核糖核苷酸热稳定性的比较研究。
Nucleic Acids Res. 1998 Jul 1;26(13):3127-35. doi: 10.1093/nar/26.13.3127.
3
Structure-activity relationships and conformational features of antiherpetic pyrimidine and purine nucleoside analogues. A review.抗疱疹嘧啶和嘌呤核苷类似物的构效关系及构象特征。综述。
Pharm World Sci. 1994 Apr 15;16(2):127-38. doi: 10.1007/BF01880663.
4
Uracil in deoxyribonucleotide polymers reduces their template-primer activity for E. coli DNA polymerase I.脱氧核糖核苷酸聚合物中的尿嘧啶会降低其作为大肠杆菌DNA聚合酶I模板引物的活性。
Nucleic Acids Res. 1983 Jun 11;11(11):3753-65. doi: 10.1093/nar/11.11.3753.
5
Modified polynucleotides. VII. Impaired integrity of a synthetic DNA containing the antiherpetic agent 5-isopropyl-2'-deoxyuridine.修饰的多核苷酸。VII. 含有抗疱疹剂5-异丙基-2'-脱氧尿苷的合成DNA的完整性受损。
Nucleic Acids Res. 1986 Apr 25;14(8):3449-62. doi: 10.1093/nar/14.8.3449.
6
C4-methyldeoxythymidine replacing deoxythymidine in poly[d(A-T)] renders the polymer resistant to the 3'----5' exonuclease activity of the Klenow and T4 DNA polymerases.在聚[d(A-T)]中用C4-甲基脱氧胸苷取代脱氧胸苷，可使该聚合物对Klenow和T4 DNA聚合酶的3'→5'核酸外切酶活性具有抗性。
Nucleic Acids Res. 1986 Aug 26;14(16):6735-43. doi: 10.1093/nar/14.16.6735.

本文引用的文献

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HELIX--RANDOM COIL TRANSITIONS IN DNA HOMOPOLYMER PAIRS.DNA同聚物对中的螺旋-无规卷曲转变
J Mol Biol. 1964 Apr;8:452-69. doi: 10.1016/s0022-2836(64)80003-6.
2
Enzymatic synthesis of deoxyribonucleic acid. VII. Synthesis of a polymer of deoxyadenylate and deoxythymidylate.脱氧核糖核酸的酶促合成。VII. 脱氧腺苷酸和脱氧胸苷酸聚合物的合成。
J Biol Chem. 1960 Nov;235:3242-9.
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(E)-5-(2-bromovinyl)-2'-Deoxyuridine in the treatment of experimental herpes simplex keratitis.（E）-5-（2-溴乙烯基）-2'-脱氧尿苷治疗实验性单纯疱疹性角膜炎
Antimicrob Agents Chemother. 1980 Jan;17(1):8-12. doi: 10.1128/AAC.17.1.8.
4
(E)-5-(2-bromovinyl)-2'-deoxyuridine-5'-triphosphate as a DNA polymerase substrate.（E）-5-（2-溴乙烯基）-2'-脱氧尿苷-5'-三磷酸作为DNA聚合酶底物
Nucleic Acids Res. 1981 Dec 21;9(24):6985-94. doi: 10.1093/nar/9.24.6985.
5
Digestion of highly modified bacteriophage DNA by restriction endonucleases.用限制性内切核酸酶消化高度修饰的噬菌体DNA。
Nucleic Acids Res. 1982 Mar 11;10(5):1579-91. doi: 10.1093/nar/10.5.1579.
6
Incorporation of E-5-(2-halovinyl)-2'-deoxyuridines into deoxyribonucleic acids of herpes simplex virus type 1-infected cells.E-5-(2-卤代乙烯基)-2'-脱氧尿苷掺入单纯疱疹病毒1型感染细胞的脱氧核糖核酸中。
J Biol Chem. 1982 Jan 25;257(2):603-6.
7
Nucleoside analogues with clinical potential in antivirus chemotherapy. The effect of several thymidine and 2'-deoxycytidine analogue 5'-triphosphates on purified human (alpha, beta) and herpes simplex virus (types 1, 2) DNA polymerases.具有抗病毒化疗临床潜力的核苷类似物。几种胸苷和2'-脱氧胞苷类似物5'-三磷酸对纯化的人（α，β）和单纯疱疹病毒（1型、2型）DNA聚合酶的作用。
Mol Pharmacol. 1981 Sep;20(2):415-22.
8
Selective inhibition of herpesvirus deoxyribonucleic acid synthesis by acycloguanosine, 2'-fluoro-5-iodo-aracytosine, and (E)-5-(2-bromovinyl)-2'-deoxyuridine.阿昔洛韦、2'-氟-5-碘阿糖胞苷和（E）-5-（2-溴乙烯基）-2'-脱氧尿苷对疱疹病毒脱氧核糖核酸合成的选择性抑制作用。
Antimicrob Agents Chemother. 1981 May;19(5):927-9. doi: 10.1128/AAC.19.5.927.
9
Differential affinities of 5-(2-halogenovinyl)-2'-deoxyuridines for deoxythymidine kinases of various origins.5-（2-卤代乙烯基）-2'-脱氧尿苷对不同来源的脱氧胸苷激酶的差异亲和力。
Mol Pharmacol. 1981 Jul;20(1):230-3.
10
On the mechanism of selective inhibition of herpesvirus replication by (E)-5-(2-bromovinyl)-2'-deoxyuridine.关于（E）-5-（2-溴乙烯基）-2'-脱氧尿苷对疱疹病毒复制的选择性抑制机制
Proc Natl Acad Sci U S A. 1981 May;78(5):2698-702. doi: 10.1073/pnas.78.5.2698.