小沟结合剂吡咯聚酰胺-2'-脱氧鸟苷杂合物的设计、合成与分析。
Design, synthesis, and analysis of minor groove binder pyrrolepolyamide-2'-deoxyguanosine hybrids.
作者信息
Kawashima Etsuko, Ohba Yusuke, Terui Yusuke, Kamaike Kazuo
机构信息
School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.
出版信息
J Nucleic Acids. 2010;2010. doi: 10.4061/2010/235240. Epub 2010 Feb 16.
Abstract
Pyrrolepolyamide-2'-deoxyguanosine hybrids (Hybrid 2 and Hybrid 3) incorporating the 3-aminopropionyl or 3-aminopropyl linker were designed and synthesized on the basis of previously reported results of a pyrrolepolyamide-adenosine hybrid (Hybrid 1). Evaluation of the DNA binding sequence selectivity of pyrrolepolyamide-2'-deoxyguanosine hybrids was performed by CD spectral and T(m) analyses. It was shown that Hybrid 3 possessed greater binding specificity than distamycin A, Hybrid 1 and Hybrid 2.
摘要
基于先前报道的吡咯聚酰胺-腺苷杂合物（杂合物1）的结果，设计并合成了包含3-氨基丙酰基或3-氨基丙基连接体的吡咯聚酰胺-2'-脱氧鸟苷杂合物（杂合物2和杂合物3）。通过圆二色光谱（CD）和熔点（T(m)）分析对吡咯聚酰胺-2'-脱氧鸟苷杂合物的DNA结合序列选择性进行了评估。结果表明，杂合物3比Distamycin A、杂合物1和杂合物2具有更高的结合特异性。
相似文献
1
Design, synthesis, and analysis of minor groove binder pyrrolepolyamide-2'-deoxyguanosine hybrids.
J Nucleic Acids. 2010;2010. doi: 10.4061/2010/235240. Epub 2010 Feb 16.
2
[Design, synthesis and evaluation of polyamide-nucleoside hybrids and oligonucleotides conjugated hybrid as a novel gene expression control compound].
Yakugaku Zasshi. 2010 Mar;130(3):355-75. doi: 10.1248/yakushi.130.355.
3
Design, synthesis and analysis of a pyrrolepolyamide-nucleoside hybrid.
Nucleic Acids Symp Ser (Oxf). 2004(48):55-6. doi: 10.1093/nass/48.1.55.
4
Design, synthesis and evaluation of oligomer conjugated MGBpolyamide-nucleoside hybrid as a novel gene expression control compound.
Nucleic Acids Symp Ser (Oxf). 2005(49):327-8. doi: 10.1093/nass/49.1.327.
5
Synthesis and evaluation of 2-pyrrolepolyamide-2'-deoxyguanosine 5'-phosphate.
Nucleic Acids Symp Ser (Oxf). 2007(51):263-4. doi: 10.1093/nass/nrm132.
6
Design, synthesis, and biological activity of hybrid compounds between uramustine and DNA minor groove binder distamycin A.
J Med Chem. 2002 Aug 15;45(17):3630-8. doi: 10.1021/jm011113b.
7
Synthesis of oligonucleotide conjugated pyrrolepolyamide- and pyrrole-imidazole polyamide-2'-deoxyguanosine hybrids as novel gene expression control compounds.
Nucleic Acids Symp Ser (Oxf). 2008(52):387-8. doi: 10.1093/nass/nrn197.
8
Design, synthesis and analysis of antiviral nucleosides bearing pyrrolepolyamide binding to nucleic acid (II): N2-pyrrolepolyamidopropylguanosine.
Nucleic Acids Res Suppl. 2003(3):29-30. doi: 10.1093/nass/3.1.29.
9
Design, synthesis, DNA binding, and biological evaluation of water-soluble hybrid molecules containing two pyrazole analogues of the alkylating cyclopropylpyrroloindole (CPI) subunit of the antitumor agent CC-1065 and polypyrrole minor groove binders.
J Med Chem. 2001 Aug 2;44(16):2536-43. doi: 10.1021/jm0108404.
10
Distamycin A as stem of DNA minor groove alkylating agents.
Curr Top Med Chem. 2004;4(2):231-9. doi: 10.2174/1568026043451474.
引用本文的文献
1
Synthesis and Evaluation of MGB Polyamide-Oligonucleotide Conjugates as Gene Expression Control Compounds.
J Nucleic Acids. 2023 Mar 14;2023:2447998. doi: 10.1155/2023/2447998. eCollection 2023.
本文引用的文献
1
A brief history, status, and perspective of modified oligonucleotides for chemotherapeutic applications.
Curr Protoc Nucleic Acid Chem. 2001 May;Chapter 4:Unit 4.1. doi: 10.1002/0471142700.nc0401s00.
2
Sequence recognition in the minor groove of DNA by covalently linked formamido imidazole-pyrrole-imidazole polyamides: effect of H-pin linkage and linker length on selectivity and affinity.
Biochemistry. 2007 Oct 23;46(42):11661-70. doi: 10.1021/bi701053a. Epub 2007 Oct 2.
3
Use of ferrocene scaffolds as pendant groups in hairpin-type pyrrole-imidazole polyamide molecules showing sequence-selective binding to DNA duplexes.
J Org Chem. 2005 Dec 9;70(25):10311-22. doi: 10.1021/jo051247n.
4
Influence of structural variation on nuclear localization of DNA-binding polyamide-fluorophore conjugates.
Nucleic Acids Res. 2004 May 20;32(9):2802-18. doi: 10.1093/nar/gkh609. Print 2004.
5
Design, synthesis, and biological evaluation of hybrid molecules containing alpha-methylene-gamma-butyrolactones and polypyrrole minor groove binders.
J Med Chem. 2004 May 20;47(11):2877-86. doi: 10.1021/jm031104y.
6
Synthesis and analysis of nucleosides bearing pyrrolepolyamide binding to DNA.
Nucleosides Nucleotides Nucleic Acids. 2003 May-Aug;22(5-8):1309-11. doi: 10.1081/NCN-120022953.
7
Design, synthesis and analysis of antiviral nucleosides bearing pyrrolepolyamide binding to nucleic acid (II): N2-pyrrolepolyamidopropylguanosine.
Nucleic Acids Res Suppl. 2003(3):29-30. doi: 10.1093/nass/3.1.29.
8
Design, synthesis, and biological activity of hybrid compounds between uramustine and DNA minor groove binder distamycin A.
J Med Chem. 2002 Aug 15;45(17):3630-8. doi: 10.1021/jm011113b.
9
Cellular uptake of N-methylpyrrole/N-methylimidazole polyamide-dye conjugates.
Bioorg Med Chem. 2002 Oct;10(10):3313-8. doi: 10.1016/s0968-0896(02)00204-3.
10
Efficient methods for the synthesis of [2-15N]guanosine and 2'-deoxy[2-15N]guanosine derivatives.
Nucleosides Nucleotides Nucleic Acids. 2001 Jan-Feb;20(1-2):59-75. doi: 10.1081/NCN-100001437.
Zotero 插件