• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利：CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法，用中文像聊天一样搜索，搜遍4000万医学文献。AI智能推荐，让科研检索更轻松。

立即免费搜索

文件翻译

保留排版，准确专业，支持PDF/Word/PPT等文件格式，支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述，25分钟生成高质量综述，智能提取关键信息，辅助科研写作。

立即免费体验

双链 DNA 模板引导的寡核苷酸断裂，其中包含 P3'->N5' 键，由三链体形成触发：化学修饰的影响和反应性的显著增强。

Double-stranded DNA-templated cleavage of oligonucleotides containing a P3'->N5' linkage triggered by triplex formation: the effects of chemical modifications and remarkable enhancement in reactivity.

机构信息

Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan.

出版信息

Nucleic Acids Res. 2010 Nov;38(20):7332-42. doi: 10.1093/nar/gkq600. Epub 2010 Jul 8.

DOI:10.1093/nar/gkq600
PMID:20615902
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2978371/
Abstract

We recently reported double-stranded DNA-templated cleavage of oligonucleotides as a sequence-specific DNA-detecting method. In this method, triplex-forming oligonucleotides (TFOs) modified with 5'-amino-2',4'-BNA were used as a DNA-detecting probe. This modification introduced a P3'→N5' linkage (P-N linkage) in the backbone of the TFO, which was quickly cleaved under acidic conditions when it formed a triplex. The prompt fission of the P-N linkage was assumed to be driven by a conformational strain placed on the linkage upon triplex formation. Therefore, chemical modifications around the P-N linkage should change the reactivity by altering the microenvironment. We synthesized 5'-aminomethyl type nucleic acids, and incorporated them into TFOs instead of 5'-amino-2',4'-BNA to investigate the effect of 5'-elongation. In addition, 2',4'-BNA/LNA or 2',5'-linked DNA were introduced at the 3'- and/or 5'-neighboring residues of 5'-amino-2',4'-BNA to reveal neighboring residual effects. We evaluated the triplex stability and reaction properties of these TFOs, and found out that chemical modifications around the P-N linkage greatly affected their reaction properties. Notably, 2',5'-linked DNA at the 3' position flanking 5'-amino-2',4'-BNA brought significantly higher reactivity, and we succeeded in indicating that a TFO with this modification is promising as a DNA analysis tool.

摘要

我们最近报道了双链 DNA 模板切割寡核苷酸作为一种序列特异性的 DNA 检测方法。在该方法中，用 5'-氨基-2'，4'-BNA 修饰的三聚体形成寡核苷酸（TFOs）被用作 DNA 检测探针。这种修饰在 TFO 的主链中引入了 P3'→N5'键（P-N 键），当它形成三聚体时，该键在酸性条件下迅速断裂。P-N 键的快速断裂被认为是由三聚体形成时键上的构象应变驱动的。因此，P-N 键周围的化学修饰应该通过改变微环境来改变反应性。我们合成了 5'-氨基甲基型核酸，并将其引入 TFO 中，而不是 5'-氨基-2'，4'-BNA，以研究 5'-延伸的影响。此外，在 5'-氨基-2'，4'-BNA 的 3'和/或 5'相邻残基处引入了 2'，4'-BNA/LNA 或 2'，5'-连接的 DNA，以揭示相邻残基的影响。我们评估了这些 TFO 的三聚体稳定性和反应性质，发现 P-N 键周围的化学修饰极大地影响了它们的反应性质。值得注意的是，在 5'-氨基-2'，4'-BNA 的 3'位置侧翼引入 2'，5'-连接的 DNA 带来了更高的反应性，我们成功地表明，具有这种修饰的 TFO 有望成为一种 DNA 分析工具。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4fd1/2978371/84e117b2d13d/gkq600s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4fd1/2978371/d710e307133e/gkq600s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4fd1/2978371/74a5c90a66b3/gkq600f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4fd1/2978371/fdf15de7e4c7/gkq600s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4fd1/2978371/81ea5be48353/gkq600s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4fd1/2978371/8ddbc48d2edc/gkq600f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4fd1/2978371/49c8d99fbcb2/gkq600f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4fd1/2978371/866046b67edf/gkq600f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4fd1/2978371/4ae563a1f041/gkq600f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4fd1/2978371/244eb52bccd8/gkq600s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4fd1/2978371/84e117b2d13d/gkq600s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4fd1/2978371/d710e307133e/gkq600s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4fd1/2978371/74a5c90a66b3/gkq600f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4fd1/2978371/fdf15de7e4c7/gkq600s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4fd1/2978371/81ea5be48353/gkq600s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4fd1/2978371/8ddbc48d2edc/gkq600f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4fd1/2978371/49c8d99fbcb2/gkq600f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4fd1/2978371/866046b67edf/gkq600f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4fd1/2978371/4ae563a1f041/gkq600f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4fd1/2978371/244eb52bccd8/gkq600s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4fd1/2978371/84e117b2d13d/gkq600s5.jpg

相似文献

1
Double-stranded DNA-templated cleavage of oligonucleotides containing a P3'->N5' linkage triggered by triplex formation: the effects of chemical modifications and remarkable enhancement in reactivity.双链 DNA 模板引导的寡核苷酸断裂，其中包含 P3'->N5' 键，由三链体形成触发：化学修饰的影响和反应性的显著增强。
Nucleic Acids Res. 2010 Nov;38(20):7332-42. doi: 10.1093/nar/gkq600. Epub 2010 Jul 8.
2
Acid-mediated cleavage of oligonucleotide P3' --> N5' phosphoramidates triggered by sequence-specific triplex formation.由序列特异性三链体形成引发的酸介导的寡核苷酸P3'→N5'氨基磷酸酯的切割。
Nucleosides Nucleotides Nucleic Acids. 2007;26(8-9):893-6. doi: 10.1080/15257770701505741.
3
Synthesis and properties of 5'-amino-2',4'-BNA modified oligonucleotides with P3'-->N5' phosphoramidate linkages.具有3'-磷酰胺基-5'-氮基连接的5'-氨基-2',4'-双环核苷酸修饰寡核苷酸的合成与性质
Nucleic Acids Res Suppl. 2002(2):25-6. doi: 10.1093/nass/2.1.25.
4
Stable oligonucleotide-directed triplex formation at target sites with CG interruptions: strong sequence-specific recognition by 2',4'-bridged nucleic-acid-containing 2-pyridones under physiological conditions.在含有CG间断的靶位点形成稳定的寡核苷酸定向三链体：在生理条件下含2',4'-桥连核酸的2-吡啶酮对序列具有强特异性识别作用。
Chemistry. 2002 Oct 18;8(20):4796-802. doi: 10.1002/1521-3765(20021018)8:20<4796::AID-CHEM4796>3.0.CO;2-O.
5
Synthesis and properties of a novel bridged nucleic acid analogue bearing a P3'-->N5' phosphoroamidate linkage, 5'-amino-3', 5'-BNA.一种带有P3'→N5'氨基磷酸酯键的新型桥连核酸类似物5'-氨基-3', 5'-BNA的合成与性质
Nucleic Acids Symp Ser (Oxf). 2004(48):7-8. doi: 10.1093/nass/48.1.7.
6
Cleavage of oligonucleotides containing a P3'→N5' phosphoramidate linkage mediated by single-stranded oligonucleotide templates.寡核苷酸中 P3'→N5' 膦酸酰胺键的断裂由单链寡核苷酸模板介导。
Molecules. 2011 Dec 20;16(12):10695-708. doi: 10.3390/molecules161210695.
7
Promotion of acid-mediated cleavage of oligonucleotide P3'->N5' phosphoroamidates by triplex formation: a novel approach to sequence-specific DNA detection.通过三链体形成促进酸介导的寡核苷酸P3'→N5'氨基磷酸酯的切割：一种序列特异性DNA检测的新方法。
Nucleic Acids Symp Ser (Oxf). 2005(49):157-8. doi: 10.1093/nass/49.1.157.
8
Synthesis and properties of a novel bridged nucleic acid with a P3' --> N5' phosphoramidate linkage, 5'-amino-2',4'-BNA.一种具有P3'→N5'氨基磷酸酯键的新型桥连核酸5'-氨基-2',4'-BNA的合成与性质
Chem Commun (Camb). 2003 Sep 7(17):2202-3. doi: 10.1039/b307290h.
9
Synthesis and properties of a novel bridged nucleic acid analogue, 5'-amino-3',5'-BNA.一种新型桥连核酸类似物5'-氨基-3',5'-BNA的合成与性质
Nucleosides Nucleotides Nucleic Acids. 2005;24(5-7):1097-100. doi: 10.1081/ncn-200061836.
10
2'-O,4'-C-aminomethylene-bridged nucleic acid modification with enhancement of nuclease resistance promotes pyrimidine motif triplex nucleic acid formation at physiological pH.2'-O,4'-C-亚甲基桥连核酸修饰物增强了抗核酸酶的能力，促进了嘧啶基 motif 三链核酸在生理 pH 下的形成。
Chemistry. 2011 Feb 25;17(9):2742-51. doi: 10.1002/chem.201002745. Epub 2011 Jan 24.

引用本文的文献

1
Oligonucleotide-templated reactions for sensing nucleic acids.寡核苷酸模板反应在核酸检测中的应用。
Molecules. 2012 Feb 29;17(3):2446-63. doi: 10.3390/molecules17032446.
2
Cleavage of oligonucleotides containing a P3'→N5' phosphoramidate linkage mediated by single-stranded oligonucleotide templates.寡核苷酸中 P3'→N5' 膦酸酰胺键的断裂由单链寡核苷酸模板介导。
Molecules. 2011 Dec 20;16(12):10695-708. doi: 10.3390/molecules161210695.

本文引用的文献

1
A 2',4'-Bridged Nucleic Acid Containing 2-Pyridone as a Nucleobase: Efficient Recognition of a C⋅G Interruption by Triplex Formation with a Pyrimidine Motif.一种以2-吡啶酮作为碱基的2',4'-桥连核酸：通过与嘧啶基序形成三链体有效识别C⋅G中断。
Angew Chem Int Ed Engl. 2001 Jun 1;40(11):2079-2081. doi: 10.1002/1521-3773(20010601)40:11<2079::AID-ANIE2079>3.0.CO;2-Z.
2
Streamlining hit discovery and optimization with a yoctoliter scale DNA reactor.利用微微升级 DNA 反应器简化命中发现和优化。
Expert Opin Drug Discov. 2009 Nov;4(11):1201-13. doi: 10.1517/17460440903206940. Epub 2009 Sep 13.
3
Efficient nucleic acid detection by templated reductive quencher release.
通过模板还原抑制剂释放实现高效核酸检测。
J Am Chem Soc. 2009 Nov 11;131(44):16021-3. doi: 10.1021/ja904138v.
4
Nucleic acid templated reactions: consequences of probe reactivity and readout strategy for amplified signaling and sequence selectivity.核酸模板反应：探针反应性及读出策略对信号放大和序列选择性的影响
Chemistry. 2009 Jul 6;15(27):6723-30. doi: 10.1002/chem.200900025.
5
Reduction-triggered red fluorescent probes for dual-color detection of oligonucleotide sequences.用于寡核苷酸序列双色检测的还原触发红色荧光探针。
Org Biomol Chem. 2009 Feb 21;7(4):671-7. doi: 10.1039/b817228e. Epub 2008 Dec 12.
6
7-Azidomethoxy-coumarins as profluorophores for templated nucleic acid detection.7-叠氮甲氧基香豆素作为用于模板核酸检测的前体荧光团。
Chembiochem. 2008 Dec 15;9(18):2981-8. doi: 10.1002/cbic.200800507.
7
Target-catalyzed transfer reactions for the amplified detection of RNA.用于RNA扩增检测的靶标催化转移反应
Angew Chem Int Ed Engl. 2008;47(37):7119-22. doi: 10.1002/anie.200801355.
8
Organometallic activation of a fluorogen for templated nucleic acid detection.用于模板核酸检测的荧光团的有机金属活化
Org Lett. 2008 Jul 17;10(14):2935-8. doi: 10.1021/ol800878b. Epub 2008 Jun 13.
9
Facile SNP detection using bifunctional, cross-linking oligonucleotide probes.使用双功能交联寡核苷酸探针进行便捷的单核苷酸多态性检测。
Nucleic Acids Res. 2008 Mar;36(5):e31. doi: 10.1093/nar/gkn052. Epub 2008 Feb 16.
10
Fluorescence-based detection of single nucleotide permutation in DNA via catalytically templated reaction.
Chem Commun (Camb). 2007 Oct 7(37):3820-2. doi: 10.1039/b709611a.