Suppr超能文献

21 世纪菲啶和菲啶鎓衍生物的复兴。

Come-back of phenanthridine and phenanthridinium derivatives in the 21st century.

机构信息

Laboratory for Study of Interactions of Biomacromolecules, Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, PO Box 180, HR-10002 Zagreb, Croatia.

出版信息

Beilstein J Org Chem. 2014 Dec 10;10:2930-54. doi: 10.3762/bjoc.10.312. eCollection 2014.

Abstract

Phenanthridine derivatives are one of the most intensively studied families of biologically active compounds with efficient DNA binding capability. Attracting attention since DNA structure discovery (1960s), they were early recognized as a symbol of DNA intercalative binding, for many decades applied as gold-standard DNA- and RNA-fluorescent markers (ethidium bromide), probes for cell viability (propidium iodide), but also "ill-famed" for various toxic (genotoxic) and mutagenic effects. After two decades of low interest, the discovery of phenanthridine alkaloids and new studies of antiparasitic/antitumor properties of phenanthridine derivatives resulted in the strong increase of the scientific interest about the turn of this century. Here are summarized phenanthridine-related advances in the 21st century (2000-present period) with emphasis on the supramolecular interactions and bioorganic chemistry, as well as novel or improved synthetic approaches.

摘要

菲啶衍生物是生物活性化合物中研究最广泛的家族之一,具有高效的 DNA 结合能力。自 DNA 结构发现(20 世纪 60 年代)以来,它们就引起了人们的关注,它们很早就被认为是 DNA 嵌入结合的标志,几十年来一直被用作 DNA 和 RNA 荧光标记物的金标准(溴化乙锭)、细胞活力探针(碘化丙啶),但也因各种毒性(遗传毒性)和诱变作用而声名狼藉。经过二十年的低关注度后,菲啶生物碱的发现以及菲啶衍生物的抗寄生虫/抗肿瘤特性的新研究,在本世纪之交强烈增加了人们对它们的科学兴趣。本文总结了 21 世纪(2000 年至今)与菲啶相关的进展,重点介绍超分子相互作用和生物有机化学,以及新颖或改进的合成方法。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e954/4273281/871c13a4abdf/Beilstein_J_Org_Chem-10-2930-g014.jpg

相似文献

1
Come-back of phenanthridine and phenanthridinium derivatives in the 21st century.
Beilstein J Org Chem. 2014 Dec 10;10:2930-54. doi: 10.3762/bjoc.10.312. eCollection 2014.
2
Permanent positive charge strongly influences DNA/RNA binding and antiproliferative activity of urea-phenanthridinium conjugates.
Eur J Med Chem. 2010 Aug;45(8):3281-92. doi: 10.1016/j.ejmech.2010.04.006. Epub 2010 Apr 14.
3
Synthesis, photophysical properties, and nucleic acid binding of phenanthridinium derivatives based on ethidium.
Bioorg Med Chem. 2003 Nov 17;11(23):5235-47. doi: 10.1016/j.bmc.2003.08.006.
4
Synthesis of DNA with phenanthridinium as an artificial DNA base.
J Org Chem. 2004 Feb 6;69(3):744-51. doi: 10.1021/jo0355404.
5
A novel bis-phenanthridine triamine with pH controlled binding to nucleotides and nucleic acids.
Org Biomol Chem. 2005 Dec 21;3(24):4373-81. doi: 10.1039/b509094f. Epub 2005 Nov 7.
7
Synthesis, DNA-binding and biological activity of a double intercalating analog of ethidium bromide.
Nucleic Acids Res. 1978 Jul;5(7):2629-41. doi: 10.1093/nar/5.7.2629.

引用本文的文献

2
Distinctive Nucleic Acid Recognition by Lysine-Embedded Phenanthridine Peptides.
Int J Mol Sci. 2024 Apr 29;25(9):4866. doi: 10.3390/ijms25094866.
3
Photoinduced in situ generation of DNA-targeting ligands: DNA-binding and DNA-photodamaging properties of benzo[]quinolizinium ions.
Beilstein J Org Chem. 2024 Jan 18;20:101-117. doi: 10.3762/bjoc.20.11. eCollection 2024.
4
The Effective Synthesis of New Benzoquinoline Derivatives as Small Molecules with Anticancer Activity.
Pharmaceuticals (Basel). 2023 Dec 28;17(1):52. doi: 10.3390/ph17010052.
5
Difluoromethylborates and Muonium for the Study of Isonitrile Insertion Affording Phenanthridines via Imidoyl Radicals.
J Org Chem. 2023 Jul 7;88(13):8042-8054. doi: 10.1021/acs.joc.3c00056. Epub 2023 Jun 23.
6
Synthesis of phenanthridines via a novel photochemically-mediated cyclization and application to the synthesis of triphaeridine.
Beilstein J Org Chem. 2021 Sep 8;17:2340-2347. doi: 10.3762/bjoc.17.152. eCollection 2021.
8
Phenanthridine derivatives as potential HIV-1 protease inhibitors.
Biomed Rep. 2020 Dec;13(6):66. doi: 10.3892/br.2020.1373. Epub 2020 Oct 20.
10
A Triptycene-Based Enantiopure Bis(Diazadibenzoanthracene) by a Chirality-Assisted Synthesis Approach.
Chemistry. 2020 Dec 4;26(68):16036-16042. doi: 10.1002/chem.202002781. Epub 2020 Oct 27.

本文引用的文献

2
6-Phosphorylated phenanthridines from 2-isocyanobiphenyls via radical C-P and C-C bond formation.
Org Lett. 2014 Jan 3;16(1):250-3. doi: 10.1021/ol403256e. Epub 2013 Dec 9.
3
6-Aroylated phenanthridines via base promoted homolytic aromatic substitution (BHAS).
Org Lett. 2013 Dec 20;15(24):6286-9. doi: 10.1021/ol403147v. Epub 2013 Nov 25.
4
Synthesis of 6-alkylated phenanthridine derivatives using photoredox neutral somophilic isocyanide insertion.
Angew Chem Int Ed Engl. 2013 Dec 9;52(50):13289-92. doi: 10.1002/anie.201308376. Epub 2013 Nov 12.
9
6-Trifluoromethyl-phenanthridines through radical trifluoromethylation of isonitriles.
Angew Chem Int Ed Engl. 2013 Oct 4;52(41):10792-5. doi: 10.1002/anie.201306082. Epub 2013 Sep 2.
10
Phenanthridine synthesis through iron-catalyzed intramolecular N-arylation of O-acetyl oxime.
Org Lett. 2013 Aug 16;15(16):4254-7. doi: 10.1021/ol4020392. Epub 2013 Aug 8.

文献AI研究员

20分钟写一篇综述,助力文献阅读效率提升50倍。

立即体验

用中文搜PubMed

大模型驱动的PubMed中文搜索引擎

马上搜索

文档翻译

学术文献翻译模型,支持多种主流文档格式。

立即体验