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