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茚并异喹啉的 UV-Vis 光谱的溶剂依赖性：酮氧作为极性相互作用探针的作用。

Solvent dependency of the UV-Vis spectrum of indenoisoquinolines: role of keto-oxygens as polarity interaction probes.

机构信息

Dipartimento di Biologia, Università degli Studi di Roma "Tor Vergata", Roma, Italy.

出版信息

PLoS One. 2013 Sep 26;8(9):e73881. doi: 10.1371/journal.pone.0073881. eCollection 2013.

DOI:10.1371/journal.pone.0073881
PMID:24086299
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3784438/
Abstract

Indenoisoquinolines are the most promising non-campthotecins topoisomerase IB inhibitors. We present an integrated experimental/computational investigation of the UV-Vis spectra of the IQNs parental compound (NSC314622) and two of its derivatives (NSC724998 and NSC725776) currently undergoing Phase I clinical trials. In all the three compounds a similar dependence of the relative absorption intensities at 270 nm and 290 nm on solvent polarity is found. The keto-oxygens in positions 5 and 11 of the molecular scaffold of the molecule are the principal chromophores involved in this dependence. Protic interactions on these sites are also found to give rise to absorptions at wavelength <250 nm observed in water solution, due to the stabilization of highly polarized tautomers of the molecule. These results suggest that the keto-oxygens are important polarizable groups that can act as useful interactors with the molecular receptor, providing at the same time an useful fingerprint for the monitoring of the drug binding to topoisomerase IB.

摘要

吲哚并喹啉类化合物是最有前途的非喜树碱拓扑异构酶 IB 抑制剂。我们对正在进行 I 期临床试验的 IQN 母体化合物（NSC314622）及其两种衍生物（NSC724998 和 NSC725776）的紫外-可见光谱进行了综合的实验/计算研究。在所有这三种化合物中，在 270nm 和 290nm 处的相对吸收强度与溶剂极性的依赖性相似。分子骨架中 5 位和 11 位的酮氧是参与这种依赖性的主要发色团。在这些位置上的质子相互作用也被发现会导致在水溶液中观察到波长<250nm 的吸收，这是由于分子的高度极化互变异构体的稳定化。这些结果表明，酮氧是重要的可极化基团，可以作为与分子受体的有用相互作用物，同时为监测药物与拓扑异构酶 IB 的结合提供有用的指纹。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2108/3784438/2ce92fb1901d/pone.0073881.g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2108/3784438/72ad003d1312/pone.0073881.g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2108/3784438/a7d674d34713/pone.0073881.g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2108/3784438/3b711b9908b4/pone.0073881.g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2108/3784438/e657113b988c/pone.0073881.g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2108/3784438/442855890b0d/pone.0073881.g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2108/3784438/05e3bc257fc6/pone.0073881.g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2108/3784438/0beac690f7dc/pone.0073881.g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2108/3784438/2ce92fb1901d/pone.0073881.g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2108/3784438/72ad003d1312/pone.0073881.g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2108/3784438/a7d674d34713/pone.0073881.g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2108/3784438/3b711b9908b4/pone.0073881.g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2108/3784438/e657113b988c/pone.0073881.g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2108/3784438/442855890b0d/pone.0073881.g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2108/3784438/05e3bc257fc6/pone.0073881.g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2108/3784438/0beac690f7dc/pone.0073881.g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2108/3784438/2ce92fb1901d/pone.0073881.g008.jpg

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