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含查耳酮部分的异香豆素作为同工型选择性肿瘤相关碳酸酐酶抑制剂。

Isocoumarins incorporating chalcone moieties act as isoform selective tumor-associated carbonic anhydrase inhibitors.

机构信息

Faculty of Science & Arts, Department of Chemistry, Harran University, Sanliurfa 63290, Turkey.

Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Adiyaman University, Adıyaman 02040, Turkey.

出版信息

Future Med Chem. 2024 Jul 2;16(13):1347-1355. doi: 10.1080/17568919.2024.2350875. Epub 2024 May 28.

DOI:10.1080/17568919.2024.2350875
PMID:39109432
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11318696/
Abstract

A series of isocoumarin-chalcone hybrids were prepared and assays for the inhibition of four isoforms of human carbonic anhydrase (hCA; EC 4.2.1.1), hCA I, II, IX and XII. Isocoumarin-chalcone hybrids were synthesized by condensing acetyl-isocoumarin with aromatic aldehydes. They did not significantly inhibit off-target cytosolic isoforms hCA I and II (K >100 μM) but acted as low micromolar or submicromolar inhibitors for the tumor-associated isoforms hCA IX and XII. Our work provides insights into a new and scarcely investigated chemotype which provides interesting tumor-associated CA inhibitors, considering that some such derivatives like sulfonamide SLC-0111 are in advanced clinical trials for the management of metastatic advanced solid tumors.

摘要

一系列异香豆素-查耳酮类混合物被制备出来，并对四种人碳酸酐酶（hCA；EC 4.2.1.1）同工酶 hCA I、II、IX 和 XII 的抑制作用进行了检测。异香豆素-查耳酮类混合物是通过乙酰基异香豆素与芳香醛缩合而成的。它们对非靶标胞质同工酶 hCA I 和 II 的抑制作用不明显（K > 100 μM），但对肿瘤相关同工酶 hCA IX 和 XII 具有低微摩尔或亚微摩尔的抑制作用。我们的工作为一种新的、研究甚少的化学型提供了深入了解，该化学型提供了有趣的肿瘤相关 CA 抑制剂，考虑到一些这样的衍生物，如磺胺 SLC-0111，正在进行晚期临床研究，用于治疗转移性晚期实体肿瘤。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6e5/11318696/db533fd476df/IFMC_A_2350875_UF0001_C.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6e5/11318696/db533fd476df/IFMC_A_2350875_UF0001_C.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6e5/11318696/db533fd476df/IFMC_A_2350875_UF0001_C.jpg

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Anticancer Potential of Natural Chalcones: In Vitro and In Vivo Evidence.天然查耳酮的抗癌潜力：体外和体内证据。
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Terminators or Guardians? Design, Synthesis, and Cytotoxicity Profiling of Chalcone-Sulfonamide Hybrids.终结者还是守护者？查耳酮-磺酰胺杂化物的设计、合成及细胞毒性分析
ACS Omega. 2023 Feb 17;8(8):7666-7683. doi: 10.1021/acsomega.2c07285. eCollection 2023 Feb 28.
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