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具有一氧化氮合酶/单羧酸转运体抑制作用的异硫脲和肉桂酸衍生物的体外和体内抗肿瘤活性

In Vitro and In Vivo Antitumor Activities of Isothiourea and Cinnamic Acid Derivative with NOS/MCT Inhibitory Effect.

作者信息

Shitova A A, Filimonova M V, Soldatova O V, Volkova I K, Rybachuk V A, Shevchenko L I, Surinova V I, Kaprin A D, Shegay P V, Ivanov S A, Shlyakhto E V, Filimonov A S

机构信息

Almazov National Medical Research Centre, Ministry of Health of the Russian Federation, St. Petersburg, Russia.

A. Tsyb Medical Radiological Research Centre - Branch of the National Medical Research Radiological Centre, Ministry of Health of the Russian Federation, Obninsk, Russia.

出版信息

Bull Exp Biol Med. 2024 Nov;178(1):68-74. doi: 10.1007/s10517-024-06284-9. Epub 2024 Nov 22.

DOI:10.1007/s10517-024-06284-9
PMID:39572496
Abstract

This work presents the method of synthesis and physicochemical characterization of isothiourea and cinnamic acid original derivative α-cyano-4-hydroxycinnamate 1-cyclohexanoy-l-2-ethylisothiourea (T1114). In studies of the cytotoxic and antitumor activity of T1114, it has been found that the combination in one molecular structure of NOS-inhibitory fragment (1-cyclohexanoyl-2-ethylisothiourea) and a fragment inhibiting monocarboxylate lactate transporters (MCT) (α-cyano-4-hydroxycinnamic acid) does not modify the cytotoxic activity of bifunctional NOS/MCT-inhibitor T1114 in vitro. But in vivo inhibition of NOS and MCT is able to realize effects on the tumor microenvironment and hypoxic tumor cells. Such structural and functional modification has significantly extended the antitumor activity of the new NOS/MCT inhibitor. The bifunctional compound not only realized a more pronounced antitumor effect, but also prevented the development of hypoxic adaptation in solid Ehrlich carcinoma and acquired the ability to overcome the resistance of mouse cervical cancer (RShM-5). Therefore, the combination of NOS-inhibitory, anti-vasculogenic and hypoxia-oriented toxic effects can create new opportunities in antiangiogenic therapy of malignant neoplasms.

摘要

这项工作介绍了异硫脲和肉桂酸原衍生物α-氰基-4-羟基肉桂酸1-环己酰基-2-乙基异硫脲(T1114)的合成方法及理化特性。在对T1114的细胞毒性和抗肿瘤活性研究中发现,一氧化氮合酶(NOS)抑制片段(1-环己酰基-2-乙基异硫脲)和抑制单羧酸乳酸转运蛋白(MCT)的片段(α-氰基-4-羟基肉桂酸)在一个分子结构中的组合,并未改变双功能NOS/MCT抑制剂T1114在体外的细胞毒性活性。但在体内对NOS和MCT的抑制能够对肿瘤微环境和缺氧肿瘤细胞产生作用。这种结构和功能的修饰显著扩展了新型NOS/MCT抑制剂的抗肿瘤活性。该双功能化合物不仅实现了更显著的抗肿瘤效果,还阻止了实体艾氏癌中缺氧适应的发展,并获得了克服小鼠宫颈癌(RShM-5)耐药性的能力。因此,NOS抑制、抗血管生成和缺氧导向的毒性作用的联合可以为恶性肿瘤的抗血管生成治疗创造新的机会。

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本文引用的文献

1
Preclinical studies of NOS inhibitor T1059 vasopressor activity on the models of acute hemorrhagic shock in rats and dogs.一氧化氮合酶抑制剂T1059对大鼠和犬急性失血性休克模型血管升压活性的临床前研究。
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Combination of NOS- and PDK-Inhibitory Activity: Possible Way to Enhance Antitumor Effects.
一氧化氮合酶(NOS)抑制活性与丙酮酸脱氢酶激酶(PDK)抑制活性的联合:增强抗肿瘤作用的可能途径。
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In Vitro and In Vivo Efficacy of AZD3965 and Alpha-Cyano-4-Hydroxycinnamic Acid in the Murine 4T1 Breast Tumor Model.在小鼠 4T1 乳腺癌模型中 AZD3965 和 Alpha-氰基-4-羟基肉桂酸的体外和体内疗效。
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Bull Exp Biol Med. 2019 Nov;168(1):92-94. doi: 10.1007/s10517-019-04655-1. Epub 2019 Nov 25.
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Use of Computational Biochemistry for Elucidating Molecular Mechanisms of Nitric Oxide Synthase.利用计算生物化学阐明一氧化氮合酶的分子机制。
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8
Nitric oxide synthase inhibitors 1400W and L-NIO inhibit angiogenesis pathway of colorectal cancer.一氧化氮合酶抑制剂 1400W 和 L-NIO 抑制结直肠癌的血管生成途径。
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