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单硫代草酰胺对人红细胞、卤虫和果蝇的合成及毒性

Synthesis and toxicity of monothiooxalamides against human red blood cells, brine shrimp (), and fruit fly ( ).

作者信息

Romero-Chávez María M, Macías-Hernández Carlos Eduardo, Ramos-Organillo Angel, Jiménez-Ruiz Edgar Iván, Robles-Machuca Marcela, Ocaño-Higuera Victor Manuel, Sumaya-Martínez María Teresa

机构信息

Unidad de Tecnología de Alimentos, Secretaría de Investigación y Posgrado, Universidad Autónoma de Nayarit, Ciudad de la Cultura s/n, Tepic, 63000, Mexico.

Facultad de Ciencias Químicas, Universidad de Colima, Km 9 Carretera Colima-Coquimatlán, Coquimatlán, Colima, C.P. 28400, Mexico.

出版信息

Heliyon. 2024 Aug 14;10(16):e36182. doi: 10.1016/j.heliyon.2024.e36182. eCollection 2024 Aug 30.

DOI:10.1016/j.heliyon.2024.e36182
PMID:39253194
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11382093/
Abstract

A new family of monothiooxalamides derived from 2-aminobenzimidazole was synthesized, and their structures were confirmed by H and C one-dimensional and 2D NMR experiments (COSY, HSQC, and HMBC). The antioxidant capacity was evaluated by free radical scavenging assays: 1,1-diphenyl-2-picrylhydrazyl (DPPH•), 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) radical cation (ABTS•), ferric reducing antioxidant power (FRAP), oxygen radical absorbance capacity (ORAC), and the Fe(II) chelating ability. Our work group has previously reported the synthesis and antioxidant activity of monothiooxalamides derived from 2-aminopyridine (). In this study, the hemolytic activity of compounds from the 2-aminopyridine () and 2-aminobenzimidazole () families was evaluated against human red blood cells (RBCs). The concentration at which monothiooxalamides showed no hemolytic activity was chosen to assess their ability to inhibit free radical-induced membrane damage in human RBCs, acute toxicity in brine shrimp, and toxicity against . Compounds with morpholine fragments (, , , and ) showed time- and concentration-dependent protective effects against radical-induced oxidative hemolysis. Moreover, they had the lowest acute toxicity in the brine shrimp lethality assay and a significant increase in chelating activity compared with the other molecules. In particular, monothiooxalamide showed lower toxicity and can be considered for further biological screening and application trials.

摘要

合成了一类源自2-氨基苯并咪唑的新型单硫代草酰胺，并通过氢和碳的一维及二维核磁共振实验（COSY、HSQC和HMBC）对其结构进行了确证。通过自由基清除试验评估抗氧化能力：1,1-二苯基-2-苦基肼基（DPPH•）、2,2'-偶氮双（3-乙基苯并噻唑啉-6-磺酸）自由基阳离子（ABTS•）、铁还原抗氧化能力（FRAP）、氧自由基吸收能力（ORAC）以及亚铁离子螯合能力。我们的研究小组之前报道过源自2-氨基吡啶的单硫代草酰胺的合成及抗氧化活性（）。在本研究中，评估了源自2-氨基吡啶（）和2-氨基苯并咪唑（）家族的化合物对人红细胞（RBC）的溶血活性。选择单硫代草酰胺不表现溶血活性的浓度来评估它们抑制人红细胞中自由基诱导的膜损伤的能力、对卤虫的急性毒性以及对……的毒性。具有吗啉片段的化合物（、、、和）对自由基诱导的氧化溶血表现出时间和浓度依赖性的保护作用。此外，在卤虫致死试验中它们的急性毒性最低，并且与其他分子相比螯合活性显著增加。特别是，单硫代草酰胺表现出较低的毒性，可考虑用于进一步的生物筛选和应用试验。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3cfc/11382093/e24d1cc20c29/gr7.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3cfc/11382093/ee63f749fb8f/sc1.jpg
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