Isolation of a jadomycin incorporating L-ornithine, analysis of antimicrobial activity and jadomycin reactive oxygen species (ROS) generation in MDA-MB-231 breast cancer cells

Forget Stephanie M.; Robertson Andrew W.; Hall Steven R.; MacLeod Jeanna M.; Overy David P.; Kerr Russell G.; Goralski Kerry B.; Jakeman David L.

首页> 外文期刊>The Journal of Antibiotics: An International Journal >Isolation of a jadomycin incorporating L-ornithine, analysis of antimicrobial activity and jadomycin reactive oxygen species (ROS) generation in MDA-MB-231 breast cancer cells

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Isolation of a jadomycin incorporating L-ornithine, analysis of antimicrobial activity and jadomycin reactive oxygen species (ROS) generation in MDA-MB-231 breast cancer cells

机译：掺入L-鸟氨酸的Jadomycin的分离，分析MDA-MB-231乳腺癌细胞中的抗菌活性和Jadomycin反应性氧物质（ROS）产生

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Herein, we report the characterization and antimicrobial activity of a previously unreported jadomycin (1) obtained from a culture of S. venezuelae ISP5230 with L-ornithine (Orn). 1 arises from the rearrangement of a putative five-membered ring containing jadomycin incorporating Orn, whereby intramolecular attack of the E-ring carbonyl from the delta-NH2 group of the Orn side chain results in collapse of the oxazolone ring and formation of a stable six-membered lactam. This rearrangement produces a jadomycin with a 3a hemiaminal position that is susceptible to solvolysis. A structure-activity relationship is discussed based on the antimicrobial activity of 1 compared to previously reported jadomycins, providing evidence that the presence of a 3a hemiaminal enhances activity against Gram-positive bacteria. Additionally, assays to quantify reactive oxygen species (ROS) generation and cell viability were performed using a series of nine jadomycins. Compound 1 was found to produce the highest ROS activity and to possess the greatest cytotoxicity against MDA-MB-231 breast cancer cells.

机译：在此，我们报告了用L-鸟嘌呤（ORN）从S. venezuelae ISP5230的培养物中获得的先前未报告的Jadomycin（1）的表征和抗微生物活性。从含有掺入ORN的推定的五元环的重新排列出来，从而从δ-NH2组的E-环羰基的分子内发作导致恶唑酮环的塌陷并形成稳定的六个 - MEMBERED的内酰胺。这种重排产生Jadomycin，其具有易溶解的3A半骨膜位置。与先前报道的Jadomycins相比，基于1的抗微生物活性讨论了结构 - 活性关系，提供了3A半骨苷的存在对抗革兰氏阳性细菌的证据。另外，使用一系列九个jadomycins进行量化反应性氧物质（ROS）产生和细胞活力的测定。发现化合物1产生最高的ROS活性，并具有对MDA-MB-231乳腺癌细胞的最大细胞毒性。

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《The Journal of Antibiotics: An International Journal》 |2018年第8期|共9页
作者
Forget Stephanie M.; Robertson Andrew W.; Hall Steven R.; MacLeod Jeanna M.; Overy David P.; Kerr Russell G.; Goralski Kerry B.; Jakeman David L.;
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Dalhousie Univ Dept Chem Halifax NS B3H 4R2 Canada;

Dalhousie Univ Dept Chem Halifax NS B3H 4R2 Canada;

Dalhousie Univ Coll Pharm Halifax NS B3H 4R2 Canada;

Dalhousie Univ Coll Pharm Halifax NS B3H 4R2 Canada;

Univ Prince Edward Isl Dept Chem Charlottetown PE C1A 4P3 Canada;

Univ Prince Edward Isl Dept Chem Charlottetown PE C1A 4P3 Canada;

Dalhousie Univ Coll Pharm Halifax NS B3H 4R2 Canada;

Dalhousie Univ Dept Chem Halifax NS B3H 4R2 Canada;

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正文语种 eng
中图分类药学;
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1. Isolation of a jadomycin incorporating L-ornithine, analysis of antimicrobial activity and jadomycin reactive oxygen species (ROS) generation in MDA-MB-231 breast cancer cells [J] . Forget Stephanie M., Robertson Andrew W., Hall Steven R., The Journal of Antibiotics: An International Journal . 2018,第8期

机译：掺入L-鸟氨酸的Jadomycin的分离，分析MDA-MB-231乳腺癌细胞中的抗菌活性和Jadomycin反应性氧物质（ROS）产生
2. Apoptosis induction by alantolactone in breast cancer MDA-MB-231 cells through reactive oxygen species-mediated mitochondrion-dependent pathway [J] . Cui Li, Bu Weiquan, Song Jie, Archives of pharmacal research . 2018,第3期

机译：通过反应性氧物种介导的线粒体依赖性途径乳腺癌MDA-MB-231细胞中的蛋白酰胺酮诱导凋亡诱导
3. (-)-Xanthatin up-regulation of the GADD45?? tumor suppressor gene in MDA-MB-231 breast cancer cells: Role of topoisomerase II?? inhibition and reactive oxygen species [J] . TakedaS., NoguchiM., MatsuoK., Toxicology: An International Journal Concerned with the Effects of Chemicals on Living Systems . 2013,第Null期

机译：（-）-Xantthatin上调GADD45？ MDA-MB-231乳腺癌细胞中的肿瘤抑制基因：拓扑异构酶II？抑制和活性氧
4. Jaceosidin Induces Apoptosis in ras-Transformed Human Breast Epithelial Cells through Generation of Reactive Oxygen Species [C] . MIN-JUNG KIM, DO-HEE KIM, KI WON LEE, Meeting on Cell Signaling World: Signal Transduction Pathways as Therapeutic Targets . 2007

机译：Jaceosidin通过生成活性氧物种诱导ras转化的人类乳腺癌上皮细胞凋亡。
5. Quantifying the Effects of Common in vitro Cell Culture Techniques on Glutathione Depletion and Cellular Viability via Breast Cancer Cells and Reactive Oxygen Species (ROS). [D] . Khobeir, Alexander M. 2016

机译：量化常见的体外细胞培养技术对通过乳腺癌细胞和活性氧（ROS）引起的谷胱甘肽耗竭和细胞活力的影响。
6. (−)-Xanthatin up-regulation of the GADD45γ tumor suppressor gene in MDA-MB-231 breast cancer cells: Role of topoisomerase IIα inhibition and reactive oxygen species [O] . Shuso Takeda, Momoko Noguchi, Kazumasa Matsuo, -1

机译：（ - ） - MDA-MB-231乳腺癌细胞中GADD45γ肿瘤抑制基因的Xanthatin上调：TopoisomeraseIIα抑制和活性氧的作用
7. Sulphamoylated Estradiol Analogue Induces Reactive Oxygen Species Generation to Exert Its Antiproliferative Activity in Breast Cancer Cell Lines [O] . Maphuti T. Lebelo, Anna M. Joubert, Michelle H. Visagie 2020

机译：磺酰磺酰化雌二醇类似物诱导反应性氧物种在乳腺癌细胞系中发挥其抗增殖活性

Isolation of a jadomycin incorporating L-ornithine, analysis of antimicrobial activity and jadomycin reactive oxygen species (ROS) generation in MDA-MB-231 breast cancer cells

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