海洋来源链霉菌产生的 Chromomycin SA 类似物
Chromomycin SA analogs from a marine-derived Streptomyces sp.
机构信息
Department of Biochemistry, Division of Chemistry, University of Texas Southwestern Medical Center, Dallas, TX 75390-9038, USA.
出版信息
Bioorg Med Chem. 2011 Sep 1;19(17):5183-9. doi: 10.1016/j.bmc.2011.07.013. Epub 2011 Jul 20.
Abstract
Two chromomycin SA analogs, chromomycin SA(3) and chromomycin SA(2), along with deacetylchromomycin A(3) and five previously reported chromomycin analogs were isolated from a marine-derived Streptomyces sp. The structures of the new compounds were determined by spectroscopic methods including 1D and 2D NMR techniques, HRMS and chemical methods. Chromomycin SA(3) and chromomycin SA(2) are the first naturally occuring chromomycin analogs with truncated side-chains. Biological evaluation of chromomycin analogs for cytotoxicity against two non-small cell lung cancer (NSCLC) cell-lines, A549 and HCC44, demonstrated a decrease in cytotoxicity for the truncated sides chain chromomycin analogs.
摘要
从海洋来源的链霉菌中分离得到两种柔红霉素 SA 类似物，柔红霉素 SA(3)和柔红霉素 SA(2)，以及去乙酰柔红霉素 A(3)和五种先前报道的柔红霉素类似物。新化合物的结构通过包括 1D 和 2D NMR 技术、高分辨率质谱和化学方法在内的光谱方法确定。柔红霉素 SA(3)和柔红霉素 SA(2)是具有截断侧链的第一个天然存在的柔红霉素类似物。对两种非小细胞肺癌 (NSCLC) 细胞系 A549 和 HCC44 的细胞毒性进行的柔红霉素类似物的生物学评价表明，截断侧链柔红霉素类似物的细胞毒性降低。
相似文献
1
Chromomycin SA analogs from a marine-derived Streptomyces sp.海洋来源链霉菌产生的 Chromomycin SA 类似物
Bioorg Med Chem. 2011 Sep 1;19(17):5183-9. doi: 10.1016/j.bmc.2011.07.013. Epub 2011 Jul 20.
2
Aureolic acids from a marine-derived Streptomyces sp. WBF16.海洋来源的链霉菌 WBF16 中的 aureolic 酸。
Microbiol Res. 2012 Dec 20;167(10):590-5. doi: 10.1016/j.micres.2012.06.001. Epub 2012 Jul 11.
3
Antibacterial Activity of Chromomycins from a Marine-Derived .海洋来源的Chromomycins 的抗菌活性。
Mar Drugs. 2020 Oct 21;18(10):522. doi: 10.3390/md18100522.
4
5
Carpatamides A-C, cytotoxic arylamine derivatives from a marine-derived Streptomyces sp.Carpatamides A-C，来自海洋来源的链霉菌属的细胞毒性芳基胺衍生物。
J Nat Prod. 2014 May 23;77(5):1245-8. doi: 10.1021/np500207p. Epub 2014 Apr 23.
6
Chromomycins from soil-derived sp. inhibit the growth of human non-small cell lung cancer cells by targeting c-FLIP.从土壤来源的菌种中提取的色霉素通过靶向c-FLIP抑制人非小细胞肺癌细胞的生长。
J Asian Nat Prod Res. 2025 Feb;27(2):153-168. doi: 10.1080/10286020.2024.2375288. Epub 2024 Jul 8.
7
Antitumor compounds from Streptomyces sp. KML-2, isolated from Khewra salt mines, Pakistan.从巴基斯坦克赫瓦拉盐矿分离出的链霉菌属KML-2中的抗肿瘤化合物。
Biol Res. 2015 Oct 14;48:58. doi: 10.1186/s40659-015-0046-3.
8
Tartrolon D, a cytotoxic macrodiolide from the marine-derived actinomycete Streptomyces sp. MDG-04-17-069.Tartrolon D，一种来自海洋来源放线菌链霉菌 sp. MDG-04-17-069 的细胞毒性大环二萜。
J Nat Prod. 2009 Dec;72(12):2192-4. doi: 10.1021/np9006603.
9
Anthraquinones from a marine-derived Streptomyces spinoverrucosus.海洋来源的棘孢小单孢菌中的蒽醌类化合物。
J Nat Prod. 2012 Oct 26;75(10):1759-64. doi: 10.1021/np3004326. Epub 2012 Oct 11.
10
A new quinoline derivative with cytotoxic activity from Streptomyces sp. neau50.一株链霉菌 NEAU50 来源的具有细胞毒活性的新型喹啉衍生物。
Bioorg Med Chem Lett. 2011 Apr 15;21(8):2313-5. doi: 10.1016/j.bmcl.2011.02.095. Epub 2011 Mar 14.
引用本文的文献
1
Natural Products from Singapore Soil-Derived Family and Evaluation of Their Biological Activities.新加坡土壤来源真菌家族的天然产物及其生物活性评价。
Molecules. 2023 Aug 2;28(15):5832. doi: 10.3390/molecules28155832.
2
Development of Marine-Derived Compounds for Cancer Therapy.海洋来源化合物在癌症治疗中的发展。
Mar Drugs. 2021 Jun 15;19(6):342. doi: 10.3390/md19060342.
3
Antibacterial Activity of Chromomycins from a Marine-Derived .海洋来源的Chromomycins 的抗菌活性。
Mar Drugs. 2020 Oct 21;18(10):522. doi: 10.3390/md18100522.
4
An "olivomycin A" derivative from a sponge-associated sp. strain SP 85.一种来自海绵相关菌株SP 85的“橄榄霉素A”衍生物。
3 Biotech. 2019 Dec;9(12):439. doi: 10.1007/s13205-019-1964-5. Epub 2019 Nov 7.
5
Staurosporine from Streptomyces sanyensis activates Programmed Cell Death in Acanthamoeba via the mitochondrial pathway and presents low in vitro cytotoxicity levels in a macrophage cell line.链霉菌属发酵产生的星形孢菌素通过线粒体途径激活棘阿米巴中的细胞程序性死亡，并且在巨噬细胞系中表现出低体外细胞毒性水平。
Sci Rep. 2019 Aug 12;9(1):11651. doi: 10.1038/s41598-019-48261-7.
6
Bacteria in Cancer Therapeutics: A Framework for Effective Therapeutic Bacterial Screening and Identification.癌症治疗中的细菌：有效治疗性细菌筛选与鉴定框架
J Cancer. 2019 Apr 21;10(8):1781-1793. doi: 10.7150/jca.31699. eCollection 2019.
7
Chromomycin A potently inhibits glucose-stimulated insulin secretion from pancreatic β cells.色霉素 A 能强烈抑制胰岛 β 细胞的葡萄糖刺激的胰岛素分泌。
J Gen Physiol. 2018 Dec 3;150(12):1747-1757. doi: 10.1085/jgp.201812177. Epub 2018 Oct 23.
8
Antitumor compounds from Streptomyces sp. KML-2, isolated from Khewra salt mines, Pakistan.从巴基斯坦克赫瓦拉盐矿分离出的链霉菌属KML-2中的抗肿瘤化合物。
Biol Res. 2015 Oct 14;48:58. doi: 10.1186/s40659-015-0046-3.
9
Chromomycin A2 induces autophagy in melanoma cells.放线菌素A2可诱导黑色素瘤细胞发生自噬。
Mar Drugs. 2014 Dec 4;12(12):5839-55. doi: 10.3390/md12125839.
10
Chromomycins A2 and A3 from marine actinomycetes with TRAIL resistance-overcoming and Wnt signal inhibitory activities.来自海洋放线菌的嗜铬霉素A2和A3具有克服TRAIL抗性和抑制Wnt信号的活性。
Mar Drugs. 2014 Jun 5;12(6):3466-76. doi: 10.3390/md12063466.
本文引用的文献
1
Characterization of the terminal activation step catalyzed by oxygenase CmmOIV of the chromomycin biosynthetic pathway from Streptomyces griseus.氧合酶 CmmOIV 催化灰霉素生物合成途径中末端激活步骤的特性。
Biochemistry. 2011 Mar 1;50(8):1421-8. doi: 10.1021/bi1016205. Epub 2011 Feb 2.
2
DNA binding characteristics of mithramycin and chromomycin analogues obtained by combinatorial biosynthesis.通过组合生物合成获得的密螺旋霉素和柔红霉素类似物的 DNA 结合特性。
Biochemistry. 2010 Dec 14;49(49):10543-52. doi: 10.1021/bi101398s. Epub 2010 Nov 16.
3
Generation of new derivatives of the antitumor antibiotic mithramycin by altering the glycosylation pattern through combinatorial biosynthesis.通过组合生物合成改变糖基化模式来生成抗肿瘤抗生素光神霉素的新衍生物。
Chembiochem. 2008 Sep 22;9(14):2295-304. doi: 10.1002/cbic.200800299.
4
The aureolic acid family of antitumor compounds: structure, mode of action, biosynthesis, and novel derivatives.抗肿瘤化合物的金霉素酸家族：结构、作用模式、生物合成及新型衍生物
Appl Microbiol Biotechnol. 2006 Nov;73(1):1-14. doi: 10.1007/s00253-006-0511-6. Epub 2006 Sep 30.
5
Novel GC-rich DNA-binding compound produced by a genetically engineered mutant of the mithramycin producer Streptomyces argillaceus exhibits improved transcriptional repressor activity: implications for cancer therapy.由丝裂霉素产生菌阿吉链霉菌的基因工程突变体产生的新型富含鸟嘌呤的DNA结合化合物表现出增强的转录抑制活性：对癌症治疗的意义。
Nucleic Acids Res. 2006 Mar 29;34(6):1721-34. doi: 10.1093/nar/gkl063. Print 2006.
6
Characterization of kinetics and products of the Baeyer-Villiger oxygenase MtmOIV, the key enzyme of the biosynthetic pathway toward the natural product anticancer drug mithramycin from Streptomyces argillaceus.来自泥质链霉菌的天然产物抗癌药物光神霉素生物合成途径关键酶拜耳-维利格单加氧酶MtmOIV的动力学及产物表征
J Am Chem Soc. 2005 Dec 21;127(50):17594-5. doi: 10.1021/ja055750t.
7
Biosynthesis of the antitumor chromomycin A3 in Streptomyces griseus: analysis of the gene cluster and rational design of novel chromomycin analogs.灰色链霉菌中抗肿瘤放线菌素A3的生物合成：基因簇分析及新型放线菌素类似物的合理设计
Chem Biol. 2004 Jan;11(1):21-32. doi: 10.1016/j.chembiol.2003.12.011.
8
Selective incells by chromomycin A3.用放线菌素A3进行细胞筛选。 （注：原文“incells”有误，推测可能是“incubate cells”等正确表述，这里按推测的合理意思翻译）
Nature. 1963 Apr 27;198:385-6. doi: 10.1038/198385a0.
9
Studies on the antitumor activity of chromomycin A3.色霉素A3的抗肿瘤活性研究。
Sci Rep Res Inst Tohoku Univ Med. 1960 Feb;9:224-32.
10
Mithramycin SK, a novel antitumor drug with improved therapeutic index, mithramycin SA, and demycarosyl-mithramycin SK: three new products generated in the mithramycin producer Streptomyces argillaceus through combinatorial biosynthesis.光神霉素SK，一种治疗指数有所提高的新型抗肿瘤药物，光神霉素SA，以及去甲糖基光神霉素SK：通过组合生物合成在光神霉素产生菌泥质链霉菌中产生的三种新产品。
J Am Chem Soc. 2003 May 14;125(19):5745-53. doi: 10.1021/ja034162h.
Zotero 插件