120500-15-4|Leinamycin|(2Z,9E,13Z,15E)-4',11-dihydroxy-2,4',9-trimethylspiro[3-aza-1(2,4)-thiazolacyclohexadecaphanene-6,3'-[1,2]dithiolane]-9,13,15-triene-4,5',12-trione 2'-oxide|-范德生物科技公司

Leinamycin

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names：
(2Z,9E,13Z,15E)-4',11-dihydroxy-2,4',9-trimethylspiro[3-aza-1(2,4)-thiazolacyclohexadecaphanene-6,3'-[1,2]dithiolane]-9,13,15-triene-4,5',12-trione 2'-oxide
CAS号：
120500-15-4
MDL Number：
MF(分子式)： C22H26N2O6S3 MW(分子量)： 510.63
EINECS: Reaxys Number:
Pubchem ID: Brand:BIOFOUNT

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中文别名	Leinamycin
英文别名	Leinamycin; Antibiotic DC 107; DC 107; DC-107; DC107; (+)-Leinamycin;
CAS号	120500-15-4
SMILES	O=C(CC(C1(O)C)(CC/C(C)=C/C(O)C(/C=C\C=C\2)=O)S(SC1=O)=O)NC(C)C3=NC2=CS3
Inchi	InChI=1S/C22H26N2O6S3/c1-13-8-9-22(21(3,29)20(28)32-33(22)30)11-18(27)23-14(2)19-24-15(12-31-19)6-4-5-7-16(25)17(26)10-13/h4-7,10,12,14,17,26,29H,8-9,11H2,1-3H3,(H,23,27)/b6-4+,7-5-,13-10+
InchiKey	ZHTRILQJTPJGNK-WQGJMKSQSA-N
分子式 Formula	C22H26N2O6S3
分子量 Molecular Weight	510.63
闪点 FP
熔点 Melting point
沸点 Boiling point
Polarizability极化度
密度 Density
蒸汽压 Vapor Pressure
溶解度Solubility
性状	Solid powder
储藏条件 Storage conditions	Dry, dark and store at 0-4℃ for short term (days to weeks) or -20℃ for long term (Store correctly 2-3years).

产品说明	Leinamycin(CAS:120500-15-4):仅限应用于工业或者科学研究过程中非医疗目的，不应用于人类或动物的临床诊断以及治过程疗，该产品非药用，非食用。
Introduction	Leinamycin is a thiazole containing macrolide characterized by an unusual 1,3-dioxo-1,2-dithiolane moiety that is spiro fused to an 18 member macrolactam ring; isolated from Streptomyces; possible DNA alkylator; the leinamycin biosynthetic gene cluster from Streptomyces atroolivaceus S-140 consists of two polyketide synthases genes.
Application1
Application2
Application3

警示图
危险性	Warning
危险性警示
安全声明
安全防护
备注

[1]Huang SX, Yun BS, Ma M, Basu HS, Church DR, Ingenhorst G, Huang Y, Yang D, Lohman JR, Tang GL, Ju J, Liu T, Wilding G, Shen B. Leinamycin E1 acting as an anticancer prodrug activated by reactive oxygen species. Proc Natl Acad Sci U S A. 2015 Jul 7;112(27):8278-83. doi: 10.1073/pnas.1506761112. Epub 2015 Jun 8. PubMed PMID: 26056295; PubMed Central PMCID: PMC4500275.

[2]Keerthi K, Rajapakse A, Sun D, Gates KS. Synthesis and characterization of a small analogue of the anticancer natural product leinamycin. Bioorg Med Chem. 2013 Jan 1;21(1):235-41. doi: 10.1016/j.bmc.2012.10.021. Epub 2012 Oct 27. PubMed PMID: 23168080; PubMed Central PMCID: PMC3532941.

[3] Viswesh V, Hays AM, Gates K, Sun D. DNA cleavage induced by antitumor antibiotic leinamycin and its biological consequences. Bioorg Med Chem. 2012 Jul 15;20(14):4413-21. doi: 10.1016/j.bmc.2012.05.033. Epub 2012 May 23. PubMed PMID: 22682923; PubMed Central PMCID: PMC3389147.

[4] Katt WP, Cerione RA. Less than the sum of its parts, a leinamycin precursor has superior properties. Proc Natl Acad Sci U S A. 2015 Jul 7;112(27):8164-5. doi: 10.1073/pnas.1510122112. Epub 2015 Jun 23. PubMed PMID: 26106161; PubMed Central PMCID: PMC4500279.

[5] Sivaramakrishnan S, Breydo L, Sun D, Gates KS. The macrocycle of leinamycin imparts hydrolytic stability to the thiol-sensing 1,2-dithiolan-3-one 1-oxide unit of the natural product. Bioorg Med Chem Lett. 2012 Jun 1;22(11):3791-4. doi: 10.1016/j.bmcl.2012.04.003. Epub 2012 Apr 12. PubMed PMID: 22560586; PubMed Central PMCID: PMC3376404.

6: Liu T, Ma M, Ge HM, Yang C, Cleveland J, Shen B. Synthesis and evaluation of 8,4'-dideshydroxy-leinamycin revealing new insights into the structure-activity relationship of the anticancer natural product leinamycin. Bioorg Med Chem Lett. 2015 Nov 1;25(21):4899-4902. doi: 10.1016/j.bmcl.2015.05.078. Epub 2015 May 30. PubMed PMID: 26071634; PubMed Central PMCID: PMC4607584.7: Lohman JR, Bingman CA, Phillips GN Jr, Shen B. Structure of the bifunctional acyltransferase/decarboxylase LnmK from the leinamycin biosynthetic pathway revealing novel activity for a double-hot-dog fold. Biochemistry. 2013 Feb 5;52(5):902-11. doi: 10.1021/bi301652y. Epub 2013 Jan 24. PubMed PMID: 23320975; PubMed Central PMCID: PMC3567400.8: Viswesh V, Gates K, Sun D. Characterization of DNA damage induced by a natural product antitumor antibiotic leinamycin in human cancer cells. Chem Res Toxicol. 2010 Jan;23(1):99-107. doi: 10.1021/tx900301r. PubMed PMID: 20017514; PubMed Central PMCID: PMC2810146.9: Huang Y, Tang GL, Pan G, Chang CY, Shen B. Characterization of the Ketosynthase and Acyl Carrier Protein Domains at the LnmI Nonribosomal Peptide Synthetase-Polyketide Synthase Interface for Leinamycin Biosynthesis. Org Lett. 2016 Sep 2;18(17):4288-91. doi: 10.1021/acs.orglett.6b02033. Epub 2016 Aug 19. PubMed PMID: 27541042; PubMed Central PMCID: PMC5013926.10: Huang Y, Yang D, Pan G, Tang GL, Shen B. Characterization of LnmO as a pathway-specific Crp/Fnr-type positive regulator for leinamycin biosynthesis in Streptomyces atroolivaceus and its application for titer improvement. Appl Microbiol Biotechnol. 2016 Dec;100(24):10555-10562. Epub 2016 Oct 5. PubMed PMID: 27704182; PubMed Central PMCID: PMC5121087.1

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