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MedKoo Cat#: 598550 | Name: Leinamycin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Leinamycin
Leinamycin
CAS#120500-15-4

Theoretical Analysis

MedKoo Cat#: 598550

Name: Leinamycin

CAS#: 120500-15-4

Chemical Formula: C22H26N2O6S3

Exact Mass: 510.0953

Molecular Weight: 510.63

Elemental Analysis: C, 51.75; H, 5.13; N, 5.49; O, 18.80; S, 18.84

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Leinamycin; Antibiotic DC 107; DC 107; DC-107; DC107; (+)-Leinamycin;
IUPAC/Chemical Name
(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
InChi Key
ZHTRILQJTPJGNK-WQGJMKSQSA-N
InChi Code
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+
SMILES Code
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
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 510.63 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
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. 11: Fekry MI, Szekely J, Dutta S, Breydo L, Zang H, Gates KS. Noncovalent DNA binding drives DNA alkylation by leinamycin: evidence that the Z,E-5-(thiazol-4-yl)-penta-2,4-dienone moiety of the natural product serves as an atypical DNA intercalator. J Am Chem Soc. 2011 Nov 9;133(44):17641-51. doi: 10.1021/ja2046149. Epub 2011 Oct 18. PubMed PMID: 21954957; PubMed Central PMCID: PMC3268133. 12: Zang H, Gates KS. Sequence specificity of DNA alkylation by the antitumor natural product leinamycin. Chem Res Toxicol. 2003 Dec;16(12):1539-46. PubMed PMID: 14680367. 13: Hara M, Saitoh Y, Nakano H. DNA strand scission by the novel antitumor antibiotic leinamycin. Biochemistry. 1990 Jun 19;29(24):5676-81. PubMed PMID: 2383554. 14: Bassett S, Urrabaz R, Sun D. Cellular response and molecular mechanism of antitumor activity by leinamycin in MiaPaCa human pancreatic cancer cells. Anticancer Drugs. 2004 Aug;15(7):689-96. PubMed PMID: 15269600. 15: Asai A, Saito H, Saitoh Y. Thiol-independent DNA cleavage by a leinamycin degradation product. Bioorg Med Chem. 1997 Apr;5(4):723-9. PubMed PMID: 9158871. 16: Huang Y, Huang SX, Ju J, Tang G, Liu T, Shen B. Characterization of the lnmKLM genes unveiling key intermediates for β-alkylation in leinamycin biosynthesis. Org Lett. 2011 Feb 4;13(3):498-501. doi: 10.1021/ol102838y. Epub 2010 Dec 30. PubMed PMID: 21192727; PubMed Central PMCID: PMC3074603. 17: Behroozi SJ, Kim W, Dannaldson J, Gates KS. 1,2-Dithiolan-3-one 1-oxides: a class of thiol-activated DNA-cleaving agents that are structurally related to the natural product leinamycin. Biochemistry. 1996 Feb 13;35(6):1768-74. PubMed PMID: 8639657. 18: Szilagyi A, Fenyvesi F, Majercsik O, Pelyvas IF, Bacskay I, Fehér P, Varadi J, Vecsernyés M, Herczegh P. Synthesis and cytotoxicity of leinamycin antibiotic analogues. J Med Chem. 2006 Sep 7;49(18):5626-30. PubMed PMID: 16942037. 19: Ma M, Lohman JR, Liu T, Shen B. C-S bond cleavage by a polyketide synthase domain. Proc Natl Acad Sci U S A. 2015 Aug 18;112(33):10359-64. doi: 10.1073/pnas.1508437112. Epub 2015 Aug 3. PubMed PMID: 26240335; PubMed Central PMCID: PMC4547226. 20: Hara M, Asano K, Kawamoto I, Takiguchi T, Katsumata S, Takahashi K, Nakano H. Leinamycin, a new antitumor antibiotic from Streptomyces: producing organism, fermentation and isolation. J Antibiot (Tokyo). 1989 Dec;42(12):1768-74. PubMed PMID: 2621160.