Echinomycin
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MedKoo CAT#: 329824

CAS#: 512-64-1

Description: Echinomycin is a peptide antibiotic. It intercalates into DNA at two specific sites, thereby blocking the binding of hypoxia inducible factor 1 alpha (HIF1alpha).


Price and Availability

Size
Price

1mg
USD 190
Size
Price

Size
Price

Echinomycin, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 329824
Name: Echinomycin
CAS#: 512-64-1
Chemical Formula: C51H64N12O12S2
Exact Mass: 1100.4208
Molecular Weight: 1101.265
Elemental Analysis: C, 55.62; H, 5.86; N, 15.26; O, 17.43; S, 5.82


Synonym: Echinomycin; Antibiotic A 654I; NSC 13502; NSC 526417; Quinomycin A; SK 302B;

IUPAC/Chemical Name: N,N'-((1R,4S,7R,11S,14R,17S,20R,24S)-11,24-diisopropyl-2,4,12,15,17,25-hexamethyl-27-(methylthio)-3,6,10,13,16,19,23,26-octaoxo-9,22-dioxa-28-thia-2,5,12,15,18,25-hexaazabicyclo[12.12.3]nonacosane-7,20-diyl)bis(quinoxaline-2-carboxamide)

InChi Key: AUJXLBOHYWTPFV-VITLIGDRSA-N

InChi Code: InChI=1S/C51H64N12O12S2/c1-25(2)38-49(72)74-22-36(59-42(65)34-21-53-30-17-13-15-19-32(30)57-34)44(67)55-28(6)46(69)63(10)40-48(71)62(9)39(26(3)4)50(73)75-23-35(58-41(64)33-20-52-29-16-12-14-18-31(29)56-33)43(66)54-27(5)45(68)60(7)37(47(70)61(38)8)24-77-51(40)76-11/h12-21,25-28,35-40,51H,22-24H2,1-11H3,(H,54,66)(H,55,67)(H,58,64)(H,59,65)/t27-,28-,35+,36+,37-,38-,39-,40+,51?/m0/s1

SMILES Code: O=C([C@@](C(SC)SC1)([H])N(C)C([C@H](C)NC([C@H](NC(C2=NC3=CC=CC=C3N=C2)=O)COC([C@H](C(C)C)N(C)C([C@@]1([H])N(C)C([C@H](C)NC([C@H](NC(C4=NC5=CC=CC=C5N=C4)=O)CO6)=O)=O)=O)=O)=O)=O)N(C)[C@@H](C(C)C)C6=O


Technical Data

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:
>2 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).

Harmonized System Code:
293490


References

1: Yamaguchi J, Tanaka T, Saito H, Nomura S, Aburatani H, Waki H, Kadowaki T, Nangaku M. Echinomycin inhibits adipogenesis in 3T3-L1 cells in a HIF-independent manner. Sci Rep. 2017 Jul 26;7(1):6516. doi: 10.1038/s41598-017-06761-4. PubMed PMID: 28747725; PubMed Central PMCID: PMC5529514.

2: Yao Y, Wang L, Zhou J, Zhang X. HIF-1α inhibitor echinomycin reduces acute graft-versus-host disease and preserves graft-versus-leukemia effect. J Transl Med. 2017 Feb 10;15(1):28. doi: 10.1186/s12967-017-1132-9. PubMed PMID: 28183349; PubMed Central PMCID: PMC5301444.

3: Jentzsch T, Zimmermann SM, Nicholls F, Cinelli P, Simmen HP, Werner CM. Echinomycin did not affect the safety of fracture healing: an experimental pilot study on a murine femur fracture model. Patient Saf Surg. 2016 Feb 16;10:7. doi: 10.1186/s13037-016-0094-9. eCollection 2016. PubMed PMID: 26884813; PubMed Central PMCID: PMC4754826.

4: Tsuzuki T, Okada H, Shindoh H, Shimoi K, Nishigaki A, Kanzaki H. Effects of the hypoxia-inducible factor-1 inhibitor echinomycin on vascular endothelial growth factor production and apoptosis in human ectopic endometriotic stromal cells. Gynecol Endocrinol. 2016;32(4):323-8. doi: 10.3109/09513590.2015.1121225. Epub 2015 Dec 10. PubMed PMID: 26654708.

5: Zhen X, Gong T, Liu F, Zhang PC, Zhou WQ, Li Y, Zhu P. A New Analogue of Echinomycin and a New Cyclic Dipeptide from a Marine-Derived Streptomyces sp. LS298. Mar Drugs. 2015 Nov 18;13(11):6947-61. doi: 10.3390/md13116947. PubMed PMID: 26593927; PubMed Central PMCID: PMC4663560.

6: Singh V, Nand A, Chen C, Li Z, Li SJ, Wang S, Yang M, Merino A, Zhang L, Zhu J. Echinomycin, a potential binder of FKBP12, shows minor effect on calcineurin activity. J Biomol Screen. 2014 Oct;19(9):1275-81. doi: 10.1177/1087057114544742. Epub 2014 Aug 1. PubMed PMID: 25085862.

7: Wang Y, Liu Y, Tang F, Bernot KM, Schore R, Marcucci G, Caligiuri MA, Zheng P, Liu Y. Echinomycin protects mice against relapsed acute myeloid leukemia without adverse effect on hematopoietic stem cells. Blood. 2014 Aug 14;124(7):1127-35. doi: 10.1182/blood-2013-12-544221. Epub 2014 Jul 3. PubMed PMID: 24994068; PubMed Central PMCID: PMC4133485.

8: Hotta K, Keegan RM, Ranganathan S, Fang M, Bibby J, Winn MD, Sato M, Lian M, Watanabe K, Rigden DJ, Kim CY. Conversion of a disulfide bond into a thioacetal group during echinomycin biosynthesis. Angew Chem Int Ed Engl. 2014 Jan 13;53(3):824-8. PubMed PMID: 24302672.

9: Yonekura S, Itoh M, Okuhashi Y, Takahashi Y, Ono A, Nara N, Tohda S. Effects of the HIF1 inhibitor, echinomycin, on growth and NOTCH signalling in leukaemia cells. Anticancer Res. 2013 Aug;33(8):3099-103. PubMed PMID: 23898065.

10: Sato M, Nakazawa T, Tsunematsu Y, Hotta K, Watanabe K. Echinomycin biosynthesis. Curr Opin Chem Biol. 2013 Aug;17(4):537-45. doi: 10.1016/j.cbpa.2013.06.022. Epub 2013 Jul 12. Review. PubMed PMID: 23856054.

11: Zhang C, Kong L, Liu Q, Lei X, Zhu T, Yin J, Lin B, Deng Z, You D. In vitro characterization of echinomycin biosynthesis: formation and hydroxylation of L-tryptophanyl-S-enzyme and oxidation of (2S,3S) β-hydroxytryptophan. PLoS One. 2013;8(2):e56772. doi: 10.1371/journal.pone.0056772. Epub 2013 Feb 21. PubMed PMID: 23437232; PubMed Central PMCID: PMC3578932.

12: Zimmermann SM, Würgler-Hauri CC, Wanner GA, Simmen HP, Werner CM. Echinomycin in the prevention of heterotopic ossification - an experimental antibiotic agent shows promising results in a murine model. Injury. 2013 Apr;44(4):570-5. doi: 10.1016/j.injury.2012.12.030. Epub 2013 Feb 8. PubMed PMID: 23398900.

13: Wang Z, Zhang Z, Wu Y, Chen L, Luo Q, Zhang J, Chen J, Luo Z, Huang X, Cheng Y. Effects of echinomycin on endothelin-2 expression and ovulation in immature rats primed with gonadotropins. Exp Mol Med. 2012 Oct 31;44(10):615-21. doi: 10.3858/emm.2012.44.10.070. PubMed PMID: 22874467; PubMed Central PMCID: PMC3490083.

14: Espinosa A, Socha AM, Ryke E, Rowley DC. Antiamoebic properties of the actinomycete metabolites echinomycin A and tirandamycin A. Parasitol Res. 2012 Dec;111(6):2473-7. doi: 10.1007/s00436-012-3019-2. Epub 2012 Jul 5. PubMed PMID: 22763704; PubMed Central PMCID: PMC3491104.

15: Milesi-Hallé A, McCullough S, Hinson JA, Kurten RC, Lamps LW, Brown A, James LP. Echinomycin decreases induction of vascular endothelial growth factor and hepatocyte regeneration in acetaminophen toxicity in mice. Basic Clin Pharmacol Toxicol. 2012 Apr;110(4):327-34. doi: 10.1111/j.1742-7843.2011.00812.x. Epub 2011 Nov 9. PubMed PMID: 21985601; PubMed Central PMCID: PMC3289727.

16: Jarikote DV, Li W, Jiang T, Eriksson LA, Murphy PV. Towards echinomycin mimetics by grafting quinoxaline residues on glycophane scaffolds. Bioorg Med Chem. 2011 Jan 15;19(2):826-35. doi: 10.1016/j.bmc.2010.12.009. Epub 2010 Dec 13. PubMed PMID: 21195622.

17: Pfoh R, Cuesta-Seijo JA, Sheldrick GM. Interaction of an echinomycin-DNA complex with manganese ions. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2009 Jul 1;65(Pt 7):660-4. doi: 10.1107/S1744309109019654. Epub 2009 Jun 27. PubMed PMID: 19574634; PubMed Central PMCID: PMC2705629.

18: Watanabe K, Hotta K, Nakaya M, Praseuth AP, Wang CC, Inada D, Takahashi K, Fukushi E, Oguri H, Oikawa H. Escherichia coli allows efficient modular incorporation of newly isolated quinomycin biosynthetic enzyme into echinomycin biosynthetic pathway for rational design and synthesis of potent antibiotic unnatural natural product. J Am Chem Soc. 2009 Jul 8;131(26):9347-53. doi: 10.1021/ja902261a. PubMed PMID: 19514719; PubMed Central PMCID: PMC2757413.

19: Watanabe K, Oguri H, Oikawa H. Diversification of echinomycin molecular structure by way of chemoenzymatic synthesis and heterologous expression of the engineered echinomycin biosynthetic pathway. Curr Opin Chem Biol. 2009 Apr;13(2):189-96. doi: 10.1016/j.cbpa.2009.02.012. Epub 2009 Mar 9. Review. PubMed PMID: 19278894.

20: Socha AM, Laplante KL, Russell DJ, Rowley DC. Structure-activity studies of echinomycin antibiotics against drug-resistant and biofilm-forming Staphylococcus aureus and Enterococcus faecalis. Bioorg Med Chem Lett. 2009 Mar 1;19(5):1504-7. doi: 10.1016/j.bmcl.2009.01.010. Epub 2009 Jan 10. PubMed PMID: 19185486.