Myriocin | CAS#35891-70-4 | antibiotic

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

MedKoo CAT#: 561301

CAS#: 35891-70-4

Description: Myriocin, also known as antibiotic ISP-1 and thermozymocidin, is an atypical amino acid and an antibiotic derived from certain thermophilic fungi. Myriocin is a very potent inhibitor of serine palmitoyltransferase, the first step in sphingosine biosynthesis. Due to this property, it is used in biochemical research as a tool for depleting cells of sphingolipids.

Chemical Structure

Myriocin

CAS# 35891-70-4

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 561301
Name: Myriocin
CAS#: 35891-70-4
Chemical Formula: C21H39NO6
Exact Mass: 401.28
Molecular Weight: 401.544
Elemental Analysis: C, 62.82; H, 9.79; N, 3.49; O, 23.91

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 205
10mg	USD 340
25mg	USD 610
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Thermozymocidin; ISP-I; ISP-1; Myriocin;

IUPAC/Chemical Name: (2R,3R,4S,E)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid

InChi Key: ZZIKIHCNFWXKDY-ANSFIGKPSA-N

InChi Code: InChI=1S/C21H39NO6/c1-2-3-4-10-13-17(24)14-11-8-6-5-7-9-12-15-18(25)19(26)21(22,16-23)20(27)28/h9,12,18-19,23,25-26H,2-8,10-11,13-16,22H2,1H3,(H,27,28)/b12-9+/t18-,19-,21+/m0/s1

SMILES Code: CCCCCCC(CCCCCC/C=C/C[C@H](O)[C@H](O)[C@@](CO)(N)C(O)=O)=O

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).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:

Product Data

Instruction:

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Biological target:	Myriocin (Thermozymocidin) is a potent inhibitor of serine-palmitoyl-transferase (SPT). Myriocin suppresses replication of both the subgenomic HCV-1b replicon and the JFH-1 strain of genotype 2a infectious HCV, with an IC50 of 3.5 µg/mL for inhibiting HCV infection.
In vitro activity:	Using the HCV cell culture system, this study investigated the effect of myriocin, a sphingomyelin synthesis inhibitor, on HCV replication. Myriocin suppressed replication of both a genotype 1b subgenomic HCV replicon (Huh7/Rep-Feo) and genotype 2a infectious HCV (JFH-1 HCV) in a dose-dependent manner (for subgenomic HCV-1b, maximum of 79% at 1000 nmol/L; for genomic HCV-2a, maximum of 40% at 1000 nmol/L). Reference: J Infect Dis. 2008 Feb 1;197(3):361-70. https://pubmed.ncbi.nlm.nih.gov/18248300/
In vivo activity:	To evaluate the biological effects of myriocin in vivo, we investigated the levels of free sphingoid bases and expression of selected genes regulating cell growth in mouse liver. Male Balb/c mice, weighing 22 g were injected intraperitoneally with myriocin at 0, 0.1, 0.3, and 1.0 mg kg(-1) body weight daily for 5 days. Results showed that myriocin blocked de novo synthesis of sphingolipids in vivo by SPT inhibition and induced c-myc expression in liver. Reference: Mycopathologia. 2004 Apr;157(3):339-47. https://pubmed.ncbi.nlm.nih.gov/15180163/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	4.4	10.83
	Methanol	2.0	4.98

Preparing Stock Solutions

The following data is based on the product molecular weight 401.54 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.

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

Formulation protocol:	1. He L, Liu Y, Xu J, Li J, Cheng G, Cai J, Dang J, Yu M, Wang W, Duan W, Liu K. Inhibitory Effects of Myriocin on Non-Enzymatic Glycation of Bovine Serum Albumin. Molecules. 2022 Oct 18;27(20):6995. doi: 10.3390/molecules27206995. PMID: 36296589; PMCID: PMC9607541. 2. Amemiya F, Maekawa S, Itakura Y, Kanayama A, Matsui A, Takano S, Yamaguchi T, Itakura J, Kitamura T, Inoue T, Sakamoto M, Yamauchi K, Okada S, Yamashita A, Sakamoto N, Itoh M, Enomoto N. Targeting lipid metabolism in the treatment of hepatitis C virus infection. J Infect Dis. 2008 Feb 1;197(3):361-70. doi: 10.1086/525287. PMID: 18248300. 3. Yalcin EB, Tong M, Homans C, de la Monte SM. Myriocin Treatment Reverses Alcohol-Induced Alterations in Polyunsaturated Fatty Acid-Containing Phospholipid Expression in the Liver. Nutr Metab Insights. 2022 Feb 28;15:11786388221082012. doi: 10.1177/11786388221082012. PMID: 35250275; PMCID: PMC8891894. 4. He Q, Johnson VJ, Osuchowski MF, Sharma RP. Inhibition of serine palmitoyltransferase by myriocin, a natural mycotoxin, causes induction of c-myc in mouse liver. Mycopathologia. 2004 Apr;157(3):339-47. doi: 10.1023/b:myco.0000024182.04140.95. PMID: 15180163.
In vitro protocol:	1. He L, Liu Y, Xu J, Li J, Cheng G, Cai J, Dang J, Yu M, Wang W, Duan W, Liu K. Inhibitory Effects of Myriocin on Non-Enzymatic Glycation of Bovine Serum Albumin. Molecules. 2022 Oct 18;27(20):6995. doi: 10.3390/molecules27206995. PMID: 36296589; PMCID: PMC9607541. 2. Amemiya F, Maekawa S, Itakura Y, Kanayama A, Matsui A, Takano S, Yamaguchi T, Itakura J, Kitamura T, Inoue T, Sakamoto M, Yamauchi K, Okada S, Yamashita A, Sakamoto N, Itoh M, Enomoto N. Targeting lipid metabolism in the treatment of hepatitis C virus infection. J Infect Dis. 2008 Feb 1;197(3):361-70. doi: 10.1086/525287. PMID: 18248300.
In vivo protocol:	1. Yalcin EB, Tong M, Homans C, de la Monte SM. Myriocin Treatment Reverses Alcohol-Induced Alterations in Polyunsaturated Fatty Acid-Containing Phospholipid Expression in the Liver. Nutr Metab Insights. 2022 Feb 28;15:11786388221082012. doi: 10.1177/11786388221082012. PMID: 35250275; PMCID: PMC8891894. 2. He Q, Johnson VJ, Osuchowski MF, Sharma RP. Inhibition of serine palmitoyltransferase by myriocin, a natural mycotoxin, causes induction of c-myc in mouse liver. Mycopathologia. 2004 Apr;157(3):339-47. doi: 10.1023/b:myco.0000024182.04140.95. PMID: 15180163.

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1: Aburasayn H, Al Batran R, Ussher JR. Targeting ceramide metabolism in obesity. Am J Physiol Endocrinol Metab. 2016 Aug 1;311(2):E423-35. doi: 10.1152/ajpendo.00133.2016. Epub 2016 Jul 5. Review. PubMed PMID: 27382035.

2: Zécri FJ. From Natural Product to the First Oral Treatment for Multiple Sclerosis: The Discovery of FTY720 (Gilenya™)? Curr Opin Chem Biol. 2016 Jun;32:60-6. doi: 10.1016/j.cbpa.2016.04.014. Epub 2016 May 31. Review. PubMed PMID: 27258401.

3: Huang X, Withers BR, Dickson RC. Sphingolipids and lifespan regulation. Biochim Biophys Acta. 2014 May;1841(5):657-64. doi: 10.1016/j.bbalip.2013.08.006. Epub 2013 Aug 15. Review. PubMed PMID: 23954556; PubMed Central PMCID: PMC3925463.

4: Lo HC, Hsieh C, Lin FY, Hsu TH. A Systematic Review of the Mysterious Caterpillar Fungus Ophiocordyceps sinensis in Dong-ChongXiaCao ( Dōng Chóng Xià Cǎo) and Related Bioactive Ingredients. J Tradit Complement Med. 2013 Jan;3(1):16-32. doi: 10.4103/2225-4110.106538. Review. PubMed PMID: 24716152; PubMed Central PMCID: PMC3924981.

5: Chiba K, Adachi K. Discovery of fingolimod, the sphingosine 1-phosphate receptor modulator and its application for the therapy of multiple sclerosis. Future Med Chem. 2012 Apr;4(6):771-81. doi: 10.4155/fmc.12.25. Review. PubMed PMID: 22530640.

6: Podbielska M, Krotkiewski H, Hogan EL. Signaling and regulatory functions of bioactive sphingolipids as therapeutic targets in multiple sclerosis. Neurochem Res. 2012 Jun;37(6):1154-69. doi: 10.1007/s11064-012-0728-y. Epub 2012 Mar 27. Review. PubMed PMID: 22451227.

7: Jiang XC, Goldberg IJ, Park TS. Sphingolipids and cardiovascular diseases: lipoprotein metabolism, atherosclerosis and cardiomyopathy. Adv Exp Med Biol. 2011;721:19-39. doi: 10.1007/978-1-4614-0650-1_2. Review. PubMed PMID: 21910080.

8: Yeung BK. Natural product drug discovery: the successful optimization of ISP-1 and halichondrin B. Curr Opin Chem Biol. 2011 Aug;15(4):523-8. doi: 10.1016/j.cbpa.2011.05.019. Epub 2011 Jun 22. Review. PubMed PMID: 21684798.

9: Strader CR, Pearce CJ, Oberlies NH. Fingolimod (FTY720): a recently approved multiple sclerosis drug based on a fungal secondary metabolite. J Nat Prod. 2011 Apr 25;74(4):900-7. doi: 10.1021/np2000528. Epub 2011 Apr 1. Review. PubMed PMID: 21456524.

10: Friedrich FW, Eschenhagen T. [Fingolimod - a new immunomodulator]. Dtsch Med Wochenschr. 2009 Oct;134(42):2127-31. doi: 10.1055/s-0029-1241903. Epub 2009 Oct 6. Review. German. PubMed PMID: 19809964.

11: Chiba K. [New therapeutic approach for autoimmune diseases by the sphingosine 1-phosphate receptor modulator, fingolimod (FTY720)]. Yakugaku Zasshi. 2009 Jun;129(6):655-65. Review. Japanese. PubMed PMID: 19483408.

12: Chiba K. [A new therapeutic approach for autoimmune diseases by the sphingosine 1-phosphate receptor modulator, fingolimod (FTY720)]. Nihon Rinsho Meneki Gakkai Kaishi. 2009 Apr;32(2):92-101. Review. Japanese. PubMed PMID: 19404007.

13: Hiestand PC, Rausch M, Meier DP, Foster CA. Ascomycete derivative to MS therapeutic: S1P receptor modulator FTY720. Prog Drug Res. 2008;66:361, 363-81. Review. PubMed PMID: 18416311.

14: Bismuth J, Lin P, Yao Q, Chen C. Ceramide: a common pathway for atherosclerosis? Atherosclerosis. 2008 Feb;196(2):497-504. Epub 2007 Oct 25. Review. PubMed PMID: 17963772; PubMed Central PMCID: PMC2924671.

15: Baumruker T, Billich A, Brinkmann V. FTY720, an immunomodulatory sphingolipid mimetic: translation of a novel mechanism into clinical benefit in multiple sclerosis. Expert Opin Investig Drugs. 2007 Mar;16(3):283-9. Review. PubMed PMID: 17302523.

16: Chiba K, Matsuyuki H, Maeda Y, Sugahara K. Role of sphingosine 1-phosphate receptor type 1 in lymphocyte egress from secondary lymphoid tissues and thymus. Cell Mol Immunol. 2006 Feb;3(1):11-9. Review. PubMed PMID: 16549044.

17: Nishikido M, Kanekake H, Harada T. [Molecular action mechanisms of the therapeutic agents for kidney diseases: Immunosuppressants]. Nihon Rinsho. 2006 Feb;64 Suppl 2:634-8. Review. Japanese. PubMed PMID: 16523968.

18: Chiba K. FTY720, a new class of immunomodulator, inhibits lymphocyte egress from secondary lymphoid tissues and thymus by agonistic activity at sphingosine 1-phosphate receptors. Pharmacol Ther. 2005 Dec;108(3):308-19. Epub 2005 Jun 13. Review. PubMed PMID: 15951022.

19: Kahan BD. FTY720: from bench to bedside. Transplant Proc. 2004 Mar;36(2 Suppl):531S-543S. Review. PubMed PMID: 15041402.

20: Aki FT, Kahan BD. FTY720: A new kid on the block for transplant immunosuppression. Expert Opin Biol Ther. 2003 Jul;3(4):665-81. Review. PubMed PMID: 12831371.

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