35891-70-4 Usage
Description
Myriocin, an amino fatty acid antibiotic, is derived from certain thermophilic fungi, such as Mycelia sterilia, Myriococcum, Melanconis, and Isaria. It is a potent immunosuppressant with 10to 100-fold more activity than cyclosporin A. Myriocin acts as a potent inhibitor of serine palmitoyltransferase (SPT), the enzyme that catalyzes the first step in sphingolipid biosynthesis. It is a useful biochemical research tool for depleting cells of sphingolipids and has been shown to induce apoptosis, disrupt substratum adhesion of melanoma cells, and suppress cell proliferation.
Uses
1. Used in Biochemical Research:
MYRIOCIN is used as a research tool for depleting cells of sphingolipids, which aids in understanding the role of these lipids in various cellular processes.
2. Used in Immunosuppression:
MYRIOCIN is used as an immunosuppressant due to its potent activity, which is 10to 100-fold more potent than cyclosporin A. It is particularly effective in suppressing the proliferation of IL-2-dependent mouse cytotoxic cells and inducing apoptosis in the cytotoxic T-cell line CTTL-2.
3. Used in Anticancer Applications:
MYRIOCIN is used as an anticancer agent, as it disrupts substratum adhesion of melanoma cells and suppresses cell proliferation. It also induces apoptosis by depleting cellular sphingolipids.
4. Used in Antiviral Applications:
MYRIOCIN is used as an antiviral agent, specifically in suppressing the replication of the hepatitis C virus in a murine model.
5. Used in Drug Development:
MYRIOCIN is used in the development of novel drug delivery systems to enhance its applications and efficacy against cancer cells. Various organic and metallic nanoparticles have been employed as carriers for MYRIOCIN delivery, aiming to improve its delivery, bioavailability, and therapeutic outcomes.
Chemical Properties:
MYRIOCIN is a white powder with potent immunosuppressant activity and is a very potent inhibitor of serine palmitoyltransferase, blocking the synthesis of ceramide.
Biochem/physiol Actions
Product does not compete with ATP.
References
1) Fujita et al.(1994) Fungal metabolites. Part 11. A potent immunosuppressive activity found in Isaria sinclairii metabolite; J. Antibiot. 47 208
2) Miyake et al. (1995) Serine palmitoyltransferase is the primary target of a sphingosine-like immunosuppressant ISP-1/myriocin; Biochem. Biophys. Res. Commun. 211 396
3) Lee et al. (2012) Myriocin, a serine palmitoyltransferase inhibitor, suppresses tumor growth in a murine melanoma model by inhibiting de novo sphingolipid synthesis; Cancer Biol Ther. 13 92
Check Digit Verification of cas no
The CAS Registry Mumber 35891-70-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,5,8,9 and 1 respectively; the second part has 2 digits, 7 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 35891-70:
(7*3)+(6*5)+(5*8)+(4*9)+(3*1)+(2*7)+(1*0)=144
144 % 10 = 4
So 35891-70-4 is a valid CAS Registry Number.
InChI:InChI=1/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
35891-70-4Relevant articles and documents
Construction of Quaternary Carbon Stereocenter of α-Tertiary Amine through Remote C-H Functionalization of Tris Derivatives: Enantioselective Total Synthesis of Myriocin
Miyagawa, Takashi,Inuki, Shinsuke,Oishi, Shinya,Ohno, Hiroaki
, p. 5485 - 5490 (2019)
We describe the development of a strategy for the construction of the quaternary carbon stereocenter of α-tertiary amines. This strategy highlights a site-selective C-H functionalization involving an alkoxy-radical-triggered 1,5-hydrogen transfer (1,5-HAT
Total synthesis of the immunosuppressants myriocin and 2-epi-myriocin
Jones, Matthew C.,Marsden, Stephen P.
supporting information; experimental part, p. 4125 - 4128 (2009/05/27)
(Chemical Equation Presented) Total syntheses of the natural immunosuppressant myriocin (1) and the equipotent unnatural analogue 2-epi-myriocin (in protected form) have been achieved through a common strategy. The key transformations are the efficient synthesis of a quaternary (E)-vinylglycine by asymmetric deconjugative alkylation of a dehydroamino acid and an unusually highly diastereoselective dihydroxylation of the vinylglycine alkene.
Total synthesis of (+)-myriocin and (-)-sphingofungin E from aldohexoses using overman rearrangement as the key reaction
Oishi, Takeshi,Ando, Koji,Inomiya, Kenjin,Sato, Hideyuki,Iida, Masatoshi,Chida, Noritaka
, p. 1927 - 1947 (2007/10/03)
Total synthesis starting from aldohexoses of naturally occurring α-substituted α-amino acids, (+)-myriocin (1) and (-)-sphingofungin E (2), is described. Overman rearrangement of allylic trichloroacetimidate 6E derived from D-mannose effectively generated the tetrasubstituted carbon with nitrogen, and subsequent Wittig olefination afforded the highly functionalized moiety 3 of myriocin stereoselectively. Sulfone-mediated coupling reaction of the allyl bromide 3 with C12 hydrophobic part 4 successfully constructed the carbon framework possessing E-olefin 28. Removal of the sulfone and protecting groups completed the chiral and stereoselective total synthesis of (+)-myriocin (1). A similar transformation starting from D-glucose also accomplished the total synthesis of (-)-sphingofungin E (2).
