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MedKoo Cat#: 412709 | Name: Biotin Sphingosine
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Description:

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

Biotin Sphingosine has been used as a substrate in sphingosine kinases (SphK) assay. It has also been used to label wt- ceramide synthase 1 (CerS1) expressed in UM-SCC-22A cells, to study the interaction between CerS1-generated C18-ceramide and light chain 3 β (LC3B).

Chemical Structure

Biotin Sphingosine
Biotin Sphingosine
CAS#752987-57-8

Theoretical Analysis

MedKoo Cat#: 412709

Name: Biotin Sphingosine

CAS#: 752987-57-8

Chemical Formula: C28H52N4O4S

Exact Mass: 540.3709

Molecular Weight: 540.81

Elemental Analysis: C, 62.19; H, 9.69; N, 10.36; O, 11.83; S, 5.93

Price and Availability

Size Price Availability Quantity
1mg USD 1,150.00 2 Weeks
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Related CAS #
No Data
Synonym
Biotin Sphingosine; omega-biotinyl D-erythro-sphingosine
IUPAC/Chemical Name
N-((16R,17S,E)-17-amino-16,18-dihydroxyoctadec-14-en-1-yl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide
InChi Key
NYQVYZZGZCNEMF-RPRIXWAOSA-N
InChi Code
InChI=1S/C28H52N4O4S/c29-22(20-33)24(34)16-12-10-8-6-4-2-1-3-5-7-9-11-15-19-30-26(35)18-14-13-17-25-27-23(21-37-25)31-28(36)32-27/h12,16,22-25,27,33-34H,1-11,13-15,17-21,29H2,(H,30,35)(H2,31,32,36)/b16-12+/t22-,23-,24+,25-,27-/m0/s1
SMILES Code
[H][C@]1(SC[C@]2([C@@]1(NC(N2)=O)[H])[H])CCCCC(NCCCCCCCCCCCCC/C=C/[C@@](O)([C@]([H])(CO)N)[H])=O
Appearance
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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 540.81 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: Shirani A, Okuda DT, Stüve O. Therapeutic Advances and Future Prospects in Progressive Forms of Multiple Sclerosis. Neurotherapeutics. 2016 Jan;13(1):58-69. doi: 10.1007/s13311-015-0409-z. PMID: 26729332; PMCID: PMC4720678. 2: Fournie P, Galiacy S, Ranty ML, Rico-Lattes I, Malecaze F, Quintyn JC. Sphingosine-1 phosphate prevents ethanol-induced corneal epithelial apoptosis. Indian J Ophthalmol. 2012 Mar-Apr;60(2):115-8. doi: 10.4103/0301-4738.94052. PMID: 22446906; PMCID: PMC3339070. 3: Lv M, Zhang D, Dai D, Zhang W, Zhang L. Sphingosine kinase 1/sphingosine-1-phosphate regulates the expression of interleukin-17A in activated microglia in cerebral ischemia/reperfusion. Inflamm Res. 2016 Jul;65(7):551-62. doi: 10.1007/s00011-016-0939-9. Epub 2016 Mar 22. PMID: 27002656. 4: Kashem MA, Wa C, Wolak JP, Grafos NS, Ryan KR, Sanville-Ross ML, Fogarty KE, Rybina IV, Shoultz A, Molinaro T, Desai SN, Rajan A, Huber JD, Nelson RM. A high-throughput scintillation proximity assay for sphingosine-1-phosphate lyase. Assay Drug Dev Technol. 2014 Jun;12(5):293-302. doi: 10.1089/adt.2014.575. Epub 2014 May 20. PMID: 24846303. 5: Hasegawa Y, Suzuki H, Sozen T, Rolland W, Zhang JH. Activation of sphingosine 1-phosphate receptor-1 by FTY720 is neuroprotective after ischemic stroke in rats. Stroke. 2010 Feb;41(2):368-74. doi: 10.1161/STROKEAHA.109.568899. Epub 2009 Nov 25. PMID: 19940275; PMCID: PMC2811754. 6: Altay O, Hasegawa Y, Sherchan P, Suzuki H, Khatibi NH, Tang J, Zhang JH. Isoflurane delays the development of early brain injury after subarachnoid hemorrhage through sphingosine-related pathway activation in mice. Crit Care Med. 2012 Jun;40(6):1908-13. doi: 10.1097/CCM.0b013e3182474bc1. PMID: 22488000; PMCID: PMC3358576. 7: Roberts JL, Moretti PA, Darrow AL, Derian CK, Vadas MA, Pitson SM. An assay for sphingosine kinase activity using biotinylated sphingosine and streptavidin- coated membranes. Anal Biochem. 2004 Aug 1;331(1):122-9. doi: 10.1016/j.ab.2004.03.030. PMID: 15246004. 8: Zhao Y, Kalari SK, Usatyuk PV, Gorshkova I, He D, Watkins T, Brindley DN, Sun C, Bittman R, Garcia JG, Berdyshev EV, Natarajan V. Intracellular generation of sphingosine 1-phosphate in human lung endothelial cells: role of lipid phosphate phosphatase-1 and sphingosine kinase 1. J Biol Chem. 2007 May 11;282(19):14165-77. doi: 10.1074/jbc.M701279200. Epub 2007 Mar 22. PMID: 17379599; PMCID: PMC2659598. 9: Bakar AM, Park SW, Kim M, Lee HT. Isoflurane protects against human endothelial cell apoptosis by inducing sphingosine kinase-1 via ERK MAPK. Int J Mol Sci. 2012;13(1):977-93. doi: 10.3390/ijms13010977. Epub 2012 Jan 17. PMID: 22312298; PMCID: PMC3269732. 10: Altay O, Suzuki H, Altay BN, Calisir V, Tang J, Zhang JH. Isoflurane versus sevoflurane for early brain injury and expression of sphingosine kinase 1 after experimental subarachnoid hemorrhage. Neurosci Lett. 2020 Aug 10;733:135142. doi: 10.1016/j.neulet.2020.135142. Epub 2020 Jun 6. PMID: 32522601; PMCID: PMC7351136.