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860493P

Avanti

1-deoxysphinganine

Avanti Research™ - A Croda Brand 860493P, powder

Synonyme(s) :

1-deoxysphinganine (m18:0)

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About This Item

Formule empirique (notation de Hill):
C18H39NO
Numéro CAS:
196497-48-0
Poids moléculaire :
285.51
Code UNSPSC :
12352211
Nomenclature NACRES :
NA.25

Forme

powder

Conditionnement

pkg of 1 × 1 mg (860493P-1mg)
pkg of 1 × 10 mg (860493P-10mg)

Fabricant/nom de marque

Avanti Research™ - A Croda Brand 860493P

Type de lipide

bioactive lipids
sphingolipids

Conditions d'expédition

dry ice

Température de stockage

−20°C

Chaîne SMILES 

C[C@@](N)([H])[C@]([H])(O)CCCCCCCCCCCCCCC

InChI

1S/C18H39NO/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-18(20)17(2)19/h17-18,20H,3-16,19H2,1-2H3/t17-,18+/m0/s1

Clé InChI

YRYJJIXWWQLGGV-ZWKOTPCHSA-N

Description générale

1-deoxysphinganine is synthesized by the condensation of palmitic acid with alanine or glycine in the presence of enzyme serine palmitoyltransferase (SPT). It is metabolized to 1-deoxyceramides.

Application

1-deoxysphinganine may be used for the complex preparation with bovine serum albumin for cytotoxicity testing in MN9D dopaminergic neuroblastoma cell line. It is also suitable for use as a neurotoxic agent in human CD8+ T cells.

Actions biochimiques/physiologiques

1-deoxysphinganine elicits cytotoxicity towards dorsal root ganglion (DRG) neurons by disrupting the neuronal cytoskeleton formation. High levels of 1-deoxysphinganine in diabetic patients may contribute to the reduction of pancreatic β cell functionality. In hereditary sensory and autonomic neuropathy type I, mutation in the serine palmitoyltransferase gene results in altered substrate specificity, resulting in the accumulation of 1-deoxysphinganine.

Conditionnement

5 mL Amber Glass Screw Cap Vial (860493P-10mg)
5 mL Amber Glass Screw Cap Vial (860493P-1mg)

Informations légales

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Code de la classe de stockage

11 - Combustible Solids

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Deoxysphingolipids, novel biomarkers for type 2 diabetes, are cytotoxic for insulin-producing cells
Zuellig RA, et al.
Diabetes, 63(4), 1326-1339 (2014)
Loss of Neurological Disease HSAN-I-Associated Gene SPTLC2 Impairs CD8+ T Cell Responses to Infection by Inhibiting T Cell Metabolic Fitness
Wu J, et al.
Immunity, 50(5), 1218-1231 (2019)
Nicholas C Zitomer et al.
The Journal of biological chemistry, 284(8), 4786-4795 (2008-12-20)
Fumonisin B(1) (FB(1)) is a mycotoxin that inhibits ceramide synthases (CerS) and causes kidney and liver toxicity and other disease. Inhibition of CerS by FB(1) increases sphinganine (Sa), Sa 1-phosphate, and a previously unidentified metabolite. Analysis of the latter by
M F Dohrn et al.
European journal of neurology, 22(5), 806-814 (2015-01-28)
Diabetic distal sensorimotor polyneuropathy (DSPN) is a frequent, disabling complication of diabetes mellitus. There is increasing evidence that sphingolipids play a role in insulin resistance and type 2 diabetes (T2DM). Whether neurotoxic 1-deoxy-sphingolipids are elevated in DSPN patients' plasma and
Irina Alecu et al.
Journal of lipid research, 58(1), 60-71 (2016-11-23)
The 1-deoxysphingolipids (1-deoxySLs) are atypical sphingolipids (SLs) that are formed when serine palmitoyltransferase condenses palmitoyl-CoA with alanine instead of serine during SL synthesis. The 1-deoxySLs are toxic to neurons and pancreatic β-cells. Pathologically elevated 1-deoxySLs cause the inherited neuropathy, hereditary
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