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SML3679

Sigma-Aldrich

SLM6031434 hydrochloride

≥98% (HPLC)

Synonym(s):

(2S)-2-[3-[4-(Octyloxy)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl]-1-pyrrolidinecarboximidamide, hydrochloride, (S)-2-(3-(4-(Octyloxy)-3-(trifluoromethyl)phenyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide, hydrochloride, (S)-Amino(2-(3-(4-(octyloxy)-3-(trifluoromethyl)phenyl)-1,2,4-oxadiazol-5-yl)pyrrolidin-1-yl)methaniminium chloride, SLM 6031434 HCl, SLM 6081442 (S)-enantiomer HCl, SLM-6031434 HCl, SLM-6081442 (S)-enantiomer HCl, SLM6081442 (S)-enantiomer HCl

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About This Item

Empirical Formula (Hill Notation):
C22H30F3N5O2·HCl
CAS Number:
1897379-34-8
Molecular Weight:
489.96
MDL number:
MFCD31689247
UNSPSC Code:
51111800
UNSPSC Code:
12352200
NACRES:
NA.21

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

water: ≥2 mg/mL

storage temp.

-10 to -25°C

Biochem/physiol Actions

SLM6031434 is a selective sphingosine (Sph) kinase 2 (SK2, SphK2, SpK2) inhibitor (r/m SphK2 Ki = 400/500 nM, r/m SphK1 Ki >20 μM) that effectively downregulates cellular sphingosine 1-phosphate (S1P) level (47% S1P & 143% Sph of control in U937 post 2h 100 nM SLM6031434 treatment) and selectively reduces plasma S1P in Sphk1-/-, but not Sphk2-/- mice in vivo (5 mg/kg i.v.). In contrary to Sphk2-KO mice, SLM6031434 treatment enhances plasma S1P in wild-type mice and offers neuroprotective efficacy against ischemic stroke (2 mg/kg i.v. 2h prior to tMCAO).

Caution

Hygroscopic

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Mateusz Adamiak et al.
Oncotarget, 8(39), 65588-65600 (2017-10-17)
Sphingosine-1-phosphate (S1P) is a bioactive lipid involved in cell signaling and, if released from cells, also plays a crucial role in regulating the trafficking of lympho-hematopoietic cells, including primitive hematopoietic stem/progenitor cells (HSPCs). It has been demonstrated that S1P chemoattracts
Yugesh Kharel et al.
The Journal of pharmacology and experimental therapeutics, 355(1), 23-31 (2015-08-06)
Sphingosine 1-phosphate (S1P) levels are significantly higher in blood and lymph than in tissues. This S1P concentration difference is necessary for proper lymphocyte egress from secondary lymphoid tissue and to maintain endothelial barrier integrity. Studies with mice lacking either sphingosine
Gaurav Ahuja et al.
EMBO reports, 20(4) (2019-03-20)
Cardiac dysfunctions dramatically increase with age. Revealing a currently unknown contributor to cardiac ageing, we report the age-dependent, cardiac-specific accumulation of the lysosphingolipid sphinganine (dihydrosphingosine, DHS) as an evolutionarily conserved hallmark of the aged vertebrate heart. Mechanistically, the DHS-derivative sphinganine-1-phosphate
Yugesh Kharel et al.
PloS one, 13(4), e0192179-e0192179 (2018-04-20)
Successful medicinal chemistry campaigns to discover and optimize sphingosine kinase inhibitors require a robust assay for screening chemical libraries and for determining rank order potencies. Existing assays for these enzymes are laborious, expensive and/or low throughput. The toxicity of excessive
Rui Cao et al.
Theranostics, 8(22), 6111-6120 (2019-01-08)
Rationale: Emerging evidence has suggested that sphingosine 1-phosphate (S1P), a bioactive metabolite of sphingolipids, may play an important role in the pathophysiological processes of cerebral hypoxia and ischemia. However, the influence of S1P on cerebral hemodynamics and metabolism remains unclear.
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