SK1-I - ≥98% , CAS No.1072443-89-0

CAS: 1072443-89-0 Cat. No.: S647696 Molecular Weight: 277.40 PubChem CID: 49793059

GRADE & PURITY ≥98%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

SK1-I (BML-258), an analog of sphingosine, is an isozyme-specific competitive SPHK1 inhibitor with a K i value of 10 µM SK1-I shows no activity at SPHK1 PKCα, PKCδ , PKA , AKT1 , ERK1 , EGFR , CDK2 , IKKβ or CamK2β. SK1-I enhances autophagy and has antitumor activity .

In Vitro

SK1-I (0-10 μM; 24 hours) attenuates cancer cell growth and survival in a TP53-dependent manner in HCT116 cells and HCT116 cells bearing TP53 cancer. SK1-I (0-20 μM; 12 hours) induces more CASP3 cleavage in HCT116 cells, compared to HCT116 cells lacking TP53, leading to a hallmark of apoptosis. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Cell Viability AssayCell Line: HCT116 cells and HCT116 cells bearing TP53 cancer Concentration: 0 µM, 2.5 µM, 5 µM, 7.5 µM, 10 µM Incubation Time: 24 hours Result: Decreased cancer cell growth and survival. Western Blot AnalysisCell Line: HCT116 cells and HCT116 cells bearing TP53 cancer Concentration: 0 µM, 5 µM, 10 µM, 20 µM Incubation Time: 12 hours Result: Induced more CASP3 cleavage in HCT116 cells, compared to HCT116 cells lacking TP53.

In Vivo

Pre-treatment with SK1-I (BML-258; intraperitoneal (i.p.) injection; once; 24 hours prior to baseline mean arterial blood pressure (MAP) measurement; 75 mg/kg) before anandamide (i.v. injection; two doses; 1 and 10 mg/kg) significantly decreases the hypotensive response. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Animal Model: Male C57BL/6 mice (24 ± 3.5 g)Dosage: 75 mg/kg Administration: Intraperitoneal (i.p.) injection; once; 24 hours prior to baseline MAP measurement Result: Significantly lowered baseline mean arterial blood pressure (MAP).

Form:Solid

IC50& Target:Ki: 10 µM (SPHK1)

Specifications

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

SK1-I (BML-258), an analog of sphingosine, is an isozyme-specific competitive SPHK1 inhibitor with a K i value of 10 µM. SK1-I shows no activity at SPHK1 PKCα, PKCδ , PKA , AKT1 , ERK1 , EGFR , CDK2 , IKKβ or CamK2β. SK1-I enhances autophagy and has

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CCCCCC1=CC=C(C=C1)C=CC(C(CO)NC)O.Cl
• IUPAC Name: (E,2R,3S)-2-(methylamino)-5-(4-pentylphenyl)pent-4-ene-1,3-diol;hydrochloride
• InChIKey: SGCJOKUPGVFNKS-UUCPMUBFSA-N
• INCHI: 1S/C17H27NO2.ClH/c1-3-4-5-6-14-7-9-15(10-8-14)11-12-17(20)16(13-19)18-2;/h7-12,16-20H,3-6,13H2,1-2H3;1H/b12-11+;/t16-,17+;/m1./s1
• Isomeric SMILES: CCCCCC1=CC=C(C=C1)/C=C/[C@@H]([C@@H](CO)NC)O.Cl
• PubChem CID: 49793059
• MeSH Entry Terms: BML 258;BML-258;BML258;N-methyl-5-(4'-pentylphenyl)-2-aminopent-4-ene-1,3-diol;SK1-I cpd
• Molecular Weight: 277.40

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Cinnamyl alcohols

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Cinnamyl alcohols
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Cinnamyl alcohols
• Alternative Parents: Styrenes Secondary alcohols 1,2-aminoalcohols Dialkylamines Primary alcohols Hydrochlorides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Cinnamyl alcohol - Styrene - Monocyclic benzene moiety - Benzenoid - Secondary alcohol - 1,2-aminoalcohol - Secondary amine - Secondary aliphatic amine - Alcohol - Organic oxygen compound - Primary alcohol - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Amine - Hydrochloride - Hydrocarbon derivative - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as cinnamyl alcohols. These are aromatic alcohols containing a 3-phenylprop-2-en-1-ol moiety.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO : 100 mg/mL (360.49 mM; Need ultrasonic)
• Molecular Weight: 313.900 g/mol
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 9
• Exact Mass: 313.181 Da
• Monoisotopic Mass: 313.181 Da
• Topological Polar Surface Area: 52.500 Ų
• Heavy Atom Count: 21
• Formal Charge: 0
• Complexity: 260.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 2

XLogP3