BML-258 HCl

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

MedKoo CAT#: 406472

CAS#: 1072443-89-0

Description: BML-258, also known as SK1-I, is a potent, water-soluble, isoenzyme-specific inhibitor of SphK1. In contrast to pan-SphK inhibitors, SK1-I did not inhibit SphK2, PKC, or numerous other protein kinases. SK1-I decreased growth and survival of human leukemia U937 and Jurkat cells, and enhanced apoptosis and cleavage of Bcl-2. Notably, SK1-I potently induced apoptosis in leukemic blasts isolated from patients with acute myelogenous leukemia but was relatively sparing of normal peripheral blood mononuclear leukocytes. Moreover, SK1-I markedly reduced growth of AML xenograft tumors. Specific inhibitors of SphK1 warrant attention as potential additions to the therapeutic armamentarium in leukemia.


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BML258 HCl, purity > 98%, is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 406472
Name: BML-258 HCl
CAS#: 1072443-89-0
Chemical Formula: C17H28ClNO2
Exact Mass:
Molecular Weight: 313.86272
Elemental Analysis: C, 65.05; H, 8.99; Cl, 11.30; N, 4.46; O, 10.20


Synonym: BML258; BML 258; BML-258; SK1I.

IUPAC/Chemical Name: (2R,3S,E)-2-(methylamino)-5-(4-pentylphenyl)pent-4-ene-1,3-diol hydrochloride

InChi Key: SGCJOKUPGVFNKS-UUCPMUBFSA-N

InChi Code: 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

SMILES Code: OC[C@@H](NC)[C@@H](O)/C=C/C1=CC=C(CCCCC)C=C1.[H]Cl


Technical Data

Appearance:
white solid powder

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, not in water

Shelf Life:
>2 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).

Harmonized System Code:
293490


Additional Information

  
 
 
 


References

1: Price MM, Oskeritzian CA, Falanga YT, Harikumar KB, Allegood JC, Alvarez SE, Conrad D, Ryan JJ, Milstien S, Spiegel S. A specific sphingosine kinase 1 inhibitor attenuates airway hyperresponsiveness and inflammation in a mast cell-dependent murine model of allergic asthma. J Allergy Clin Immunol. 2013 Feb;131(2):501-11.e1. doi: 10.1016/j.jaci.2012.07.014. Epub 2012 Aug 30. PubMed PMID: 22939756; PubMed Central PMCID: PMC3563730.

2: Nagahashi M, Ramachandran S, Kim EY, Allegood JC, Rashid OM, Yamada A, Zhao R, Milstien S, Zhou H, Spiegel S, Takabe K. Sphingosine-1-phosphate produced by sphingosine kinase 1 promotes breast cancer progression by stimulating angiogenesis and lymphangiogenesis. Cancer Res. 2012 Feb 1;72(3):726-35. doi: 10.1158/0008-5472.CAN-11-2167. PubMed PMID: 22298596; PubMed Central PMCID: PMC3289261.

3: Cakir Z, Saydam G, Sahin F, Baran Y. The roles of bioactive sphingolipids in resveratrol-induced apoptosis in HL60: acute myeloid leukemia cells. J Cancer Res Clin Oncol. 2011 Feb;137(2):279-86. doi: 10.1007/s00432-010-0884-x. Epub 2010 Apr 18. PubMed PMID: 20401667.

4: Kapitonov D, Allegood JC, Mitchell C, Hait NC, Almenara JA, Adams JK, Zipkin RE, Dent P, Kordula T, Milstien S, Spiegel S. Targeting sphingosine kinase 1 inhibits Akt signaling, induces apoptosis, and suppresses growth of human glioblastoma cells and xenografts. Cancer Res. 2009 Sep 1;69(17):6915-23. doi: 10.1158/0008-5472.CAN-09-0664. PubMed PMID: 19723667; PubMed Central PMCID: PMC2752891.

5: Paugh SW, Paugh BS, Rahmani M, Kapitonov D, Almenara JA, Kordula T, Milstien S, Adams JK, Zipkin RE, Grant S, Spiegel S. A selective sphingosine kinase 1 inhibitor integrates multiple molecular therapeutic targets in human leukemia. Blood. 2008 Aug 15;112(4):1382-91. doi: 10.1182/blood-2008-02-138958. Epub 2008 May 29. PubMed PMID: 18511810; PubMed Central PMCID: PMC2515133.