Molecular structure of D-erythro-Sphingosine, CAS Number: 123-78-4
D-erythro-Sphingosine (CAS 123-78-4)
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Alternate Names:
trans-4-Sphingenine
Application:
D-erythro-Sphingosine is a potent, highly selective PKC inhibitor
CAS Number:
123-78-4
Purity:
≥97%
Molecular Weight:
299.49
Molecular Formula:
C18H37NO2
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
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SDS & Certificate of Analysis
D-erythro-Sphingosine, a natural sphingosine isomer, selectively inhibits protein kinase C and activates casein kinase II, without affecting protein kinase A or myosin light chain kinase. It also inhibits several enzymes and interactions within cells, including those in HL-60 cells and various rat and mouse tissues, showcasing broad biological activity. This compound plays a role in cell membrane function, cell signaling pathways, and exhibits potential anti-inflammatory, anti-apoptotic, and anti-tumor effects. Its involvement in regulating cell growth, survival, and disease processes, particularly cancer, highlights its significance in biological research.
D-erythro-Sphingosine (CAS 123-78-4) References
- The total syntheses of D-erythro-sphingosine, N-palmitoylsphingosine (ceramide), and glucosylceramide (cerebroside) via an azidosphingosine analog. | Duclos, RI. 2001. Chem Phys Lipids. 111: 111-38. PMID: 11457441
- Retinoblastoma protein dephosphorylation induced by D-erythro-sphingosine. | Chao, R., et al. 1992. J Biol Chem. 267: 23459-62. PMID: 1385423
- Inhibition of arachidonic acid release and cytosolic phospholipase A2 alpha activity by D-erythro-sphingosine. | Nakamura, H., et al. 2004. Eur J Pharmacol. 484: 9-17. PMID: 14729377
- A practical synthesis of D-erythro-sphingosine using a cross-metathesis approach. | Torssell, S. and Somfai, P. 2004. Org Biomol Chem. 2: 1643-6. PMID: 15162217
- A concise synthesis of a promising protein kinase C inhibitor: D-erythro-sphingosine. | Pham, VT., et al. 2007. Arch Pharm Res. 30: 22-7. PMID: 17328238
- Asymmetric sulfur ylide based enantioselective synthesis of D-erythro-sphingosine. | Morales-Serna, JA., et al. 2008. Org Biomol Chem. 6: 4502-4. PMID: 19039356
- Activation of casein kinase II by sphingosine. | McDonald, OB., et al. 1991. J Biol Chem. 266: 21773-6. PMID: 1939200
- Sphingosine inhibits the activity of rat liver CTP:phosphocholine cytidylyltransferase. | Sohal, PS. and Cornell, RB. 1990. J Biol Chem. 265: 11746-50. PMID: 2164014
- Protein kinase C and platelet inhibition by D-erythro-sphingosine: comparison with N,N-dimethylsphingosine and commercial preparation. | Khan, WA., et al. 1990. Biochem Biophys Res Commun. 172: 683-91. PMID: 2241961
- Structural requirements for long-chain (sphingoid) base inhibition of protein kinase C in vitro and for the cellular effects of these compounds. | Merrill, AH., et al. 1989. Biochemistry. 28: 3138-45. PMID: 2742830
- Inhibition of the oxidative burst in human neutrophils by sphingoid long-chain bases. Role of protein kinase C in activation of the burst. | Wilson, E., et al. 1986. J Biol Chem. 261: 12616-23. PMID: 3017982
- Modulation of the free sphingosine levels in human neutrophils by phorbol esters and other factors. | Wilson, E., et al. 1988. J Biol Chem. 263: 9304-9. PMID: 3132460
- Sphingosine inhibition of protein kinase C activity and of phorbol dibutyrate binding in vitro and in human platelets. | Hannun, YA., et al. 1986. J Biol Chem. 261: 12604-9. PMID: 3462188
- Inhibition of phorbol ester-dependent differentiation of human promyelocytic leukemic (HL-60) cells by sphinganine and other long-chain bases. | Merrill, AH., et al. 1986. J Biol Chem. 261: 12610-5. PMID: 3462189
- Stereoselectivity of induction of the retinoblastoma gene product (pRb) dephosphorylation by D-erythro-sphingosine supports a role for pRb in growth suppression by sphingosine. | Pushkareva, M., et al. 1995. Biochemistry. 34: 1885-92. PMID: 7849048
Inhibitor of:
4932429P05Rik, apoL7b, ATPase, CCT, Cd1d2, Ceramide Kinase, CERKL, CMPK2, DGK-β, DGK-η, DGK-ι, DGK-κ, GIMAP4, GIMAP7, GLTPD1, Gm438, GSDML, LANCL3, LASS1, LCE1B, LCE1C, MARCKS, MUP20, p55 CDC, PAP, PIG-K, PITPβ, PKC, PKC-d2, PKN, PLSCR5, Polyoma virus VP1, Ser/Thr Protein Kinase, SMPD5, SPACA5, SPHKAP, SUSD3, Synapsin Ia, and Ypk1.Activator of:
1700110M21Rik, 4930525M21Rik, 4930526D03Rik, 4931417E11Rik, 5330437I02Rik, 6330403A02Rik, 9130409I23Rik, 9430007A20Rik, ACT, AGXT2L1, APHC, ASAH2B, ASAH3, Atlastin-2, C11orf74, Casein Kinase, caspase-13, CD17, CD1E, CD60b, ChoK, cPKC βI, CWH43, CXorf49B, CYB5R3, CYLC1, dachsous, DMRTC2, DSCR 5, EDG-4, EDG-6, EG629667, Ethanolamine kinase 2, FADS7_Degs1, FAN, FBXW27, FIG4, Flotillin-1, GAL3ST2, GD3 Synthase, GLB1L2, GM2-AP, GM2/GD2 Synthase, Gm70, GUP1, Hantavirus, HS1BP3, KEPI, Keratin 38, KRTAP5-4, LASS2, LASS3, LASS5, LASS6, LOC730005, LPPR3, MASP-1, MBOAT1, MBOAT5, MORN4, MTMR4, mucolipin 3, Mumps, murinoglobulin 1, myotubularin, MYPT3, N-SMase3, neutral ceramidase, NMT1, Obox2, OCR1, ORMDL3, PAcP, PC-PLD, PC-PLD1A, periaxin, PGRMC2, PI 3-kinase p101, PI 4-kinase α, PIG-V, PIG-Y, PITP, PKC delta, Pkc1, PLC ζ, PLC 2, PLC-XD3, PLD6, PLEKHS1, PP2A-β, PP2A-B55-γ, PP2A-B56-δ, PP2A-B72/B130, PRP4 kinase, PSAPL1, PSS2, Rab 4B, RAM, Respiratory Syncytial Virus fusion protein, SAMD8, SEC14L2, SERINC1, SMPD5, SMS1, SMS2, SO, SPTLC2, SPTLC3, SPTSSA, stefin A2l1, stefin A3L1, Streptolysin, Synaptotagmin VIII, TCP11L2, Tctex5, TEX261, TEX37, THUMPD2, TM4SF20, TM7SF3, Tmed11, TMEM106C, TMEM131, TMEM132C, Tropomyosin β, TSPYL3, Tsx, TTC24, TTP-α, U90926, v-SNARE Ykt6p, VPS13A, WBP2, XYLB, Ypk2, ZDHHC14, ZDHHC15, ZDHHC24, ZDHHC25, ZDHHC7, and ZDHHC9.Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
D-erythro-Sphingosine, 10 mg | sc-3546 | 10 mg | $90.00 | |||
D-erythro-Sphingosine, 25 mg | sc-3546A | 25 mg | $194.00 | |||
D-erythro-Sphingosine, 100 mg | sc-3546B | 100 mg | $510.00 | |||
D-erythro-Sphingosine, 1 g | sc-3546C | 1 g | $2448.00 | |||
D-erythro-Sphingosine, 5 g | sc-3546D | 5 g | $9384.00 | |||
D-erythro-Sphingosine, 10 g | sc-3546E | 10 g | $15300.00 |