1-O-(α-D-galactosyl)-N-hexacosanoylphytosphingosine

Names

[ Name ]:
1-O-(α-D-galactosyl)-N-hexacosanoylphytosphingosine

[Synonym ]:
Krn 7000
Galalpha-Cer(t18:0/26:0)
Hexacosanamide, N-[(1S,2S,3R)-1-[(α-D-galactopyranosyloxy)methyl]-2,3-dihydroxyheptadecyl]-
N-[(2S,3S,4R)-3,4-dihydroxy-1-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadecan-2-yl]hexacosanamide
AGL-582
1-O-(alpha-D-galactosyl)-N-hexacosanoylphytosphingosine
N-[(2S,3S,4R)-1-(α-D-Galactopyranosyloxy)-3,4-dihydroxy-2-octadecanyl]hexacosanamide
1-O-(α-D-galactosyl)-N-hexacosanoylphytosphingosine

Biological Activity

[Description]:

α-Galactosylceramide (α-GalCer) is a synthetic glycolipid with antitumorial and immunostimulatory. α-Galactosylceramide is a very potent NKT cell agonist and binds effectively to CD1d. The complex of α-Galactosylceramide plus CD1d binds the NKT cell TCR (T cell antigen receptor)[1][2][3][4].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Others >> Others

Research Areas >> Inflammation/Immunology

[Target]

NKT cell[3]

[In Vitro]

Culture supernatants of activated Vα24+NKT-cell cultures stimulated with α-Galactosylceramide pulsed monocyte-derived dendritic cells (Mo-DCs) exhibits antiproliferative activities against melanoma cells. This effect is predominantly due to release of IFN-γ, and to a lesser extent IL-12. Other cytokines, including IL-4 and IL-10, are released but these cytokines have less antiproliferative effects. Vα24+NKT-cells stimulated by α-Galactosylceramide-pulsed Mo-DCs have anti-tumour activities against human melanoma through antiproliferative effects exerted by soluble mediators[3].

[In Vivo]

α-Galactosylceramide treatment can protect against spontaneous, carcinogen-, or oncogene-induced primary tumor formation in mice. Consistent with a prime role for IFN-γ in NKT cell-mediated tumor responses, a C-glycoside analog of α-Galactosylceramide that preferentially stimulated IFN-γ production is even more effective than α-Galactosylceramide at preventing metastases of the B16 melanoma[1]. Since α-Galactosylceramide shows a potent antitumor activity and stimulates the lymphocyte proliferation (LP) on allogeneic mixed lymphocyte reaction (MLR) in the mouse, α-Galactosylceramide is considered to be a nonspecific immunostimulating agent which is a biological response modifier[4].

[References]

[1]. Godfrey DI, et al. Going both ways: immune regulation via CD1d-dependent NKT cells. J Clin Invest. 2004 Nov;114(10):1379-88.

[2]. Morita M, et al. Practical Total Synthesis of (2S,3S,4R)-1-O-(α-D-Galactopyranosyl)-N-hexacosanoyl-2-amino-1,3,4-octadecanetriol, the Antitumorial and Immunostimulatory α-Galactosylcer-amide, KRN7000. Biosci Biotechnol Biochem. 1996 Jan;60(2):288-92.

[3]. Kikuchi A, et al. In vitro anti-tumour activity of alpha-galactosylceramide-stimulated human invariant Valpha24+NKT cells against melanoma. Br J Cancer. 2001 Sep 1;85(5):741-6.

[4]. Masahiro Morita, et al. Structure-Activity Relationship of .alpha.-Galactosylceramides against B16-Bearing Mice. J. Med. Chem. 1995, 38, 12, 2176-2187.

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
939.8±65.0 °C at 760 mmHg

[ Melting Point ]:
190 °C

[ Molecular Formula ]:
C₅₀H₉₉NO₉

[ Molecular Weight ]:
858.322

[ Flash Point ]:
522.2±34.3 °C

[ Exact Mass ]:
857.731995

[ PSA ]:
168.94000

[ LogP ]:
15.96

[ Vapour Pressure ]:
0.0±0.6 mmHg at 25°C

[ Index of Refraction ]:
1.512