9008-22-4

9008-22-4 structure

Name: Laminaran
Chemical Name: (2S,3R,4S,5R,6R)-4-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-(hydroxymethyl)oxane-2,3,5-triol
CAS Number: 9008-22-4
Molecular Formula: C₁₈H₃₂O₁₆
Molecular Weight: 504.437
Catalog: Biochemical Plant extracts
Create Date: 2018-02-13 08:00:00
Modify Date: 2024-01-02 15:47:39
Laminaran is a neutral water-soluble β-1-3-glucan and a typical ligand for Dectin-1 isolated from the brown alga D. dichotoma, has potent immunomodulating, radioprotective, and anticancer activities[1]. Laminaran is made up of β (1→3)-glucan with β (1→6)-branches and can be catalyzed by enzymes such as laminarinase (EC 3.2.1.6) that breaks the β (1→3) bonds[2]. Laminaran is a promising immune stimulatory molecule for use in cancer immunotherapy[3].

Name	(2S,3R,4S,5R,6R)-4-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-(hydroxymethyl)oxane-2,3,5-triol
Synonyms	D-Glucopyranosyl-(1->3)-D-glucopyranosyl-(1->3)-D-glucopyranose Laminarin D-Glucopyranose, O-D-glucopyranosyl-(1->3)-O-D-glucopyranosyl-(1->3)- Laminaran MFCD00466918

Description	Laminaran is a neutral water-soluble β-1-3-glucan and a typical ligand for Dectin-1 isolated from the brown alga D. dichotoma, has potent immunomodulating, radioprotective, and anticancer activities[1]. Laminaran is made up of β (1→3)-glucan with β (1→6)-branches and can be catalyzed by enzymes such as laminarinase (EC 3.2.1.6) that breaks the β (1→3) bonds[2]. Laminaran is a promising immune stimulatory molecule for use in cancer immunotherapy[3].
Related Catalog	Research Areas >> Cancer Signaling Pathways >> Others >> Others
In Vitro	Laminaran (100-800 µg/mL; 24 hours) is not cytotoxic against normal epidermal cells JB6 Cl41 and human melanoma cells SK-MEL-28, the percentage of inhibition of living cells number is less than 15 % at concentrations range up to 800 µg/mL after 24 h of treatment[1]. Laminaran (200 µg/mL; 24-72 hours)does not cause any growth inhibition of SK-MEL-28 cells after 24 and 48 h of treatment, but decreases cells proliferation by 36 % after 72 h of treatment[1]. Laminaran (25-50 µg/mL; 24 hours) at low concentration does not influence the phosphorylation of c-Raf (Ser259), ERK1/2 (Tyr202/Tyr204), and MEK1/2 (Ser 221) kinases as well as total expression level of investigated proteins. But decreases p-MEK, p-ERK1/2 at 50 µg/mL[1]. Cell Viability Assay[1] Cell Line: JB6 Cl41 and SK-MEL-28 cells Concentration: 100, 200, 400, and 800 µg/mL Incubation Time: 24 hours Result: Showed no cytotoxic against normal epidermal cells JB6 Cl41 and human melanoma cells SK-MEL-28. Cell Proliferation Assay[1] Cell Line: SK-MEL-28 cells Concentration: 200 µg/mL Incubation Time: 24 hours Result: Decreased cell proliferation at 72 hours. Western Blot Analysis[1] Cell Line: SK-MEL-28 cells Concentration: 25 µg/mL; 50 µg/mL Incubation Time: 24 hours Result: Inhibited phosphorylation of c-Raf, MEK1/2, and ERK1/2 kinases.
In Vivo	Laminaran (intravenous injection; 12.5, 25, and 50 mg/kg; 21 days) and OVA (50 μg) combination significanly decreases the tumor masses when it compares with the PBS-, OVA-, and laminarin-treated mice[3]. Animal Model: C57BL/6 mice injected s.c. with B16-OVA cells[3] Dosage: 12.5, 25, and 50 mg/kg; 21 days Administration: Intravenous injection Result: Prevented B16-OVA tumor growth by inducing Ag-specific immune responses.
References	[1]. Malyarenko OS, et al. Laminaran from brown alga Dictyota dichotoma and its sulfated derivative as radioprotectors and radiosensitizers in melanoma therapy.Carbohydr Polym. 2019 Feb 15;206:539-547. [2]. Laminaran [3]. Song K, et al. Laminarin promotes anti-cancer immunity by the maturation of dendritic cells.Oncotarget. 2017 Jun 13;8(24):38554-38567.

Density	1.8±0.1 g/cm3
Boiling Point	902.8±65.0 °C at 760 mmHg
Molecular Formula	C₁₈H₃₂O₁₆
Molecular Weight	504.437
Flash Point	499.8±34.3 °C
Exact Mass	504.169037
PSA	268.68000
LogP	-6.08
Appearance	powder \| White to Off-white
Vapour Pressure	0.0±0.6 mmHg at 25°C
Index of Refraction	1.673
Storage condition	2-8°C
Water Solubility	H2O: 20 mg/mL, clear, faintly yellow \| Soluble in dimethyl sulfoxide (slightly, heated). Slightly soluble in water.

Personal Protective Equipment	Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes	Xn
Safety Phrases	22-24/25
RIDADR	NONH for all modes of transport
WGK Germany	3
RTECS	LZ3985000

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