1-Dodecylimidazole

Names

[ Name ]:
1-Dodecylimidazole

[Synonym ]:
Imidazole,1-dodecyl
1-n-dodecanylimidazole
1H-Imidazole,1-dodecyl
dodecylimidazole
EINECS 224-314-4
N-dodecyl imidazole
1-Laurylimidazole
1-Dodecylimidazole
1-Dodecyl-1H-imidazole
N-Laurylimidazole

Biological Activity

[Description]:

1-Dodecylimidazole (N-Dodecylimidazole) is a lysosomotropic detergent and a cytotoxic agent. 1-Dodecylimidazole causes cell death by its acid-dependent accumulation in lysosomes, disruption of the lysosomal membrane, and releaseof cysteine proteases into the cytoplasm. 1-Dodecylimidazole has hypocholesterolaemic activity and broad-spectrum antifungal activity[1][2][3].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Anti-infection >> Fungal

[In Vitro]

N-dodecylimidazole, an acid activated detergent with a pKa of 6.3, has been shown to be cytotoxic to cells in culture. N-dodecylimidazole displayed extracellular pH (pHe)-dependent cytotoxicity against EMT-6 and MGH U1 cells. cell killing was dose dependent and was 100-fold greater at pHe 6.0 than pHe 7.0[4].

[In Vivo]

The hypocholesterolaemic activity of 1-dodecylimidazole results in part from the inhibition of cholesterol biosynthesis at the level of 2,3-oxidosqualene sterol cyclase[2]. 1-dodecylimidazole (150 mg/kg body wt; by stomach tube; daily for 10 days) has lower serum cholesterol concentrations than control rats[2]. Animal Model: Male rats[2] Dosage: 150 mg/kg body wt Administration: By stomach tube; daily for 10 days Result: Had significantly lower serum cholesterol concentrations than untreated animals.

[References]

[1]. Wilson PD, et al. A relationship between multidrug resistance and growth-state dependent cytotoxicity of the lysosomotropic detergent N-dodecylimidazole. Biochem Biophys Res Commun. 1991;176(3):1377-1382.

[2]. Atkin SD, et al. The isolation of 2,3-oxidosqualene from the liver of rats treated with 1-dodecylimidazole, a novel hypocholesterolaemic agent. Biochem J. 1972;130(1):153-157.

[3]. Firestone RA, et al. Lysosomotropic agents. 7. Broad-spectrum antifungal activity of lysosomotropic detergents. J Med Chem. 1987;30(8):1519-1521.

[4]. Boyer MJ, et al. pH dependent cytotoxicity of N-dodecylimidazole: a compound that acquires detergent properties under acidic conditions. Br J Cancer. 1993;67(1):81-87.

Chemical & Physical Properties

[ Molecular Formula ]:
C₁₅H₂₈N₂

[ Molecular Weight ]:
236.39600

[ Exact Mass ]:
236.22500

[ PSA ]:
17.82000

[ LogP ]:
4.80400

[ Storage condition ]:
2~8℃，Seal

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NI5290000

CHEMICAL NAME :: Imidazole, 1-dodecyl-

CAS REGISTRY NUMBER :: 4303-67-7

BEILSTEIN REFERENCE NO. :: 0609993

LAST UPDATED :: 199701

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C15-H28-N2

MOLECULAR WEIGHT :: 236.45

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :: Cytogenetic analysis

TEST SYSTEM :: Rodent - hamster Ovary

DOSE/DURATION :: 29 mg/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 189,69,1987

Safety Information

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
36/37/38

[ Safety Phrases ]:
37/39-26

[ HS Code ]:
2933290090

Synthetic Route

Click to get detail synthetic route

Customs

[ HS Code ]: 2933290090

[ Summary ]:
2933290090. other compounds containing an unfused imidazole ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%