1-Dodecylimidazole (N-Dodecylimidazole) is a lysosomally active detergent and cytotoxic agent. 1-Dodecylimidazole causes cell death through its acid-dependent accumulation in lysosomes, disruption of lysosomal membranes, and release of caspases into the cytoplasm. 1-Dodecylimidazole has cholesterol-lowering and broad-spectrum antifungal activity.

Physicochemical Properties

Molecular Formula	C15H28N2
Molecular Weight	236.40
Exact Mass	236.225
CAS #	4303-67-7
PubChem CID	78002
Appearance	Colorless to light yellow liquid
LogP	4.804
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	11
Heavy Atom Count	17
Complexity	159
Defined Atom Stereocenter Count	0
SMILES	N1(C=NC=C1)CCCCCCCCCCCC
InChi Key	JMTFLSQHQSFNTE-UHFFFAOYSA-N
InChi Code	InChI=1S/C15H28N2/c1-2-3-4-5-6-7-8-9-10-11-13-17-14-12-16-15-17/h12,14-15H,2-11,13H2,1H3
Chemical Name	1-dodecylimidazole
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	It has been demonstrated that the acid-activated detergent N-dodecylimidazole, which has a pKa of 6.3, is cytotoxic to cultured cells. On EMT-6 and MGH U1 cells, N-docecylimidazole exhibited cytotoxicity that was dependent on extracellular pH (pHe). Cell death is 100 times more common at pH 6.0 than pH 7.0 and is dose-dependent [4].
ln Vivo	The inhibition of cholesterol biosynthesis at the level of 2,3-oxidosqualene sterol cyclase contributes to 1-dodecylimidazole's ability to decrease cholesterol [2]. 1. Rats given dodecylimidazole (150 mg/kg body weight; given daily for 10 days via gastric tube) had lower serum cholesterol concentrations than control rats [2].
Animal Protocol	Animal/Disease Models: Male rats[2] Doses: 150 mg/kg body wt Route of Administration: By stomach tube; daily for 10 days Experimental Results: Had Dramatically lower serum cholesterol concentrations than untreated animals.
References	[1]. 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]. 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]. Lysosomotropic agents. 7. Broad-spectrum antifungal activity of lysosomotropic detergents. J Med Chem. 1987;30(8):1519-1521. [4]. pH dependent cytotoxicity of N-dodecylimidazole: a compound that acquires detergent properties under acidic conditions. Br J Cancer. 1993;67(1):81-87.

Solubility Data

Solubility (In Vitro)

DMSO : 100 mg/mL (423.01 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (10.58 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (10.58 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (10.58 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	4.2301 mL	21.1506 mL	42.3012 mL
	5 mM	0.8460 mL	4.2301 mL	8.4602 mL
	10 mM	0.4230 mL	2.1151 mL	4.2301 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.