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Dimethyldioctadecylammonium (bromide) Sale

(Synonyms: 双十八烷基二甲基溴化铵) 目录号 : GC43467

A cationic amphipathic lipid

Dimethyldioctadecylammonium (bromide) Chemical Structure

Cas No.:3700-67-2

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产品描述

Dimethyldioctadecylammonium (DDA) is a cationic amphipathic lipid. DDA liposomes containing an Ag85B-ESAT-6 antigen induce antigen deposition at an intramuscular or subcutaneous injection site in mice, increasing immune cell exposure to the antigen. In a guinea pig model of M. tuberculosis infection, spleen bacterial load is reduced and lung and spleen lesion numbers are decreased when the mycobacterial lipid antigens Ac2SGL and PIM2 are administered in liposomes comprised of DDA and a synthetic analog of the mycobacterial cord factor trehalose 6,6-dibehenate (TDB). DDA has also been used in the study of lipid bilayer dynamics.

Chemical Properties

Cas No. 3700-67-2 SDF
别名 双十八烷基二甲基溴化铵
Canonical SMILES CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC.[Br-]
分子式 C38H80N•Br 分子量 631
溶解度 DMF: 2 mg/ml,DMSO: 16 mg/ml,Ethanol: 33 mg/ml,PBS (pH 7.2): 5 mg/ml 储存条件 Store at -20°C
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1 mg 5 mg 10 mg
1 mM 1.5848 mL 7.9239 mL 15.8479 mL
5 mM 0.317 mL 1.5848 mL 3.1696 mL
10 mM 0.1585 mL 0.7924 mL 1.5848 mL
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Research Update

Immunological Effects of Dimethyldioctadecylammonium bromide and Saponin as Adjuvants for Outer Membrane Vesicles from Neisseria meningitidis

Diseases 2022 Jul 19;10(3):46.PMID:35892740DOI:10.3390/diseases10030046.

The meningococcal disease is a global health threat, but is preventable through vaccination. Adjuvants improve meningococcal vaccines and are able to trigger different aspects of the immune response. The present work evaluated the immune response of mice against Neisseria meningitidis outer membrane vesicles (OMV) complexed with the adjuvants aluminium hydroxide (AH), via subcutaneous route; and Dimethyldioctadecylammonium bromide (DDA) or Saponin (Sap), via intranasal/subcutaneous routes. ELISA demonstrated that all adjuvants increased IgG titers after the booster dose, remaining elevated for 18 months. Additionally, adjuvants increased the avidity of the antibodies and the bactericidal titer: OMVs alone were bactericidal until 1:4 dilution but, when adjuvanted by Alum, DDA or Sap, it increased to 1/32. DDA and Sap increased all IgG isotypes, while AH improved IgG1 and IgG2a levels. Thus, Sap led to the recognition of more proteins in Immunoblot, followed by DDA and AH. Sap and AH induced higher IL-4 and IL-17 release, respectively. The use of adjuvants improved both cellular and humoral immune response, however, each adjuvant contributed to particular parameters. This demonstrates the importance of studying different adjuvant options and their suitability to stimulate different immune mechanisms, modulating the immune response.

Effect of salts on size and morphology of extruded Dimethyldioctadecylammonium bromide or chloride vesicle for polymeric nanocapsules synthesis via templating emulsion polymerization

J Colloid Interface Sci 2021 Apr;587:393-401.PMID:33370661DOI:10.1016/j.jcis.2020.11.116.

In preparing polymer capsules by vesicle templated emulsion polymerization, the initial size and morphology of the biomimetic vesicle template dictate the final size and morphology of the capsules. The presence of salts (NaCl, NaBr and LiCl) influences the size, dispersity (PDI) and morphology of Dimethyldioctadecylammonium bromide or chloride (DODAX, X = Br- or Cl-) vesicles, prepared via membrane extrusion. DODAX vesicles in pure water exhibit broad size distributions with PDI of 0.5 and 0.3 for DODAB and DODAC, respectively. Addition of salts in water before (pre-addition) and after (post-addition) extrusion reduces the size and PDI of the vesicles significantly and results in various morphology investigated with cryo-TEM. It is observed that at low salt concentration (≤0.5 mM) in pre-addition, DODAX exists as a nice quasi spherical unilamellar vesicle, suitable for vesicle templated polymerization whereas in post-addition of salt at any concentration, the morphology is dominated by structures not suitable for templating application. The information obtained here is crucial for vesicle templated emulsion polymerization and it will be shown that there is a relationship between vesicle template morphology and final polymer capsule morphology.

Effects of Dimethyldioctadecylammonium bromide on phagocytosis and digestion of Listeria monocytogenes by mouse peritoneal macrophages

Immunology 1981 Jul;43(3):425-31.PMID:6788683doi

Listeria monocytogenes was labelled with [3H]-thymidine and phagocytosis in vivo, measured after the intraperitoneal injection of killed or viable listeria. The loss of intracellular radioactivity after incubation in vitro was used as a measure for digestion. Killing was assessed by counting the numbers of viable listeria before and after in vitro incubation. Peritoneal macrophages from mice immunized with viable listeria showed better phagocytosis and digestion of both killed and viable listeria than macrophages from normal mice. Viable listeria were digested to a lesser degree than killed ones by both normal and immune macrophages. The simultaneous injection of the surfactant Dimethyldioctadecylammonium bromide (DDA) with killed or viable listeria greatly depressed the digestion of listeria. Phagocytosis of viable listeria was not affected whereas that of killed listeria was slightly enhanced. The injection of 10(8) killed listeria mixed with DDA greatly impaired the digestion of viable listeria 7 days but not 1 day after injection. The impairment of digestion was accompanied by an increase in the number of intracellular viable listeria.

Effect of Dimethyldioctadecylammonium bromide induced macrophages on malignant cell proliferation

Cancer Lett 1985 Jun;27(2):225-32.PMID:4005832DOI:10.1016/0304-3835(85)90112-0.

Murine peritoneal macrophages elicited by Dimethyldioctadecylammonium bromide (DDA), which is a potent immunologic adjuvant, were examined for cytotoxic and growth inhibiting activity for malignant cells. DDA macrophages had no cytolytic activity for murine B16BL-6 melanoma or human SMS-SB pre-B leukemia cells even in the presence of up to 1 microgram bacterial endotoxin (lipopolysaccharide, LPS)/ml. However, they exhibited a variable inhibitory effect on the growth of several lines of leukemia cells. The number of SMS-SB and human NALL cells remained essentially static in the presence of DDA macrophages while they increased significantly when cultured with resident macrophages. In contrast, L1210 cells increased 5-8-fold in the presence of macrophages elicited either by DDA or the inflammatory agent proteose peptone (PP). Although DDA macrophages retarded L1210 growth relative to PP macrophages, both populations responded to LPS in a comparable dose dependent manner to become essentially cytostatic at 1 microgram LPS/ml.

Protective antiviral immune responses to pseudorabies virus induced by DNA vaccination using Dimethyldioctadecylammonium bromide as an adjuvant

J Virol 2002 Oct;76(20):10540-5.PMID:12239334DOI:10.1128/jvi.76.20.10540-10545.2002.

To enhance the efficacy of a DNA vaccine against pseudorabies virus (PRV), we evaluated the adjuvant properties of plasmids coding for gamma interferon or interleukin-12, of CpG immunostimulatory motifs, and of the conventional adjuvants Dimethyldioctadecylammonium bromide in water (DDA) and sulfolipo-cyclodextrin in squalene in water. We demonstrate that a DNA vaccine combined with DDA, but not with the other adjuvants, induced significantly stronger immune responses than plasmid vaccination alone. Moreover, pigs vaccinated in the presence of DDA were protected against clinical disease and shed significantly less PRV after challenge infection. This is the first study to demonstrate that DDA, a conventional adjuvant, enhances DNA vaccine-induced antiviral immunity.