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Dimethyldioctadecylammonium bromide

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Category	Adjuvants
Catalog NO.	BPG-3012
Product Name	Dimethyldioctadecylammonium bromide
CAS	3700-67-2
Molecular Formula	C38H80BrN
Molecular Weight	630.95

Scheme Design
Custom Synthesis
cGMP Manufacturing
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Product Information
Application
References
Documents
Reviews

Product Information

Description	Dimethyldioctadecylammonium Bromide 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.
Synonyms	DDAB; N,N-dimethyl-N-octadecyloctadecan-1-aminium bromide; 1-Octadecanaminium, N,N-dimethyl-N-octadecyl-, bromide; Dimethyldistearylammonium bromide; Distearyldimethylammonium bromide; Dimethyldioctadecylazanium bromide; Dioctadecyldimethylammonium bromide; di-n-Octadecyldimethylammonium bromide; N,N-Distearyl-N,N-dimethylammonium bromide; 18:0 DDAB; DODAB
IUPAC Name	dimethyl(dioctadecyl)azanium;bromide
Canonical SMILES	CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC.[Br-]
InChI	InChI=1S/C38H80N.BrH/c1-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-39(3,4)38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-2;/h5-38H2,1-4H3;1H/q+1;/p-1
InChIKey	PSLWZOIUBRXAQW-UHFFFAOYSA-M
Boiling Point	159-160 °C at 760 mmHg
Melting Point	151-157 °C
Purity	≥98%
Density	1.05 g/cm3
Solubility	Soluble in Acetone, Acetonitrile, Ethanol, Methanol, Water
Appearance	White powder
Shelf Life	1 Year
Storage	Store at -20 °C
Exact Mass	629.547
Hygroscopic	No
Light Sensitive	No
Percent Composition	C 72.34%, H 12.78%, Br 12.66%, N 2.22%
Pictogram(s)	Irritant
Signal	Warning
Precautionary Statement Codes	P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

References

1. Lou G, Anderluzzi G, Tandrup Schmidt S, Woods S, Gallorini S, Brazzoli M, Giusti F, Ferlenghi I, Johnson R, Roberts CW, O'Hagan DT, Baudner BC, Perrie Y. Delivery of self-amplifying mRNA vaccines by cationic lipid nanoparticles: The impact of cationic lipid selection. J Control Release. 2020 Jun 30:S0168-3659(20)30362-X. doi: 10.1016/j.jconrel.2020.06.027. Epub ahead of print. PMID: 32619745. PubMed ID: 32619745.
2. Lee H, Jiang D, Pardridge WM. Lyoprotectant Optimization for the Freeze-Drying of Receptor-Targeted Trojan Horse Liposomes for Plasmid DNA Delivery. Mol Pharm. 2020 Apr 29. doi: 10.1021/acs.molpharmaceut.0c00310. Epub ahead of print. PMID: 32315188. PubMed ID: 32315188.
3. Cheng Q, Wei T, Farbiak L, Johnson LT, Dilliard SA, Siegwart DJ. Selective organ targeting (SORT) nanoparticles for tissue-specific mRNA delivery and CRISPR-Cas gene editing. Nat Nanotechnol. 2020 Apr;15(4):313-320. doi: 10.1038/s41565-020-0669-6. Epub 2020 Apr 6. PMID: 32251383. PubMed ID: 32251383.
4. Chatzikleanthous D, Schmidt ST, Buffi G, Paciello I, Cunliffe R, Carboni F, Romano MR, O'Hagan DT, D'Oro U, Woods S, Roberts CW, Perrie Y, Adamo R. Design of a novel vaccine nanotechnology-based delivery system comprising CpGODN-protein conjugate anchored to liposomes. J Control Release. 2020 Apr 2:S0168-3659(20)30211-X. doi: 10.1016/j.jconrel.2020.04.001. Epub ahead of print. PMID: 32247804. PubMed ID: 32247804.
5. Larrouy-Maumus G, Layre E, Clark S, Prandi J, Rayner E, Lepore M, de Libero G, Williams A, Puzo G, Gilleron M. Protective efficacy of a lipid antigen vaccine in a guinea pig model of tuberculosis. Vaccine. 2017 Mar 7;35(10):1395-1402. doi: 10.1016/j.vaccine.2017.01.079. Epub 2017 Feb 9. PMID: 28190740. PubMed ID: 28190740.
6. Derrick SC, Yabe I, Morris S, Cowley S. Induction of Unconventional T Cells by a Mutant Mycobacterium bovis BCG Strain Formulated in Cationic Liposomes Correlates with Protection against Mycobacterium tuberculosis Infections of Immunocompromised Mice. Clin Vaccine Immunol. 2016 Jul 5;23(7):638-47. doi: 10.1128/CVI.00232-16. PMID: 27226281; PMCID: PMC4933783. PubMed ID: 27226281.
7. Rose F, Wern JE, Ingvarsson PT, van de Weert M, Andersen P, Follmann F, Foged C. Engineering of a novel adjuvant based on lipid-polymer hybrid nanoparticles: A quality-by-design approach. J Control Release. 2015 Jul 28;210:48-57. doi: 10.1016/j.jconrel.2015.05.004. Epub 2015 May 6. PMID: 25957906. PubMed ID: 25957906.
8. Teng X, Tian M, Li J, Tan S, Yuan X, Yu Q, Jing Y, Zhang Z, Yue T, Zhou L, Fan X. Immunogenicity and protective efficacy of DMT liposome-adjuvanted tuberculosis subunit CTT3H vaccine. Hum Vaccin Immunother. 2015;11(6):1456-64. doi: 10.1080/21645515.2015.1037057. PMID: 25905680; PMCID: PMC4514263. PubMed ID: 25905680.
9. Gallez A, Palazzo C, Blacher S, Tskitishvili E, Noël A, Foidart JM, Evrard B, Pequeux C, Piel G. Liposomes and drug-in-cyclodextrin-in-liposomes formulations encapsulating 17β-estradiol: An innovative drug delivery system that prevents the activation of the membrane-initiated steroid signaling (MISS) of estrogen receptor α. Int J Pharm. 2020 Jan 5;573:118861. doi: 10.1016/j.ijpharm.2019.118861. Epub 2019 Nov 22. PubMed ID: 31765774.
10. Faria MJ, Machado R, Ribeiro A, Gonçalves H, Real Oliveira MECD, Viseu T, das Neves J, Lúcio M. Rational Development of Liposomal Hydrogels: A Strategy for Topical Vaginal Antiretroviral Drug Delivery in the Context of HIV Prevention. Pharmaceutics. 2019 Sep 18;11(9). pii: E485. doi: 10.3390/pharmaceutics11090485. PubMed ID: 31540519.

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