Trehalose-6,6'-dibehenate

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Category	Adjuvants
Catalog NO.	BPG-3011
Product Name	Trehalose-6,6'-dibehenate
CAS	66758-35-8
Molecular Formula	C56H106O13
Molecular Weight	987.43

Scheme Design
Custom Synthesis
cGMP Manufacturing
Quality Assurance

Product Information
References
Documents
Reviews

Product Information

Description	Trehalose-6,6'-dibehenate is a bioactive glycolipid and an analog of mycobacterial cord factor. Trehalose-6,6'-dibehenate is considered less toxic and an efficient vaccine adjuvant for tuberculosis.
Synonyms	22:0 Trehalose; D-(+)-trehalose 6,6'-dibehenate; 6,6'-didocosanoyl-α,α'-trehalose; TDB
IUPAC Name	[(2R,3S,4S,5R,6R)-6-[(2R,3R,4S,5S,6R)-6-(docosanoyloxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl docosanoate
Canonical SMILES	CCCCCCCCCCCCCCCCCCCCCC(=O)OCC1C(C(C(C(O1)OC2C(C(C(C(O2)COC(=O)CCCCCCCCCCCCCCCCCCCCC)O)O)O)O)O)O
InChI	InChI=1S/C56H106O13/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-39-41-47(57)65-43-45-49(59)51(61)53(63)55(67-45)69-56-54(64)52(62)50(60)46(68-56)44-66-48(58)42-40-38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h45-46,49-56,59-64H,3-44H2,1-2H3/t45-,46-,49-,50-,51+,52+,53-,54-,55-,56-/m1/s1
InChIKey	ZLJJDBSDZSZVTF-LXOQPCSCSA-N
Boiling Point	945.8±65.0°C at 760 mmHg
Purity	>99%
Density	1.08±0.1 g/cm3
Appearance	White solid
Shelf Life	1 Year
Storage	Store at -20°C
Exact Mass	986.763
Hygroscopic	No
Light Sensitive	No
Percent Composition	C 68.12%, H 10.82%, O 21.06%

References

1. 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.
2. 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.
3. 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.
4. 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.
5. Hansen M, Peltier J, Killy B, Amin B, Bodendorfer B, Härtlova A, Uebel S, Bosmann M, Hofmann J, Büttner C, Ekici AB, Kuttke M, Franzyk H, Foged C, Beer-Hammer S, Schabbauer G, Trost M, Lang R. Macrophage phosphoproteome analysis reveals MINCLE-dependent and -independent mycobacterial cord factor signaling. Mol Cell Proteomics. 2019 Jan 11. pii: mcp.RA118.000929. doi: 10.1074/mcp.RA118.000929. [Epub ahead of print]...PubMed ID: 30635358.
6. Fomsgaard, A., Karlsson, I., Gram, G., Schou, C., Tang, S., Bang, P., Kromann, I., Andersen, P., Andreasen, L.V. (2011) Development and preclinical safety evaluation of a new therapeutic HIV-1 vaccine based on 18 T-cell minimal epitope peptides applying a novel cationic adjuvant CAF01. Vaccine. 29:7067-74. PubMed ID: 21767590.
7. Nordly, P., Agger, E.M., Andersen, P., Nielsen, H.M., Foged, C. (2011) Incorporation of the TLR4 agonist monophosphoryl lipid A into the bilayer of DDA/TDB liposomes: physico-chemical characterization and induction of CD8+ T-cell responses in vivo. Pharm Res. 28:553-62. PubMed ID: 21042837.
8. Gram, G.J., Karlsson, I., Agger, E.M., Andersen, P., Fomsgaard, A. (2009) A novel liposome-based adjuvant CAF01 for induction of CD8(+) cytotoxic T-lymphocytes (CTL) to HIV-1 minimal CTL peptides in HLA-A*0201 transgenic mice. PLoS One. 4:e6950. PubMed ID: 19759892.
9. Davidsen, J., Rosenkrands, I., Christensen, D., Vangala, A., Kirby, D., Perrie, Y., Agger, E.M., Andersen, P. (2005) Characterization of cationic liposomes based on dimethyldioctadecylammonium and synthetic cord factor from M. tuberculosis (trehalose 6,6'-dibehenate)-a novel adjuvant inducing both strong CMI and antibody responses. Biochim Biophys Acta. 1718:22-31. PubMed ID: 16321607.

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