Trehalose-6,6'-dibehenate

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; α-D-Glucopyranoside, 6-O-(1-oxodocosyl)-α-D-glucopyranosyl, 6-docosanoate
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
Related CAS	73078-77-0 (Deleted CAS) 160112-43-6 (Deleted CAS)
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%

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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