Compounds > trehalose 6,6'-dibehenate
Page last updated: 2024-11-12

trehalose 6,6'-dibehenate

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

trehalose 6,6'-dibehenate: an analog of cord factor [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID11170611
CHEMBL ID4070777
CHEBI ID82287
MeSH IDM0494910

Synonyms (21)

Synonym
66758-35-8
C19190
trehalose-6,6'-dibehenate
CHEBI:82287
trehalose-6,6-dibehenate
DTXSID30457482
alpha-d-glucopyranoside, 6-o-(1-oxodocosyl)-alpha-d-glucopyranosyl, 6-docosanoate
Q27155858
6,6'-dibehenoyl-alpha,alpha'-trehalose
CHEMBL4070777
MS-31841
[(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
CS-0043454
HY-112137
alpha-d-glucopyranoside,6-o-(1-oxodocosyl)-alpha-d-glucopyranosyl,6-docosanoate
E86706
22:0 trehalose
672NB7JH7R
trehalose 6,6'-dibehenate
((2r,3s,4s,5s,6s)-6-((2r,3s,4r,5s,6s)-6-(docosanoyloxymethyl)-3,4,5-tris(oxidanyl)oxan-2-yl)oxy-3,4,5-tris(oxidanyl)oxan-2-yl)methyl docosanoate
((2r,2'r,3s,3's,4s,4's,5r,5'r,6r,6'r)-oxybis(3,4,5-trihydroxytetrahydro-2h-pyran-6,2-diyl))bis(methylene) didocosanoate

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Comprehensive toxicity studies of the CAF01 adjuvant-alone and together with different vaccines showed that CAF01 when tested at human dose levels was safe and well tolerated with only local inflammation at the site of injection and no systemic reactions."( 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.
Andersen, P; Andreasen, LV; Bang, P; Fomsgaard, A; Gram, G; Karlsson, I; Kromann, I; Schou, C; Tang, S, 2011)		0.37

Pharmacokinetics

ExcerptReferenceRelevance
" Therefore the aim of this study was to investigate the impact of a combination of reduced vesicle size and surface pegylation on the biodistribution and adjuvanticity of the formulations, in a bid to further manipulate the pharmacokinetic profiles of these adjuvants."( Manipulation of the surface pegylation in combination with reduced vesicle size of cationic liposomal adjuvants modifies their clearance kinetics from the injection site, and the rate and type of T cell response.
Bramwell, VW; Kaur, R; Kirby, DJ; Perrie, Y, 2012)		0.38
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
fatty acid derivativeAny organic molecular entity derived from a fatty acid.
O-acyl carbohydrateA carbohydrate derivative in which the hydrogen atom of at least one alcoholic hydroxy group of a carbohydrate has been replaced by an acyl substituent.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (19)

Assay IDTitleYearJournalArticle
AID1454999Adjuvant activity in immunized C57BL/6 mouse assessed as increase in OVA-specific IgG1 production in serum at 0.3 umol treated with ovalbumin for 7 days followed by stimulation with OVA for 7 days and restimulation with OVA measured 24 to 48 hrs post OVA 2018Journal of medicinal chemistry, 02-08, Volume: 61, Issue:3
Lipidated Brartemicin Analogues Are Potent Th1-Stimulating Vaccine Adjuvants.
AID1454980Agonist activity at mincle in wild type C57BL/6 mouse GM-CSF derived BMDM assessed as increase in TNF release at 0.1 to 1 nmol after 24 hrs by sandwich ELISA2018Journal of medicinal chemistry, 02-08, Volume: 61, Issue:3
Lipidated Brartemicin Analogues Are Potent Th1-Stimulating Vaccine Adjuvants.
AID1454978Agonist activity at mincle in wild type C57BL/6 mouse GM-CSF derived BMDM assessed as increase in IL-1beta release at 0.1 to 1 nmol after 24 hrs by sandwich ELISA2018Journal of medicinal chemistry, 02-08, Volume: 61, Issue:3
Lipidated Brartemicin Analogues Are Potent Th1-Stimulating Vaccine Adjuvants.
AID1581622Immuno-adjuvant activity in M72-immunized BALB/c mouse assessed as potentiation of antibody response to M72 by measuring IL-5 at 2 to 50 nmol, im administered immediately and 14 and measured after 5 days by immuno staining based flow cytometry2020Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1
Aryl Trehalose Derivatives as Vaccine Adjuvants for
AID1454974Adjuvant activity in immunized C57BL/6 mouse assessed as increase in OVA-specific IgG production in serum at 0.3 umol treated with ovalbumin for 7 days followed by stimulation with OVA for 7 days and restimulation with OVA measured 24 to 48 hrs post OVA c2018Journal of medicinal chemistry, 02-08, Volume: 61, Issue:3
Lipidated Brartemicin Analogues Are Potent Th1-Stimulating Vaccine Adjuvants.
AID1581614Agonist activity at human Mincle receptor expressed in human HEK cells assessed as NF-kappaB activation incubated for 24 hrs by SEAP reporter gene assay2020Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1
Aryl Trehalose Derivatives as Vaccine Adjuvants for
AID1454998Adjuvant activity in immunized C57BL/6 mouse assessed as increase in OVA-specific IgG2b production in serum at 0.3 umol treated with ovalbumin for 7 days followed by stimulation with OVA for 7 days and restimulation with OVA measured 24 to 48 hrs post OVA2018Journal of medicinal chemistry, 02-08, Volume: 61, Issue:3
Lipidated Brartemicin Analogues Are Potent Th1-Stimulating Vaccine Adjuvants.
AID1581619Immuno-adjuvant activity in M72-immunized BALB/c mouse assessed as potentiation of antibody response to M72 by measuring CD4+ IL-17A T-cells at 2 to 50 nmol, im administered immediately and 14 and measured after 5 days by immuno staining based flow cytome2020Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1
Aryl Trehalose Derivatives as Vaccine Adjuvants for
AID1454979Agonist activity at mincle in wild type C57BL/6 mouse GM-CSF derived BMDM assessed as increase in MIP2 release at 0.1 to 1 nmol after 24 hrs by sandwich ELISA2018Journal of medicinal chemistry, 02-08, Volume: 61, Issue:3
Lipidated Brartemicin Analogues Are Potent Th1-Stimulating Vaccine Adjuvants.
AID1454995Adjuvant activity in immunized C57BL/6 mouse assessed as footpad swelling at 0.3 umol treated with ovalbumin for 7 days followed by stimulation with OVA for 7 days measured 24 to 48 hrs post OVA challenge2018Journal of medicinal chemistry, 02-08, Volume: 61, Issue:3
Lipidated Brartemicin Analogues Are Potent Th1-Stimulating Vaccine Adjuvants.
AID1581618Immuno-adjuvant activity in M72-immunized BALB/c mouse assessed as potentiation of antibody response to M72 by measuring serum anti-M72 IgG2a level at 10 nmol, im administered immediately and 14 and measured after 14 days by ELISA2020Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1
Aryl Trehalose Derivatives as Vaccine Adjuvants for
AID1581620Immuno-adjuvant activity in B42-immunized BALB/c mouse assessed as potentiation of antibody response to B42 by measuring CD4+ IL-17A T-cells at 2 to 50 nmol, im administered immediately and 14 and measured after 5 days by immuno staining based flow cytome2020Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1
Aryl Trehalose Derivatives as Vaccine Adjuvants for
AID1455000Adjuvant activity in immunized C57BL/6 mouse assessed as increase in OVA-specific IgG2c production in serum at 0.3 umol treated with ovalbumin for 7 days followed by stimulation with OVA for 7 days and restimulation with OVA measured 24 to 48 hrs post OVA2018Journal of medicinal chemistry, 02-08, Volume: 61, Issue:3
Lipidated Brartemicin Analogues Are Potent Th1-Stimulating Vaccine Adjuvants.
AID1454977Agonist activity at mincle in wild type C57BL/6 mouse GM-CSF derived BMDM assessed as increase in IL-6 release at 0.1 to 1 nmol after 24 hrs by sandwich ELISA2018Journal of medicinal chemistry, 02-08, Volume: 61, Issue:3
Lipidated Brartemicin Analogues Are Potent Th1-Stimulating Vaccine Adjuvants.
AID1581615Agonist activity at mouse Mincle receptor expressed in human HEK cells assessed as NF-kappaB activation incubated for 24 hrs by SEAP reporter gene assay2020Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1
Aryl Trehalose Derivatives as Vaccine Adjuvants for
AID1454975Adjuvant activity in immunized C57BL/6 mouse assessed as increase in antigen specific IFNgamma production in spelnocytes at 0.3 umol treated with ovalbumin for 7 days followed by stimulation with OVA for 7 days and restimulation with OVA measured 24 to 482018Journal of medicinal chemistry, 02-08, Volume: 61, Issue:3
Lipidated Brartemicin Analogues Are Potent Th1-Stimulating Vaccine Adjuvants.
AID1664128Agonist activity at human Mincle receptor expressed in HEK cells cotransfected with NF-kappaB SEAP reporter gene assessed as increase in production of SEAP measured after 18 to 24 hrs by SEAP reporter gene-based spectrophotometric method2020Bioorganic & medicinal chemistry, 07-15, Volume: 28, Issue:14
6,6'-Aryl trehalose analogs as potential Mincle ligands.
AID1454976Adjuvant activity in immunized C57BL/6 mouse assessed as increase in IL-17 production in spelnocytes at 0.3 umol treated with ovalbumin for 7 days followed by stimulation with OVA for 7 days and restimulation with OVA measured 24 to 48 hrs post OVA challe2018Journal of medicinal chemistry, 02-08, Volume: 61, Issue:3
Lipidated Brartemicin Analogues Are Potent Th1-Stimulating Vaccine Adjuvants.
AID1581621Immuno-adjuvant activity in M72-immunized BALB/c mouse assessed as potentiation of antibody response to M72 by measuring IFNgamma at 2 to 50 nmol, im administered immediately and 14 and measured after 5 days by immuno staining based flow cytometry2020Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1
Aryl Trehalose Derivatives as Vaccine Adjuvants for
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (51)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's9 (17.65)29.6817
2010's38 (74.51)24.3611
2020's4 (7.84)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 18.63

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index18.63 (24.57)
Research Supply Index3.95 (2.92)
Research Growth Index4.95 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (18.63)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (5.88%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other48 (94.12%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
curdlan
D-hexose : A hexose that has D-configuration at position 5.		3.3110hexose
lactic acid
Lactic Acid: A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed). 2-hydroxypropanoic acid : A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group.		2.47202-hydroxy monocarboxylic acidalgal metabolite;
Daphnia magna metabolite
ddt
1,1-bis(p-chlorophenyl)-2,2,2-trichloroethane: structure in first source		2.1710benzenoid aromatic compound;
chlorophenylethane;
monochlorobenzenes;
organochlorine insecticide		bridged diphenyl acaricide;
carcinogenic agent;
endocrine disruptor;
persistent organic pollutant
lactose
Lactose: A disaccharide of GLUCOSE and GALACTOSE in human and cow milk. It is used in pharmacy for tablets, in medicine as a nutrient, and in industry.. lactose : A glycosylglucose disaccharide, found most notably in milk, that consists of D-galactose and D-glucose fragments bonded through a beta-1->4 glycosidic linkage. The glucose fragment can be in either the alpha- or beta-pyranose form, whereas the galactose fragment can only have the beta-pyranose form.. beta-lactose : The beta-anomer of lactose.		2.0810lactose
mannitol
[no description available]		2.4720mannitolallergen;
antiglaucoma drug;
compatible osmolytes;
Escherichia coli metabolite;
food anticaking agent;
food bulking agent;
food humectant;
food stabiliser;
food thickening agent;
hapten;
metabolite;
osmotic diuretic;
sweetening agent
bis(p-chlorophenyl)acetic acid
bis(p-chlorophenyl)acetic acid: a metabolite of DDT; RN given refers to parent cpd.. bis(4-chlorophenyl)acetic acid : A organochlorine compound comprising acetic acid having two 4-chlorophenyl substituents attached at the 2-position.		2.1710monocarboxylic acid;
monochlorobenzenes
trehalose
alpha,alpha-trehalose : A trehalose in which both glucose residues have alpha-configuration at the anomeric carbon.		7.9640trehaloseEscherichia coli metabolite;
geroprotector;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
dimethyldioctadecylammonium
dimethyldioctadecylammonium: a cationic lipid analog; RN given refers to parent cpd		11.55340
1,2-distearoyllecithin
[no description available]		3.0140
resiquimod
S 28463: structure given in first source		2.1710imidazoquinoline
epiglucan
epiglucan: a highly side-chain/branched alkali-insoluble cell wall glucan from fungus such as Epicoccum nigrum, Botrytis cinerea, ascomycetes & basidiomycetes; also isolated S-4001 from Lei Wan (polyporus mylitiae), HA-beta-glucan from mushroom Pleutotus ostreatus (Fr.) Quel., and translam from seaweed Laminaria cichorioides; with commercially important functional properties including emulsification and friction reduction.		3.3110
ovalbumin
Ovalbumin: An albumin obtained from the white of eggs. It is a member of the serpin superfamily.		2.9940
lipid a
Lipid A: Lipid A is the biologically active component of lipopolysaccharides. It shows strong endotoxic activity and exhibits immunogenic properties.. lipid A : The glycolipid moiety of bacterial lipopolysaccharide (R can be either hydrogen or a fatty acyl group).		3.9330dodecanoate ester;
lipid A;
tetradecanoate ester		Escherichia coli metabolite
phosphatidylcholines
Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.		3.01401,2-diacyl-sn-glycero-3-phosphocholine
chitosan
[no description available]		2.1710
brartemicin
brartemicin: an inhibitor of tumor cell invasion from the actinomycete Nonomuraea sp.; structure in first source. brartemicin : A glycosyl glycoside derivative that consists of alpha,alpha-trehalose substituted at positions 6 and 6' by O-2,4-dihydroxy-6-methylbenzoyl groups. It is isolated from the culture broth of actinomycete, Nonomuraea, and has antitumor activity.		2.1710benzoate ester;
glycosyl glycoside derivative;
resorcinols		antimicrobial agent;
metabolite
glycolipids
[no description available]		8.15480
interleukin-8
Interleukin-8: A member of the CXC chemokine family that plays a role in the regulation of the acute inflammatory response. It is secreted by variety of cell types and induces CHEMOTAXIS of NEUTROPHILS and other inflammatory cells.		2.0710
minocycline
Minocycline: A TETRACYCLINE analog, having a 7-dimethylamino and lacking the 5 methyl and hydroxyl groups, which is effective against tetracycline-resistant STAPHYLOCOCCUS infections.. minocycline : A tetracycline analogue having a dimethylamino group at position 7 and lacking the methyl and hydroxy groups at position 5.		2.2110
muramidase
Muramidase: A basic enzyme that is present in saliva, tears, egg white, and many animal fluids. It functions as an antibacterial agent. The enzyme catalyzes the hydrolysis of 1,4-beta-linkages between N-acetylmuramic acid and N-acetyl-D-glucosamine residues in peptidoglycan and between N-acetyl-D-glucosamine residues in chitodextrin. EC 3.2.1.17.		2.5520
cord factors
Cord Factors: Toxic glycolipids composed of trehalose dimycolate derivatives. They are produced by MYCOBACTERIUM TUBERCULOSIS and other species of MYCOBACTERIUM. They induce cellular dysfunction in animals.		2.9840
guanosine
ribonucleoside : Any nucleoside where the sugar component is D-ribose.		2.0610guanosines;
purines D-ribonucleoside		fundamental metabolite
ConditionIndicatedRelationship StrengthStudiesTrials
Koch's Disease
[description not available]		04.1750
Tuberculosis
Any of the infectious diseases of man and other animals caused by species of MYCOBACTERIUM TUBERCULOSIS.		04.1750
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.6120
Pulmonary Consumption
[description not available]		03.7330
Tuberculosis, Pulmonary
MYCOBACTERIUM infections of the lung.		03.7330
Innate Inflammatory Response
[description not available]		02.2110
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		02.2110
Allodynia
[description not available]		02.2110
Disbacteriosis
[description not available]		03.1210
Infections, Plasmodium
[description not available]		02.0410
Malaria
A protozoan disease caused in humans by four species of the PLASMODIUM genus: PLASMODIUM FALCIPARUM; PLASMODIUM VIVAX; PLASMODIUM OVALE; and PLASMODIUM MALARIAE; and transmitted by the bite of an infected female mosquito of the genus ANOPHELES. Malaria is endemic in parts of Asia, Africa, Central and South America, Oceania, and certain Caribbean islands. It is characterized by extreme exhaustion associated with paroxysms of high FEVER; SWEATING; shaking CHILLS; and ANEMIA. Malaria in ANIMALS is caused by other species of plasmodia.		02.0410
HIV Coinfection
[description not available]		02.0610
HIV Infections
Includes the spectrum of human immunodeficiency virus infections that range from asymptomatic seropositivity, thru AIDS-related complex (ARC), to acquired immunodeficiency syndrome (AIDS).		02.0610