Page last updated: 2024-11-07

dodecyl-beta-d-maltoside

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

Description

Dodecyl-beta-d-maltoside (DDM) is a non-ionic detergent commonly used in biochemistry and structural biology for solubilizing and stabilizing membrane proteins. It is synthesized by attaching a dodecyl (C12) hydrocarbon chain to the reducing end of beta-maltose. DDM is a mild detergent that can effectively extract and maintain the native structure of membrane proteins, making it suitable for various applications, including protein purification, crystallization, and spectroscopy. The detergent disrupts the hydrophobic interactions within the membrane, allowing the protein to be solubilized in aqueous solution. It is particularly effective for solubilizing and stabilizing integral membrane proteins, which are difficult to study due to their hydrophobic nature. DDM's ability to maintain protein structure and function makes it a valuable tool for studying membrane protein dynamics, interactions, and mechanisms of action. It is commonly used in research areas such as drug discovery, biophysics, and cell biology.'

dodecyl beta-D-maltoside : A glycoside resulting from attachment of a dodecyl group to the reducing-end anomeric centre of a beta-maltose molecule. [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]

Cross-References

ID SourceID
PubMed CID114880
CHEMBL ID1234047
CHEBI ID43769
SCHEMBL ID411624
MeSH IDM0120216

Synonyms (41)

Synonym
chebi:43769 ,
CHEMBL1234047
dodecyl-beta-d-maltoside
n-dodecyl beta-d-maltoside, >=98% (gc)
n-dodecyl beta-d-maltoside, bioxtra, >=98% (gc)
n-dodecyl-beta-d-maltoside
lauryl maltoside
69227-93-6
(2r,3r,4s,5s,6r)-2-[(2r,3s,4r,5r,6r)-6-dodecoxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
beta-d-glucopyranoside, dodecyl 4-o-alpha-d-glucopyranosyl-
di107e57b4 ,
unii-di107e57b4
dodecyl maltoside
AKOS016011222
n-dodecyl b-d-maltoside
n-dodecyl beta-d-maltoside
dodecyl beta-maltoside
lauryl-.beta.-d-maltoside
n-dodecyl .beta.-d-maltoside
1-o-n-dodecyl-.beta.-dmaltopyranoside
SCHEMBL411624
dodecyl beta-d-maltoside
lauryl beta-d-maltoside
lauryl beta-maltoside
dodecyl 4-o-alpha-d-glucopyranosyl-beta-d-glucopyranoside
dodecyl alpha-d-glucopyranosyl-9(1->4)-beta-d-glucopyranoside
(2r,3r,4s,5s,6r)-2-(((2r,3s,4r,5r,6r)-6-(dodecyloxy)-4,5-dihydroxy-2-(hydroxymethyl)tetrahydro-2h-pyran-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2h-pyran-3,4,5-triol
mfcd00043012
(2r,3r,4s,5s,6r)-2-((2r,3s,4r,5r,6r)-6-(dodecyloxy)-4,5-dihydroxy-2-(hydroxymethyl)tetrahydro-2h-pyran-3-yloxy)-6-(hydroxymethyl)tetrahydro-2h-pyran-3,4,5-triol
n-dodecyl-i(2)-d-maltoside
n-dodecyl-b-d-maltoside
DS-6568
HY-128974
n-dodecyl-|a-d-maltoside
dodecyl 4-o-hexopyranosylhexopyranoside
DTXSID30988948
Q27120527
b-d-glucopyranoside, dodecyl 4-o-a-d-glucopyranosyl-
CS-0102968
A866883
F14800

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"Oral bioavailability of biologically active peptides and proteins is generally very low because they are extensively degraded by peptidases and proteases in the gastrointestinal tract and impermeable through the intestinal mucosal membrane."( [Methodologies for regulation of intestinal absorption of biologically active peptides].
Fujita, T; Muranishi, S, 1998
)
0.3
"The efficacy of n-lauryl-beta-D-maltopyranoside, (dodecylmaltoside, DDM) as a permeability-enhancer for tiludronate and cromolyn (BCS Class III, water-soluble compounds with oral bioavailability < 5%) was evaluated in Caco-2 cell monolayers and rat intestinal sacs."( Effect of dodecylmaltoside (DDM) on uptake of BCS III compounds, tiludronate and cromolyn, in Caco-2 cells and rat intestine model.
Betageri, GV; Deshmukh, DD; Nagilla, R; Ravis, WR, 2010
)
0.36

Dosage Studied

ExcerptRelevanceReference
" These approaches include (1) to use additives such as absorption enhancers and protease inhibitors, (2) to modify the peptide molecules to produce prodrugs and analogs, (3) to develop an administration method for peptides that can serve as an alternative to oral and injection administration and (4) to use the dosage forms to these peptide drugs."( [Methodologies for regulation of intestinal absorption of biologically active peptides].
Fujita, T; Muranishi, S, 1998
)
0.3
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
detergentA surfactant (or a mixture containing one or more surfactants) having cleaning properties in dilute solutions.
[role 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]

Drug Classes (2)

ClassDescription
glycosideA glycosyl compound resulting from the attachment of a glycosyl group to a non-acyl group RO-, RS-, RSe-, etc. The bond between the glycosyl group and the non-acyl group is called a glycosidic bond. By extension, the terms N-glycosides and C-glycosides are used as class names for glycosylamines and for compounds having a glycosyl group attached to a hydrocarbyl group respectively. These terms are misnomers and should not be used. The preferred terms are glycosylamines and C-glycosyl compounds, respectively.
disaccharide derivativeA carbohydrate derivative that is formally obtained from a disaccharide.
[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 (15)

Assay IDTitleYearJournalArticle
AID1439534Induction of biofilm formation in Pseudomonas aeruginosa PW6886 harboring rhlA-E08::ISphoA/hah mutant at 20 to 170 uM after 24 hrs under non-shaking condition by crystal-violet staining based assay2017Bioorganic & medicinal chemistry, 03-15, Volume: 25, Issue:6
Synthetic analogs of rhamnolipids modulate structured biofilms formed by rhamnolipid-nonproducing mutant of Pseudomonas aeruginosa.
AID1439546Inhibition of biofilm formation in eGFP-fused Pseudomonas aeruginosa PW6886 harboring rhlA-E08::ISphoA/hah mutant at 340 uM after 24 hrs under shaking condition by confocal laser scanning microscopy2017Bioorganic & medicinal chemistry, 03-15, Volume: 25, Issue:6
Synthetic analogs of rhamnolipids modulate structured biofilms formed by rhamnolipid-nonproducing mutant of Pseudomonas aeruginosa.
AID1439548Inhibition of biofilm formation in eGFP-fused Pseudomonas aeruginosa PW6886 harboring rhlA-E08::ISphoA/hah mutant at 340 uM after 48 hrs under shaking condition by confocal laser scanning microscopy2017Bioorganic & medicinal chemistry, 03-15, Volume: 25, Issue:6
Synthetic analogs of rhamnolipids modulate structured biofilms formed by rhamnolipid-nonproducing mutant of Pseudomonas aeruginosa.
AID1439539Bactericidal activity against Pseudomonas aeruginosa PW6886 harboring rhlA-E08::ISphoA/hah mutant at 20 to 340 uM under shaking condition2017Bioorganic & medicinal chemistry, 03-15, Volume: 25, Issue:6
Synthetic analogs of rhamnolipids modulate structured biofilms formed by rhamnolipid-nonproducing mutant of Pseudomonas aeruginosa.
AID1439541Induction of tendril formation in Pseudomonas aeruginosa PW6886 harboring rhlA-E08::ISphoA/hah mutant at 5 to 100 uM after 24 hrs2017Bioorganic & medicinal chemistry, 03-15, Volume: 25, Issue:6
Synthetic analogs of rhamnolipids modulate structured biofilms formed by rhamnolipid-nonproducing mutant of Pseudomonas aeruginosa.
AID1439549Induction of biofilm formation in eGFP-fused Pseudomonas aeruginosa PW6886 harboring rhlA-E08::ISphoA/hah mutant at 20 to 40 uM by COMSTAT based quantification relative to control2017Bioorganic & medicinal chemistry, 03-15, Volume: 25, Issue:6
Synthetic analogs of rhamnolipids modulate structured biofilms formed by rhamnolipid-nonproducing mutant of Pseudomonas aeruginosa.
AID1439547Induction of biofilm formation in eGFP-fused Pseudomonas aeruginosa PW6886 harboring rhlA-E08::ISphoA/hah mutant at 20 uM after 48 hrs under shaking condition by confocal laser scanning microscopy2017Bioorganic & medicinal chemistry, 03-15, Volume: 25, Issue:6
Synthetic analogs of rhamnolipids modulate structured biofilms formed by rhamnolipid-nonproducing mutant of Pseudomonas aeruginosa.
AID1439544Induction of tendril formation in Pseudomonas aeruginosa PAO1 at > 85 uM after 24 hrs2017Bioorganic & medicinal chemistry, 03-15, Volume: 25, Issue:6
Synthetic analogs of rhamnolipids modulate structured biofilms formed by rhamnolipid-nonproducing mutant of Pseudomonas aeruginosa.
AID1439543Induction of swarming motility of wild-type Pseudomonas aeruginosa PAO1 at 50 uM after 24 hrs2017Bioorganic & medicinal chemistry, 03-15, Volume: 25, Issue:6
Synthetic analogs of rhamnolipids modulate structured biofilms formed by rhamnolipid-nonproducing mutant of Pseudomonas aeruginosa.
AID1439550Inhibition of biofilm formation in eGFP-fused Pseudomonas aeruginosa PW6886 harboring rhlA-E08::ISphoA/hah mutant at 340 uM by COMSTAT based quantification relative to control2017Bioorganic & medicinal chemistry, 03-15, Volume: 25, Issue:6
Synthetic analogs of rhamnolipids modulate structured biofilms formed by rhamnolipid-nonproducing mutant of Pseudomonas aeruginosa.
AID1439555Antibiofilm activity against Pseudomonas aeruginosa PW6886 harboring rhlA-E08::ISphoA/hah mutant preformed biofilms assessed as reduction in biofilm bacterial count at 340 uM preincubated for 24 hrs under non-shaking condition followed by second incubatio2017Bioorganic & medicinal chemistry, 03-15, Volume: 25, Issue:6
Synthetic analogs of rhamnolipids modulate structured biofilms formed by rhamnolipid-nonproducing mutant of Pseudomonas aeruginosa.
AID1439537Antibiofilm activity against Pseudomonas aeruginosa PW6886 harboring rhlA-E08::ISphoA/hah mutant preformed biofilms assessed as reduction in biofilm bacterial count at 20 to 40 uM preincubated for 24 hrs under non-shaking condition followed by second incu2017Bioorganic & medicinal chemistry, 03-15, Volume: 25, Issue:6
Synthetic analogs of rhamnolipids modulate structured biofilms formed by rhamnolipid-nonproducing mutant of Pseudomonas aeruginosa.
AID1439545Induction of structured biofilm formation in eGFP-fused Pseudomonas aeruginosa PW6886 harboring rhlA-E08::ISphoA/hah mutant at 20 uM after 24 hrs under shaking condition by confocal laser scanning microscopy2017Bioorganic & medicinal chemistry, 03-15, Volume: 25, Issue:6
Synthetic analogs of rhamnolipids modulate structured biofilms formed by rhamnolipid-nonproducing mutant of Pseudomonas aeruginosa.
AID1439540Induction of swarming motility of Pseudomonas aeruginosa PW6886 harboring rhlA-E08::ISphoA/hah mutant at 5 to 100 uM after 24 hrs2017Bioorganic & medicinal chemistry, 03-15, Volume: 25, Issue:6
Synthetic analogs of rhamnolipids modulate structured biofilms formed by rhamnolipid-nonproducing mutant of Pseudomonas aeruginosa.
AID1438600Surfactant property of the compound in aqueous solution assessed as critical micelle concentration or minimal hydrotropic concentration2017European journal of medicinal chemistry, Mar-10, Volume: 128Synthesis, surfactant properties and antimicrobial activities of methyl glycopyranoside ethers.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (312)

TimeframeStudies, This Drug (%)All Drugs %
pre-199020 (6.41)18.7374
1990's73 (23.40)18.2507
2000's105 (33.65)29.6817
2010's107 (34.29)24.3611
2020's7 (2.24)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 31.02

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 Index31.02 (24.57)
Research Supply Index5.77 (2.92)
Research Growth Index4.97 (4.65)
Search Engine Demand Index39.53 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (31.02)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews5 (1.57%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other314 (98.43%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]