Page last updated: 2024-12-09

isopropyl thiogalactoside

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

Description

Isopropyl Thiogalactoside: A non-metabolizable galactose analog that induces expression of the LAC OPERON. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

isopropyl beta-D-thiogalactopyranoside : An S-glycosyl compound consisting of beta-D-1-thiogalactose having an isopropyl group attached to the anomeric sulfur. [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 CID656894
CHEBI ID61448
SCHEMBL ID25476
MeSH IDM0011780

Synonyms (90)

Synonym
c9h18o5s
1-methylethyl 1-thio-beta-d-galactopyranoside
isopropyl-1-beta-d-thiogalactoside
iptg, >=99% (tlc), <=0.1% dioxane
isopropyl beta-d-1-thiogalactopyranoside, >=99% (tlc)
1PX4
isopropyl beta-d-1-thiogalactopyranoside
isopropyl beta-d-thiogalactoside
iptg
isopropyl thiogalactoside
DB01862
isopropyl beta-d-thiogalactopyranoside
isopropyl-beta-d-thiogalactoside
367-93-1
isopropyl-beta-d-thiogalactopyranoside
propan-2-yl 1-thio-beta-d-galactopyranoside
isopropyl 1-thio-beta-d-galactopyranoside
16096F13-BE3A-44D0-88E0-01D116E70779
beta-d-galactopyranoside, 1-isopropyl-, 1-thio-
isopropyl-?-d-thiogalactopyranoside
CHEBI:61448
I0328
(2r,3r,4s,5r,6s)-2-(hydroxymethyl)-6-propan-2-ylsulfanyloxane-3,4,5-triol
AKOS005259707
A823371
AKOS016003761
unii-x73vv2246b
einecs 206-703-0
isopropy-beta-d-thiogalactopyranoside
x73vv2246b ,
isopropyl beta- thiogalactoside
105431-82-1
S6826
HY-15921
SCHEMBL25476
3MUZ
3VDC
3I3D
3VD9
3DYO
3T08
3T2P
3T0B
3VD4
(2r,3r,4s,5r,6s)-2-(hydroxymethyl)-6-(isopropylthio)tetrahydro-2h-pyran-3,4,5-triol
I-8070
isopropyl-.beta.-d-thiogalactopyranoside
isopropyl 1-thiohexopyranoside #
isopropyl-.beta.-d-thiogalactoside
1-methylethyl 1-thio-?-d-galactopyranoside
isopropyl .beta.-thiogalactoside
iptg [mi]
thioisopropyl .beta.-d-galactopyranoside
isopropyl .beta.-d-thiogalactopyranoside
isopropyl .beta.-thiogalactopyranoside
1-methylethyl 1-thio-.beta.-d-galactopyranoside
isopropyl thio-.beta.-d-galactoside
.beta.-d-galactopyranoside, 1-methylethyl 1-thio-
HB3941
AC-30877
mfcd00063273
bdbm192770
DTXSID6041052
4OUE
(2s,3r,4s,5r,6r)-2-(isopropylthio)-6-methylol-tetrahydropyran-3,4,5-triol
(2r,3r,4s,5r,6s)-2-(hydroxymethyl)-6-propan-2-ylsulfanyl-oxane-3,4,5-triol
M02725
isopropyl-ss-d-thiogalactopyranoside, dioxane free (iptg)
isopropyl ss-d-thiogalactoside
isopropyl-?-d-thiogalactoside, dioxane-free
isopropyl beta-d-1-thiogalactopyranoside, >=99.0%
isopropyl beta-d-1-thiogalactopyranoside, >=99.0% (tlc)
isopropyl beta-d-thiogalactoside, vetec(tm) reagent grade, >=99%
(2r,3r,4s,5r,6s)-2-(hydroxymethyl)-6-(propan-2-ylsulfanyl)oxane-3,4,5-triol
|a-d-galactopyranoside,1-methylethyl 1-thio-
isopropyl |a-d-thiogalactoside
isopropyl beta-d thiogalactopyranoside
Q419229
isopropyl-beta-d-thiogalactoside, dioxane free
AS-14787
AMY3361
isopropyl b-d-thiogalactoside
isopropyl-beta-d-thiogalactopyranosid
isopropyl beta-d-thiogalactopyranosid
iptg (animal free)
isopropyl |a-d-thiogalactoside(iptg)
EN300-7369863
iptg, dioxane-free
isopropyl-beta-d-thiogalactoside and isopropyl-beta-d-thiogalactoside
Z1741982662

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" coli BL21(DE3) strain and three different recombinants carrying a synthetic metabolic pathway for biodegradation of the toxic anthropogenic pollutant 1,2,3-trichloropropane (TCP) were investigated using plating, flow cytometry, and electron microscopy."( Exacerbation of substrate toxicity by IPTG in Escherichia coli BL21(DE3) carrying a synthetic metabolic pathway.
Chaloupkova, R; Chrast, L; Damborsky, J; de Lorenzo, V; Dvorak, P; Fedr, R; Nikel, PI; Prokop, Z; Sedlackova, M; Soucek, K, 2015
)
0.42

Dosage Studied

ExcerptRelevanceReference
" This inhibition of division could be prevented by an increased gene dosage of ftsZ or the presence of the sulB allele of ftsZ, which is known to code for an altered but functional ftsZ protein."( A lacZ-ftsZ gene fusion is an analog of the cell division inhibitor sulA.
Lutkenhaus, JF; Ward, JE, 1984
)
0.27
"Runaway plasmid replication can be used to increase target gene dosage and thereby overproduce proteins within the bacterium Escherichia coli."( Effects of plasmid copy number and runaway plasmid replication on overproduction and excretion of beta-lactamase from Escherichia coli.
Shuler, ML; Togna, AP; Wilson, DB,
)
0.13
" The expression level was closely related to the cell density, induction temperature and medium but not to the inductor dosage and the induction period within certain range."( Construction and expression of high efficiency expressing plasmid of transforming growth factor alpha-Pseudomonas aeruginosa exotoxin fusion protein TGF alpha-PE40.
Shen, M; Xu, Y; Zhang, H; Zhao, Q, 1994
)
0.29
" Each antagonist alone caused smaller shifts to the right in the dose-response curve to NE and, when present simultaneously, completely abolished the NE response."( Inducible expression of beta 1- and beta 2-adrenergic receptors in rat C6 glioma cells: functional interactions between closely related subtypes.
Esbenshade, TA; Guerrero, SW; Minneman, KP; Zhong, H, 1996
)
0.29
" By inducing the biosensor with varying amounts of L-arabinose and a constant amount of IPTG, it was possible to obtain a dose-response curve for L-arabinose, together with a constant production of EYFP, which allowed for a dynamic evaluation of the metabolic activity of the cell."( Internal response correction for fluorescent whole-cell biosensors.
Daunert, S; Feliciano, J; Michelini, E; Mirasoli, M; Roda, A, 2002
)
0.31
"Control of mammalian gene promoters by the bacterial LacI repressor provides reversible regulation and dose-response levels of derepressed expression by the lactose analog isopropyl thiogalactose (IPTG)."( The Lac repressor provides a reversible gene expression system in undifferentiated and differentiated embryonic stem cell.
Binétruy, B; Bost, F; Caron, L; Prot, M; Rolando, M; Rouleau, M, 2005
)
0.33
" To efficiently induce gene expression, a sufficient dosage of an inducer, usually that of 500-1000 µM isopropyl β-D-1-thiogalactopyranoside (IPTG), is required to keep repressor LacI from its binding sites, which is a heavy cost burden in low-value-added products."( Establishment of a low-dosage-IPTG inducible expression system construction method in Escherichia coli.
Ren, YH; Tao, XY; Wang, FQ; Wei, DZ; Zhao, M, 2018
)
0.48
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
S-glycosyl compoundA glycosyl compound arising formally from the elimination of water from a glycosidic hydroxy group and a S atom bound to a carbon atom, thus creating a C-S bond.
[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]

Protein Targets (16)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, beta-galactosidaseEscherichia coliKi590.0000590.0000590.0000590.0000AID977610
Chain A, Beta-galactosidaseEscherichia coli K-12Ki5,000.00005,000.00005,000.00005,000.0000AID977610
Chain A, Beta-galactosidaseEscherichia coli K-12Ki10,300.000010,300.000010,300.000010,300.0000AID977610
Chain A, Beta-galactosidaseEscherichia coli K-12Ki10,300.000010,300.000010,300.000010,300.0000AID977610
Chain A, Beta-galactosidaseEscherichia coli K-12Ki403.333350.0000403.3333910.0000AID977610
Chain A, Beta-galactosidaseEscherichia coli K-12Ki403.333350.0000403.3333910.0000AID977610
Chain A, Beta-galactosidaseEscherichia coli K-12Ki403.333350.0000403.3333910.0000AID977610
Chain A, Beta-galactosidaseEscherichia coli K-12Ki403.333350.0000403.3333910.0000AID977610
Chain A, Beta-galactosidaseEscherichia coli K-12Ki403.333350.0000403.3333910.0000AID977610
Chain A, Beta-galactosidaseEscherichia coli K-12Ki403.333350.0000403.3333910.0000AID977610
Chain A, Beta-galactosidaseEscherichia coliKi42.333312.000042.3333100.0000AID977610
Chain A, Beta-galactosidaseEscherichia coliKi42.333312.000042.3333100.0000AID977610
Chain A, Beta-galactosidaseEscherichia coliKi42.333312.000042.3333100.0000AID977610
Chain A, Beta-galactosidaseEscherichia coliKi42.333312.000042.3333100.0000AID977610
Chain A, Beta-galactosidaseEscherichia coliKi42.333312.000042.3333100.0000AID977610
Beta-galactosidaseEscherichia coli K-12Ki76.00004.30004.30004.3000AID1801922
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (2)

Processvia Protein(s)Taxonomy
lactose catabolic processBeta-galactosidaseEscherichia coli K-12
carbohydrate metabolic processBeta-galactosidaseEscherichia coli K-12
lactose catabolic processBeta-galactosidaseEscherichia coli K-12
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (7)

Processvia Protein(s)Taxonomy
magnesium ion bindingBeta-galactosidaseEscherichia coli K-12
beta-galactosidase activityBeta-galactosidaseEscherichia coli K-12
hydrolase activity, acting on glycosyl bondsBeta-galactosidaseEscherichia coli K-12
carbohydrate bindingBeta-galactosidaseEscherichia coli K-12
alkali metal ion bindingBeta-galactosidaseEscherichia coli K-12
identical protein bindingBeta-galactosidaseEscherichia coli K-12
metal ion bindingBeta-galactosidaseEscherichia coli K-12
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
beta-galactosidase complexBeta-galactosidaseEscherichia coli K-12
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (8)

Assay IDTitleYearJournalArticle
AID977610Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB2014Biochemistry, Mar-11, Volume: 53, Issue:9
Unraveling the substrate recognition mechanism and specificity of the unusual glycosyl hydrolase family 29 BT2192 from Bacteroides thetaiotaomicron.
AID977610Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB2012Archives of biochemistry and biophysics, Jan-15, Volume: 517, Issue:2
Ser-796 of β-galactosidase (Escherichia coli) plays a key role in maintaining a balance between the opened and closed conformations of the catalytically important active site loop.
AID977610Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB2010Biochemistry and cell biology = Biochimie et biologie cellulaire, Oct, Volume: 88, Issue:5
Role of Met-542 as a guide for the conformational changes of Phe-601 that occur during the reaction of β-galactosidase (Escherichia coli).
AID977610Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB2012Archives of biochemistry and biophysics, May, Volume: 521, Issue:1-2
Substitution for Asn460 cripples β-galactosidase (Escherichia coli) by increasing substrate affinity and decreasing transition state stability.
AID1811Experimentally measured binding affinity data derived from PDB2003Biochemistry, Nov-25, Volume: 42, Issue:46
Structural basis for the altered activity of Gly794 variants of Escherichia coli beta-galactosidase.
AID977610Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB2003Biochemistry, Nov-25, Volume: 42, Issue:46
Structural basis for the altered activity of Gly794 variants of Escherichia coli beta-galactosidase.
AID1801922beta-Galactosidase Assay from Article 10.1002/cbic.201600267: \\Capture-Tag-Release: A Strategy for Small Molecule Labeling of Native Enzymes.\\2016Chembiochem : a European journal of chemical biology, 09-02, Volume: 17, Issue:17
Capture-Tag-Release: A Strategy for Small Molecule Labeling of Native Enzymes.
AID977610Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB2009Protein science : a publication of the Protein Society, Jun, Volume: 18, Issue:6
Direct and indirect roles of His-418 in metal binding and in the activity of beta-galactosidase (E. coli).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (1,029)

TimeframeStudies, This Drug (%)All Drugs %
pre-199072 (7.00)18.7374
1990's340 (33.04)18.2507
2000's330 (32.07)29.6817
2010's233 (22.64)24.3611
2020's54 (5.25)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (0.09%)5.53%
Reviews10 (0.95%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other1,044 (98.96%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]