Page last updated: 2024-11-07

1-((3,5-dichloro)-2,6-dihydroxy-4-methoxyphenyl)-1-hexanone

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

Description

1-((3,5-dichloro)-2,6-dihydroxy-4-methoxyphenyl)-1-hexanone: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

1-(3,5-dichloro-2,6-dihydroxy-4-methoxyphenyl)hexan-1-one : A differentiation-inducing factor that is hexaphenone bearing two chloro substituents at positions 3 and 5, two hydroxy substituents at positions 2 and 6 as well as a single methoxy substituent at position 4. A secreted, chlorinated molecule that controls cell fate during development of Dictyostelium cells. [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 CID123886
CHEMBL ID2409648
CHEBI ID64598
SCHEMBL ID3515213
MeSH IDM0151397

Synonyms (21)

Synonym
1-(3,5-dichloro-2,6-dihydroxy-4-methoxyphenyl)hexan-1-one
CHEMBL2409648
differentiation-inducing factor 1
CHEBI:64598 ,
dif-1
differentiation-inducing factor-1
dif 1
dif factor
1-((3,5-dichloro)-2,6-dihydroxy-4-methoxyphenyl)-1-hexanone
differentiation inducing factor
dif-1 (dictyostelium)
morphogen differentiation inducing factor (dictyostelium)
1-hexanone, 1-(3,5-dichloro-2,6-dihydroxy-4-methoxyphenyl)-
111050-72-7
SCHEMBL3515213
c13h16cl2o4
DTXSID10149474
J-002512
dictyostelium
1-(3,5-dichloro-2,6-dihydroxy-4-methoxyphenyl)-1-hexanone
Q27133348

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Copolymers of D11Q and wild type actins bound cofilin, but cofilin-induced depolymerization of the copolymers was slower than that of wild type filaments, which may presumably be the primary reason why this mutant actin is dominantly toxic in vivo."( Rapid nucleotide exchange renders Asp-11 mutant actins resistant to depolymerizing activity of cofilin, leading to dominant toxicity in vivo.
Hirose, K; Ito, K; Nagasaki, A; Nakajima, J; Noguchi, TQ; Tokuraku, K; Umeki, N; Uyeda, TQ, 2013
)
0.39
" A second objective of the solid phase DDDC assay is to identify potential mechanisms of toxic action on the developmental cycle, for which three checkpoints are examined: (a) aggregation arrest, (b) migration arrest, and (c) culmination arrest."( Dictyostelium discoideum developmental cycle (DDDC) assay: a tool for Hg toxicity assessment and soil health screening.
Boatti, L; Marigómez, I; Rodríguez-Ruiz, A; Viarengo, A, 2013
)
0.39
" The elutriates of both soils provoked toxic effects, but toxicity was markedly lower in the aged soil."( Toxicity assessment of diesel- and metal-contaminated soils through elutriate and solid phase assays with the slime mold Dictyostelium discoideum.
Dondero, F; Marigómez, I; Rodríguez-Ruiz, A; Viarengo, A, 2016
)
0.43

Bioavailability

ExcerptReferenceRelevance
"The insulin-like growth factor-II/mannose 6-phosphate receptor (IGF-II/MPR) is a type I glycoprotein that mediates both the intracellular sorting of lysosomal enzymes bearing mannose 6-phosphate (Man-6-P) residues to the lysosome and the bioavailability of IGF-II."( Recognition of Dictyostelium discoideum lysosomal enzymes is conferred by the amino-terminal carbohydrate binding site of the insulin-like growth factor II/mannose 6-phosphate receptor.
Dahms, NM; Hancock, MK; Haskins, DJ; Marron-Terada, PG, 2000
)
0.31
" In line with the biological results, the chemical data showed that the concentration of DDX in the pore water (in general a highly bioavailable phase) showed a minimal value (0."( Relevance of the bioavailable fraction of DDT and its metabolites in freshwater sediment toxicity: New insight into the mode of action of these chemicals on Dictyostelium discoideum.
Boeri, M; Borrelli, R; Governa, D; Oldani, A; Oliveri, L; Sforzini, S; Vago, F; Viarengo, A, 2016
)
0.43
"Iron, zinc, and copper play fundamental roles in eucaryotes and procaryotes, and their bioavailability regulates host-pathogen interactions."( Differential Effects of Iron, Zinc, and Copper on
Andreini, C; Bozzaro, S; Bracco, E; Buracco, S; Peracino, B, 2017
)
0.46

Dosage Studied

ExcerptRelevanceReference
" In diploids these mutations show a gene dosage effect and are all alleles."( The structural gene for alpha-mannosidase-1 in Dictyostellium discoideum.
Free, SJ; Schimke, RT, 1976
)
0.26
" A dose-response curve for GTP gamma S indicated a concentration for half-maximal stimulation of approximately 8 microM."( GTP analogues stimulate inositol trisphosphate formation transiently in Dictyostelium.
Europe-Finner, GN; Newell, PC, 1987
)
0.27
" The phorbol ester was shown to affect the dose-response relationship between the cAMP concentration and the relative amplitude of the light-scattering change, more by decreasing the number of cAMP receptors than by decreasing their apparent affinity for cAMP."( Phorbol 12-myristate 13-acetate modulates the cAMP-induced light-scattering response of a Dictyostelium discoïdeum cell population.
Klein, R; Tatischeff, I; Thiery, R, 1988
)
0.27
" 1) The dose-response curves for the responses to Enterobacter contact are clearly different."( Contact alters cAMP metabolism in aggregation-competent Dictyostelium amoebae.
Fontana, DR; Price, PL, 1988
)
0.27
" Dose-response curves with cAMP and adenosine 3',5'-monophosphorothioate, a nonhydrolyzable analog, revealed that the requirement for high concentrations of exogenous cAMP for regulating gene expression is due to the rapid degradation of cAMP by phosphodiesterase."( Pharmacological characterization of cyclic AMP receptors mediating gene regulation in Dictyostelium discoideum.
Dottin, RP; Haribabu, B, 1986
)
0.27
" Binding of 125I-labeled fusion proteins PA80I (containing the Val123 to Ile514 fragment of gp80) and PA80II (Val123 to Ala258) was dosage dependent and could be inhibited by precoating cells with the cell cohesion-blocking mAb 80L5C4."( Mapping of a cell-binding domain in the cell adhesion molecule gp80 of Dictyostelium discoideum.
Kamboj, RK; Lam, TY; Siu, CH; Wong, LM, 1988
)
0.27
" The shape of the dose-response curves shows a paradox: the activity of a derivative, when applied at receptor-saturating concentrations, is inversely related to its affinity."( Evidence that the rate of association of adenosine 3',5'-monophosphate to its chemotactic receptor induces phosphodiesterase activity in Dictyostelium discoideum.
Konijn, TM; Van Der Meer, RC; Van Haastert, PJ, 1981
)
0.26
" Dose-response curves relating the accuracies of phototaxis and negative chemotaxis to STF concentration indicate that, in both phototaxis and chemotaxis, slugs "measure" the ratios of STF concentrations on their opposite sides."( An extracellular chemical signal controlling phototactic behavior by D. discoideum slugs.
Fisher, PR; Smith, E; Williams, KL, 1981
)
0.26
" A dose-response curve was obtained; 5,5'-difluoro-BAPTA was the most potent analogue."( Introduction of calcium buffers into the cytosol of Dictyostelium discoideum amoebae alters cell morphology and inhibits chemotaxis.
Schlatterer, C; Unterweger, N, 1995
)
0.29
" We found that the cyclic AMP-induced cytoskeletal actin response was similar to that of the parental strain in this mutant (although showing a slight displacement in the dose-response curve) but the cytoskeletal myosin II heavy chain response was abolished."( The role of cyclic GMP in regulating myosin during chemotaxis of Dictyostelium: evidence from a mutant lacking the normal cyclic GMP response to cyclic AMP.
Ishida, S; Kuwayama, H; Liu, G; Newell, PC, 1993
)
0.29
" Overexpression of these mutant G alpha5 genes by increased gene dosage resulted in cell death, suggesting that high levels of the altered subunits have detrimental effects during vegetative growth."( Mutations in the Dictyostelium heterotrimeric G protein alpha subunit G alpha5 alter the kinetics of tip morphogenesis.
Firtel, RA; Hadwiger, JA; Natarajan, K, 1996
)
0.29
" In this study, cells overexpressing the wild type Galpha4 gene, due to high copy gene dosage (Galpha4HC), were found to be defective in the ability to form the anterior prestalk cell region, express prespore- and prestalk-cell specific genes, and undergo spore formation."( Folic acid stimulation of the Galpha4 G protein-mediated signal transduction pathway inhibits anterior prestalk cell development in Dictyostelium.
Hadwiger, JA; Srinivasan, J, 1999
)
0.3
" Data from emission spectra were used to detect the FRET fluorescence and to determine kinetics and dose-response curves of bound ligand and analogs."( Monitoring receptor-mediated activation of heterotrimeric G-proteins by fluorescence resonance energy transfer.
Devreotes, P; Janetopoulos, C, 2002
)
0.31
" The expression level of many duplicated genes is increased with dosage, but for others it appears that some form of dosage compensation occurs."( Widespread duplications in the genomes of laboratory stocks of Dictyostelium discoideum.
Bloomfield, G; Ivens, A; Kay, RR; Skelton, J; Tanaka, Y, 2008
)
0.35
" SDS-related somatic EIF6 missense mutations that reduce eIF6 dosage or eIF6 binding to the 60S subunit suppress the defects in ribosome assembly and protein synthesis across multiple SBDS-deficient species including yeast, Dictyostelium and Drosophila."( Somatic genetic rescue of a germline ribosome assembly defect.
Alibeu, O; Beaupain, B; Bellanné-Chantelot, C; Bertrand, A; Bôle-Feysot, C; Bond, PJ; Boukerrou, AZ; Callebaut, I; de Villartay, JP; Delhommeau, F; Donadieu, J; Escudero-Urquijo, N; Faille, A; Fumagalli, S; Goyenechea, B; Hilcenko, C; Jin, L; Kaltenbach, S; Kargas, V; Kermasson, L; Koh, AL; Martignoles, JA; Masson, C; Moreil, J; Nitschké, P; Parisot, M; Phua, KB; Pouliet, A; Radford-Weiss, I; Reversade, B; Revy, P; Rossmann, M; Tan, S; Tores, F; Traynor, D; Warren, AJ; Zarhrate, M, 2021
)
0.62
" In addition, the adverse effects did not show a dose-response relationship with increased imidacloprid concentrations, where no significant difference was observed among the treatment groups."( The neonicotinoid insecticide imidacloprid has unexpected effects on the growth and development of soil amoebae.
He, Z; Huang, W; Liu, Z; Shu, L; Wang, Z; Zeng, J, 2023
)
0.91
" Single-cell data reproduced the dose-response observed in ensemble measurements by CE-LIF, superimposed with high levels of heterogeneity."( Microfluidic single-cell measurements of oxidative stress as a function of cell cycle position.
Allcroft, TJ; Duong, JT; Kovarik, ML; Skardal, PS, 2023
)
0.91
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
eukaryotic metaboliteAny metabolite produced during a metabolic reaction in eukaryotes, the taxon that include members of the fungi, plantae and animalia kingdoms.
signalling moleculeA molecular messenger in which the molecule is specifically involved in transmitting information between cells. Such molecules are released from the cell sending the signal, cross over the gap between cells by diffusion, and interact with specific receptors in another cell, triggering a response in that cell by activating a series of enzyme controlled reactions which lead to changes inside the cell.
[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 (4)

ClassDescription
monomethoxybenzeneCompounds containing a benzene skeleton substituted with one methoxy group.
resorcinolsAny benzenediol in which the two hydroxy groups are meta to one another.
differentiation-inducing factorAn aromatic ketone that is penta- or hexaphenone bearing chloro, hydroxy and methoxy substituents on the benzene ring. A class of effector molecules isolated from Dictyostelium discoideum.
dichlorobenzeneAny member of the class of chlorobenzenes carrying two chloro groups at unspecified positions.
[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 (4)

Assay IDTitleYearJournalArticle
AID1235104Immunosuppressive activity in Drosophila S2 cells expressing att-luc reporter gene assessed as inhibition of peptidoglycan-induced attacin production pre-treated for 1.5 hrs before peptidoglycan stimulation for 8 hrs by luciferase reporter gene assay2015Bioorganic & medicinal chemistry, Aug-01, Volume: 23, Issue:15
Development of novel DIF-1 derivatives that selectively suppress innate immune responses.
AID761205Induction of stalk cell differentiation in Dictyostelium discoideum HM44 at 1 nM after 2 days by phase-contrast microscopy2013Bioorganic & medicinal chemistry, Aug-01, Volume: 21, Issue:15
Novel chlorinated dibenzofurans isolated from the cellular slime mold, Polysphondylium filamentosum, and their biological activities.
AID1235105Cytotoxicity against Drosophila S2 assessed as reduction in cell proliferation by WST8 assay2015Bioorganic & medicinal chemistry, Aug-01, Volume: 23, Issue:15
Development of novel DIF-1 derivatives that selectively suppress innate immune responses.
AID1235106Selectivity index, ratio of CC50 for Drosophila S2 by WST8 assay to IC50 for immunosuppressive activity in Drosophila S2 cells expressing att-luc reporter gene assessed as inhibition of attacin production2015Bioorganic & medicinal chemistry, Aug-01, Volume: 23, Issue:15
Development of novel DIF-1 derivatives that selectively suppress innate immune responses.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7,550)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902043 (27.06)18.7374
1990's1815 (24.04)18.2507
2000's1855 (24.57)29.6817
2010's1511 (20.01)24.3611
2020's326 (4.32)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 5.54

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index5.54 (24.57)
Research Supply Index8.94 (2.92)
Research Growth Index4.49 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (5.54)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews712 (9.29%)6.00%
Case Studies13 (0.17%)4.05%
Observational0 (0.00%)0.25%
Other6,941 (90.54%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]