Page last updated: 2024-11-12

dictyostatin

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

Description

dictyostatin: a macrocyclic compound; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID11353099
CHEMBL ID226880
SCHEMBL ID14094924
MeSH IDM0445373

Synonyms (7)

Synonym
CHEMBL226880
dictyostatin
SCHEMBL14094924
(3z,5e,7r,8s,10s,11z,13s,14r,15s,17s,20r,21s,22s)-22-[(2s,3z)-hexa-3,5-dien-2-yl]-8,10,14,20-tetrahydroxy-7,13,15,17,21-pentamethyl-1-oxacyclodocosa-3,5,11-trien-2-one
(3~{z},5~{e},7~{r},8~{s},10~{s},11~{z},13~{s},14~{r},15~{s},17~{s},20~{r},21~{s},22~{s})-22-[(2~{s},3~{z})-hexa-3,5-dien-2-yl]-7,13,15,17,21-pentamethyl-8,10,14,20-tetrakis(oxidanyl)-1-oxacyclodocosa-3,5,11-trien-2-one
(-)-dictyostatin
Q43297542

Research Excerpts

Overview

Dictyostatin (DCT, 1) is a complex, flexible polyketide macrolide that demonstrates potent microtubule-polymerization activity. It causes cells to accumulate in the G2/M phase of the cell cycle.

ExcerptReferenceRelevance
"The dictyostatins are a promising class of potential anti-cancer drugs because they are powerful microtubule-stabilizing agents, but the complexity of their chemical structures is a severe impediment to their further development. "( Streamlined syntheses of (-)-dictyostatin, 16-desmethyl-25,26-dihydrodictyostatin, and 6-epi-16-desmethyl-25,26-dihydrodictyostatin.
Balachandran, R; Camarco, DP; Curran, DP; Day, BW; Jiménez, M; Jung, WH; Vogt, A; Zhu, W, 2010
)
1.21
"Dictyostatin (DCT, 1) is a complex, flexible polyketide macrolide that demonstrates potent microtubule-polymerization activity. "( Dictyostatin flexibility bridges conformations in solution and in the β-tubulin taxane binding site.
Alcaraz, AA; Curran, DP; Damodaran, K; Jogalekar, AS; Jung, WH; Kriel, FH; Snyder, JP; Zhong, S, 2011
)
3.25
"(-)-Dictyostatin is a sponge-derived, 22-member macrolactone natural product shown to cause cells to accumulate in the G2/M phase of the cell cycle, with changes in intracellular microtubules analogous to those observed with paclitaxel treatment. "( Tubulin assembly, taxoid site binding, and cellular effects of the microtubule-stabilizing agent dictyostatin.
Balachandran, R; Brückner, AM; Curran, DP; Day, BW; Edler, MC; Fournier, JH; Fukui, Y; Giuliano, KA; Hamel, E; Madiraju, C; Raccor, BS; Shin, Y; Vogt, A; Zhu, G, 2005
)
1.1
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (36)

Assay IDTitleYearJournalArticle
AID294923Cytotoxicity against human PANC1 cells after 72 hrs by MTT assay2007Bioorganic & medicinal chemistry letters, May-01, Volume: 17, Issue:9
Synthesis and biological evaluation of novel analogues of dictyostatin.
AID772395Stabilization of microtubule in HEK293 cells assessed as increase in acetylated alpha-tubulin after 4 hrs by ELISA2013ACS medicinal chemistry letters, Sep-12, Volume: 4, Issue:9
MT-Stabilizer, Dictyostatin, Exhibits Prolonged Brain Retention and Activity: Potential Therapeutic Implications.
AID417071Growth inhibition of human AsPC1 cells after 72 hrs by MTT assay2009Bioorganic & medicinal chemistry, Mar-15, Volume: 17, Issue:6
Total synthesis and biological evaluation of novel C2-C6 region analogues of dictyostatin.
AID772392Fraction unbound in CD1 mouse plasma at 5 mg/kg, ip dministered as single dose2013ACS medicinal chemistry letters, Sep-12, Volume: 4, Issue:9
MT-Stabilizer, Dictyostatin, Exhibits Prolonged Brain Retention and Activity: Potential Therapeutic Implications.
AID417074Growth inhibition of paclitaxel-resistant human NCI/ADR cells after 72 hrs by MTT assay2009Bioorganic & medicinal chemistry, Mar-15, Volume: 17, Issue:6
Total synthesis and biological evaluation of novel C2-C6 region analogues of dictyostatin.
AID772384Fraction unbound in CD1 mouse brain at 5 mg/kg, ip administered as single dose2013ACS medicinal chemistry letters, Sep-12, Volume: 4, Issue:9
MT-Stabilizer, Dictyostatin, Exhibits Prolonged Brain Retention and Activity: Potential Therapeutic Implications.
AID294921Cytotoxicity against human AsPC1 cells after 72 hrs by MTT assay2007Bioorganic & medicinal chemistry letters, May-01, Volume: 17, Issue:9
Synthesis and biological evaluation of novel analogues of dictyostatin.
AID772391Plasma concentration in CD1 mouse at 5 mg/kg, ip administered as single dose at 4 hrs2013ACS medicinal chemistry letters, Sep-12, Volume: 4, Issue:9
MT-Stabilizer, Dictyostatin, Exhibits Prolonged Brain Retention and Activity: Potential Therapeutic Implications.
AID410180Cytotoxicity against taxol-resistant human NCI/ADR-RES cells after 72 hrs by MTT assay2008Bioorganic & medicinal chemistry letters, Dec-01, Volume: 18, Issue:23
Total synthesis and biological evaluation of potent analogues of dictyostatin: modification of the C2-C6 dienoate region.
AID772393Stabilization of microtubule in HEK293 cells assessed as increase in acetylated alpha-tubulin at 1to 10 nM after 4 hrs by ELISA2013ACS medicinal chemistry letters, Sep-12, Volume: 4, Issue:9
MT-Stabilizer, Dictyostatin, Exhibits Prolonged Brain Retention and Activity: Potential Therapeutic Implications.
AID294924Cytotoxicity against human Taxol-adriamycin-resistant NCI cells after 72 hrs by MTT assay2007Bioorganic & medicinal chemistry letters, May-01, Volume: 17, Issue:9
Synthesis and biological evaluation of novel analogues of dictyostatin.
AID410177Cytotoxicity against taxol-sensitive human AsPC1 cells after 72 hrs by MTT assay2008Bioorganic & medicinal chemistry letters, Dec-01, Volume: 18, Issue:23
Total synthesis and biological evaluation of potent analogues of dictyostatin: modification of the C2-C6 dienoate region.
AID291081Displacement of [3H]paclitaxel from bovine brain tubulin at 4 uM2007Journal of medicinal chemistry, Jun-28, Volume: 50, Issue:13
Total synthesis and biological evaluation of C16 analogs of (-)-dictyostatin.
AID410178Cytotoxicity against taxol-sensitive human DLD1 cells after 72 hrs by MTT assay2008Bioorganic & medicinal chemistry letters, Dec-01, Volume: 18, Issue:23
Total synthesis and biological evaluation of potent analogues of dictyostatin: modification of the C2-C6 dienoate region.
AID417076Cell cycle arrest in human PANC1 cells assessed as accumulation at S phase at 100 nM after 24 hrs by flow cytometry2009Bioorganic & medicinal chemistry, Mar-15, Volume: 17, Issue:6
Total synthesis and biological evaluation of novel C2-C6 region analogues of dictyostatin.
AID318809Cytotoxicity against human PANC1 cells after 72 hrs by MTT assay2008Journal of natural products, Mar, Volume: 71, Issue:3
Synthesis and biological evaluation of 10,11-dihydrodictyostatin, a potent analogue of the marine anticancer agent dictyostatin.
AID318807Cytotoxicity against human AsPC1 cells after 72 hrs by MTT assay2008Journal of natural products, Mar, Volume: 71, Issue:3
Synthesis and biological evaluation of 10,11-dihydrodictyostatin, a potent analogue of the marine anticancer agent dictyostatin.
AID291078Growth inhibition of beta tubulin Phe270Val mutant expressing human 1A9/Ptx10 cells after 72 hrs2007Journal of medicinal chemistry, Jun-28, Volume: 50, Issue:13
Total synthesis and biological evaluation of C16 analogs of (-)-dictyostatin.
AID772386Drug uptake in CD1 mouse brain at 5 mg/kg, ip administered as single dose at 4 hrs2013ACS medicinal chemistry letters, Sep-12, Volume: 4, Issue:9
MT-Stabilizer, Dictyostatin, Exhibits Prolonged Brain Retention and Activity: Potential Therapeutic Implications.
AID291076Increase in cellular tubulin polymer mass in HeLa cells assessed as minimum detectable effective concentration after 21 hrs2007Journal of medicinal chemistry, Jun-28, Volume: 50, Issue:13
Total synthesis and biological evaluation of C16 analogs of (-)-dictyostatin.
AID291079Growth inhibition of beta tubulin A364T mutant expressing human 1A9/Ptx22 cells after 72 hrs2007Journal of medicinal chemistry, Jun-28, Volume: 50, Issue:13
Total synthesis and biological evaluation of C16 analogs of (-)-dictyostatin.
AID291080Inhibition of bovine brain tubulin polymerization at 10 uM relative to paclitaxel2007Journal of medicinal chemistry, Jun-28, Volume: 50, Issue:13
Total synthesis and biological evaluation of C16 analogs of (-)-dictyostatin.
AID772383Stabilization of microtubule brain in CD1 mouse assessed as increase in acetylated alpha-tubulin at 5 mg/kg, ip administered as single dose measured after 7 days relative to vehicle-treated control2013ACS medicinal chemistry letters, Sep-12, Volume: 4, Issue:9
MT-Stabilizer, Dictyostatin, Exhibits Prolonged Brain Retention and Activity: Potential Therapeutic Implications.
AID291077Growth inhibition of human 1A9 cells after 72 hrs2007Journal of medicinal chemistry, Jun-28, Volume: 50, Issue:13
Total synthesis and biological evaluation of C16 analogs of (-)-dictyostatin.
AID410179Cytotoxicity against taxol-sensitive human PANC1 cells after 72 hrs by MTT assay2008Bioorganic & medicinal chemistry letters, Dec-01, Volume: 18, Issue:23
Total synthesis and biological evaluation of potent analogues of dictyostatin: modification of the C2-C6 dienoate region.
AID772388Plasma concentration in CD1 mouse at 5 mg/kg, ip administered as single dose at 16 hrs2013ACS medicinal chemistry letters, Sep-12, Volume: 4, Issue:9
MT-Stabilizer, Dictyostatin, Exhibits Prolonged Brain Retention and Activity: Potential Therapeutic Implications.
AID318808Cytotoxicity against human DLD1 cells after 72 hrs by MTT assay2008Journal of natural products, Mar, Volume: 71, Issue:3
Synthesis and biological evaluation of 10,11-dihydrodictyostatin, a potent analogue of the marine anticancer agent dictyostatin.
AID417075Cell cycle arrest in human PANC1 cells assessed as accumulation at G1 phase at 100 nM after 24 hrs by flow cytometry2009Bioorganic & medicinal chemistry, Mar-15, Volume: 17, Issue:6
Total synthesis and biological evaluation of novel C2-C6 region analogues of dictyostatin.
AID318810Cytotoxicity against taxol-resistant human NCI/ADR cells after 72 hrs by MTT assay2008Journal of natural products, Mar, Volume: 71, Issue:3
Synthesis and biological evaluation of 10,11-dihydrodictyostatin, a potent analogue of the marine anticancer agent dictyostatin.
AID772387Drug uptake in CD1 mouse brain at 5 mg/kg, ip administered as single dose at 16 hrs2013ACS medicinal chemistry letters, Sep-12, Volume: 4, Issue:9
MT-Stabilizer, Dictyostatin, Exhibits Prolonged Brain Retention and Activity: Potential Therapeutic Implications.
AID294922Cytotoxicity against human DLD1 cells after 72 hrs by MTT assay2007Bioorganic & medicinal chemistry letters, May-01, Volume: 17, Issue:9
Synthesis and biological evaluation of novel analogues of dictyostatin.
AID772390AUC (0.25 to 4 hrs) in CD1 mouse plasma at 5 mg/kg, ip administered as single dose at 4 hrs2013ACS medicinal chemistry letters, Sep-12, Volume: 4, Issue:9
MT-Stabilizer, Dictyostatin, Exhibits Prolonged Brain Retention and Activity: Potential Therapeutic Implications.
AID417073Growth inhibition of human PANC1 cells after 72 hrs by MTT assay2009Bioorganic & medicinal chemistry, Mar-15, Volume: 17, Issue:6
Total synthesis and biological evaluation of novel C2-C6 region analogues of dictyostatin.
AID772385AUC (0.5 to 16 hrs) in CD1 mouse brain at 5 mg/kg, ip administered as single dose at 4 hrs2013ACS medicinal chemistry letters, Sep-12, Volume: 4, Issue:9
MT-Stabilizer, Dictyostatin, Exhibits Prolonged Brain Retention and Activity: Potential Therapeutic Implications.
AID417072Growth inhibition of human DLD1 cells after 72 hrs by MTT assay2009Bioorganic & medicinal chemistry, Mar-15, Volume: 17, Issue:6
Total synthesis and biological evaluation of novel C2-C6 region analogues of dictyostatin.
AID417077Cell cycle arrest in human PANC1 cells assessed as accumulation at G2/M phase at 100 nM after 24 hrs by flow cytometry2009Bioorganic & medicinal chemistry, Mar-15, Volume: 17, Issue:6
Total synthesis and biological evaluation of novel C2-C6 region analogues of dictyostatin.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (41)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's31 (75.61)29.6817
2010's10 (24.39)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 18.19

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 Index18.19 (24.57)
Research Supply Index3.74 (2.92)
Research Growth Index4.29 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (18.19)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews5 (12.20%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other36 (87.80%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]