Page last updated: 2024-11-11

cytochalasin d

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Description

Cytochalasin D: A fungal metabolite that blocks cytoplasmic cleavage by blocking formation of contractile microfilament structures resulting in multinucleated cell formation, reversible inhibition of cell movement, and the induction of cellular extrusion. Additional reported effects include the inhibition of actin polymerization, DNA synthesis, sperm motility, glucose transport, thyroid secretion, and growth hormone release. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

cytochalasin D : An organic heterotricyclic compound that is a mycotoxin produced by Helminthosporium and other moulds which is cell permeable and a potent inhibitor of actin polymerisation and DNA synthesis. [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 CID5458428
CHEMBL ID260287
SCHEMBL ID33529
MeSH IDM0023976
PubMed CID124523547
MeSH IDM0023976

Synonyms (31)

Synonym
7(s),18(r)-dihydroxy-16(s),18-dimethyl-10-phenyl(11)cytochalasa-6(12),13(e),19(e)-triene-1,17-dione 21(r)-acetate
1h-cycloundec(d)isoindole-1,11(2h)-dione, 15-(acetyloxy)-3,3a,4,5,6,6a,9,10,12,15-decahydro-6,12-dihydroxy-4,10,12-trimethyl-5-methylene-3-(phenylmethyl)-, (3s-(3r*,3as*,4r*,6r*,6as*,7e,10r*,12s*,13e,15s*,15as*))-
einecs 244-804-1
1h-cycloundec(d)isoindole-1,11(2h)-dione, 3-benzyl-3,3-alpha,4,5,6,6-alpha,9,10,12,15-decahydro-6,12,15-trihydroxy-4,10,12-trimethyl-5-methylene-, 15-acetate
nsc 209835
(11)cytochalasa-6(12),13,19-triene-1,17-dione, 21-(acetyloxy)-7,18-dihydroxy-16,18-dimethyl-10-phenyl-, (7s,13e,16s,18r,19e,21r)-
hsdb 3549
1h-cycloundec(d)isoindole-1,11(2h)-dione, 3-benzyl-3,3-alpha4,5,6,6-alpha,9,10,12,15-decahydro-6,12,15-trihydroxy-4,10,12-trimethyl-5-methylene-, 15-acetate
1h-cycloundec[d]isoindole-1,11(2h)-dione, 15-(acetyloxy)-3,3a,4,5,6,6a,9,10,12,15-decahydro-6-12-dihydroxy-4,10,12-trimethyl-5-methylene-3-(phenylmethyl)-, (3s,3ar,4s,6s,6ar,7e,10s,12r,13e,15r,15ar)-
(benzyl-dihydroxy-trimethyl-methylene-dioxo-[?]yl) acetate
NSC209835 ,
cytochalasin d, from zygosporium mansonii, >=98% (tlc and hplc), powder
nsc-209835
CHEMBL260287
sy9f0fz3to ,
unii-sy9f0fz3to
1h-cycloundec(d)isoindole-1,11(2h)-dione, 15-(acetyloxy)-3,3a,4,5,6,6a,9,10,12,15-decahydro-6,12-dihydroxy-4,10,12-trimethyl-5-methylene-3-(phenylmethyl)-, (3s,3ar,4s,6s,6ar,7e,10s,12r,13e,15r,15ar)-
cytochalasin d [hsdb]
(-)-cytochalasin d
SCHEMBL33529
3EKS
mfcd00077706
AKOS030213128
cytochalasin d, from zygosporium mansonii
Q5201339
(3s,3ar,4s,6s,6ar,7e,10s,12r,13e,15r,151r)-3-benzyl-6,12-dihydroxy-4,10,12-trimethyl-5-methylene-1,11-dioxo-2,3,3a,4,5,6,6a,9,10,11,12,15-dodecahydro-1h-cycloundeca[d]isoindol-15-yl acetate
CS-0012977
HY-N6682
F82057
cytochalasin d
22144-77-0

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" The adult LD50 for CD (1."( Differences in the toxicity and teratogenicity of cytochalasins D and E in various mouse strains.
Austin, WL; Brown, KS; Wind, M, 1982
)
0.26
" In addition, bvg mutants were poorly cytotoxic for the eukaryotic cells, while a prn mutant was significantly less toxic than wild-type bacteria."( Bordetella bronchiseptica-mediated cytotoxicity to macrophages is dependent on bvg-regulated factors, including pertactin.
Forde, CB; Li, J; Roberts, M; Shi, X, 1999
)
0.3
" From the viewpoint of developing effective and safe protein transduction technology, although Tat was the most versatile carrier among the peptides studied, PTDs should be selected based on their individual characteristics."( Comparative study on transduction and toxicity of protein transduction domains.
Imai, S; Kamada, H; Mukai, Y; Nagano, K; Nakagawa, S; Shibata, H; Sugita, T; Tsunoda, SI; Tsutsumi, Y; Yamanada, N; Yoshida, Y; Yoshikawa, T; Yoshioka, Y, 2008
)
0.35
" The excess calories are stored as triglycerides in adipose tissue, but also may accumulate ectopically in other organs, including the kidney, which contributes to the damage through a toxic process named lipotoxicity."( Renal Lipotoxicity-Associated Inflammation and Insulin Resistance Affects Actin Cytoskeleton Organization in Podocytes.
Chen, S; Izquierdo-Lahuerta, A; Martínez-García, C; Medina-Gomez, G; Velasco, I; Vivas, Y; Yeo, TK, 2015
)
0.42

Bioavailability

ExcerptReferenceRelevance
"A decrease in the bioavailability of endothelium-derived nitric oxide (NO) is linked to hypercholesterolemia."( Low density lipoprotein induces eNOS translocation to membrane caveolae: the role of RhoA activation and stress fiber formation.
Liao, HL; Lin, T; Niu, XL; Stemerman, MB; Verna, L; Yuan, Y; Zhu, Y, 2003
)
0.32

Dosage Studied

ExcerptRelevanceReference
" This effect was rapid (t1/2 less than 5 min) and had a similar dose-response relationship as the effect on glucose transport."( Insulin can rapidly increase cell surface insulin binding capacity in rat adipocytes. A novel mechanism related to insulin sensitivity.
Eriksson, J; Lönnroth, P; Smith, U, 1992
)
0.28
" In measurements of cytosolic free calcium concentration ([Ca2+]i) by flow cytometry in Indo-1-loaded platelets, ADP's dose-response for actin polymerization was similar to that for calcium mobilization."( Heterogeneity in filamentous actin content among individual human blood platelets.
Cabral, C; Daley, JF; Kang, JH; Oda, A; Salzman, EW; Smith, M, 1992
)
0.28
" Inhibition of specific-granule release by GTP[S] was observed at low Ca2+ concentrations and resulted from shifting the Ca2+ dose-response curves to the right."( Dual effects of guanosine 5'-[gamma-thio]triphosphate on secretion by electroporated human neutrophils.
Koh, EK; Kuczynski, B; Omann, GM; Smolen, JE; Stoehr, SJ, 1991
)
0.28
" The dose-response effect for the two different cytochalasins differed in accordance with the different cell specificity of their membrane binding."( Kinetic and morphological changes induced in human blood leucocytes by cytochalasin D and E.
Boll, I; Lichter, JH, 1988
)
0.27
" The changes in rate of LH release investigated were the initial response to GnRH, desensitization, change of dose-response during desensitization, and recovery of sensitivity between pulses of stimulation."( Effects of modifiers of cytoskeletal structures on the dynamics of release of LH from sheep anterior pituitary cells stimulated with gonadotrophin-releasing hormone, K+ or phorbol ester.
McIntosh, JE; McIntosh, RP; Starling, L, 1987
)
0.27
" Maximal decrements in transepithelial resistance and junctional charge selectivity were obtained with 10 micrograms/ml CD and the dose-response curves for these two functional parameters were highly similar."( Effects of cytochalasin D on occluding junctions of intestinal absorptive cells: further evidence that the cytoskeleton may influence paracellular permeability and junctional charge selectivity.
Barenberg, D; Carlson, S; Madara, JL, 1986
)
0.27
" The dose-response relationship was observed in all of the groups tested."( Teratogenicity of cytochalasin D in chick embryos.
Gilani, SH; Kreshal, C,
)
0.13
" Dose-response studies and "time-addition" experiments performed with NH4Cl, which raises the pH of acidic vesicles and organelles, showed that ricin uptake as well as the movement of the toxin to the translocation site were affected in the differentiated cells."( Requirement of either the NH4Cl-sensitive or the cytochalasin D-sensitive pathway for ricin toxicity depends upon the enterocytic state of differentiation of HT-29 cells.
Aubery, M; Bauvy, C; Chazaud, B; Codogno, P; Decastel, M; Muriel, MP, 1994
)
0.29
" Thus, Cas exhibits an unusual bell-shaped dose-response curve in response to EGF stimulation."( Epidermal growth factor modulates tyrosine phosphorylation of p130Cas. Involvement of phosphatidylinositol 3'-kinase and actin cytoskeleton.
Ojaniemi, M; Vuori, K, 1997
)
0.3
" Only cytochalasin A and 2-deoxy-D-glucose (2dG) affected bacterial internalisation, whereas intracellular multiplication was inhibited by cytochalasins A, B, C, D and J (D being the most active) and by 2dG with a dose-response effect."( Multiplication of Legionella pneumophila in HeLa cells in the presence of cytoskeleton and metabolic inhibitors.
Carrara, S; Cattani, L; Goldoni, P; Orsi, N; Pastoris, MC; Sinibaldi, L, 1998
)
0.3
" Dose-response studies show a good correlation between inhibition of actin polymerization and increased degranulation."( The role of actin microfilaments in the down-regulation of the degranulation response in RBL-2H3 mast cells.
Apgar, JR; Frigeri, L, 1999
)
0.3
" The problem with most cytogenetic indicators is, that the response levels off at doses starting around 5-7Gy of low LET radiation and that the dose-response curve even declines after doses exceeding about 10Gy."( The micronucleus assay in human lymphocytes after high radiation doses (5-15 Gy).
Müller, WU; Rode, A, 2002
)
0.31
" PDGF (1-250 ng/ml) stimulated migration, FAK tyrosine phosphorylation, and actin polymerization with a bell-shape dose-response characterized by a maximum at 10-25 ng/ml."( Platelet-derived growth factor-BB and lysophosphatidic acid distinctly regulate hepatic myofibroblast migration through focal adhesion kinase.
Chitapanarux, T; Han, J; Melton, AC; Tangkijvanich, P; Yee, HF, 2002
)
0.31
" The antisecretory effect persisted for more than 24 hrs in the case of Wortmannin and 9 hr in the case of ME 3407 at a dosage 1 and 3 mg/pouch for 30 min, respectively."( [New target for the inhibitors of gastric acid secretion. Inhibition of myosin and actin activities via the apical membrane of parietal cells in dogs].
Fujishita, T; Jinbo, K; Okabe, S, 2003
)
0.32
" The sensitivity of the high-throughput cell mechanical measurements to the cytoskeletal modifications we present in this study opens up new possibilities for label-free dose-response assays of cytoskeletal modifications."( High-throughput cell mechanical phenotyping for label-free titration assays of cytoskeletal modifications.
Golfier, S; Guck, J; Herbig, M; Mietke, A; Otto, O; Rosendahl, P, 2017
)
0.46
" To demonstrate the technique, we measured shear modulus and phase disorder strength using QPI, as well as Young's modulus using AFM, across two breast cancer cell-line populations dosed with three different concentrations of cytochalasin D, an actin-depolymerizing toxin."( Shear Modulus Measurement by Quantitative Phase Imaging and Correlation with Atomic Force Microscopy.
Ceballos, S; Eldridge, WJ; Park, HS; Shah, T; Steelman, ZA; Wax, A; Zauscher, S, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Actin-5CDrosophila melanogaster (fruit fly)Kd2.00002.00002.00002.0000AID977611
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (25)

Assay IDTitleYearJournalArticle
AID425713Antimicrobial activity against Balamuthia mandrillaris ATCC 50209 infected in HBMEC assessed as inhibition of encystment at 100 uM after 7 days2007Antimicrobial agents and chemotherapy, Dec, Volume: 51, Issue:12
Effect of antimicrobial compounds on Balamuthia mandrillaris encystment and human brain microvascular endothelial cell cytopathogenicity.
AID1656623Antiinvasive activity in human SW620 cells assessed as reduction in cell invasion at 2 uM incubated for 72 hrs by crystal violet staining based assay relative to untreated control2020Bioorganic & medicinal chemistry, 02-01, Volume: 28, Issue:3
Targeted suppression of metastasis regulatory transcription factor SOX2 in various cancer cell lines using a sequence-specific designer pyrrole-imidazole polyamide.
AID425711Antimicrobial activity against Balamuthia mandrillaris ATCC 50209 infected in HBMEC assessed as inhibition of encystment at 10 uM after 7 days2007Antimicrobial agents and chemotherapy, Dec, Volume: 51, Issue:12
Effect of antimicrobial compounds on Balamuthia mandrillaris encystment and human brain microvascular endothelial cell cytopathogenicity.
AID425719Antimicrobial activity against Balamuthia mandrillaris ATCC 50209 infected in HBMEC assessed as inhibition of amoeba-induced cytopathogenicity at 50 uM after 24 hrs by LDH release assay2007Antimicrobial agents and chemotherapy, Dec, Volume: 51, Issue:12
Effect of antimicrobial compounds on Balamuthia mandrillaris encystment and human brain microvascular endothelial cell cytopathogenicity.
AID1610505Cytotoxicity against Flt3L-cultured mouse pDC-rich bone marrow cells assessed as cell viability at 1 to 10 uM incubated for 24 hrs by MTT assay2019Bioorganic & medicinal chemistry, 12-01, Volume: 27, Issue:23
A mouse model-based screening platform for the identification of immune activating compounds such as natural products for novel cancer immunotherapies.
AID1610506Cytotoxicity against M-CSF-cultured mouse macrophage-rich bone marrow cells assessed as cell viability at 1 to 10 uM incubated for 24 hrs by MTT assay2019Bioorganic & medicinal chemistry, 12-01, Volume: 27, Issue:23
A mouse model-based screening platform for the identification of immune activating compounds such as natural products for novel cancer immunotherapies.
AID324419Increase in light chain 3-GFP+ autophagosome vesicle number per cell in human H4 cells at 4.9 uM after 24 hrs by high throughput fluorescence microscopy relative to control2007Proceedings of the National Academy of Sciences of the United States of America, Nov-27, Volume: 104, Issue:48
Small molecule regulators of autophagy identified by an image-based high-throughput screen.
AID341225Inhibition of actin polymerization in human HaCaT cells assessed as aggregate-like structure at 1 ug/mL by immunofluorescence technique2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
Hanultarin, a cytotoxic lignan as an inhibitor of actin cytoskeleton polymerization from the seeds of Trichosanthes kirilowii.
AID1610504Cytotoxicity against GM-CSF-cultured mouse cDC-rich bone marrow cells assessed as cell viability at 1 to 10 uM incubated for 24 hrs by MTT assay2019Bioorganic & medicinal chemistry, 12-01, Volume: 27, Issue:23
A mouse model-based screening platform for the identification of immune activating compounds such as natural products for novel cancer immunotherapies.
AID324367Induction of light chain 3-GFP level in human H4 cells at 4.9 uM after 24 hrs by high throughput fluorescence microscopy relative to control2007Proceedings of the National Academy of Sciences of the United States of America, Nov-27, Volume: 104, Issue:48
Small molecule regulators of autophagy identified by an image-based high-throughput screen.
AID1610512Cytotoxicity against human Jurkat cells2019Bioorganic & medicinal chemistry, 12-01, Volume: 27, Issue:23
A mouse model-based screening platform for the identification of immune activating compounds such as natural products for novel cancer immunotherapies.
AID1610508Immunostimulatory activity in GM-CSF-cultured bone marrow-derived dendritic cells isolated from get40 cytokine reporter mouse model assessed as induction of IL12p40 production at 0.1 to 10 uM incubated for 16 hrs by flow cytometry relative to control2019Bioorganic & medicinal chemistry, 12-01, Volume: 27, Issue:23
A mouse model-based screening platform for the identification of immune activating compounds such as natural products for novel cancer immunotherapies.
AID1610513Cytotoxicity against human Ramos cells2019Bioorganic & medicinal chemistry, 12-01, Volume: 27, Issue:23
A mouse model-based screening platform for the identification of immune activating compounds such as natural products for novel cancer immunotherapies.
AID425712Antimicrobial activity against Balamuthia mandrillaris ATCC 50209 infected in HBMEC assessed as inhibition of encystment at 50 uM after 7 days2007Antimicrobial agents and chemotherapy, Dec, Volume: 51, Issue:12
Effect of antimicrobial compounds on Balamuthia mandrillaris encystment and human brain microvascular endothelial cell cytopathogenicity.
AID697852Inhibition of electric eel AChE at 2 mg/ml by Ellman's method2012Bioorganic & medicinal chemistry, Nov-15, Volume: 20, Issue:22
Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.
AID1610509Immunostimulatory activity in CD4-positive T cells isolated from OVA-specific OT-II TCR transgenic mouse model assessed as T cell activation by measuring increase in IL-2 production at 1 uM compound incubated with GM-CSF cultured mouse bone marrow cells i2019Bioorganic & medicinal chemistry, 12-01, Volume: 27, Issue:23
A mouse model-based screening platform for the identification of immune activating compounds such as natural products for novel cancer immunotherapies.
AID1610507Immunostimulatory activity in GM-CSF-cultured bone marrow-derived dendritic cells isolated from get40 cytokine reporter mouse model assessed as induction of IL12p40 production at 0.1 to 10 uM incubated for 16 hrs in presence of CpG 2216 by flow cytometry 2019Bioorganic & medicinal chemistry, 12-01, Volume: 27, Issue:23
A mouse model-based screening platform for the identification of immune activating compounds such as natural products for novel cancer immunotherapies.
AID324471Increase in light chain 3-GFP+ autophagosome vesicle area per cell in human H4 cells at 4.9 uM after 24 hrs by high throughput fluorescence microscopy relative to control2007Proceedings of the National Academy of Sciences of the United States of America, Nov-27, Volume: 104, Issue:48
Small molecule regulators of autophagy identified by an image-based high-throughput screen.
AID554740Inhibition of Candida krusei ABC1 expressed in Saccharomyces cerevisiae isolate ADdelta at 20 nM2009Antimicrobial agents and chemotherapy, Feb, Volume: 53, Issue:2
Abc1p is a multidrug efflux transporter that tips the balance in favor of innate azole resistance in Candida krusei.
AID697853Inhibition of horse BChE at 2 mg/ml by Ellman's method2012Bioorganic & medicinal chemistry, Nov-15, Volume: 20, Issue:22
Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.
AID425718Antimicrobial activity against Balamuthia mandrillaris ATCC 50209 infected in HBMEC assessed as inhibition of amoeba-induced cytopathogenicity at 10 uM after 24 hrs by LDH release assay2007Antimicrobial agents and chemotherapy, Dec, Volume: 51, Issue:12
Effect of antimicrobial compounds on Balamuthia mandrillaris encystment and human brain microvascular endothelial cell cytopathogenicity.
AID1610511Immunostimulatory activity in GM-CSF-cultured bone marrow-derived dendritic cells isolated from get40 cytokine reporter mouse model assessed as induction of IL12p40 production at 0.1 to 10 uM incubated for 16 hrs in presence of LPS by flow cytometry relat2019Bioorganic & medicinal chemistry, 12-01, Volume: 27, Issue:23
A mouse model-based screening platform for the identification of immune activating compounds such as natural products for novel cancer immunotherapies.
AID1399113Antagonist activity at TLR2/TLR1 in mouse BMDM assessed as inhibition of Rhodamine-labeled Pam3CSK4-stimulated receptor internalization at 1 uM preincubated for 1 hr followed by Rhodamine-Pam3CSK4 stimulation for 20 mins by FACS analysis2018Bioorganic & medicinal chemistry, 09-01, Volume: 26, Issue:16
Decoy peptides derived from the extracellular domain of toll-like receptor 2 (TLR2) show anti-inflammatory properties.
AID324523Increase in light chain 3-GFP+ autophagosome vesicle intensity per cell in human H4 cells at 4.9 uM after 24 hrs by high throughput fluorescence microscopy relative to control2007Proceedings of the National Academy of Sciences of the United States of America, Nov-27, Volume: 104, Issue:48
Small molecule regulators of autophagy identified by an image-based high-throughput screen.
AID977611Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB2008Journal of molecular biology, Dec-26, Volume: 384, Issue:4
Crystal structures of monomeric actin bound to cytochalasin D.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (2,822)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990319 (11.30)18.7374
1990's953 (33.77)18.2507
2000's1045 (37.03)29.6817
2010's463 (16.41)24.3611
2020's42 (1.49)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 55.09

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 very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index55.09 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index4.46 (4.65)
Search Engine Demand Index83.81 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (55.09)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Reviews21 (0.73%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies1 (0.03%)4.05%
Observational0 (0.00%)0.25%
Observational1 (0.03%)0.25%
Other9 (100.00%)84.16%
Other2,848 (99.20%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (1)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
Cytochalasin D Supplementation to ICSI Handling Medium [NCT03677492]300 participants (Actual)Interventional2018-09-25Completed
[information is prepared from clinicaltrials.gov, extracted Sep-2024]