Page last updated: 2024-11-12

tryprostatin a

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

Description

tryprostatin A: isolated from Aspergillus fumigatus; a mammalian cell cycle inhibitor; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

tryprostatin A : A cyclic dipeptide that is brevianamide F (cyclo-L-Trp-L-Pro) substituted at positions 2 and 6 on the indole ring by prenyl and methoxy groups respectively. [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 CID9929833
CHEMBL ID289159
CHEBI ID72761
SCHEMBL ID21263139
MeSH IDM0257174

Synonyms (18)

Synonym
(3s,8as)-3-{[6-methoxy-2-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
MEGXM0_000107
tps-a
tryprostatin a
CHEMBL289159
chebi:72761 ,
C20607
bdbm50198769
tryprostatina
171864-80-5
Q27140127
(3s,8as)-3-((6-methoxy-2-(3-methylbut-2-en-1-yl)-1h-indol-3-yl)methyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
DTXSID701017629
SCHEMBL21263139
(3s,8as)-3-[[6-methoxy-2-(3-methylbut-2-enyl)-1h-indol-3-yl]methyl]-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
AKOS040762456
HY-N7291
CS-0113194

Research Excerpts

Overview

Tryprostatin A is an inhibitor of breast cancer resistance protein, consequently a series of structure-activity studies on the cell cycle inhibitory effects of tryprostatiin A analogues have been carried out.

ExcerptReferenceRelevance
"Tryprostatin A is an inhibitor of breast cancer resistance protein, consequently a series of structure-activity studies on the cell cycle inhibitory effects of tryprostatin A analogues as potential antitumor antimitotic agents have been carried out. "( Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
Cook, JM; Deveau, AM; Dieckhaus, CM; Jain, HD; Johnson, MA; Kakeya, H; Liao, X; Liu, X; Ma, J; Macdonald, TL; Osada, H; Smith, KS; Zhang, C; Zhou, H; Zhou, S, 2008
)
2.03
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
breast cancer resistance protein inhibitorAny inhibitor of breast cancer resistance protein (ABCG2).
[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 (5)

ClassDescription
dipeptideAny molecule that contains two amino-acid residues connected by peptide linkages.
indolesAny compound containing an indole skeleton.
pyrrolopyrazine
aromatic etherAny ether in which the oxygen is attached to at least one aryl substituent.
indole alkaloidAn alkaloid containing an indole skeleton.
[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]

Pathways (2)

PathwayProteinsCompounds
fumitremorgin C biosynthesis518
superpathway of fumitremorgin biosynthesis925

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
CDGSH iron-sulfur domain-containing protein 1Homo sapiens (human)IC50 (µMol)3.38700.73103.79949.0780AID1323834
CDGSH iron-sulfur domain-containing protein 1Homo sapiens (human)Ki0.14500.03101.20547.2910AID1323835
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (3)

Processvia Protein(s)Taxonomy
regulation of autophagyCDGSH iron-sulfur domain-containing protein 1Homo sapiens (human)
regulation of cellular respirationCDGSH iron-sulfur domain-containing protein 1Homo sapiens (human)
protein maturation by [2Fe-2S] cluster transferCDGSH iron-sulfur domain-containing protein 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (6)

Processvia Protein(s)Taxonomy
pyridoxal phosphate bindingCDGSH iron-sulfur domain-containing protein 1Homo sapiens (human)
identical protein bindingCDGSH iron-sulfur domain-containing protein 1Homo sapiens (human)
protein homodimerization activityCDGSH iron-sulfur domain-containing protein 1Homo sapiens (human)
metal ion bindingCDGSH iron-sulfur domain-containing protein 1Homo sapiens (human)
L-cysteine transaminase activityCDGSH iron-sulfur domain-containing protein 1Homo sapiens (human)
2 iron, 2 sulfur cluster bindingCDGSH iron-sulfur domain-containing protein 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (2)

Processvia Protein(s)Taxonomy
mitochondrionCDGSH iron-sulfur domain-containing protein 1Homo sapiens (human)
mitochondrial outer membraneCDGSH iron-sulfur domain-containing protein 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (47)

Assay IDTitleYearJournalArticle
AID327219Cytotoxicity against human K562 cells2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID327230Cytotoxicity against human MDA-MB-23212008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID679624TP_TRANSPORTER: inhibition of C6-NBD-PS efflux in BCRP-expressing EPG85-257 cells2003The Biochemical journal, Dec-01, Volume: 376, Issue:Pt 2
Enhanced exposure of phosphatidylserine in human gastric carcinoma cells overexpressing the half-size ABC transporter BCRP (ABCG2).
AID327229Cytotoxicity against human DU145 cells2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID327224Cytotoxicity against human EKVX cells2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID1323835Displacement of [3H]rosiglitazone from recombinant human C-terminal His-tagged MitoNEET cytosolic domain (32 to 108 residues) expressed in Escherichia coli BL21 by Cheng-Prusoff analysis2016Bioorganic & medicinal chemistry letters, 11-01, Volume: 26, Issue:21
Identification of small molecules that bind to the mitochondrial protein mitoNEET.
AID327227Cytotoxicity against human OVCAR-3 cells2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID1336111Inhibition of BCRP (unknown origin)-dependent ATPase activity at 50 uM after 30 mins by malachite green method2016Bioorganic & medicinal chemistry letters, 12-15, Volume: 26, Issue:24
Biosynthetic approaches to creating bioactive fungal metabolites: Pathway engineering and activation of secondary metabolism.
AID327223Cytotoxicity against human HOP92 cells2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID1587849Inhibition of bovine brain microtubule assembly at 250 uM by turbidimetric assay relative to control2019European journal of medicinal chemistry, Jun-01, Volume: 171Anti-tubulin agents of natural origin: Targeting taxol, vinca, and colchicine binding domains.
AID327234Cell cycle arrest in mouse tsFT210 cells assessed as accumulation at M phase at 30 uM after 18 hrs by flow cytometry2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID327226Cytotoxicity against human HT29 cells2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID103404Growth inhibitory activity against MCF-7 (human breast) cancer cell line at 10 uM dose.2002Journal of medicinal chemistry, Apr-11, Volume: 45, Issue:8
Biological activity of the tryprostatins and their diastereomers on human carcinoma cell lines.
AID327217Cytotoxicity against human CCRF-CEM cells2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID327233Antiproliferative activity against mouse tsFT210 cells after 48 hrs by WST-8 assay2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID156013Growth inhibitory activity against PC-3 (human prostate) cancer cell line at 10 uM dose.2002Journal of medicinal chemistry, Apr-11, Volume: 45, Issue:8
Biological activity of the tryprostatins and their diastereomers on human carcinoma cell lines.
AID78423Growth inhibitory activity against H520 (human lung) cancer cell line at 10 uM dose2002Journal of medicinal chemistry, Apr-11, Volume: 45, Issue:8
Biological activity of the tryprostatins and their diastereomers on human carcinoma cell lines.
AID327206Inhibition of tubulin polymerization in presence of microtubule-associated proteins2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID103406Growth inhibitory activity against MCF-7 (human breast) cancer cell line at 100 uM dose.2002Journal of medicinal chemistry, Apr-11, Volume: 45, Issue:8
Biological activity of the tryprostatins and their diastereomers on human carcinoma cell lines.
AID423398Cytotoxicity against human MCF7 cells after 48 hrs by MTT assay2009Journal of natural products, Apr, Volume: 72, Issue:4
Bioactive alkaloids from endophytic Aspergillus fumigatus.
AID78425Growth inhibitory activity against H520 (human lung) cancer cell line at 100 uM dose.2002Journal of medicinal chemistry, Apr-11, Volume: 45, Issue:8
Biological activity of the tryprostatins and their diastereomers on human carcinoma cell lines.
AID327216Cytotoxicity against human PC3 cells after 72 hrs by Cell Titer 96 Aqueous Non-Radioactive assay2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID1587848Cytotoxicity against mouse tsFT210 cells2019European journal of medicinal chemistry, Jun-01, Volume: 171Anti-tubulin agents of natural origin: Targeting taxol, vinca, and colchicine binding domains.
AID327218Cytotoxicity against human HL60 (TB) cells2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID327222Cytotoxicity against human SR cells2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID680139TP_TRANSPORTER: inhibition of C6-NBD-PS efflux in MDR1-expressing EPG85-257 cells2003The Biochemical journal, Dec-01, Volume: 376, Issue:Pt 2
Enhanced exposure of phosphatidylserine in human gastric carcinoma cells overexpressing the half-size ABC transporter BCRP (ABCG2).
AID1336110Inhibition of BCRP in human K562 cells assessed as potentiation of SN38-mediated growth inhibition at 3 uM after 4 days by coulter counter method2016Bioorganic & medicinal chemistry letters, 12-15, Volume: 26, Issue:24
Biosynthetic approaches to creating bioactive fungal metabolites: Pathway engineering and activation of secondary metabolism.
AID327215Cytotoxicity against human MCF7 cells after 72 hrs by Cell Titer 96 Aqueous Non-Radioactive assay2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID327231Cytotoxicity against human BT549 cells2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID156015Growth inhibitory activity against PC-3 (human prostate) cancer cell line at 100 uM dose.2002Journal of medicinal chemistry, Apr-11, Volume: 45, Issue:8
Biological activity of the tryprostatins and their diastereomers on human carcinoma cell lines.
AID327208Cytotoxicity against human H520 cells at 10 uM after 72 hrs by Cell Titer 96 Aqueous Non-Radioactive assay2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID327240Cytotoxicity against human LOX IMVI cells2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID327232Cytotoxicity against human UO31 cells2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID327225Cytotoxicity against human COLO205 cells2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID327213Cytotoxicity against human PC3 cells at 100 uM after 72 hrs by Cell Titer 96 Aqueous Non-Radioactive assay2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID423397Cytotoxicity against human K562 cells after 48 hrs by MTT assay2009Journal of natural products, Apr, Volume: 72, Issue:4
Bioactive alkaloids from endophytic Aspergillus fumigatus.
AID327221Cytotoxicity against human RPMI8226 cells2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID327211Cytotoxicity against human MCF7 cells at 100 uM after 72 hrs by Cell Titer 96 Aqueous Non-Radioactive assay2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID327209Cytotoxicity against human H520 cells at 100 uM after 72 hrs by Cell Titer 96 Aqueous Non-Radioactive assay2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID327212Cytotoxicity against human PC3 cells at 10 uM after 72 hrs by Cell Titer 96 Aqueous Non-Radioactive assay2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID327228Cytotoxicity against human IGROV1 cells2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID1323834Displacement of [3H]rosiglitazone from recombinant human C-terminal His-tagged MitoNEET cytosolic domain (32 to 108 residues) expressed in Escherichia coli BL21 by scintillation proximity assay2016Bioorganic & medicinal chemistry letters, 11-01, Volume: 26, Issue:21
Identification of small molecules that bind to the mitochondrial protein mitoNEET.
AID327220Cytotoxicity against human MOLT4 cells2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID423399Induction of neurite outgrowth in rat PC12 cells at 10 uM after 2 days by phase-contrast microscope2009Journal of natural products, Apr, Volume: 72, Issue:4
Bioactive alkaloids from endophytic Aspergillus fumigatus.
AID327210Cytotoxicity against human MCF7 cells at 10 uM after 72 hrs by Cell Titer 96 Aqueous Non-Radioactive assay2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID1082823Toxicity in Artemia salina (brine shrimp) at 28 degC after 48 hr2012Journal of agricultural and food chemistry, Apr-04, Volume: 60, Issue:13
Metabolites from Aspergillus fumigatus, an endophytic fungus associated with Melia azedarach, and their antifungal, antifeedant, and toxic activities.
AID423396Cytotoxicity against human KB cells after 48 hrs by MTT assay2009Journal of natural products, Apr, Volume: 72, Issue:4
Bioactive alkaloids from endophytic Aspergillus fumigatus.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (20)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's5 (25.00)18.2507
2000's8 (40.00)29.6817
2010's7 (35.00)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: 19.14

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 Index19.14 (24.57)
Research Supply Index3.04 (2.92)
Research Growth Index4.56 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (19.14)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (15.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other17 (85.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]