T-2 TOXIN

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C24H34O9
Molecular Weight	466.5214
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)CC(=O)O[C@H]1C[C@@]2(COC(C)=O)[C@H](O[C@@H]3[C@H](O)[C@@H](OC(C)=O)[C@@]2(C)[C@]34CO4)C=C1C

InChI

InChIKey=BXFOFFBJRFZBQZ-QYWOHJEZSA-N

InChI=1S/C24H34O9/c1-12(2)7-18(27)32-16-9-23(10-29-14(4)25)17(8-13(16)3)33-21-19(28)20(31-15(5)26)22(23,6)24(21)11-30-24/h8,12,16-17,19-21,28H,7,9-11H2,1-6H3/t16-,17+,19+,20+,21+,22+,23+,24-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21417259
Curator's Comment: description was created based on several sources, including

Among the naturally occurring trichothecenes in food and feed, T-2 toxin is a cytotoxic fungal secondary metabolite produced by various species of Fusarium. Following ingestion, T-2 toxin causes acute and chronic toxicity and induces apoptosis in the immune system and fetal tissues. T-2 toxin is usually metabolized and eliminated after ingestion, yielding more than 20 metabolites. Consequently, there is a possibility of human consumption of animal products contaminated with T-2 toxin and its metabolites. The molecular mechanism of inhibition of protein synthesis may be the high affinity of T-2 toxin for the 60S ribosomal subunit.

CNS Activity

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Developmental exposure to T-2 toxin reversibly affects postnatal hippocampal neurogenesis and reduces neural stem cells and progenitor cells in mice.	2016-08	26314264
Toxic effects of HT-2 toxin on mouse oocytes and its possible mechanisms.	2016-06	26138683
Toxicity and oxidative stress induced by T-2 toxin and HT-2 toxin in broilers and broiler hepatocytes.	2016-01	26683309
Delay of the onset of puberty in female rats by prepubertal exposure to T-2 toxin.	2015-11-09	26569305
Integrated Transcriptional and Proteomic Analysis of Growth Hormone Suppression Mediated by Trichothecene T-2 Toxin in Rat GH3 Cells.	2015-10	26141394
T-2 toxin inhibits gene expression and activity of key steroidogenesis enzymes in mouse Leydig cells.	2015-08	25962641
T-2 toxin regulates steroid hormone secretion of rat ovarian granulosa cells through cAMP-PKA pathway.	2015-02-03	25542145
Differential effects of route of T-2 toxin exposure on hepatic oxidative damage in mice.	2015-01	23929680
Toxicity induced by F. poae-contaminated feed and the protective effect of Montmorillonite supplementation in broilers.	2014-12	25296281
Toxic effects of dietary exposure to T-2 toxin on intestinal and hepatic biotransformation enzymes and drug transporter systems in broiler chickens.	2013-05	23313610
Toxic effects of T-2 toxin and deoxynivalenol on the mitochondrial electron transport system of cardiomyocytes in rats.	2013	23719927
T-2 toxin induced skin inflammation and cutaneous injury in mice.	2012-12-16	22960706
An in vitro investigation of endocrine disrupting effects of trichothecenes deoxynivalenol (DON), T-2 and HT-2 toxins.	2012-11-15	22982764
T-2 toxin enhances catabolic activity of hypertrophic chondrocytes through ROS-NF-κB-HIF-2α pathway.	2012-10	22800716
JAK/STAT pathway plays a critical role in the proinflammatory gene expression and apoptosis of RAW264.7 cells induced by trichothecenes as DON and T-2 toxin.	2012-06	22454431
T-2 toxin is a cytochrome P450 1A1 inducer and leads to MAPK/p38- but not aryl hydrocarbon receptor-dependent interleukin-8 secretion in the human intestinal epithelial cell line Caco-2.	2011-06-18	21453744
T-2 toxin induces apoptosis in ovarian granulosa cells of rats through reactive oxygen species-mediated mitochondrial pathway.	2011-05-10	21296132
Cytotoxicity and accumulation of ergot alkaloids in human primary cells.	2011-04-11	21295106
Effects of T-2 toxin and selenium on chondrocyte expression of matrix metalloproteinases (MMP-1, MMP-13), α2-macroglobulin (α2M) and TIMPs.	2011-03	21144892
Alteration of blood brain barrier permeability by T-2 toxin: Role of MMP-9 and inflammatory cytokines.	2011-02-04	21112371
Brain oxidative stress after dermal and subcutaneous exposure of T-2 toxin in mice.	2010-12	20854872
Immunopathological effects of ochratoxin A and T-2 toxin combination on broilers.	2010-06	20460662
DNA damage and DNA damage responses in THP-1 monocytes after exposure to spores of either Stachybotrys chartarum or Aspergillus versicolor or to T-2 toxin.	2010-05	20150440
Oxidative stress induction by T-2 toxin causes DNA damage and triggers apoptosis via caspase pathway in human cervical cancer cells.	2009-08-03	19524637
Fusarial toxin-induced toxicity in cultured cells and in isolated mitochondria involves PTPC-dependent activation of the mitochondrial pathway of apoptosis.	2009-08	19541794
Oxidative damage and gene expression profile of antioxidant enzymes after T-2 toxin exposure in mice.	2009-06-16	19526462
Role of GRP78/BiP degradation and ER stress in deoxynivalenol-induced interleukin-6 upregulation in the macrophage.	2009-06	19336499
Metabolism and cytotoxic effects of T-2 toxin and its metabolites on human cells in primary culture.	2009-04-28	19428930
Promotion of the articular cartilage proteoglycan degradation by T-2 toxin and selenium protective effect.	2008-01	18196609
[Protective effect of selenium against T-2 toxin-induced inhibition of chondrocyte aggrecan and collagen II synthesis].	2006-04	16624732
T-2 toxin induces apoptosis, and selenium partly blocks, T-2 toxin induced apoptosis in chondrocytes through modulation of the Bax/Bcl-2 ratio.	2006-04	16307838
Effects of trichothecene structure on cytokine secretion and gene expression in murine CD4+ T-cells.	1995-12-15	8560498
Direct and reflex cardiovascular effects of trichothecene mycotoxins.	1987	3590213
Synthesis of DNA in human fibroblasts treated with T-2 toxin and HT-2 toxin (the trichothecene metabolites of Fusarium species) and the effects of hydroxyurea.	1980-02	7466841
T-2 toxin production by Fusarium tricinctum on solid substrate.	1971-04	5103481

Patents

Sample Use Guides

In Vivo Use Guide

in mice toxic effect: Groups of 50 male and 50 female CD-1 mice, six weeks of age, were fed a semi-synthetic diet containing 0, 1.5 or 3.0 mg/kg T-2 toxin for 71 weeks. in rats toxic effect: 40 weanling male and female Wistar- Porton rats were administered one to eight doses of 0.2-4 mg/kg bw T-2 toxin intragastrically at approximately monthly intervals (duration unspecified).

Route of Administration: Other

In Vitro Use Guide

Embryos were cultured in media supplemented with 0.5, 0.75 and 1 ng/ml T-2. Different exposure times were applied [96 h (treatment I) or 24 h following 72 h in toxin-free media (treatment II)]. Blastomere number, nuclear chromatin status and blastocoel formation were investigated in blastocysts. After 24 h of exposure applied following a 72-h culture, blastomeres had a higher level of chromatin damage, although their developmental potential was the same as in the control embryos. In both cases, decreased mitotic rate was found, which resulted in decreased blastomere number even at low toxin concentration.

Name

Type

Language

FUSARIOTOXIN T-2

Preferred Name

English

T-2 TOXIN

Common Name

English

TRICHOTHEC-9-ENE-3.ALPHA.,4.BETA.,8.ALPHA.,15-TETROL, 12,13-EPOXY-, 4,15-DIACETATE 8-ISOVALERATE

Common Name

English

T 2 TOXIN

Common Name

English

T2-TRICHOTHECENE

Common Name

English

TOXIN T 2

Common Name

English

T2-TRICHOTHECENE [IARC]

Common Name

English

MYCOTOXIN T-2

Brand Name

English

T-2 TOXIN [HSDB]

Common Name

English

NSC-138780

Code

English

T 2 MYCOTOXIN

Common Name

English

T-2 LIENOMYCIN

Common Name

English

T-2 TOXIN [MI]

Common Name

English

4.BETA.,15-DIACETOXY-8.ALPHA.-(3-METHYLBUTYRYLOXY)-12,13-EPOXYTRICHOTHEC-9-EN-3.ALPHA.-OL

Common Name

English

8.ALPHA.-(3-METHYLBUTYRYLOXY)-4.BETA.,15-DIACETOXYSCIRP-9-EN-3.ALPHA.-OL

Common Name

English

INSARIOTOXIN

Brand Name

English

Code System Code Type Description

NSC

138780