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T6137

Sigma-Aldrich

Trioxsalen

≥98% (HPLC), powder, photochemical DNA crosslinker

Synonyme(s) :

2,5,9-Trimethylfuro[3,2-g]benzopyran-7-one, 4,5′,8-Trimethylpsoralen, TMP, Trisoralen

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About This Item

Formule empirique (notation de Hill):
C14H12O3
Numéro CAS:
3902-71-4
Poids moléculaire :
228.24
Numéro Beilstein :
221723
Numéro CE :
223-459-0
Numéro MDL:
MFCD00005010
Code UNSPSC :
12352200
ID de substance PubChem :
24900351
Nomenclature NACRES :
NA.77

product name

Trioxsalen, ≥98% (HPLC), powder

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white

Pf

229-231 °C (lit.)

Solubilité

chloroform: soluble 50 mg/mL, clear, colorless to faintly yellow

Fluorescence

λex 269 nm; λem 445 nm in methanol
λex 321 nm; λem 445 nm (bound to DNA in Tris, pH 8.1)

Auteur

Valeant

Température de stockage

−20°C

Chaîne SMILES 

Cc1cc2cc3C(C)=CC(=O)Oc3c(C)c2o1

InChI

1S/C14H12O3/c1-7-4-12(15)17-14-9(3)13-10(6-11(7)14)5-8(2)16-13/h4-6H,1-3H3

Clé InChI

FMHHVULEAZTJMA-UHFFFAOYSA-N

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Application

Trioxsalen has been used for mutagenesis of N2 worms4,5.
Trioxsalen has been used:
  • to induce small deletion mutations in worms
  • in combination with ultraviolet A (UVA)
  • to induce interstrand crosslinks (ICLs) in DNA
  • for the preparation and photoactivation of trimethyl psoralen

Actions biochimiques/physiologiques

Photochemical crosslinker of DNA that has been used as a probe for nucleic acid structure and function. Trioxsalen has also been used to crosslink DNA onto mica surfaces.
Trioxsalen (TRX) is a 4,5′,8-trimethylated psoralen analog, which belongs to the family of furocoumarins. It is mostly used to treat psoriasis.

Caractéristiques et avantages

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by Valeant. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Notes préparatoires

Trioxsalen is soluble in chloroform at 50 mg/ml and yields a clear, colorless to faint yellow solution.

Pictogrammes

Health hazardCorrosionExclamation mark
GHS08,GHS05,GHS07

Mention d'avertissement

Danger

Mentions de danger

H312 + H332,H314,H341

Classification des risques

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Eye Dam. 1 - Muta. 2 - Skin Corr. 1B

Code de la classe de stockage

8A - Combustible corrosive hazardous materials

Classe de danger pour l'eau (WGK)

WGK 2

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Methoxsalen United States Pharmacopeia (USP) Reference Standard

USP

1417001

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Methodological considerations for mutagen exposure in C. elegans
Kessler Z and Yanowitz J
Methods, 68(3), 441-449 (2014)
Filippo Doria et al.
Journal of medicinal chemistry, 50(26), 6570-6579 (2007-12-01)
Mild photoactivation of new BINOL-amino acid and -amino ester conjugates (BINOLAMs) yielded alkylating and DNA cross-linking agents with high photoefficiency and superior cytotoxicity. Detection of the transient electrophile, by laser flash photolysis (LFP), suggests that BINOL-quinone methides (QMs) are key
Aurèle Piazza et al.
Methods in molecular biology (Clifton, N.J.), 2153, 535-554 (2020-08-26)
DNA double-strand breaks (DSBs) are genotoxic lesions that can be repaired in a templated fashion by homologous recombination (HR). HR is a complex pathway that involves the formation of DNA joint molecules (JMs) containing heteroduplex DNA. Various types of JMs
UHRF1 is a sensor for DNA interstrand crosslinks and recruits FANCD2 to initiate the Fanconi anemia pathway
Liang CC, et al.
Cell Reports, 10(12), 1947-1956 (2015)
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Nucleic acids research, 47(22), 11691-11708 (2019-10-17)
We have explored the meiotic roles of cohesin modulators Pds5 and Rad61/Wapl, in relation to one another, and to meiotic kleisin Rec8, for homolog pairing, all physically definable steps of recombination, prophase axis length and S-phase progression, in budding yeast.
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