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Merck

T6137

Sigma-Aldrich

Trioxsalen

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

Synonym(e):

2,5,9-Trimethylfuro[3,2-g]benzopyran-7-on, 4,5′,8-Trimethyl-psoralen, TMP, Trisoralen

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About This Item

Empirische Formel (Hill-System):
C14H12O3
CAS-Nummer:
Molekulargewicht:
228.24
Beilstein:
221723
EG-Nummer:
MDL-Nummer:
UNSPSC-Code:
12352200
PubChem Substanz-ID:
NACRES:
NA.77

product name

Trioxsalen, ≥98% (HPLC), powder

Assay

≥98% (HPLC)

Form

powder

Farbe

white

mp (Schmelzpunkt)

229-231 °C (lit.)

Löslichkeit

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

Fluoreszenz

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

Ersteller

Valeant

Lagertemp.

−20°C

SMILES String

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

InChIKey

FMHHVULEAZTJMA-UHFFFAOYSA-N

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Anwendung

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

Biochem./physiol. Wirkung

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.

Leistungsmerkmale und Vorteile

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.

Angaben zur Herstellung

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

Signalwort

Danger

Gefahreneinstufungen

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

Lagerklassenschlüssel

8A - Combustible corrosive hazardous materials

WGK

WGK 2

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

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


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Kunden haben sich ebenfalls angesehen

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)
Methodological considerations for mutagen exposure in C. elegans
Kessler Z and Yanowitz J
Methods, 68(3), 441-449 (2014)
Isolation of deletion mutants by reverse genetics in Caenorhabditis elegans
Park BJ, et al.
Korean Journal of Biological Sciences, 5(1), 65-69 (2001)

Artikel

DNA damage and repair mechanism is vital for maintaining DNA integrity. Damage to cellular DNA is involved in mutagenesis, the development of cancer among others.

Cell cycle phases (G1, S, G2, M) regulate cell growth, DNA replication, and division in proliferating cells.

Apoptosis regulation involves multiple pathways and molecules for cellular homeostasis.

Unser Team von Wissenschaftlern verfügt über Erfahrung in allen Forschungsbereichen einschließlich Life Science, Materialwissenschaften, chemischer Synthese, Chromatographie, Analytik und vielen mehr..

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