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Merck

T6137

Sigma-Aldrich

Trioxsalen

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

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C14H12O3
Número de CAS:
Peso molecular:
228.24
Beilstein:
221723
Número CE:
Número MDL:
Código UNSPSC:
12352200
ID de la sustancia en PubChem:
NACRES:
NA.77

product name

Trioxsalen, ≥98% (HPLC), powder

Nivel de calidad

Análisis

≥98% (HPLC)

formulario

powder

color

white

mp

229-231 °C (lit.)

solubilidad

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

fluorescencia

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

emisor

Valeant

temp. de almacenamiento

−20°C

cadena 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

Clave InChI

FMHHVULEAZTJMA-UHFFFAOYSA-N

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Aplicación

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

Acciones bioquímicas o fisiológicas

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.

Características y beneficios

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.

Nota de preparación

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

Palabra de señalización

Danger

Frases de peligro

Clasificaciones de peligro

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

Código de clase de almacenamiento

8A - Combustible corrosive hazardous materials

Clase de riesgo para el agua (WGK)

WGK 2

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

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


Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Visite la Librería de documentos

Isolation of deletion mutants by reverse genetics in Caenorhabditis elegans
Park BJ, et al.
Korean Journal of Biological Sciences, 5(1), 65-69 (2001)
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)
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
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
Chunru Lin et al.
Molecular and cellular biology, 25(17), 7484-7493 (2005-08-19)
We have previously demonstrated that p68 RNA helicase, as an essential human splicing factor, acts at the U1 snRNA and 5' splice site (5'ss) duplex in the pre-mRNA splicing process. To further analyze the function of p68 in the spliceosome

Artículos

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.

Contenido relacionado

Apoptosis, or programmed cell death (PCD), is a selective process for the removal of unnecessary, infected or transformed cells in various biological systems. As it plays a role in the homeostasis of multicellular organisms, apoptosis is tightly regulated through two principal pathways by a number of regulatory and effector molecules.

n proliferating cells, the cell cycle consists of four phases. Gap 1 (G1) is the interval between mitosis and DNA replication that is characterized by cell growth. Replication of DNA occurs during the synthesis (S) phase, which is followed by a second gap phase (G2) during which growth and preparation for cell division occurs. Together, these three stages comprise the interphase phase of the cell cycle. Interphase is followed by the mitotic (M) phase.

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