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T6137 Sigma

Trioxsalen

≥98% (HPLC), powder

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

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Properties

Related Categories Apoptosis and Cell Cycle, Approved Therapeutics/Drug Candidates, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Biochemicals and Reagents,
assay   ≥98% (HPLC)
form   powder
color   white
mp   229-231 °C(lit.)
solubility   chloroform: soluble50  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)
originator   Valeant
storage temp.   −20°C

Description

Packaging

1 g in glass bottle

100, 500 mg in glass bottle

Preparation Note

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

Application

Trioxsalen has been used for mutagenesis of N2 worms4,5.

Biochem/physiol Actions

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.

Features and Benefits

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.

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Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 1759 8 / PGII
WGK Germany 
2
RTECS 
LV1576000

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Articles

DNA Damage and Repair

Damage to cellular DNA is involved in mutagenesis and the development of cancer. The DNA in a human cell undergoes several thousand to a million damaging events per day, generated by both external (e...
BioFiles 2007, 2.4, 20.
Keywords: AGE, Alkylations, Apoptosis, Applications, Biochemistry, Cancer, Carcinogens, Catalysis, Clinical, DNA replication, Deaminations, Environmental, Error, Events, Gene expression, Metabolites, Methylations, Mutagens, Oxidations, Polymorphisms, Rearrangements, Recombination, Sequences, Substitutions, Transcription, Type

Discover Bioactive Small Molecules for Apoptosis

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...
Keywords: Apoptosis, Bioactive small molecules, Cancer, Clinical, Diseases, Ligands, Neurodegenerative Diseases

Discover Bioactive Small Molecules for Cell Cycle Research

In 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 t...
Keywords: Apoptosis, Bioactive small molecules, Cancer, Cell division, Cell proliferation, DNA replication, Diseases, Genetic

Peer-Reviewed Papers

References

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Whole-genome profiling of mutagenesis in Caenorhabditis elegans. Flibotte S, Edgley ML, Chaudhry I, et al. Genetics 185(2), 431-41, (2010)

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Relationship between chromatin bridges in anaphase and chromosomal aberrations induced by TMP + UVA (365 nm) in CHO cells. Botta, R., and Gustavino, B. Mutat. Res. 374, 253-259, (1997)

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Localized domains of DNA supercoiling: topological coupling between promoters. Mojica, F.J., and Higgins, C.F. Mol. Microbiol. 22, 919, (1996)

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Atomic force microscopy imaging of DNA covalently immobilized on a functionalized mica substrate. Shlyakhtenko, L.S., et al. Biophys. J. 77, 568-576, (1999)

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Psoralens as photoactive probes of nucleic acid structure and function: organic chemistry, photochemistry, and biochemistry. Cimino, G.D., et al. Annu. Rev. Biochem. 54, 1151-1193, (1985)

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Calreticulin, a calcium-binding molecular chaperone, is required for stress response and fertility in Caenorhabditis elegans. Park BJ, Lee DG, Yu JR, et al. Mol. Biol. Cell 12(9), 2835-45, (2001)

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BINOL-amino acid conjugates as triggerable carriers of DNA-targeted potent photocytotoxic agents. Filippo Doria et al J. Med. Chem. 50, 6570-9, (2007)

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An introduction to worm lab: from culturing worms to mutagenesis. Chaudhuri J, Parihar M, and Pires-daSilva A J. Vis. Exp. (47), doi:10.3791/2293, (2011)

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Electron microscopy methods for studying in vivo DNA replication intermediates. Lopes M Methods Mol. Biol. 521, 605-31, (2009)

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Synthesis and properties of photo-reactive antisense oligonucleotides containing 2'-O-psoralen-conjugated adenosine. Higuchi M, Yamayoshi A, Kobori A, et al. Nucleic Acids Symp. Ser. (49), 331-2, (2005)

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Occupational allergic contact dermatitis disseminated from multifunctional acrylates in ultraviolet-cured lacquers. Kieć-Swierczyńska M, Krecisz B, and Swierczyńska-Machura D Int. J. Occup. Med. Environ. Health 19(1), 77-8, (2006)

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Trimethylangelicin reduces IL-8 transcription and potentiates CFTR function. Tamanini A, Borgatti M, Finotti A, et al. Am. J. Physiol. Lung Cell. Mol. Physiol. 300(3), L380-90, (2011)

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A method for genome-wide analysis of DNA helical tension by means of psoralen-DNA photobinding. Bermúdez I, García-Martínez J, Pérez-Ortín JE, et al. Nucleic Acids Res. 38(19), e182, (2010)

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Psoralen conjugates for visualization of genomic interstrand cross-links localized by laser photoactivation. Thazhathveetil AK, Liu ST, Indig FE, et al. Bioconjug. Chem. 18(2), 431-7, (2007)

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ATPase/helicase activities of p68 RNA helicase are required for pre-mRNA splicing but not for assembly of the spliceosome. Lin C, Yang L, Yang JJ, et al. Mol. Cell. Biol. 25(17), 7484-93, (2005)

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Single/low-copy integration of transgenes in Caenorhabditis elegans using an ultraviolet trimethylpsoralen method. Kage-Nakadai E, Kobuna H, Funatsu O, et al. BMC Biotechnol. 12, 1, (2012)

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Development of a novel furocoumarin derivative inhibiting NF-?B dependent biological functions: design, synthesis and biological effects. Monica Borgatti et al Eur. J. Med. Chem. 46, 4870-7, (2011)

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In vivo footprint of a picornavirus internal ribosome entry site reveals differences in accessibility to specific RNA structural elements. Fernández-Miragall O and Martínez-Salas E J. Gen. Virol. 88(Pt 11), 3053-62, (2007)

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Scoring function for DNA-drug docking of anticancer and antiparasitic compounds based on spectral moments of 2D lattice graphs for molecular dynamics trajectories. Lázaro G Pérez-Montoto et al Eur. J. Med. Chem. 44, 4461-9, (2009)

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Photoallergic contact dermatitis to 8-methoxypsoralen in Ficus carica. Bonamonte D, Foti C, Lionetti N, et al. Contact Dermatitis 62(6), 343-8, (2010)

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Efficient processing of TFO-directed psoralen DNA interstrand crosslinks by the UvrABC nuclease. Christensen LA, Wang H, Van Houten B, et al. Nucleic Acids Res. 36(22), 7136-45, (2008)

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Specific apoptosis induction in human papillomavirus-positive cervical carcinoma cells by photodynamic antisense regulation. Yamayoshi A, Kato K, Suga S, et al. Oligonucleotides 17(1), 66-79, (2007)

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Interplay between human high mobility group protein 1 and replication protein A on psoralen-cross-linked DNA. Reddy MC, Christensen J, and Vasquez KM Biochemistry 44(11), 4188-95, (2005)

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'RNA walk' a novel approach to study RNA-RNA interactions between a small RNA and its target. Lustig Y, Wachtel C, Safro M, et al. Nucleic Acids Res. 38(1), e5, (2010)

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Enhanced repair of DNA interstrand crosslinks in S phase. Mladenova V and Russev G FEBS Lett. 580(6), 1631-4, (2006)

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Inhibition of interferon-gamma signaling by a mercurio-substituted dihydropsoralen in murine keratinocytes. Martey CA, Vetrano AM, Whittemore MS, et al. Biochem. Pharmacol. 70(12), 1726-34, (2005)

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Repair of DNA interstrand crosslinks may take place at the nuclear matrix. Atanassov B, Gospodinov A, Stoimenov I, et al. J. Cell. Biochem. 96(1), 126-36, (2005)

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Psoralen photocrosslinking, a tool to study the chromatin structure of RNA polymerase I--transcribed ribosomal genes. Toussaint M, Levasseur G, Tremblay M, et al. Biochem. Cell Biol. 83(4), 449-59, (2005)

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Trioxsalen derivatives with lipoxygenase inhibitory activity. Hadjipavlou-Litina D, E Bariamis S, Militsopoulou M, et al. J. Enzyme Inhib. Med. Chem. 24(6), 1351-6, (2009)

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Photoreaction of skin-sensitizing trimethyl psoralen with lipid membrane models. Li XY and Eriksson LA Photochem. Photobiol. 81(5), 1153-60, (2005)

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Spectral study of interactions of 4,8,4'-trimethylpsoralen and 4,4'-dimethylangelicin dyes with DNA. Sibirtsev VS, Tolmachev AY, Kovaleva MV, et al. Biochemistry. (Mosc.) 70(7), 822-32, (2005)

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DNA interstrand crosslinks repair in mammalian cells. Mladenova V and Russev G Z. Naturforsch. C 63(3-4), 289-96, (2008)

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Role of tacrolimus (FK506) 0.1% ointment WW in vitiligo in children and imperatives of combine therapy with Trioxsalen and Silymarin suspension in progressive vitiligo. Sehgal VN J. Eur. Acad. Dermatol. Venereol. 23(10), 1218-9, (2009)

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Merck 14,9735

Beil. 19,V,4,472

Aldrich MSDS 1, 1795:D / Corp MSDS 1 (2), 3494:B / FT-IR 1 (2), 684:C / FT-IR 2 (3), 3619:D / RegBook 1 (2), 2433:C / Sigma FT-IR 1 (1), 731:D / Structure Index 1, 385:D:6

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