T6137 Sigma


≥98% (HPLC), powder

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



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



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.


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

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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

Signal word 
Hazard statements 
Precautionary statements 
UN 1759 8 / PGII
WGK Germany 


Certificate of Analysis

Certificate of Origin

Protocols & 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...
Keywords: AGE, Alkylations, Apoptosis, Cancer, Carcinogens, Catalysis, Clinical, DNA replication, Deaminations, Environmental, Gene expression, Metabolites, Methylations, Mutagens, Oxidations, Polymorphisms, Rearrangements, Recombination, Substitutions, Transcription

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


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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)


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)


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


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


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)


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)


Rad51-mediated replication fork reversal is a global response to genotoxic treatments in human cells. Zellweger R, Dalcher D, Mutreja K, et al. J. Cell Biol. 208(5), 563-79, (2015)


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


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)


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


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)


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)


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)


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)


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)


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)


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)


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)


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)


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)


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


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)


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)


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)


'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)


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


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)


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)


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)


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)


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


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)


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


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)


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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