2,5,9-trimethyl-7H-furo[3,2-g]chromen-7-one

• ChemBase ID: 4139
• Molecular Formular: C14H12O3
• Molecular Mass: 228.24328
• Monoisotopic Mass: 228.07864424
• SMILES: Cc1cc(=O)oc2c1cc1cc(oc1c2C)C
• Canonical SMILES: Cc1cc2c(o1)c(C)c1c(c2)c(C)cc(=O)o1
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5,9-trimethyl-7H-furo[3,2-g]chromen-7-one
• IUPAC Traditional name: 2,5,9-trimethyl-7H-furo[3,2-g]chromen-7-one; trioxsalen
• Synonyms: TMP; Trioxsalen; 4,5′,8-Trimethylpsoralen; Levrison; Tripsos; 4,5',8-Trimethylpsoralen; Trioxysalen; Dermetrix; 2,5,9-trimethyl-7H-furo[3,2-g]chromen-7-one; trimethylpsoralen; trioxysalen; trisoralen; Trioxsalen; Trioxsalen; 2,5,9-Trimethylfuro[3,2-g]benzopyran-7-one; 4,5',8-TRIMETHYLPSORALEN; 2,5,9-三甲基呋[3,2-g]苯并吡喃-7-酮; 4,5′,8-三甲基补骨脂素; 三甲补骨脂内酯; 三甲沙林

Database IDs

• CAS Number: 3902-71-4
• EC Number: 223-459-0
• MDL Number: MFCD00005010
• Beilstein Number: 221723
• PubChem SID: 160967571; 24889644; 24900351
• PubChem CID: 5585
• CHEBI ID: 28329
• ATC CODE: D05AD01; D05BA01
• CHEMBL: 1475
• Chemspider ID: 5383
• DrugBank ID: DB04571
• KEGG ID: D01034
• Unique Ingredient Identifier: Y6UY8OV51T
• Wikipedia Title: Trioxsalen

CALCULATED PROPERTIES

JChem

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.9548604
• LogD (pH = 7.4): 2.9548604
• Log P: 2.9548604
• Molar Refractivity: 64.8626 cm^3
• Polarizability: 25.444344 Å^3
• Polar Surface Area: 39.44 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.26
• LOG S: -3.56
• Solubility (Water): 6.27e-02 g/l

PROPERTIES

Physical Property

• Solubility: chloroform: soluble; DMSO: soluble; methanol: soluble
• Apperance: white powder
• Melting Point: 229 - 231°C; 229-231 °C(lit.); 233-235 °C
• Hydrophobicity(logP): 3.469
• Fluorescence: λex 269 nm; λem 445 nm in methanol; λex 321 nm; λem 445 nm (bound to DNA in Tris, pH 8.1); λex 321 nm; λem 445 nm in 10 mM Tris; 1 mM EDTA; pH 8.0; DNA

Safety Information

• Storage Condition: -20°C; Room Temperature (15-30°C), Protect from light
• RTECS: LV1576000
• European Hazard Symbols: Corrosive (C)
• UN Number: 1759
• German water hazard class: 2
• Hazard Class: 8
• Packing Group: 1
• Risk Statements: 34-40; R:34
• Safety Statements: 26-36/37/39-45; S:26-27/28-36/37/39-46-64
• GHS Pictograms: GHS05; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H314-H351
• GHS Precautionary statements: P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 1759 8/PG 1
• Storage Temperature: -20°C; 2-8°C

Pharmacology Properties

• Mechanism of Action: Action depends on the presence of functional melanocytes and their proliferation by photoactivated drug; Conjugates and forms covalent-bonds with DNA which leads to the formation of both monofunctional and bifunctional adducts upon photoactivation; Exact mechanism with epidermal melanocytes and keratinocytes unknown.

Product Information

• Purity: ≥97.0% (HPLC); ≥98% (HPLC); 95%; 98%
• Salt Data: Free Base
• Suitability: suitable for fluorescence
• Biological Source: Phytotoxic metab. of pink rot disease, produced by Sclerotinia sclerotiorum
• Application(s): Dermatological agent; Medicinal pigmentation agent; Photosensitiser; Radiosensitizer; Tool used in molecular biology for labelling and isolating nascent DNA fragments
• Empirical Formula (Hill Notation): C14H12O3

DETAILS

MP Biomedicals - 02154157

Potent photosensitizing agent; rapid and sensitive assay for interstrand DNA cross links: Biochemistry, 20: 143, (1981).

DrugBank - DB04571

• Drug Groups: approved
• Description: Trioxsalen (trimethylpsoralen, trioxysalen or trisoralen) is a furanocoumarin and a psoralen derivative. It is obtained from several plants, mainly Psoralea corylifolia. Like other psoralens it causes photosensitization of the skin. It is administered either topically or orally in conjunction with UV-A (the least damaging form of ultraviolet light) for phototherapy treatment of vitiligo[1] and hand eczema.[2] After photoactivation it creates interstrand cross-links in DNA, which can cause programmed cell death unless repaired by cellular mechanisms. In research it can be conjugated to dyes for confocal microscopy and used to visualize sites of DNA damage.[3] The compound is also being explored for development of antisense oligonucleotides that can be cross-linked specifically to a mutant mRNA sequence without affecting normal transcripts differing at even a single base pair.
• Indication: Trioxsalen is a pigmenting photosensitizing agent used in conjunction with ultraviolet light in the treatment of vitiligo.
• Pharmacology: Trioxsalen ispharmacologically inactive but when exposed to ultraviolet radiation or sunlight it is converted to its active metabolite to produce a beneficial reaction affecting the diseased tissue.
• References: van Coevorden AM, Kamphof WG, van Sonderen E, Bruynzeel DP, Coenraads PJ: Comparison of oral psoralen-UV-A with a portable tanning unit at home vs hospital-administered bath psoralen-UV-A in patients with chronic hand eczema: an open-label randomized controlled trial of efficacy. Arch Dermatol. 2004 Dec;140(12):1463-6. [Pubmed] ; Thazhathveetil AK, Liu ST, Indig FE, Seidman MM: Psoralen conjugates for visualization of genomic interstrand cross-links localized by laser photoactivation. Bioconjug Chem. 2007 Mar-Apr;18(2):431-7. [Pubmed] ; Higuchi M, Yamayoshi A, Kobori A, Yamaoka T, Murakami A: Synthesis and properties of photo-reactive antisense oligonucleotides containing 2'-O-psoralen-conjugated adenosine. Nucleic Acids Symp Ser (Oxf). 2005;(49):331-2. [Pubmed]
• External Links: Wikipedia; Drugs.com

Selleck Chemicals - S2022

Research Area: Immunology
Biological Activity:
Trioxsalen(Trisoralen) is a furanocoumarin and a psoralen derivative. It is obtained from several plants, mainly Psoralea corylifolia. Like other psoralens it causes photosensitization of the skin. It is administered either topically or orally in conjunction with UV-A (the least damaging form of ultraviolet light) for phototherapy treatment of vitiligo and hand eczema. After photoactivation it creates interstrand cross-links in DNA, which can cause programmed cell death unless repaired by cellular mechanisms. In research it can be conjugated to dyes for confocal microscopy and used to visualize sites of DNA damage. The compound is also being explored for development of antisense oligonucleotides that can be cross-linked specifically to a mutant mRNA sequence without affecting normal transcripts differing at even a single base pair. [1]

Sigma Aldrich - T6137

包装
1 g in glass bottle
100, 500 mg in glass bottle
Biochem/physiol Actions
DNA 的光化学交联剂，可作为探针用于核酸结构和功能研究。三甲沙林也用于使 DNA 在云母表面交联。

Sigma Aldrich - 861391

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.

Sigma Aldrich - 92895

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.

REFERENCES

• van Coevorden AM, Kamphof WG, van Sonderen E, Bruynzeel DP, Coenraads PJ: Comparison of oral psoralen-UV-A with a portable tanning unit at home vs hospital-administered bath psoralen-UV-A in patients with chronic hand eczema: an open-label randomized controlled trial of efficacy. Arch Dermatol. 2004 Dec;140(12):1463-6. Pubmed
• Thazhathveetil AK, Liu ST, Indig FE, Seidman MM: Psoralen conjugates for visualization of genomic interstrand cross-links localized by laser photoactivation. Bioconjug Chem. 2007 Mar-Apr;18(2):431-7. Pubmed
• Higuchi M, Yamayoshi A, Kobori A, Yamaoka T, Murakami A: Synthesis and properties of photo-reactive antisense oligonucleotides containing 2'-O-psoralen-conjugated adenosine. Nucleic Acids Symp Ser (Oxf). 2005;(49):331-2. Pubmed
• http://en.wikipedia.org/wiki/Trioxsalen
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 684C, (ir)
• Kaufman, K.D., J.O.C., 1961, 26, 117; 1980, 45, 738, (synth, uv)
• Scheel, L.D. et al., Biochemistry, 1963, 2, 1127, (isol)
• Caporale, G. et al., Experientia, 1967, 23, 985, (pharmacol)
• Bender, D.R. et al., J.O.C., 1979, 44, 2176, (synth)
• Elgamal, M.H.A. et al., Phytochemistry, 1979, 18, 139, (cmr)
• Taskineu, J. et al., Biomed. Mass Spectrom., 1980, 7, 556, (ms)
• Hassan, M.A., Anal. Profiles Drug Subst., 1981, 10, 705, (rev)
• Russev, G. et al., J. Mol. Biol., 1982, 161, 77, (pharmacol)
• Thompson, H.J. et al., J. Chromatogr., 1984, 314, 323, (hplc)
• IARC Monog., 1986, 40, 357; Suppl. 7, 366; Suppl. 6, 541, (rev, tox)
• Dimitrova, D. et al., Nucleic Acids Res., 1993, 21, 5554, (pharmacol)
• Nivsarkar, M. et al., Biochem. Mol. Biol. Int., 1996, 38, 625, (pharmacol)
• Gencheva, M. et al., J. Biol. Chem., 1996, 271, 2608, (pharmacol)
• Martindale, The Extra Pharmacopoeia, 31st edn., Pharmaceutical Press, 1996, 1098