Trioxsalen

• CAT Number: I003433
• CAS Number: 3902-71-4
• Molecular Formula: C14H12O3
• Molecular Weight: 228.24
• Purity: ≥95%
• Synonyms: 2,5,9-trimethylfuro[3,2-g]chromen-7-one
• 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
• SMILES: CC1=CC(=O)OC2=C1C=C3C=C(OC3=C2C)C

Trioxsalen (Trisoralen), a psoralen derivative, is a photochemical DNA crosslinker. Trioxsalen only works after photoactivation with near ultraviolet light. Trioxsalen is a photosensitizer that can be used for the research of vitiligo and hand eczema. Trioxsalen is used for visualization of genomic interstrand cross-links localized by laser photoactivation[1][2][3].
Trioxsalen (200 nM) plus 365 nm light produce DNA crosslinks but not breaks in mouse L1210 leukemia cells[4].
Trioxsalen/UVA treatment of HaCaT keratinocytes induces NF-kappaB binding activity, and that this is a synergistic effect[5].
Trioxsalen shows anti-inflammatory capacities in vitro[5].
Trioxsalen induces dose-dependent depletion of ATPase-positive LCs, with a maximal depletion of 80%, in oral mucous membrane (OMM) with PUVA (UVA doses of 1-8 J/cm2) in rat[3].

Reference

[1]. M T Chuan, et al. Effectiveness of psoralen photochemotherapy for vitiligo. J Formos Med Assoc. 1999 May;98(5):335-40.
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[2]. A Marco van Coevorden, et al. 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.
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[3]. A Kuusilehto, et al. The effect of PUVA on langerhans cells in rat oral epithelium photosensitized with systemic methoxsalen or topical trioxsalen. Photodermatol Photoimmunol Photomed. 2000 Jun;16(3):129-33.
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[4]. L F Cohen, et al. Interstrand DNA crosslinking by 4,5’8-trimethylpsoralen plus monochromatic ultraviolet light. Studies by alkaline elution in mouse L1210 leukemia cells. Biochim Biophys Acta. 1980 Nov 14;610(1):56-63.
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[5]. H Sánchez Ruderisch, et al. Trioxsalen in the presence of UVA is able to induce nuclear factor kappa B binding activity in HaCaT keratinocytes. Skin Pharmacol Appl Skin Physiol. Sep-Oct 2002;15(5):335-41.
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