Methoxsalen

SKU: orb2281208

Description

Methoxsalen is a psoralen-based small molecule that acts as a photosensitizer, generating reactive species upon photoactivation with UVA light. It is widely used in research applications such as studying DNA intercalation, crosslinking (in vitro), and in photochemotherapy (PUVA) models for dermatological conditions (in vivo).

Research Area

Metabolism Research, Molecular Biology

Key Properties

• CAS Number: 298-81-7
• MW: 216.19
• Purity: 99.86%
• Formula: C₁₂H₈O₄
• SMILES: COc1c2occc2cc2ccc(=O)oc12
• Target: Cytochromes P450,DNA
• Solubility: H2O:< 1 mg/mL (insoluble or slightly soluble);10% DMSO+40% PEG300+5% Tween 80+45% Saline:2 mg/mL (9.25 mM);DMSO:51 mg/mL (235.9 mM);Ethanol:5 mg/mL (23.13 mM)

Bioactivity

• In Vivo:
  Methoxsalen results in a significant decrease in the following factors: number and diameter of corpus lutei, Graafian follicles, diameter of granulosa cell layer and oocytes, number of primordial and primary and growing follicles, while the number of atretic follicle is increased. Methoxsalen also significantly reduces circulating estrogen levels in blood serum of oogenesis Balb/C mice. Methoxsalen dose-dependently stimulates a sustained increase in short-circuit current in the mouse jejunum. Methoxsalen increases the open probability of the basolateral IK(Ca) channel of isolated crypts in the mouse jejunum. Methoxsalen effectively reverses trimethyltin (TMT)-induced memory impairment on both Y-maze and passive avoidance tests in mice. Methoxsalen inhibits brain AchE activity. Methoxsalen significantly ameliorates the level of oxidative stress.
• In Vitro:
  Methoxsalen inhibits CYP2A6 (Ki = 0.8 μM) with about 3.5- 94-fold greater potency than other P450s, except for CYP1A2 (Ki = 0.2 μM). Methoxsalen shows noncompetitive inhibition of nicotine metabolism, with an apparent Ki value of 0.1 μM in cDNA-expressing microsomes. Methoxsalen is metabolized in human liver microsomes at the rate of 50-100 pmol/mg protein/min (approx. 30% of the activity in mouse liver microsomes). Methoxsalen is a very potent inhibitor of human cytochrome P450 2A6 (CYP2A6) and mouse Cyp2a-5-mediated coumarin 7-hydroxylation in vitro.

Storage & Handling

• Storage: Powder: -20°C for 3 years | In solvent: -80°C for 1 year | Shipping with blue ice/Shipping at ambient temperature.
• Expiration Date: 12 months from date of receipt.
• Disclaimer: For research use only

Alternative Names

CYPs, Cytochrome P450, DNA, 8-MOP, 8-Methoxypsoralen, NCI-C 55903, NCI-C55903, NCI-C-55903, Methoxsalen, inhibit, Inhibitor, Xanthotoxin

Compound Identifiers

PubChem CID

4114