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Trioxsalen

Alias: NSC71047 NSC 71047 NSC-71047
Cat No.:V6425 Purity: ≥98%
Trioxsalen (Trisoralen) is an analogue of psoralen.
Trioxsalen
Trioxsalen Chemical Structure CAS No.: 3902-71-4
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
250mg
500mg
Other Sizes
Official Supplier of:
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Product Description
Trioxsalen (Trisoralen) is an analogue of psoralen. Trioxsalen is a photochemical DNA cross-linker that only works when activated by near-UV light. Trioxsalen is a photosensitizer utilized in the research on vitiligo and hand eczema. Trioxsalen may be utilized to visualize laser-activated localized genomic interstrand cross-links.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
In mouse L1210 leukemia cells, trichomsalen (200 nM) combined with 365 nm light causes DNA cross-links but not breaks [4]. A synergistic effect of treating HaCaT keratinocytes with trioxsalen and UVA is the induction of NF-kappaB binding activity [5]. In vitro, trichsalen has demonstrated anti-inflammatory properties [5].
ln Vivo
In rat oral mucosa (OMM), doxsalen induces dose-dependent depletion of ATPase-positive LC using PUVA (UVA dose of 1-8 J/cm2), with a maximum depletion of 80% [3].
References

[1]. Effectiveness of psoralen photochemotherapy for vitiligo. J Formos Med Assoc. 1999 May;98(5):335-40.

[2]. 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. 200.

[3]. 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.

[4]. 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.

[5]. 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.

Additional Infomation
Trioxsalen is a 7H-furan[3,2-g]chromen-7-one with methyl groups at positions 2, 5, and 9. Like other psoralen compounds, trioxsalen causes photosensitivity in the skin. It is used orally in combination with UV-A for phototherapy of vitiligo. Upon photoactivation, it forms interstrand crosslinks in DNA, inhibiting DNA synthesis and cell division, and may cause cell damage; after cell damage heals, epidermal melanin deposition may increase. It is both a photosensitizer and a dermatological drug. Trioxsalen (trimethylpsoralen, trioxsalen, or tripsoralen) is a furanocoumarin compound and a psoralen derivative extracted from various plants (primarily psoralen). Like other psoralen compounds, it causes photosensitivity in the skin. It can be administered topically or orally and in combination with UV-A (the least damaging form of ultraviolet radiation) for phototherapy of vitiligo and hand eczema. The photoactivated form creates interstrand crosslinks in DNA, leading to apoptosis. In studies, it can be combined with confocal microscopy dyes for visualization of DNA damage sites. [3] This compound has been used to develop antisense oligonucleotides that can specifically crosslink with mutant mRNA sequences without affecting normal transcripts even if there is only one base pair different.
Trioxalin is a psoralen.
Trioxalin has been reported to be found in celery (Apium graveolens), and there is relevant data.
A pigment photosensitizer extracted from a variety of plants, primarily Psoralea corylifolia. It can be administered topically or orally and in combination with ultraviolet light for the treatment of vitiligo.
Drug Indications
Trioxalin is a pigment photosensitizer used in combination with ultraviolet light for the treatment of vitiligo.
Mechanism of Action
Upon photoactivation, it forms interstrand crosslinks in DNA, leading to programmed cell death.
Pharmacodynamics
Trioxazone itself has no pharmacological activity, but when exposed to ultraviolet light or sunlight, it is converted into its active metabolites, which can have a beneficial effect on diseased tissues.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Exact Mass
228.078
CAS #
3902-71-4
PubChem CID
5585
Appearance
White to off-white solid powder
Density
1.2±0.1 g/cm3
Boiling Point
389.0±30.0 °C at 760 mmHg
Melting Point
229-231ºC(lit.)
Flash Point
189.1±24.6 °C
Vapour Pressure
0.0±0.9 mmHg at 25°C
Index of Refraction
1.613
LogP
3.8
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
0
Heavy Atom Count
17
Complexity
374
Defined Atom Stereocenter Count
0
SMILES
O1C(C([H])([H])[H])=C([H])C2=C([H])C3C(C([H])([H])[H])=C([H])C(=O)OC=3C(C([H])([H])[H])=C12
InChi Key
FMHHVULEAZTJMA-UHFFFAOYSA-N
InChi Code
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
Chemical Name
2,5,9-trimethylfuro[3,2-g]chromen-7-one
Synonyms
NSC71047 NSC 71047 NSC-71047
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~6.6 mg/mL (~28.92 mM)
H2O : ~1 mg/mL (~4.38 mM)
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
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  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
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  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT03727061 RECRUITING Biological: Nivolumab
Drug: Porfimer Sodium
Procedure: Interstitial Illumination Photodynamic Therapy
Other: Quality of Life Assessment
Locally Advanced Head and Neck Carcinoma
Recurrent Head and Neck Carcinoma
Roswell Park Cancer Institute 2019-07-10 Phase 1
NCT03344861 COMPLETEDWITH RESULTS Drug: Porfimer Sodium
Device: Fiber optic
Lung Cancer
Lung Cancer Metastatic
Concordia Laboratories Inc 2017-08-14 Phase 1
NCT04425746 COMPLETEDWITH RESULTS Drug: Afamelanotide
Drug: Placebo
Patients Undergoing Photodynamic Therapy
Using Porfimer Sodium
Clinuvel Pharmaceuticals Limited 2008-08-05 Phase 2
NCT02082522 TERMINATEDWITH RESULTS Drug: Photodynamic therapy-Photofrin
Procedure: Stenting procedure
Drug: Chemotherapy regimen
Hilar Cholangiocarcinoma Concordia Laboratories Inc 2014-11-12 Phase 3
NCT00118222 COMPLETED Drug: porfimer sodium
Procedure: adjuvant therapy
Procedure: conventional surgery
Brain and Central Nervous System Tumors Case Comprehensive Cancer Center 2005-03 Phase 3
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