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Description: Photoswitchable inhibitor of human dihydrofolate reductase
Chemical Name: N-[4-[(1E)-2-(2,4-Diamino-6-quinazolinyl)diazenyl]benzoyl]-L-glutamic acid
Purity: ≥95% (HPLC)

Biological Activity for Phototrexate

Phototrexate is a photoswitchable potent inhibitor of human dihydrofolate reductase (DHFR). Phototrexate is a photochromic analog of Methotrexate (Cat. No. 1230). Antifolate activity is switched on (cis-Phototrexate) by UVA (375 nm) light; it can be switched off (trans-Phototrexate) by blue or white light and by thermal relaxation in the dark. cis-Phototrexate (IC50 = 6 nM) significantly reduces the viability of HeLa cells compared with trans-Phototrexate (IC50 = 34 μM).

Scientific Data

Photoswitching activity of Phototrexate Antifolate activity is switched on (cis-Phototrexate) by UVA (375 nm) light; it can be switched off (trans-Phototrexate) by blue or white light and by thermal relaxation in the dark.

Licensing Information

Sold with permission of IBEC.

Technical Data for Phototrexate

M. Wt 437.42
Formula C20H19N7O5
Storage Store at -20°C
Purity ≥95% (HPLC)
CAS Number 2268033-83-4
PubChem ID 142608675
Smiles NC1=NC2=C(C(N)=N1)C=C(/N=N/C3=CC=C(C(N[C@H](C(O)=O)CCC(O)=O)=O)C=C3)C=C2

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility Data for Phototrexate

Solvent Max Conc. mg/mL Max Conc. mM
DMSO 1.75 4

Preparing Stock Solutions for Phototrexate

The following data is based on the product molecular weight 437.42. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
0.04 mM 57.15 mL 285.77 mL 571.53 mL
0.2 mM 11.43 mL 57.15 mL 114.31 mL
0.4 mM 5.72 mL 28.58 mL 57.15 mL
2 mM 1.14 mL 5.72 mL 11.43 mL

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References for Phototrexate

References are publications that support the biological activity of the product.

Matera et al (2018) Photoswitchable antimetabolite for targeted photoactivated chemotherapy. J.Am.Chem.Soc. 140 15764 PMID: 30346152

Mashita et al (2019) Light-wavelength-based quantitative control of dihydrofolate reductase activity by using a photochromic isostere of an inhibitor. Chembiochem. 20 1382 PMID: 30656808

If you know of a relevant reference for Phototrexate, please let us know.

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Citations for Phototrexate

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