MedKoo Cat#: 466238 | Name: Phototrexate
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Phototrexate is a photoswitchable potent inhibitor of human dihydrofolate reductase (DHFR). Phototrexate is a photochromic analog of Methotrexate. 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).

Chemical Structure

Phototrexate
Phototrexate
CAS#2268033-83-4

Theoretical Analysis

MedKoo Cat#: 466238

Name: Phototrexate

CAS#: 2268033-83-4

Chemical Formula: C20H19N7O5

Exact Mass: 437.1448

Molecular Weight: 437.42

Elemental Analysis: C, 54.92; H, 4.38; N, 22.42; O, 18.29

Price and Availability

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5mg USD 700.00 2 Weeks
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Related CAS #
No Data
Synonym
Phototrexate;
IUPAC/Chemical Name
(E)-(4-((2,4-diaminoquinazolin-6-yl)diazenyl)benzoyl)-L-glutamic acid
InChi Key
IODLJULYGHWOLC-HIUCBWPRSA-N
InChi Code
InChI=1S/C20H19N7O5/c21-17-13-9-12(5-6-14(13)24-20(22)25-17)27-26-11-3-1-10(2-4-11)18(30)23-15(19(31)32)7-8-16(28)29/h1-6,9,15H,7-8H2,(H,23,30)(H,28,29)(H,31,32)(H4,21,22,24,25)/b27-26+/t15-/m0/s1
SMILES Code
NC1=NC2=C(C=C(C=C2)/N=N/C3=CC=C(C=C3)C(N[C@@H](CCC(O)=O)C(O)=O)=O)C(N)=N1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

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.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Siddique F, Anwaar A, Bashir M, Nadeem S, Rawat R, Eyupoglu V, Afzal S, Bibi M, Bin Jardan YA, Bourhia M. Revisiting methotrexate and phototrexate Zinc15 library-based derivatives using deep learning in-silico drug design approach. Front Chem. 2024 Mar 21;12:1380266. doi: 10.3389/fchem.2024.1380266. PMID: 38576849; PMCID: PMC10991842. 2: Liang R, Bakhtiiari A. Multiscale simulation unravels the light-regulated reversible inhibition of dihydrofolate reductase by phototrexate. J Chem Phys. 2022 Jun 28;156(24):245102. doi: 10.1063/5.0096349. PMID: 35778097. 3: Liang R, Bakhtiiari A. Effects of Enzyme-Ligand Interactions on the Photoisomerization of a Light-Regulated Chemotherapeutic Drug. J Phys Chem B. 2022 Mar 31;126(12):2382-2393. doi: 10.1021/acs.jpcb.1c10819. Epub 2022 Mar 17. PMID: 35297246. 4: Preisz Z, Nagymihály Z, Kollár L, Kálai T, Kunsági-Máté S. Weak Interactions of the Isomers of Phototrexate and Two Cavitand Derivatives. Int J Mol Sci. 2021 Oct 5;22(19):10764. doi: 10.3390/ijms221910764. PMID: 34639104; PMCID: PMC8509358. 5: Preisz Z, Hartvig N, Bognár B, Kálai T, Kunsági-Máté S. Comparative EPR Study on the Scavenging Effect of Methotrexate with the Isomers of Its Photoswitchable Derivative. Pharmaceuticals (Basel). 2021 Jul 11;14(7):665. doi: 10.3390/ph14070665. PMID: 34358091; PMCID: PMC8308517. 6: Mulatihan D, Guo T, Zhao Y. Azobenzene Photoswitch for Isomerization- Dependent Cancer Therapy via Azo-Combretastatin A4 and Phototrexate. Photochem Photobiol. 2020 Nov;96(6):1163-1168. doi: 10.1111/php.13292. Epub 2020 Jul 6. PMID: 32521572. 7: Matera C, Gomila AMJ, Camarero N, Libergoli M, Soler C, Gorostiza P. Photoswitchable Antimetabolite for Targeted Photoactivated Chemotherapy. J Am Chem Soc. 2018 Nov 21;140(46):15764-15773. doi: 10.1021/jacs.8b08249. Epub 2018 Oct 22. PMID: 30346152.