Phototrexate

*trans*-Phototrexate
Clinical data
ATC code	None;
Identifiers
	IUPAC name (2S)-2-[(4-[(2,4-Diaminoquinazolin-6-yl)diazenyl]benzoyl)amino]pentanedioic acid;
Chemical and physical data
Formula	C20H19N7O5
Molar mass	437.416 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1(=NC(=NC2=C1C=C(C=C2)N=NC3=CC=C(C=C3)C(=O)N[C@@H](CCC(=O)O)C(=O)O)N)N;
	InChI 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)/t15-/m0/s1; Key:IODLJULYGHWOLC-HNNXBMFYSA-N;

Phototrexate (TM pending) is a brand that distinguishes a photochromic antifolate developed at the Institute for Bioengineering of Catalonia (IBEC, The Barcelona Institute of Science and Technology). In particular, it is a photopharmacological agent^[1]^[2] that behaves as light-regulated inhibitor of the dihydrofolate reductase (DHFR).^[3]^[4] Phototrexate is a photoisomerizable structural analogue of the chemotherapy agent methotrexate. Pharmacological effects of phototrexate can be switched on and off by UVA and visible light, respectively. Phototrexate is almost inactive in its trans configuration while it behaves as a potent antifolate in its cis configuration. It can also spontaneously self-deactivate in the dark.

References

^ Velema, Willem A.; Szymanski, Wiktor; Feringa, Ben L. (2014). "Photopharmacology: Beyond Proof of Principle". Journal of the American Chemical Society. 136 (6): 2178–2191. doi:10.1021/ja413063e. ISSN 0002-7863. PMID 24456115.
^ Broichhagen, Johannes; Frank, James Allen; Trauner, Dirk (2015). "A Roadmap to Success in Photopharmacology". Accounts of Chemical Research. 48 (7): 1947–1960. doi:10.1021/acs.accounts.5b00129. ISSN 0001-4842. PMID 26103428.
^ Matera, Carlo; Gomila, Alexandre M. J.; Camarero, Núria; Libergoli, Michela; Soler, Concepció; Gorostiza, Pau (2018). "Photoswitchable Antimetabolite for Targeted Photoactivated Chemotherapy". Journal of the American Chemical Society. 140 (46): 15764–15773. doi:10.1021/jacs.8b08249. hdl:2445/126377. ISSN 0002-7863.
^ Mashita, Takato; Kowada, Toshiyuki; Takahashi, Hiroto; Matsui, Toshitaka; Mizukami, Shin (2019). "Light‐Wavelength‐Based Quantitative Control of Dihydrofolate Reductase Activity by Using a Photochromic Isostere of an Inhibitor". ChemBioChem. 20 (11): 1382–1386. doi:10.1002/cbic.201800816. ISSN 1439-4227. PMID 30656808.

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