Misplaced Pages

Phototrexate

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Photopharmacological agent Pharmaceutical compound
trans-Phototrexate
Clinical data
ATC code
  • None
Identifiers
IUPAC name
  • (2S)-2-benzoyl)amino]pentanedioic acid
CAS Number
PubChem CID
Chemical and physical data
FormulaC20H19N7O5
Molar mass437.416 g·mol
3D model (JSmol)
SMILES
  • C1(=NC(=NC2=C1C=C(C=C2)N=NC3=CC=C(C=C3)C(=O)N(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 is a photochromic antifolate drug developed at the Institute for Bioengineering of Catalonia (IBEC, The Barcelona Institute of Science and Technology). In particular, it is a photopharmacological agent that behaves as light-regulated inhibitor of the dihydrofolate reductase (DHFR) enzyme. Phototrexate is a photoisomerizable structural analogue of the chemotherapy agent methotrexate. It is also an example of "azologization". 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.

cis-Phototrexate

See also

References

  1. Velema WA, Szymanski W, Feringa BL (February 2014). "Photopharmacology: beyond proof of principle". Journal of the American Chemical Society. 136 (6): 2178–91. doi:10.1021/ja413063e. hdl:11370/d6714f52-c2c8-4e48-b345-238e98bcc776. PMID 24456115.
  2. Broichhagen J, Frank JA, Trauner D (July 2015). "A roadmap to success in photopharmacology". Accounts of Chemical Research. 48 (7): 1947–60. doi:10.1021/acs.accounts.5b00129. PMID 26103428.
  3. Matera C, Gomila AM, Camarero N, Libergoli M, Soler C, Gorostiza P (November 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. PMID 30346152.
  4. Mashita T, Kowada T, Takahashi H, Matsui T, Mizukami S (June 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. PMID 30656808. S2CID 58567138.
  5. Schoenberger M, Damijonaitis A, Zhang Z, Nagel D, Trauner D (July 2014). "Development of a new photochromic ion channel blocker via azologization of fomocaine". ACS Chemical Neuroscience. 5 (7): 514–8. doi:10.1021/cn500070w. PMC 4102962. PMID 24856540.

External links

Stub icon

This antineoplastic or immunomodulatory drug article is a stub. You can help Misplaced Pages by expanding it.

Categories: