Temoporfin

• CAT Number: I000860
• CAS Number: 122341-38-2
• Molecular Formula: C44H32N4O4
• Molecular Weight: 680.8
• Purity: ≥95%
• Synonyms: Foscan;KW 2345;m-THPC;KW2345
• Solubility: DMSO: ≥ 30 mg/mL
• Storage: -20°C
• IUPAC Name: 3-[10,15,20-tris(3-hydroxyphenyl)-2,3,22,24-tetrahydroporphyrin-5-yl]phenol
• InChI: InChI=1S/C44H32N4O4/c49-29-9-1-5-25(21-29)41-33-13-15-35(45-33)42(26-6-2-10-30(50)22-26)37-17-19-39(47-37)44(28-8-4-12-32(52)24-28)40-20-18-38(48-40)43(36-16-14-34(41)46-36)27-7-3-11-31(51)23-27/h1-17,19,21-24,46-47,49-52H,18,20H2
• InChIKey: LYPFDBRUNKHDGX-LWQDQPMZSA-N
• SMILES: C1CC2=NC1=C(C3=CC=C(N3)C(=C4C=CC(=N4)C(=C5C=CC(=C2C6=CC(=CC=C6)O)N5)C7=CC(=CC=C7)O)C8=CC(=CC=C8)O)C9=CC(=CC=C9)O

Temoporfin (CAT: I000860), also known as KW 2345, is a photosensitizing agent used in photodynamic therapy (PDT) for the treatment of squamous cell carcinoma of the head and neck. It belongs to the class of porphyrin derivatives known as second-generation photosensitizers. When activated by light of a specific wavelength, Temoporfin produces reactive oxygen species that can selectively destroy cancer cells. By targeting and destroying cancerous tissue, Temoporfin-based PDT offers a localized and minimally invasive treatment option for patients with squamous cell carcinoma of the head and neck.

Reference

1:Glycol porphyrin derivatives and temoporfin elicit resistance to photodynamic therapy by different mechanisms. Kralova J, Kolar M, Kahle M, Truksa J, Lettlova S, Balusikova K, Bartunek P.Sci Rep. 2017 Mar 15;7:44497. doi: 10.1038/srep44497. PMID: 28295025 Free PMC Article
2:Temoporfin-loaded 1-tetradecanol-based thermoresponsive solid lipid nanoparticles for photodynamic therapy. Brezaniova I, Hruby M, Kralova J, Kral V, Cernochova Z, Cernoch P, Slouf M, Kredatusova J, Stepanek P.J Control Release. 2016 Nov 10;241:34-44. doi: 10.1016/j.jconrel.2016.09.009. Epub 2016 Sep 10. PMID: 27622757
3:Intradermal drug delivery by nanogel-peptide conjugates; specific and efficient transport of temoporfin. Zabihi F, Wieczorek S, Dimde M, Hedtrich S, Börner HG, Haag R.J Control Release. 2016 Nov 28;242:35-41. doi: 10.1016/j.jconrel.2016.07.033. Epub 2016 Jul 25. PMID: 27469470
4:Online dosimetry for temoporfin-mediated interstitial photodynamic therapy using the canine prostate as model. Swartling J, Höglund OV, Hansson K, Södersten F, Axelsson J, Lagerstedt AS.J Biomed Opt. 2016 Feb;21(2):28002. doi: 10.1117/1.JBO.21.2.028002. PMID: 26886806
5:Randomised controlled trial of temoporfin photodynamic therapy plus chemotherapy in nonresectable biliary carcinoma–PCS Nordic study. Hauge T, Hauge PW, Warloe T, Drolsum A, Johansen C, Viktil E, Aabakken L, Buanes T, Konopski Z.Photodiagnosis Photodyn Ther. 2016 Mar;13:330-3. doi: 10.1016/j.pdpdt.2015.09.004. Epub 2015 Sep 28. PMID: 26415549
6:Temoporfin photodynamic therapy in advanced hilar ductal carcinoma: A promising endoscopic modality. Kumta NA, DeRoche K, Kahaleh M.Hepatology. 2015 Nov;62(5):1342-3. doi: 10.1002/hep.28021. Epub 2015 Sep 1. No abstract available. PMID: 26235213
7:Lead Structures for Applications in Photodynamic Therapy. 6. Temoporfin Anti-Inflammatory Conjugates to Target the Tumor Microenvironment for In Vitro PDT. Rogers L, Sergeeva NN, Paszko E, Vaz GM, Senge MO.PLoS One. 2015 May 19;10(5):e0125372. doi: 10.1371/journal.pone.0125372. eCollection 2015. PMID: 25992651 Free PMC Article
8:Temoporfin improves efficacy of photodynamic therapy in advanced biliary tract carcinoma: A multicenter prospective phase II study. Wagner A, Denzer UW, Neureiter D, Kiesslich T, Puespoeck A, Rauws EA, Emmanuel K, Degenhardt N, Frick U, Beuers U, Lohse AW, Berr F, Wolkersdörfer GW.Hepatology. 2015 Nov;62(5):1456-65. doi: 10.1002/hep.27905. Epub 2015 Jul 22. PMID: 25990106
9:Chemical modification of temoporfin–a second generation photosensitizer activated using upconverting nanoparticles for singlet oxygen generation. Yu Q, Rodriguez EM, Naccache R, Forgione P, Lamoureux G, Sanz-Rodriguez F, Scheglmann D, Capobianco JA.Chem Commun (Camb). 2014 Oct 18;50(81):12150-3. doi: 10.1039/c4cc05867d. PMID: 25174720
10:Photodynamic therapy with conventional and PEGylated liposomal formulations of mTHPC (temoporfin): comparison of treatment efficacy and distribution characteristics in vivo. Reshetov V, Lassalle HP, François A, Dumas D, Hupont S, Gräfe S, Filipe V, Jiskoot W, Guillemin F, Zorin V, Bezdetnaya L.Int J Nanomedicine. 2013;8:3817-31. doi: 10.2147/IJN.S51002. Epub 2013 Oct 8. PMID: 24143087 Free PMC Article