Temoporfin

Base Information

• Chemical Name: Temoporfin
• CAS No.: 122341-38-2
• Molecular Formula: C₄₄H₃₂N₄O₄
• Molecular Weight: 680.762
• Mol file: 122341-38-2.mol

Synonyms:3,3',3'',3'''-(7,8-Dihydroporphyrin-5,10,15,20-tetrayl)tetraphenol;5,10,15,20-Tetra(m-hydroxyphenyl)chlorin;5,10,15,20-Tetrakis(m-hydroxyphenyl)chlorin;8-Dihydroporphyrin-5;EF 9;Foscan;Fosgel;Foslip;Fospeg;mTHPC;

Chemical Property of Temoporfin

Chemical Property:

• Melting Point: >250 °C
• Refractive Index: 1.734
• PSA: 137.22000
• Density: 1.386 g/cm³
• LogP: 5.91260
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

Temoporfin,~90% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Temoporphin, a second generation photosensitizer, was launched in UK for the photodynamic therapy (PDT) of advanced head and neck cancers. This porphyrin derivative can be synthesized from pyrrole and 3-hydroxybenzaldehyde. The pharmacological activity is initiated, 4 days after intravenous injection, by laser-light photoactivation of temoporphin, that has selectively accumulated in cancer tissues. The resulting generation of highly reactive oxygen species leads to malignant cells death thereby inducing tumor necrosis up to a depth of 15 mm. An advantage of temoporphin over other photosensitizing agents is its extreme sensitivity to wavelengths of light that penetrate tissues, resulting in lower light/dose and irradiation time. PDT with intravenous temoporphin has produced relatively high complete and partial response rates in head and neck cancers, with higher response rates generally observed with higher light dose. Temoporphin is well-tolerated and does not preclude surgery/radiotherapy as a later option. Adverse effects were photosensitivity and pain at the injection site.
• Uses: Temoporfin is a synthetic chlorin with light-activated actions. It accumulates in tumor cells and through light activation and oxygen radical formation, it leads to necrosis and cell death. Temoporfin is a synthetic chlorin with light-activated actions. When administered systemically, temoporfin accumulates in tumor cells. When stimulated with light (650-652 nm) in the presence of oxygen, reactive oxygen species are generated, leading to necrosis within the tumor. Different approaches to using photodynamic therapy with temoporfin in palliative care are currently of interest.

Technology Process of Temoporfin

There total 5 articles about Temoporfin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 60.0%

meso-5,10,15,20-tetra(3-hydroxyphenyl)porphine (22112-79-4) → temoporfin (122341-38-2)

Guidance literature:

meso-5,10,15,20-tetra(3-hydroxyphenyl)porphine; With toluene-4-sulfonic acid hydrazide; at 140 ℃; for 0.25h; Inert atmosphere; Schlenk technique;

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; Inert atmosphere;

DOI:10.1002/chem.201304202

Reference yield:

methanol (67-56-1) + Temoporfin → Succinimide (123-56-8,89963-74-6) + methyl 3-hydroxybenzoate (19438-10-9) + temoporfin (122341-38-2) + 7,8-dihydro-1,9-bis(3-hydroxybenzoyl)-5-(3-hydroxyphenyl)pyrromethene

Guidance literature:

With air; In methanol; for 5.3h; Product distribution; Photolysis;

DOI:10.1021/ol025842c

Reference yield:

meso-5,10,15,20-tetra(3-hydroxyphenyl)porphine (22112-79-4) → temoporfin (122341-38-2) + Temoporfin

Guidance literature:

With potassium carbonate; toluene-4-sulfonic acid hydrazide; In 1,4-dioxane; at 120 ℃; for 0.416667h; Microwave irradiation; Sealed vessel;

DOI:10.1016/j.inoche.2009.12.032

upstream raw materials:

methanol

meso-5,10,15,20-tetra(3-hydroxyphenyl)porphine

meta-hydroxybenzaldehyde

Refernces

• 1、 Arnaut, Luis G.,Pereira, Mariette M.,Dabrowski, Janusz M.,Silva, Elsa F. F.,Schaberle, Fabio A.,Abreu, Artur R.,Rocha, Luis B.,Barsan, Madalina M.,Urbanska, Krystyna,Stochel, Grazyna,Brett, Christopher M. A.. "Photodynamic therapy efficacy enhanced by dynamics: The role of charge transfer and photostability in the selection of photosensitizers". . p. 5346 - 5357. Retrieved 2014.