| Size | Price | |
|---|---|---|
| 1mg | ||
| 5mg | ||
| 10mg | ||
| Other Sizes |
| Targets |
The primary molecular target of fimaporfin is not a specific receptor or enzyme but rather endosomal and lysosomal membranes. Fimaporfin incorporates into these membranes and, upon light activation, produces ROS such as singlet oxygen. This causes photochemical disruption of the membranes, enabling release of co-administered therapeutic agents from endocytic vesicles into the cytosol.
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|---|---|
| ln Vitro |
Using the drug delivery method photochemical internalization (PCI) [1], the endosome/lysosomally localized photosensitizer fimaporfin (0.35 μg/ml) is combined with medicines that are often confined in endosomes and/or lysosomes.
In vitro, fimaporfin at 0.35 μg/mL is used in PCI to enhance delivery of agents trapped in endosomes and lysosomes. PCI with fimaporfin enhances the effect of bleomycin in head and neck squamous cell carcinoma cells. It also enhances gemcitabine efficacy in cholangiocarcinoma cells. The compound shows fluorescence excitation at 420 nm and emission at 640-680 nm. |
| ln Vivo |
In vivo, fimaporfin-mediated PCI enhances bleomycin treatment in head and neck cancer models. It improves the efficacy of gemcitabine in cholangiocarcinoma models. The PCI technology uses fimaporfin to release cytotoxic agents from endo/lysosomal compartments into the tumor cell cytosol upon light activation, potentially reducing systemic toxicity while enhancing local antitumor activity.
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| Enzyme Assay |
For endosomal/lysosomal localization assays, cells are incubated with fimaporfin (0.35 μg/mL) and fluorescently labeled dextran or therapeutic agents. Colocalization with endosomal/lysosomal markers (e.g., LysoTracker) is assessed by fluorescence microscopy. For ROS generation assays, cells are loaded with ROS-sensitive probes (e.g., DCFH-DA) and irradiated at 420 nm, and fluorescence is measured.
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| Cell Assay |
For PCI-based cytotoxicity assays, cells are treated with fimaporfin (0.35 μg/mL) and a cytotoxic agent (e.g., bleomycin, gemcitabine). After incubation, cells are irradiated at 420 nm for defined periods. Cell viability is assessed by MTT or clonogenic assays. Drug release from endo/lysosomes is assessed by fluorescence microscopy or subcellular fractionation.
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| Animal Protocol |
For in vivo studies, tumor-bearing mice are injected with fimaporfin and a cytotoxic agent. After allowing for tumor accumulation, the tumor area is irradiated with light at 420 nm. Tumor growth is monitored by caliper measurement. At sacrifice, tumors are harvested for histopathological analysis of necrosis and apoptosis. Pharmacokinetic studies determine plasma and tissue concentrations of fimaporfin.
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| References |
[1]. Kaja Lund, et al. 5-FU resistant EMT-like pancreatic cancer cells are hypersensitive to photochemical internalization of the novel endoglin-targeting immunotoxin CD105-saporin. J Exp Clin Cancer Res. 2017 Dec 19;36(1):187.
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| Additional Infomation |
Fimaporfin is a synthetic photosensitizing compound composed of three benzenesulfonic acid isomers: Fimaporfin A (TPCS2a; tetraphenylchlorodisulfonate), Fimaporfin B, and Fimaporfin C, which possess potential photosensitizing activity in photodynamic therapy (PDT). Following intradermal injection, Fimaporfin can penetrate the endosome and lysosomal membranes of tumor cells. Subsequently, the cytotoxic drug is delivered and accumulates in the endosomes and lysosomes; upon activation by localized light irradiation, Fimaporfin generates reactive oxygen species (ROS), such as singlet oxygen, which damage the endosome/lysosomal membrane and release the accumulated cytotoxic drug into the tumor cell cytoplasm. This photochemical internalization (PCI) approach can improve the efficacy and selectivity of cytotoxic drugs.
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| Molecular Formula |
C44H32N4O6S2
|
|---|---|
| Molecular Weight |
776.88
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| Exact Mass |
776.176
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| CAS # |
1443547-43-0
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| PubChem CID |
135565128
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| Appearance |
Typically exists as solid at room temperature
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| Density |
1.4±0.1 g/cm3
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| Index of Refraction |
1.690
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| LogP |
8.83
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| Hydrogen Bond Donor Count |
12
|
| Hydrogen Bond Acceptor Count |
24
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| Rotatable Bond Count |
18
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| Heavy Atom Count |
168
|
| Complexity |
4360
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| Defined Atom Stereocenter Count |
0
|
| SMILES |
S(C1C([H])=C([H])C(=C([H])C=1[H])C1C2C([H])=C([H])C(=C(C3C([H])=C([H])C(=C([H])C=3[H])S(=O)(=O)O[H])C3=C([H])C([H])=C(C(C4C([H])=C([H])C([H])=C([H])C=4[H])=C4C([H])=C([H])C(C(C5C([H])=C([H])C([H])=C([H])C=5[H])=C5C([H])([H])C([H])([H])C=1N5[H])=N4)N3[H])N=2)(=O)(=O)O[H].S(C1C([H])=C([H])C(=C([H])C=1[H])C1=C2C([H])=C([H])C(=C(C3C([H])=C([H])C([H])=C([H])C=3[H])C3C([H])=C([H])C(=C(C4C([H])=C([H])C([H])=C([H])C=4[H])C4=C([H])C([H])=C(C(C5C([H])=C([H])C(=C([H])C=5[H])S(=O)(=O)O[H])=C5C([H])([H])C([H])([H])C1=N5)N4[H])N=3)N2[H])(=O)(=O)O[H].S(C1C([H])=C([H])C(=C([H])C=1[H])C1C2C([H])=C([H])C(=C(C3C([H])=C([H])C(=C([H])C=3[H])S(=O)(=O)O[H])C3=C([H])C([H])=C(C(C4C([H])=C([H])C([H])=C([H])C=4[H])=C4C([H])([H])C([H])([H])C(C(C5C([H])=C([H])C([H])=C([H])C=5[H])=C5C([H])=C([H])C=1N5[H])=N4)N3[H])N=2)(=O)(=O)O[H] |c:18,81,108,114,133,210,273,t:54,73,169,246,267|
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| InChi Key |
AINQERPKMNDVQT-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/3C44H32N4O6S2/c3*49-55(50,51)31-15-11-29(12-16-31)43-37-23-21-35(46-37)41(27-7-3-1-4-8-27)33-19-20-34(45-33)42(28-9-5-2-6-10-28)36-22-24-38(47-36)44(40-26-25-39(43)48-40)30-13-17-32(18-14-30)56(52,53)54/h1-18,21-26,46-47H,19-20H2,(H,49,50,51)(H,52,53,54);1-21,23,25-26,46-47H,22,24H2,(H,49,50,51)(H,52,53,54);1-24,46-47H,25-26H2,(H,49,50,51)(H,52,53,54)
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| Chemical Name |
4-[10,15-diphenyl-20-(4-sulfophenyl)-2,3,22,24-tetrahydroporphyrin-5-yl]benzenesulfonic acid;4-[10,15-diphenyl-20-(4-sulfophenyl)-12,13,22,24-tetrahydroporphyrin-5-yl]benzenesulfonic acid;4-[15,20-diphenyl-10-(4-sulfophenyl)-2,3,21,23-tetrahydroporphyrin-5-yl]benzenesulfonic acid
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| Synonyms |
Disulfonated tetraphenyl chlorin; TPCS2a; Fimaporfin
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.2872 mL | 6.4360 mL | 12.8720 mL | |
| 5 mM | 0.2574 mL | 1.2872 mL | 2.5744 mL | |
| 10 mM | 0.1287 mL | 0.6436 mL | 1.2872 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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