| Size | Price | Stock | Qty |
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| 50mg |
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| 100mg |
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| 250mg |
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| 500mg |
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| Other Sizes |
| Targets |
5-(4-Carboxyphenyl)-10,15,20-triphenylporphyrin acts as a photosensitizer for photodynamic therapy (PDT). Upon activation by light at specific wavelengths (typically 400-650 nm, with Soret band at ~420 nm and Q-bands at 515, 550, 590, 645 nm), the porphyrin core transfers energy to molecular oxygen, generating reactive oxygen species (ROS) such as singlet oxygen (¹O2) and superoxide anion. These ROS induce oxidative damage to cellular components, leading to cell death via apoptosis or necrosis. The compound can be conjugated to targeting ligands (e.g., antibodies, peptides) via the carboxy group for tumor-selective delivery.
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| ln Vitro |
In vitro, 5-(4-Carboxyphenyl)-10,15,20-triphenylporphyrin has been evaluated for its photodynamic activity against human cancer cell lines, including A2780 (ovarian), A549 (lung), Me300 (melanoma), and HeLa (cervical) cells. The compound exhibits concentration-dependent phototoxicity upon light irradiation (e.g., 650-670 nm, 5-20 J/cm2), with IC₅0 values in the low micromolar range depending on the cell line and light dose. In the dark, the compound shows minimal cytotoxicity at concentrations up to 50-100 microM, indicating a favorable phototoxicity index (light IC₅0/dark IC₅0). The compound also demonstrates anti-leishmanial activity with IC₅0 values lower than the reference drug glucantime.
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| ln Vivo |
In vivo, 5-(4-Carboxyphenyl)-10,15,20-triphenylporphyrin and its derivatives have been evaluated in xenograft mouse models of cancer. Following systemic administration (IV or IP, 1-10 mg/kg), the compound accumulates preferentially in tumor tissues due to the enhanced permeability and retention (EPR) effect. Upon localized light irradiation (650-670 nm, 100-200 J/cm2, 4-24 hours post-injection), the compound induces ROS-mediated tumor cell death, leading to significant tumor growth delay or regression compared to untreated or light-only controls. The compound also shows efficacy in parasite infection models (e.g., leishmaniasis) when combined with light activation.
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| Enzyme Assay |
A standard in vitro singlet oxygen generation assay: 5-(4-Carboxyphenyl)-10,15,20-triphenylporphyrin is dissolved in DMSO and diluted in PBS or methanol to final concentrations of 1-50 microM. The singlet oxygen sensor 1,3-diphenylisobenzofuran (DPBF, 50 microM) is added. The solution is irradiated with a light source (e.g., halogen lamp, 400-700 nm, 5-20 mW/cm2) for 0-10 minutes, with absorbance readings at 410 nm (DPBF) taken at 1-minute intervals. The decrease in DPBF absorbance (deltaA410) is directly proportional to singlet oxygen generation. Quantum yield (Φdelta) is calculated by comparing with a reference photosensitizer (e.g., Rose Bengal, Φdelta = 0.76). Dark controls are included to account for autoxidation.
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| Cell Assay |
A standard in vitro photodynamic therapy cytotoxicity assay: Human cancer cells (e.g., HeLa, A549, or A2780) are seeded in 96-well plates at 8,000-10,000 cells/well in DMEM with 10% FBS and incubated overnight at 37degC with 5% CO2. 5-(4-Carboxyphenyl)-10,15,20-triphenylporphyrin is dissolved in DMSO and diluted in culture medium to final concentrations of 0.01-100 microM (DMSO ≤0.5%). Cells are incubated with the compound for 4-24 hours to allow uptake, then washed with PBS. For phototoxicity assessment, cells are irradiated with a light source (e.g., LED or laser at 650 +/- 20 nm, 5-20 J/cm2, 10-50 mW/cm2). For dark toxicity (control), cells are kept in the dark under identical conditions. After 24-48 hours of further incubation, cell viability is measured using MTT or CellTiter-Glo assays. IC₅0 values (light and dark) are calculated from dose-response curves, and the phototoxicity index (dark IC₅0/light IC₅0) is determined.
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| Animal Protocol |
A standard in vivo photodynamic therapy protocol in a xenograft mouse model: Female athymic nude mice (6-8 weeks old, 18-22 g) are subcutaneously inoculated with 5 × 10⁶ human cancer cells (e.g., HeLa, A549, or A2780) suspended in 0.1 mL PBS/Matrigel (1:1) into the right flank. When tumors reach approximately 100-200 mm3 (7-14 days post-inoculation), mice are randomized into treatment groups (n=6-8 per group). 5-(4-Carboxyphenyl)-10,15,20-triphenylporphyrin is formulated in a suitable vehicle (e.g., 5% DMSO + 5% Tween 80 + 90% saline) and administered intravenously (tail vein) or intraperitoneally at doses of 1-10 mg/kg (injection volume 100-200 microL). At 4-24 hours post-injection (to allow tumor accumulation), the tumor area is irradiated with a light source (e.g., diode laser at 650-670 nm, 100-200 J/cm2, 100-200 mW/cm2) for 10-30 minutes. Control groups include: vehicle + no light, vehicle + light only, compound + no light, and positive control (e.g., Photofrin 5 mg/kg). Tumor volume is measured every 2-3 days using digital calipers (volume = length × width2/2). Body weight is monitored for toxicity. At study endpoint (e.g., day 21-28 or when tumors reach 2000 mm3), tumors are excised, weighed, and processed for histopathology (H&E staining, TUNEL assay for apoptosis, Ki-67 immunohistochemistry for proliferation).
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| ADME/Pharmacokinetics |
No specific pharmacokinetic data is available for 5-(4-Carboxyphenyl)-10,15,20-triphenylporphyrin. As a porphyrin derivative (MW 658.75), the compound is lipophilic and likely exhibits high plasma protein binding (>90%). Following IV administration, it is expected to distribute primarily to the liver, spleen, and tumors via the EPR effect. The compound may be cleared slowly (t½ of hours to days) through biliary excretion, as porphyrins are typically eliminated via the hepatobiliary route. Poor aqueous solubility requires formulation in organic solvents or liposomes. Specific Cmax, AUC, and clearance values require further investigation.
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| Toxicity/Toxicokinetics |
For 5-(4-Carboxyphenyl)-10,15,20-triphenylporphyrin, safety data indicates that the compound is not classified as a hazardous material under GHS. However, standard handling precautions should be followed: use of personal protective equipment (PPE) such as gloves, goggles, and lab coat; store in a cool, dry place, protected from light, and stored under nitrogen; avoid inhalation and skin contact. The compound is for research use only, not for diagnostic or therapeutic applications. Toxicity studies have not been systematically conducted; however, porphyrin-based photosensitizers are generally well-tolerated at therapeutic doses, with potential acute adverse effects limited to skin photosensitivity and localized pain at the irradiation site.
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| References | |
| Additional Infomation |
5-(4-Carboxyphenyl)-10,15,20-triphenylporphyrin (CAS#95051-10-8) is a research-grade porphyrin derivative used as a building block for photosensitizers in photodynamic therapy (PDT) research. The carboxy group allows conjugation to targeting ligands (antibodies, peptides, nanoparticles) for tumor-selective delivery. The compound is also used in the development of optical probes, fluorescence imaging, and as a precursor for metalloporphyrin catalysts. No FDA-approved drug contains this specific compound; however, related porphyrin-based photosensitizers (e.g., Photofrin, Temoporfin, Verteporfin) are approved for certain cancer and ophthalmic indications. For research use only, not for diagnostic or therapeutic applications.
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| Molecular Formula |
C45H30N4O2
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|---|---|
| Molecular Weight |
658.75
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| Exact Mass |
658.237
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| CAS # |
95051-10-8
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| PubChem CID |
135446084
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| Appearance |
Solid powder
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| Hydrogen Bond Donor Count |
3
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
51
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| Complexity |
1140
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=CC=C(C=C1)C2=C3C=CC(=C(C4=NC(=C(C5=CC=C(N5)C(=C6C=CC2=N6)C7=CC=CC=C7)C8=CC=C(C=C8)C(=O)O)C=C4)C9=CC=CC=C9)N3
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| InChi Key |
GZTMFXHPFNRUNU-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C45H30N4O2/c50-45(51)32-18-16-31(17-19-32)44-39-26-24-37(48-39)42(29-12-6-2-7-13-29)35-22-20-33(46-35)41(28-10-4-1-5-11-28)34-21-23-36(47-34)43(30-14-8-3-9-15-30)38-25-27-40(44)49-38/h1-27,46,49H,(H,50,51)
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| Chemical Name |
4-(10,15,20-triphenyl-21,23-dihydroporphyrin-5-yl)benzoic acid
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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 Note: (1). This product requires protection from light (avoid light exposure) during transportation and storage. (2). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| 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 | 1.5180 mL | 7.5901 mL | 15.1803 mL | |
| 5 mM | 0.3036 mL | 1.5180 mL | 3.0361 mL | |
| 10 mM | 0.1518 mL | 0.7590 mL | 1.5180 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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