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1-Palmitoyl-2-pyropheophorbide a-sn-glycero-3-pc is a phospholipid-porphyrin conjugate used for photodynamic therapy (PDT) research [13L14-L15, L23-L24]. The pyropheophorbide a moiety serves as a photosensitizer. Upon activation with light of a specific wavelength (typically 660-670 nm), the porphyrin generates reactive oxygen species (ROS), such as singlet oxygen, which are cytotoxic and can induce cell death (apoptosis or necrosis). The phospholipid anchor (sn-glycero-3-PC) facilitates incorporation into cell membranes, liposomes, or lipid nanoparticles for improved cellular uptake.
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| ln Vitro |
Not applicable. This is a photosensitizer-conjugated lipid and does not function as a typical drug acting through an enzyme or receptor target. Its biological activity is light-dependent. Upon light irradiation, the pyropheophorbide a photosensitizer undergoes photochemical reactions that generate reactive oxygen species (ROS), leading to oxidative damage to cellular components. This mechanism is evaluated in vitro by illuminating cells treated with the conjugate and assessing cell viability, ROS production, and apoptotic markers.
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| ln Vivo |
In photodynamic therapy (PDT) studies, the conjugate is expected to accumulate in tumor tissues (via passive or active targeting). Upon irradiation with light (e.g., 660 nm), it induces localized production of singlet oxygen and other ROS, resulting in tumor cell death, destruction of tumor vasculature, and activation of an anti-tumor immune response. While specific animal data for this exact conjugate is not in search results, similar porphyrin-lipid conjugates have shown effective tumor ablation in xenograft models following systemic administration and local light application.
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| Enzyme Assay |
The conjugate does not have a conventional enzyme or receptor binding assay. The singlet oxygen generation capacity of the conjugate can be measured using an anthracene-based probe. Procedure: 1-Palmitoyl-2-pyropheophorbide a-sn-glycero-3-pc is dissolved in a suitable solvent (e.g., DMSO or PBS buffer) at a concentration of 1-10 microM. A singlet oxygen sensor (e.g., 9,10-anthracenediyl-bis(methylene)dimalonic acid - ABDA) is added to the solution. The mixture is irradiated with a 660-670 nm LED lamp or laser for varying time points (0, 1, 2, 5, 10 minutes). The absorbance of ABDA at 378 nm is measured before and after irradiation. A decrease in ABDA absorbance indicates production of singlet oxygen by the photosensitizer.
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| Cell Assay |
The photodynamic activity is evaluated in cancer cell lines. Procedure: Human cancer cell lines (e.g., HeLa, A549, MCF-7) are seeded in 96-well plates at 1×10^4 cells/well. After 24 hours, cells are incubated with varying concentrations of 1-Palmitoyl-2-pyropheophorbide a-sn-glycero-3-pc (e.g., 0.1, 0.5, 1, 5, 10, 20 microM) for 4-24 hours. After removing unbound conjugate, cells are exposed to 660-670 nm light at a fluence of 2-10 J/cm2. Following irradiation, cells are incubated for an additional 24 hours. Cell viability is measured by MTT or CellTiter-Glo assay. Dark toxicity (no light exposure) is measured as a control. Cellular uptake and subcellular localization can be assessed by confocal microscopy.
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| Animal Protocol |
Animal xenograft model: 6-8 week old female BALB/c nude mice are inoculated subcutaneously with 5×10^6 tumor cells (e.g., HeLa or A549). When tumors reach approximately 100-200 mm3, mice are randomized into groups. 1-Palmitoyl-2-pyropheophorbide a-sn-glycero-3-pc is administered intravenously at a dose of 1-10 mg/kg (formulated in liposomes or cyclodextrin). At 4-24 hours post-injection (to allow for optimal tumor accumulation and normal tissue clearance), the tumor area is exposed to 660-670 nm laser light (100-200 mW/cm2, 100-200 J/cm2) for 10-20 minutes. Tumor volumes are measured every 2-3 days. Mice are monitored for survival, body weight, and tumor recurrence. Tumor and skin samples are collected for histological analysis.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties are determined for the final formulation (e.g., liposomal nanoparticles) rather than the single molecule itself. As a phospholipid-porphyrin conjugate, it has a high molecular weight (MW ~1012 Da) and amphiphilic properties, which typically lead to binding to serum proteins (e.g., albumin, lipoproteins) and relatively long circulation times, especially when formulated in lipid nanoparticles. Porphyrin derivatives are known to accumulate in the liver and spleen (reticuloendothelial system) and can persist in skin due to their high lipophilicity.
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| Toxicity/Toxicokinetics |
Specific toxicity data for this compound is not available. Photosensitizers for PDT generally have a favorable safety profile because their toxicity is light-activated, allowing for spatiotemporal control of cytotoxic effects. In the absence of light, the compound is typically non-toxic (dark toxicity). However, off-target accumulation in normal tissues (especially skin) can lead to prolonged photosensitivity, requiring patients to avoid bright light for several weeks post-treatment. The compound is for research use only.
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| References | |
| Additional Infomation |
Toxicological evaluation would focus on dark toxicity (without light) and phototoxicity (with light). The conjugate is a research chemical for PDT, a clinically approved modality for certain cancers and precancers. By conjugating a photosensitizer to a phosphatidylcholine (PC) lipid, this compound is designed to enhance delivery to tumor cells by exploiting the enhanced permeability and retention (EPR) effect or by incorporating the conjugate into the lipid bilayer of liposomal nanoparticles. Pyropheophorbide a is a chlorophyll derivative known for its strong absorption in the red/near-infrared region (660 nm), which offers deeper tissue penetration. This compound can be utilized in photodynamic therapy (PDT) research and is for laboratory use only [13L15-L16, L23-L24]. It is soluble in organic solvents such as ethanol, DMSO, and dimethyl formamide (approx. 1 mg/mL) [13L27-L30].
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| Molecular Formula |
C57H82N5O9P
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| Molecular Weight |
1012.26
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| Exact Mass |
1011.585
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| CAS # |
1287795-07-6
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| PubChem CID |
171042907
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| Appearance |
Typically exists as solids at room temperature
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
13
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| Rotatable Bond Count |
31
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| Heavy Atom Count |
72
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| Complexity |
2480
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| Defined Atom Stereocenter Count |
3
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| SMILES |
CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)CC[C@H]1[C@@H](C2=CC3=NC(=CC4=NC(=CC5=C(C6=C(CC(=C1N2)C6=N5)O)C)C(=C4C)CC)C(=C3C)C=C)C
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| InChi Key |
JNOZUNXGSWKOPZ-WXDPHDKQSA-N
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| InChi Code |
InChI=1S/C57H82N5O9P/c1-11-14-15-16-17-18-19-20-21-22-23-24-25-26-53(64)68-35-41(36-70-72(66,67)69-30-29-62(8,9)10)71-54(65)28-27-44-39(6)48-32-46-37(4)42(12-2)50(58-46)33-47-38(5)43(13-3)51(59-47)34-49-40(7)55-52(63)31-45(56(44)60-48)57(55)61-49/h12,32-34,39,41,44H,2,11,13-31,35-36H2,1,3-10H3,(H2-,58,59,60,61,63,66,67)/t39-,41+,44-/m0/s1
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| Chemical Name |
[(2R)-2-[3-[(21S,22S)-16-ethenyl-11-ethyl-4-hydroxy-12,17,21,26-tetramethyl-7,23,24,25-tetrazahexacyclo[18.2.1.15,8.110,13.115,18.02,6]hexacosa-1,4,6,8(26),9,11,13(25),14,16,18(24),19-undecaen-22-yl]propanoyloxy]-3-hexadecanoyloxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
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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 | 0.9879 mL | 4.9394 mL | 9.8789 mL | |
| 5 mM | 0.1976 mL | 0.9879 mL | 1.9758 mL | |
| 10 mM | 0.0988 mL | 0.4939 mL | 0.9879 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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