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BPD-B-1,4-diene

Cat No.:V13050 Purity: ≥98%
BPD-B-1,4-diene (Benzoporphyrin Ring B 1,4-diene), a product from the synthesis of verteporfin, is used for preparing porphyrin-related dye, nanoparticles, photosensitizers, and other photodymanic therapeutic (PDT) drugs.
BPD-B-1,4-diene
BPD-B-1,4-diene Chemical Structure CAS No.: 94238-43-4
Product category: New12
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
BPD-B-1,4-diene (Benzoporphyrin Ring B 1,4-diene), a product from the synthesis of verteporfin, is used for preparing porphyrin-related dye, nanoparticles, photosensitizers, and other photodymanic therapeutic (PDT) drugs.
BPD-B-1,4-diene (CAS#: 94238-43-4), also known as Benzoporphyrin Ring B 1,4-diene or SSN38434, is a photosensitizer compound used in photodynamic therapy (PDT) research. It is a product from the synthesis of verteporfin, a clinically approved photosensitizer. BPD-B-1,4-diene belongs to the bacteriochlorin class of compounds, which exhibit strong absorption in the near-infrared region, allowing for deeper tissue penetration during light activation. It is used for making porphyrin-related dyes, nanoparticles, and other photodynamic therapeutic drugs.
Biological Activity I Assay Protocols (From Reference)
Targets
BPD-B-1,4-diene does not have a specific biological target in the traditional sense. It is a photosensitizer that, upon activation by light, generates reactive oxygen species (ROS), particularly singlet oxygen, which cause localized cell damage and death. One source indicates it is a potent activator of the G protein-coupled receptor and has been shown to bind to and activate the mu opioid receptor. It also inhibits ion channels such as Na+ currents in neurons and glutamate neural activity.
ln Vitro
In vitro, BPD-B-1,4-diene is used as a photosensitizer in photodynamic therapy research. Its activity is assessed by measuring its ability to generate reactive oxygen species upon light activation and its subsequent cytotoxic effects on cells. The compound's strong absorption in the near-infrared region allows for deeper tissue penetration, making it suitable for PDT applications. Its photosensitizing properties are characterized by its singlet oxygen quantum yield and its phototoxicity against cancer cells.
ln Vivo
In vivo, BPD-B-1,4-diene is not typically administered as a therapeutic agent. It is a research compound and a precursor to verteporfin, which is used clinically in PDT for the treatment of certain cancers and ocular diseases. The compound's photodynamic properties are evaluated in animal models of cancer, where it is administered systemically or locally, followed by light activation. Tumor regression and tissue damage are assessed.
Enzyme Assay
The in vitro activity of BPD-B-1,4-diene is assessed using photodynamic therapy assays. Cancer cells are cultured in appropriate media and treated with various concentrations of BPD-B-1,4-diene (typically 0.01-10 µM) for defined periods (1-24 hours). Cells are then irradiated with light at a specific wavelength (typically 690 nm) and energy dose. Cell viability is assessed using MTT or CellTiter-Glo assays 24-48 hours after light activation. The photosensitizing effect is evaluated by comparing cell viability with and without light activation. Reactive oxygen species (ROS) production can be measured using DCFH-DA fluorescence.
Cell Assay
For cellular assays, cancer cell lines (e.g., HeLa, A549, HT-29) are cultured in appropriate media. Cells are treated with various concentrations of BPD-B-1,4-diene for defined periods. Cells are then irradiated with light at 690 nm (typically 1-10 J/cm²). Cell viability is assessed using MTT or CellTiter-Glo assays. Apoptosis is evaluated by flow cytometry using Annexin V/PI staining. ROS production is measured using DCFH-DA fluorescence. The subcellular localization of the photosensitizer can be assessed by fluorescence microscopy.
Animal Protocol
In vivo, BPD-B-1,4-diene is typically administered intravenously to mice bearing tumor xenografts. The compound is formulated in a suitable vehicle (e.g., 5% DMSO, 40% PEG300, 5% Tween-80, and 50% ddH2O) and administered at various doses. After a defined drug-light interval (typically 1-24 hours), the tumor is irradiated with light at 690 nm. Tumor growth is monitored by measuring tumor volume. Tumor regression, necrosis, and apoptosis are assessed by histopathological examination.
ADME/Pharmacokinetics
BPD-B-1,4-diene has a molecular formula consistent with its benzoporphyrin structure. The compound is soluble in DMSO and should be stored as a powder at -20°C under desiccated conditions, protected from light. Specific pharmacokinetic parameters such as bioavailability, half-life, and volume of distribution are not detailed in the provided search results. The compound's strong absorption in the near-infrared region is a key property for its photosensitizing activity.
Toxicity/Toxicokinetics
Specific toxicity data for BPD-B-1,4-diene is not available in the provided search results. As a photosensitizer, its toxicity is primarily related to light-activated ROS generation. The compound is intended for research purposes only and is not approved for human or veterinary use. Standard laboratory safety precautions should be followed when handling the compound. Comprehensive toxicological studies are required to establish its full safety profile.
Additional Infomation
BPD-B-1,4-diene is a research compound used in photodynamic therapy research. It is a precursor to verteporfin, a clinically approved photosensitizer used for the treatment of choroidal neovascularization and certain cancers. BPD-B-1,4-diene is used for making porphyrin-related dyes, nanoparticles, and other photodynamic therapeutic drugs. It is not approved for clinical use and is intended for research purposes only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C42H44N4O8
Molecular Weight
732.820771217346
CAS #
94238-43-4
Appearance
Typically exists as solid at room temperature
HS Tariff Code
2934.99.9001
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)
Solubility Data
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
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
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*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 : PEG300Tween 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).
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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)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL 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).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.3646 mL 6.8230 mL 13.6459 mL
5 mM 0.2729 mL 1.3646 mL 2.7292 mL
10 mM 0.1365 mL 0.6823 mL 1.3646 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.

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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