| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| 50mg |
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| 100mg |
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| 500mg | |||
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| Targets |
5-ALA benzyl ester HCl targets the heme biosynthesis pathway. As a prodrug of 5-aminolevulinic acid (5-ALA), it is converted to 5-ALA by esterases. 5-ALA is the rate-limiting precursor in heme biosynthesis. In cells, 5-ALA is converted to protoporphyrin IX (PpIX), a photosensitizer that accumulates preferentially in tumor cells. Upon light irradiation, PpIX generates reactive oxygen species, leading to cell death. The benzyl ester moiety enhances lipophilicity and cellular uptake.
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| ln Vitro |
In the colon cancer cell line SW480, 5-ALA benzylester salticide (Benzyl-ALA saltloride) (0.6-0.12 mM; 3 h) causes protoporphyrin IX (PPIX) to accumulate [2].
In vitro studies have demonstrated that 5-ALA benzyl ester HCl is a protoporphyrin precursor that induces protoporphyrin IX (PPIX) accumulation. As a lipophilic ester prodrug of 5-ALA, it shows improved cellular uptake compared to 5-ALA. The compound is used as a photodetection agent and in photodynamic therapy (PDT) research. It is valuable for studying photodynamic therapy, tumor biology, and cancer diagnostics. Further detailed in vitro characterization data are available. |
| ln Vivo |
Tumor porphyrin levels decreased dose-dependently when 5-ALA benzyl ester hydrochloride (31 mg/kg; i.v.; 1 hour) was administered [3].
In vivo studies have shown that 5-ALA benzyl ester HCl induces protoporphyrin IX (PPIX) accumulation in vivo. As a lipophilic prodrug, it shows improved bioavailability and tissue penetration compared to 5-ALA. The compound is used in photodynamic therapy (PDT) and photodiagnostic research. It is valuable for studying tumor biology and cancer diagnostics. The compound's ability to induce PpIX accumulation in tumor cells makes it useful for fluorescence-guided surgery and photodynamic therapy. |
| Enzyme Assay |
In vitro enzyme/receptor binding (non-cell) assays for 5-ALA benzyl ester HCl typically involve esterase activity studies to confirm prodrug conversion to 5-ALA. The compound is incubated with esterases (e.g., porcine liver esterase or human serum) in buffer at 37°C for various time points. The release of 5-ALA is measured by HPLC or LC-MS. For PpIX formation, cells or cell lysates are incubated with the compound and the accumulation of PpIX is measured by fluorescence spectroscopy (excitation ~405 nm, emission ~630 nm). The compound's phototoxicity can be assessed by irradiating PpIX-containing samples with light and measuring ROS production.
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| Cell Assay |
For in vitro cell-based assays, cancer cell lines are cultured in appropriate media. Cells are treated with 5-ALA benzyl ester HCl at concentrations ranging from 0.01-1 mM for 4-24 hours. PpIX accumulation is measured by flow cytometry or fluorescence microscopy. Following PpIX accumulation, cells are irradiated with light at appropriate wavelengths (e.g., 635 nm) and cell viability is assessed by MTT or LDH release assays. ROS production is measured using DCFH-DA. The compound's selectivity for tumor cells over normal cells can be assessed using matched cell lines. Cell death mechanisms (apoptosis vs. necrosis) are evaluated by Annexin V/PI staining.
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| Animal Protocol |
Animal/Disease Models: Female CBA/Gy mice (CaNT tumor model) [3]
Doses: 31 mg/kg Route of Administration: intravenous (iv) (iv)injection; 1 hour Experimental Results: Reducing the dose of 5-ALA benzyl ester hydrochloride leads to accumulation in CaNT tumors The porphyrin concentration diminished in a dose-dependent manner. In vivo animal studies with 5-ALA benzyl ester HCl typically use mouse models of cancer. Mice bearing subcutaneous tumors are administered the compound orally or intravenously at doses determined from pharmacokinetic studies. PpIX accumulation in tumors and normal tissues is measured by fluorescence imaging or by extracting PpIX from tissues and measuring fluorescence. Photodynamic therapy efficacy is assessed by irradiating tumors with light and measuring tumor growth inhibition. Survival and toxicity are monitored. The compound's utility for fluorescence-guided surgery can be assessed by imaging tumors during surgery. |
| ADME/Pharmacokinetics |
5-ALA benzyl ester HCl has a molecular weight of 257.71 g/mol and molecular formula C12H16ClNO3. The compound is soluble in water and DMSO. It is a lipophilic ester prodrug of 5-ALA. Storage recommendations: -20°C for long-term storage. Pharmacokinetic properties include improved oral bioavailability and tissue penetration compared to 5-ALA. The compound is metabolized by esterases to release 5-ALA. The compound is intended for research purposes only.
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| Toxicity/Toxicokinetics |
In preclinical studies, 5-ALA benzyl ester HCl has shown a favorable safety profile at pharmacological doses. As a prodrug of the endogenous metabolite 5-ALA, it is expected to be well-tolerated. PpIX accumulation and phototoxicity are localized to treated areas. The compound is not intended for human therapeutic use without further development. Standard laboratory safety precautions should be followed when handling the compound.
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| References |
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| Additional Infomation |
5-ALA benzyl ester HCl (Benzyl-ALA hydrochloride) is a lipophilic ester prodrug of the endogenous metabolite 5-aminolevulinic acid (5-ALA). It has a molecular weight of 257.71 g/mol and molecular formula C12H16ClNO3. The compound is a protoporphyrin IX (PpIX) precursor used as a photodetection agent and in photodynamic therapy (PDT) research. It induces protoporphyrin IX (PPIX) accumulation and is valuable for studying photodynamic therapy, tumor biology, and cancer diagnostics. 5-ALA benzyl ester HCl is not FDA-approved and is intended for research use only.
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| Molecular Formula |
C12H15NO3.HCL
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| Molecular Weight |
257.71334
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| Exact Mass |
257.081
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| CAS # |
163271-32-7
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| PubChem CID |
22253144
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| Appearance |
White to off-white solid powder
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| Boiling Point |
385.1ºC at 760 mmHg
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| Flash Point |
186.7ºC
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| Vapour Pressure |
2.61E-06mmHg at 25°C
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| LogP |
2.54
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
17
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| Complexity |
234
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
GHMCTRQKEALPCK-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C12H15NO3.ClH/c13-8-11(14)6-7-12(15)16-9-10-4-2-1-3-5-10;/h1-5H,6-9,13H2;1H
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| Chemical Name |
benzyl 5-amino-4-oxopentanoate;hydrochloride
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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: Please store this product in a sealed and protected environment, 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) |
DMSO : ~250 mg/mL (~970.08 mM)
H2O : ~100 mg/mL (~388.03 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (8.07 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (8.07 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. 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. View More
Solubility in Formulation 3: ≥ 2.08 mg/mL (8.07 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: 100 mg/mL (388.03 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.8803 mL | 19.4017 mL | 38.8033 mL | |
| 5 mM | 0.7761 mL | 3.8803 mL | 7.7607 mL | |
| 10 mM | 0.3880 mL | 1.9402 mL | 3.8803 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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