| Size | Price | Stock | Qty |
|---|---|---|---|
| 100mg |
|
| Targets |
A2E targets the mitochondrial membrane and lysosomal membrane in RPE cells. Upon blue light (430-480 nm) photoactivation, A2E acts as a photosensitizer, generating reactive oxygen species (ROS) and inducing oxidative stress. It accumulates in lysosomes and mitochondria, where it disrupts membrane integrity, activates the NLRP3 inflammasome, and triggers caspase-mediated apoptosis.
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|---|---|
| ln Vitro |
When A2E is exposed to light, it transforms into two or more other products. Hydrophilic epoxy-A2E is one of them; it can pass through the membrane and dissolve into an aqueous solution. Unidentified borrowing material is another product [3].
In vitro, A2E (10-100 uM) induces autophagy under photoactivation and damages membrane integrity in a concentration-dependent manner. Blue light exposure (430-480 nm, 1-4 J/cm2) in the presence of A2E leads to production of ROS, lipid peroxidation, and apoptosis in RPE cells (e.g., ARPE-19). A2E inhibits lysosomal function, increases lysosomal pH, and reduces cathepsin activity. |
| ln Vivo |
In vivo, A2E accumulates in the RPE with age and is associated with age-related macular degeneration (AMD) pathology. In animal models (e.g., Abca4-/- mice, which accumulate A2E in the RPE), exposure to blue light exacerbates RPE degeneration and choroidal neovascularization (CNV), recapitulating features of dry and wet AMD.
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| Enzyme Assay |
For non-cellular photochemical assessment, A2E is dissolved in ethanol or DMSO (1-100 uM) and exposed to blue light (430-480 nm, 0.5-10 J/cm2) in buffer solution. Singlet oxygen and superoxide production are measured using specific probes (e.g., Singlet Oxygen Sensor Green, dihydroethidium). Lipid peroxidation is measured by TBARS (thiobarbituric acid reactive substances) assay using liposomes.
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| Cell Assay |
For cell-based assays, human ARPE-19 or primary RPE cells are seeded in 96-well plates and treated with A2E (10-100 uM) for 24-72 hours. Cells are then exposed to blue light (430-480 nm, 1-10 J/cm2) or kept in darkness as control. Cell viability is measured by MTT, LDH release, or Calcein-AM staining. ROS production is measured using H2DCFDA or CellROX. Apoptosis is quantified by Annexin V/PI staining and caspase-3/7 activation.
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| Animal Protocol |
For in vivo evaluation, Abca4-/- mice (model of Stargardt disease and A2E accumulation) or wild-type C57BL/6 mice with exogenous A2E injection (intravitreal injection of 0.5-5 ug/eye) are exposed to blue light (430-480 nm, 50-300 J/cm2) for 1-6 hours. Retinal degeneration is assessed by fundus photography, spectral-domain OCT, electroretinography (ERG), and histology (TUNEL staining, outer nuclear layer thickness).
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| ADME/Pharmacokinetics |
Not applicable. A2E is a fluorescent pigment, not a drug candidate, and PK studies are not relevant. In vivo, A2E accumulates progressively in the RPE over time, with minimal clearance. The half-life of A2E in the RPE is estimated to be months to years. Exogenous A2E administered intravitreally is gradually phagocytosed by RPE cells.
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| Toxicity/Toxicokinetics |
A2E is cytotoxic to RPE cells upon photoactivation and is associated with dry AMD. Toxicity is light-dependent; in the absence of blue light, A2E exhibits minimal cytotoxicity. Chronic accumulation of A2E leads to RPE atrophy, sub-RPE deposits (drusen), and progressive vision loss. No acute systemic toxicity has been reported.
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| References |
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| Additional Infomation |
N-Retinaldehyde-N-Retinolethanolamine is a pyridine ion formed by the condensation of two retinol molecules and one ethanolamine amino group. It is a major component of lipofuscin in the retinal pigment epithelium and belongs to the retinoid and pyridine ion groups.
A2E is a research-grade compound, not a drug. It is widely used as a model for studying lipofuscin-mediated RPE degeneration and dry AMD pathogenesis. The compound has been used to screen for potential therapeutic agents that inhibit A2E formation, reduce A2E accumulation, or protect RPE cells from A2E-photoinduced damage (e.g., antioxidants, visual cycle modulators). No clinical trials are registered for A2E itself. |
| Molecular Formula |
C42H58NO+
|
|---|---|
| Molecular Weight |
592.91602
|
| Exact Mass |
592.452
|
| CAS # |
173449-96-2
|
| Related CAS # |
Pyridinium bisretinoid A2E TFA;1821308-73-9;Pyridinium bisretinoid A2E-d4 TFA
|
| PubChem CID |
11007064
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| Appearance |
Typically exists as solid at room temperature
|
| LogP |
10.997
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| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
11
|
| Heavy Atom Count |
44
|
| Complexity |
1250
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
OCC[N+]1=CC=C(/C=C/C=C(/C=C/C2=C(C)CCCC2(C)C)\C)C=C1/C=C(\C=C\C=C(\C=C\C1=C(C)CCCC1(C)C)/C)/C
|
| InChi Key |
WPWFMRDPTDEJJA-FAXVYDRBSA-N
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| InChi Code |
InChI=1S/C42H58NO/c1-32(20-22-39-35(4)17-12-25-41(39,6)7)14-10-16-34(3)30-38-31-37(24-27-43(38)28-29-44)19-11-15-33(2)21-23-40-36(5)18-13-26-42(40,8)9/h10-11,14-16,19-24,27,30-31,44H,12-13,17-18,25-26,28-29H2,1-9H3/q+1/b16-10+,19-11+,22-20+,23-21+,32-14+,33-15+,34-30+
|
| Chemical Name |
2-[2-[(1E,3E,5E,7E)-2,6-dimethyl-8-(2,6,6-trimethylcyclohexen-1-yl)octa-1,3,5,7-tetraenyl]-4-[(1E,3E,5E)-4-methyl-6-(2,6,6-trimethylcyclohexen-1-yl)hexa-1,3,5-trienyl]pyridin-1-ium-1-yl]ethanol
|
| Synonyms |
Pyridinium bisretinoid A2E; A2E
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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) |
DMSO: ~150 mg/mL (253.0 mM)
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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 | 1.6866 mL | 8.4328 mL | 16.8657 mL | |
| 5 mM | 0.3373 mL | 1.6866 mL | 3.3731 mL | |
| 10 mM | 0.1687 mL | 0.8433 mL | 1.6866 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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