All-trans Retinal 是一种具有活性的vitamin A aldehyde,对CRBP-I和CRBP-II蛋白的Kd值分别为50nM和90nM。
Cas No.:116-31-4
Sample solution is provided at 25 µL, 10mM.
All-trans Retinal is a reactive vitamin A aldehyde with Kd values of 50 and 90nM for CRBP-I and CRBP-II proteins, respectively [1]. All-trans Retinal can selectively inhibit the activities of bovine DNA polymerase α and DNA polymerase δ, with IC50 values of 15µM and 17µM, respectively, and interfere with the cell cycle process [2]. All-trans Retinal can disrupt cellular metabolism and the integrity of the cell membrane, promote the release of lactate dehydrogenase (LDH) and lead to the formation of lipid peroxides [3]. All-trans Retinal has been widely used to induce retinal damage and cause oxidative stress [4].
In vitro, All-trans Retinal treatment for 6 hours significantly inhibited the viability of ARPE-19 cells, with an IC50 value of 18µM[5]. Treatment with 30µM All-trans Retinal for 6 hours significantly induced apoptosis in 661W cells and promoted the expression of Bax[6]. Treatment with 5µM All-trans Retinal for 6 hours significantly increased the phosphorylation level of STAT3 (Y705) in 661W cells, promoting the accumulation of reactive oxygen species (ROS) and ferroptosis[7].
References:
[1] Noy N. Retinoid-binding proteins: mediators of retinoid action[J]. Biochemical Journal, 2000, 348(3): 481-495.
[2] Murakami C, Takemura M, Sugiyama Y, et al. Vitamin A-related compounds, All-trans Retinal and retinoic acids, selectively inhibit activities of mammalian replicative DNA polymerases[J]. Biochimica et Biophysica Acta (BBA)-Gene Structure and Expression, 2002, 1574(1): 85-92.
[3] Wielgus A R, Chignell C F, Ceger P, et al. Comparison of A2E cytotoxicity and phototoxicity with all‐trans‐retinal in human retinal pigment epithelial cells[J]. Photochemistry and photobiology, 2010, 86(4): 781-791.
[4] Maeda T, Golczak M, Maeda A. Retinal photodamage mediated by all‐trans‐retinal[J]. Photochemistry and photobiology, 2012, 88(6): 1309-1319.
[5] Han Y, Yang K H, He D X, et al. Effect of palmitoylethanolamide on degeneration of a human-derived retinal pigment epithelial cell induced by All-trans Retinal[J]. International Journal of Ophthalmology, 2023, 16(2): 191.
[6] Sawada O, Perusek L, Kohno H, et al. All-trans-retinal induces Bax activation via DNA damage to mediate retinal cell apoptosis[J]. Experimental eye research, 2014, 123: 27-36.
[7] Chen C, Yang J, Wang H, et al. Involvement of STAT3 activation in ameliorating all-trans-retinal-induced ferroptosis in photoreceptor-derived 661W cells in vitro[J]. Experimental Eye Research, 2025, 253: 110280.
All-trans Retinal是一种具有活性的vitamin A aldehyde,对CRBP-I和CRBP-II蛋白的Kd值分别为50nM和90nM[1]。All-trans Retinal可选择性地抑制牛DNA聚合酶α和DNA聚合酶δ的活性,IC50值分别为15µM和17µM,并能干扰细胞周期进程[2]。All-trans Retinal可破坏细胞代谢和细胞膜完整性,促进乳酸脱氢酶(LDH)的释放并导致脂质过氧化物的形成[3]。All-trans Retinal已被广泛用于诱导视网膜损伤和引起氧化应激[4]。
在体外,All-trans Retinal处理ARPE-19细胞6小时,显著抑制了细胞活力,IC50值为18µM[5]。30µM的All-trans Retinal处理661W细胞6小时,显著诱导了细胞凋亡并促进了Bax的表达[6]。5µM的All-trans Retinal处理661W细胞6小时,显著增加了STAT3(Y705)的磷酸化水平,促进了活性氧(ROS)的积累和铁死亡[7]。
| Cell experiment [1]: | |
Cell lines | ARPE-19 cells |
Preparation Method | ARPE-19 cells were grown in DMEM medium with 10% (v/v) fetal bovine serum (FBS), 100μg/ml streptomycin, and 100U/ml penicillin at 37°C in 5% CO2/atmosphere. 1.5×104 cells per well of ARPE-19 cells inoculated in 96-well plates and cultured overnight. All-trans Retinal (2.5, 5, 15, and 20µM) treated ARPE-19 cells for 6h and cell viability was measured. |
Reaction Conditions | 2.5, 5, 15, and 20µM; 6h |
Applications | All-trans Retinal treatment significantly reduced the cell viability of ARPE-19 cells in a concentration-dependent manner. |
References: | |
| Cas No. | 116-31-4 | SDF | |
| 别名 | 视黄醛,Retinaldehyde,Vitamin A aldehyde | ||
| 化学名 | retinal | ||
| Canonical SMILES | CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C([H])=O)C(C)(C)CCC1 | ||
| 分子式 | C20H28O | 分子量 | 284.4 |
| 溶解度 | ≥ 57.4 mg/mL in DMSO, ≥ 56.6 mg/mL in EtOH | 储存条件 | Store at -20°C,unstable in solution, ready to use. |
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.5162 mL | 17.5809 mL | 35.1617 mL |
| 5 mM | 703.2 μL | 3.5162 mL | 7.0323 mL |
| 10 mM | 351.6 μL | 1.7581 mL | 3.5162 mL |
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