9-cis-Retinoic Acid
(Synonyms: 9-顺式维甲酸,Alitretinoin) 目录号 : GC145969-cis-Retinoic Acid是一种对视黄酸受体(RAR)具有高亲和力的配体，对RARα的EC50值为0.2μM。
Cas No.:5300-03-8
Sample solution is provided at 25 µL, 10mM.
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9-cis-Retinoic Acid is a high-affinity ligand for the retinoic acid receptor (RAR), with an EC50 value of 0.2μM for RARα[1]. 9-cis-Retinoic Acid has been widely used in cell proliferation regulation studies and as a model compound to develop new analytical methods[2].
In vitro, 9-cis-Retinoic Acid treatment (24h) inhibited the cell proliferation of HL-60 cells, with an IC50 value of 30nM[3]. 9-cis-Retinoic Acid treatment (1nM; 20 days) inhibited the growth of SCC-9 cells, accompanied by increased expression of RARα and RARβ[4]. 9-cis-Retinoic Acid treatment (1nM; 5days) resulted in a significant decrease in cell migration, decreased tenascin synthesis, increased G1 phase cell cycle and enhanced α-actin expression in human aortic smooth muscle cells[5].
In vivo, 9-cis-Retinoic Acid treatment (0.08mg/kg/day; i.p.) for 4 weeks reduced the formation of the lymphedema and accelerated the resolution of the tissue swelling in the tails of mice[6]. Treatment with 9-cis-Retinoic Acid (10mg/kg) to male Wistar rats via gavage every other day for 8 weeks reduced the incidence of liver cancer and decreased the liver carcinogenesis index[7].
References:
[1] Heyman R A, Mangelsdorf D J, Dyck J A, et al. 9-cis retinoic acid is a high affinity ligand for the retinoid X receptor[J]. Cell, 1992, 68(2): 397-406.
[2] Kane M A. Analysis, occurrence, and function of 9-cis-retinoic acid[J]. Biochimica et Biophysica Acta (BBA)-Molecular and Cell Biology of Lipids, 2012, 1821(1): 10-20.
[3] Gottardis M M, Lamph W W, Shalinsky D R, et al. The efficacy of 9-cis retinoic acid in experimental models of cancer[J]. Breast cancer research and treatment, 1996, 38(1): 85-96.
[4] Giannini F, Maestro R, Vukosavijevic T, et al. All‐trans, 13‐cis and 9‐cis retinoic acids induce a fully reversible growth inhibition in HNSCC cell lines: implications for in vivo retinoic acid use[J]. International journal of cancer, 1997, 70(2): 194-200.
[5] Johst U, Betsch A, Wiskirchen J, et al. All-trans and 9-cis retinoid acids inhibit proliferation, migration, and synthesis of extracellular matrix of human vascular smooth muscle cells by inducing differentiation in vitro[J]. Journal of cardiovascular pharmacology, 2003, 41(4): 526-535.
[6] Choi I, Lee S, Kyoung Chung H, et al. 9-cis retinoic acid promotes lymphangiogenesis and enhances lymphatic vessel regeneration: therapeutic implications of 9-cis retinoic acid for secondary lymphedema[J]. Circulation, 2012, 125(7): 872-882.
[7] Silveira E R, Naves M M V, Vannucchi H, et al. Vitamin A and all-trans and 9-cis retinoic acids inhibit cell proliferation during the progression phase of hepatocarcinogenesis in Wistar rats[J]. Nutrition and cancer, 2001, 39(2): 244-251.
9-cis-Retinoic Acid是一种对视黄酸受体(RAR)具有高亲和力的配体，对RARα的EC50值为0.2μM[1]。9-cis-Retinoic Acid已被广泛应用于细胞增殖调控研究，并作为开发新型分析方法的模型化合物[2]。
在体外，用9-cis-Retinoic Acid处理24小时可抑制HL-60细胞增殖，IC50值为30nM[3]。1nM浓度的9-cis-Retinoic Acid处理20天能抑制SCC-9细胞生长，同时伴随RARα和RARβ表达增加[4]。在人主动脉平滑肌细胞中，1nM浓度的9-cis-Retinoic Acid处理5天可显著降低细胞迁移能力、减少腱蛋白合成、增加G1期细胞周期比例并增强α-肌动蛋白表达[5]。
在体内，连续4周每天腹腔注射0.08mg/kg剂量的9-cis-Retinoic Acid可减轻小鼠尾部淋巴水肿形成并加速组织肿胀消退[6]。对雄性Wistar大鼠隔天灌胃给予10mg/kg剂量的9-cis-Retinoic Acid持续8周，能降低肝癌发生率并减小肝脏致癌指数[7]。
| Cell experiment [1]: | |
Cell lines | Human aortic smooth muscle cells |
Preparation Method | Human aortic smooth muscle cells (haSMCs) were maintained in Waymouth/Ham F12 medium in a 1: 1 ratio with 20% fetal calf serum, 1% L-glutamine, and standard concentrations of antibiotics (penicillin, streptomycin) in a humidified atmosphere of 3.5% CO2 at 37°C. Only passages 21 and 22 were used for the study. Proliferation kinetics were performed by seeding 30,000 haSMCs into 25-cm2 ventilated tissue culture flasks in standard medium. After 2 days (day 0), standard medium was exchanged by a medium supplemented with 9-cis-Retinoic Acid (0.01μM, 0.1μM, and 1μM) in the treated groups. The control group was supplied with standard medium. The treated cells were further separated into one group receiving a single treatment over 5 days and one group receiving a continuous drug application over 20 days. Medium was exchanged every 5 days in the absence or presence of 9-cis-Retinoic Acid supplementation. Cells underwent trypsinization to measure their absolute numbers electronically at specified time intervals following initial treatment, which included day 5, day 10, day 15, and day 20. |
Reaction Conditions | 0.01μM, 0.1μM and 1μM; 20 days |
Applications | 9-cis-Retinoic Acid treatment inhibited cell proliferation of haSMCs in a dose-dependent and time-dependent manner. |
| Animal experiment [2]: | |
Animal models | C57BL/6J mice |
Preparation Method | The circumferential 2-mm-wide skin was removed =1cm distal of the tail base of C57BL/6J mice under dissecting microscope. The deeper lymphatics that run along the major blood vessels were severed by dissection with attention to avoid damaging blood vessels. Starting from postsurgical day 2, the control mouse group received intraperitoneal injections of 100μL vehicle (10μL of 100% ethanol, 90μL sunflower seed oil), or 100μL vehicle solution containing 9-cis-Retinoic Acid (0.08mg/kg) daily. The whole experiment lasted for 4 weeks. The diameter of the proximal and distal sides of surgical site in the tail was measured every other day. Mouse tails were surgically removed at the end of the experiments and processed for further immunohistochemical analyses. |
Dosage form | 0.08mg/kg/day for 4 weeks; i.p. |
Applications | 9-cis-Retinoic Acid treatment clearly inhibited the formation of the lymphedema and accelerated the resolution of the tissue swelling in the tails of mice. |
References: | |
| Cas No. | 5300-03-8 | SDF | |
| 别名 | 9-顺式维甲酸,Alitretinoin | ||
| 化学名 | (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid | ||
| Canonical SMILES | CC1(C)C(/C=C/C(C)=C\C=C\C(C)=C\C(O)=O)=C(C)CCC1 | ||
| 分子式 | C20H28O2 | 分子量 | 300.44 |
| 溶解度 | ≤0.5mg/ml in ethanol;20mg/ml in DMSO | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.3285 mL | 16.6423 mL | 33.2845 mL |
| 5 mM | 0.6657 mL | 3.3285 mL | 6.6569 mL |
| 10 mM | 0.3328 mL | 1.6642 mL | 3.3285 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
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| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
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2.
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