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Retinoic acid

Retinoic acid (Tretinoin) 是维生素 A 的代谢产物，结合并激活视黄酸受体，从而诱导基因表达的变化，导致细胞分化、细胞增殖减少和肿瘤发生的抑制。它是 RAR 核受体的天然激动剂，对 RARα/β/γ的 IC50为14 nM，与 PPARβ/δ结合的Kd 值为17 nM。

CAS号

302-79-4

分子式

C20H28O2

主要靶点

Endogenous Metabolite|Autophagy|Retinoid Receptor|PPAR

仅限科研使用

Cat No : CM01288

Print datasheet

Synonyms

维生素A酸|all-trans-Retinoic acid|ATRA|Vitamin A acid|Tretinoin

验证数据展示

  • CAS No.: 302-79-4

    Retinoic acid
    CAS#: 302-79-4

产品信息

Retinoic acid (Tretinoin) binds to and activates retinoic acid receptors (RARs), thereby inducing changes in gene expression that lead to cell differentiation, decreased cell proliferation, and inhibition of tumorigenesis. This agent also inhibits telomerase, resulting in telomere shortening and eventual apoptosis of some tumor cell types. Tretinoin is a naturally-occurring acid of retinol. The oral form of tretinoin has teratogenic and embryotoxic properties.

CAS号 302-79-4
分子式 C20H28O2
主要靶点 Endogenous Metabolite|Autophagy|Retinoid Receptor|PPAR
主要通路 DNA损伤和修复|代谢|自噬
分子量 300.44
纯度 99.52%， 此纯度可做参考，具体纯度与批次有关系，可咨询客服
储存条件 Powder: -20°C for 3 years | In solvent: -80°C for 1 year
别名 维生素A酸|all-trans-Retinoic acid|ATRA|Vitamin A acid|Tretinoin

靶点活性

RARβ:14 nM|RARγ:14 nM|RARα:14 nM

体内活性

在对谷胱甘肽含量和过氧化氢酶活性影响的研究中,Tretinoin以时间和剂量依赖的方式增加对应含量和活性,对人肾小球系膜细胞中的H2O2细胞毒性具有预防和降低作用。用Tretinoin培育系膜细胞,可使过氧化氢酶以及γ-谷酰基-半胱氨酸合成酶(催化亚基,还原型谷胱甘肽合成的限速步骤)mRNA水平的增加。此外,Tretinoin可使人瘢痕疙瘩衍生的成纤维细胞中基质金属蛋白酶-8/13上调。

体外活性

Tretinoin可以防止皮质类固醇诱导的无毛小鼠皮肤萎缩.在豚鼠体内,Tretinoin与咪喹莫特联用可使之出现组织病理学上的纹身褪色和中度的色素清除.在45 CD-1小鼠的皮肤切口上,Tretinoin使成纤维细胞分化增加,胶原蛋白产生量减少.与对照组老年大鼠相比,Tretinoin处理的老年雄性Fischer 344大鼠肾皮质中蛋白质含量低30%,这可能是因为其抑制了肿瘤坏死因子-β1和骨桥蛋白的表达.

溶解度

H2O:<1 mg/mL,Ethanol:6 mg/mL (19.97 mM),DMSO:56 mg/mL (186.4 mM)

细胞实验

Retinoic acid is dissolved in DMSO and stored, and then diluted with appropriate medium before use[3]. P19 cell are induced to undergo neuronal differentiation according to established procedures. Briefly, cells are cultured on 1% agarose-coated 10 cm dishes at 3×10 5 cells/mL in α-minimal essential medium supplemented with 10% FBS. Differentiation is induced by addition of Retinoic acid (1 μM) and medium containing Retinoic acid replaced 2 days later. On day 4, cell aggregates are collected by centrifugation, separated to single cells by trypsin/EDTA treatment, replated onto poly-L-lysine-coated plates, and cultured in α-minimal essential medium supplemented with 10% FBS. On day 6, medium is replaced with neurobasal medium containing B27 supplement and 2 mM GlutaMAX. Medium is replaced every 2 days for an additional week[3].

参考文献

1.Manzano VM, et al. J Pharmacol Exp Ther, 1999, 289(1), 123-132.
2.Qiu Y, Sun Y, Xu D, et al. Screening of FDA-approved drugs identifies sutent as a modulator of UCP1 expression in brown adipose tissue[J]. EBioMedicine. 2018, 37: 344-355.
3.Uchida G, et al. Exp Dermatol, 2003, 12 ,Suppl 2, 35-42.
4.Schwartz E, et al. J Invest Dermatol, 1994, 102(2), 241-246.
5.Solis RR, et al. Dermatol Surg, 2002, 28(1), 83-6, discussion 86-87.
6.Muehlberger T, et al. J Am Acad Dermatol, 2005, 52(4), 583-588.
7.Wu L, et al. Retinoid X Receptor Agonists Upregulate Genes Responsible for the Biosynthesis of All-Trans-Retinoic Acid in Human Epidermis. PLoS One. 2016 Apr 14;11(4):e0153556.
8.Wan X Q, Cai J Y, Zhu Y, et al. SENP1 has an important role in lung development and influences the differentiation of alveolar type 2 cells[J]. International journal of molecular medicine. 2019 Jan;43(1):371-381.
9.Wei Z, Li T, Sun Y, et al. Daturataturin A, a withanolide in Datura metel L., induces HaCaT autophagy through the PI3K‐Akt‐mTOR signaling pathway[J] . Phytotherapy Research. 2021
10.Yanxing Wang, Xiaodong Dou, Lan Jiang, Hongwei Jin, Lihe Zhang, Liangren Zhang, and Zhenming Liu. Discovery of novel glycogen synthase kinase-3α inhibitors: Structurebased virtual screening, preliminary SAR and biological evaluation for treatment of acute myeloid leukemia [J]. European Journal of Medicinal Chemistry. 2019 Jun 1;171:221-234.

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