9-cis-Retinoic acid (BioDeep_00000014466)

 

Secondary id: BioDeep_00000858375

human metabolite Endogenous blood metabolite


代谢物信息卡片


(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid

化学式: C20H28O2 (300.2089188)
中文名称: 9-顺式视黄酸
谱图信息: 最多检出来源 Homo sapiens(blood) 0.48%

分子结构信息

SMILES: C/C(=C/C=C/C(=C/C(=O)O)/C)/C=C/C1=C(C)CCCC1(C)C
InChI: InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8-,16-14+

描述信息

9-cis-Retinoic acid is an active retinoid that regulates expression of retinoid responsive genes, serving as a ligand for two classes of ligand-dependent transcription factors: the retinoic acid receptors and retinoid X receptors. Retinoids (vitamin A and its analogs) are essential dietary substances that are needed by mammals for reproduction, normal embryogenesis, growth, vision, and maintaining normal cellular differentiation and the integrity of the immune system. Within cells, retinoids regulate gene transcription acting through ligand-dependent transcription factors, the retinoic acid receptors (RARs), and the retinoid X receptors (RXRs). all-trans-Retinoic acid binds only to RARs with high affinity, whereas its 9-cis isomer binds with high affinity to both RARs and RXRs. The actions of all-trans- and 9-cis-retinoic acid in regulating cellular responses are distinct and not interchangeable (PMID: 9115228).
Isolated from pancreas of pig and cow. Digestive enzyme. It is used in replacement therapy. It is used to prepare protein hydrolysates for pre- and post-operative diets
D - Dermatologicals > D11 - Other dermatological preparations > D11A - Other dermatological preparations > D11AH - Agents for dermatitis, excluding corticosteroids
L - Antineoplastic and immunomodulating agents > L01 - Antineoplastic agents > L01X - Other antineoplastic agents > L01XF - Retinoids for cancer treatment
C274 - Antineoplastic Agent > C2122 - Cell Differentiating Agent > C1934 - Differentiation Inducer
C274 - Antineoplastic Agent > C163758 - Targeted Therapy Agent > C804 - Retinoic Acid Agent
C308 - Immunotherapeutic Agent > C129820 - Antineoplastic Immunomodulating Agent
D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids
D000970 - Antineoplastic Agents
D003879 - Dermatologic Agents
Same as: D02815

同义名列表

67 个代谢物同义名

(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid; (2E,4E,6Z,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid; (2E,4E,6Z,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate; Tretinoin/All-Trans Retinoic Acid; 15-apo-beta-Caroten-15-Oic acid; (7E,9Z,11E,13E)-Retinoic acid; Tretinoin/all-trans retinoate; all-trans-beta-Retinoic acid; 15-apo-beta-Caroten-15-Oate; Isotretinoin retinoic acid; all-trans- Vitamin a1 acid; (7E,9Z,11E,13E)-Retinoate; all-trans-b-Retinoic acid; all-trans-beta-Retinoate; all-trans-Vitamin a acid; Isotretinoin retinoate; all-trans-b-Retinoate; trans-Vitamin a acid; 9-cis-retinoic acid; trans-Retinoic acid; 9 cis Retinoic acid; beta-Retinoic acid; 9(Z)-Retinoic acid; alpha-Vitaminsyre; 9-cis-Tretinoin; b-Retinoic acid; trans-Retinoate; 9-Retinoic acid; 9-cis-Retinoate; beta-Retinoate; Alitretinoinum; 9(Z)-Retinoate; Alitretinoina; 9CRA compound; Retinoic Acid; Retin-a micro; Alitretinoine; Alitretinoin; Panretin gel; 9-Retinoate; b-Retinoate; Epi-aberel; Pancreatin; Tretinoin; Retinoate; Vesnaroid; Dermairol; Tretinon; Panrexin; Retacnyl; Vesanoid; Effederm; Panretyn; Retinova; Panretin; Toctino; Aberela; Avitoin; Retin a; Retin-a; Atragen; Aknoten; Aberel; Renova; Eudyna; Airol; Avita



数据库引用编号

17 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(12)

BioCyc(0)

PlantCyc(0)

代谢反应

128 个相关的代谢反应过程信息。

Reactome(118)

BioCyc(0)

WikiPathways(1)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(9)

PharmGKB(0)

2 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Venkatram R Atigadda, Mahendra P Kashyap, Zhengrong Yang, Debasish Chattopadhyay, Nathalia Melo, Rajesh Sinha, Olga V Belyaeva, Chu-Fang Chou, Pi-Ling Chang, Natalia Y Kedishvili, Clinton J Grubbs, Matthew B Renfrow, Donald D Muccio, Craig A Elmets, Mohammad Athar. Conformationally Defined Rexinoids for the Prevention of Inflammation and Nonmelanoma Skin Cancers. Journal of medicinal chemistry. 2022 11; 65(21):14409-14423. doi: 10.1021/acs.jmedchem.2c00735. [PMID: 36318154]
  • Faizul Azam, Martiniano Bello. Microsecond MD Simulations to Explore the Structural and Energetic Differences between the Human RXRα-PPARγ vs. RXRα-PPARγ-DNA. Molecules (Basel, Switzerland). 2022 Sep; 27(18):. doi: 10.3390/molecules27185778. [PMID: 36144514]
  • Jieying Luo, Junaid Ahmed Shaikh, Lei Huang, Lei Zhang, Shahid Iqbal, Yu Wang, Bojiang Liu, Quan Zhou, Aisha Ajmal, Maryam Rizvi, Maryam Ajmal, Yingwu Liu. Human Plasma Metabolomics Identify 9-cis-retinoic Acid and Dehydrophytosphingosine Levels as Novel biomarkers for Early Ventricular Fibrillation after ST-elevated Myocardial Infarction. Bioengineered. 2022 02; 13(2):3334-3350. doi: 10.1080/21655979.2022.2027067. [PMID: 35094641]
  • Maddalena Napolitano, Luca Potestio, Mario De Lucia, Mariateresa Nocerino, Gabriella Fabbrocini, Cataldo Patruno. Alitretinoin for the treatment of severe chronic eczema of the hands. Expert opinion on pharmacotherapy. 2022 Feb; 23(2):159-167. doi: 10.1080/14656566.2021.1998457. [PMID: 34789049]
  • Xingming Hou, Clemens Malainer, Atanas G Atanasov, Elke H Heiß, Verena M Dirsch, Limei Wang, KeWei Wang. Evodiamine Lowers Blood Lipids by Up-Regulating the PPARγ/ABCG1 Pathway in High-Fat-Diet-Fed Mice. Journal of natural products. 2021 12; 84(12):3110-3116. doi: 10.1021/acs.jnatprod.1c00881. [PMID: 34902249]
  • Sandra Treptow, Joachim Grün, Josephine Scholz, Andreas Radbruch, Guido Heine, Margitta Worm. 9-cis Retinoic acid and 1.25-dihydroxyvitamin D3 drive differentiation into IgA+ secreting plasmablasts in human naïve B cells. European journal of immunology. 2021 01; 51(1):125-137. doi: 10.1002/eji.202048557. [PMID: 33107588]
  • Junyou Li, Mengqi Liu, Yazhou Li, Dan-Dan Sun, Zhihao Shu, Qian Tan, Shimeng Guo, Rongrong Xie, Lixin Gao, Hongbo Ru, Yi Zang, Hong Liu, Jia Li, Yu Zhou. Discovery and Optimization of Non-bile Acid FXR Agonists as Preclinical Candidates for the Treatment of Nonalcoholic Steatohepatitis. Journal of medicinal chemistry. 2020 11; 63(21):12748-12772. doi: 10.1021/acs.jmedchem.0c01065. [PMID: 32991173]
  • Wei-Xiang Lin, Chun-Lan Xie, Mi Zhou, Man-Li Xia, Ting-Ting Zhou, Hai-Feng Chen, Xian-Wen Yang, Quan Yang. Chemical constituents from the deep sea-derived Streptomyces xiamenensis MCCC 1A01570 and their effects on RXRα transcriptional regulation. Natural product research. 2020 May; 34(10):1461-1464. doi: 10.1080/14786419.2018.1508148. [PMID: 30270742]
  • Fen Wang, Long-Sheng Wang, Yao-Hui Gao, Xu-Dong Yao. VHL enhances 9-cis-retinoic acid treatment by down-regulating retinoid X receptor α in renal cell carcinomas. Biochemical and biophysical research communications. 2020 03; 523(2):535-541. doi: 10.1016/j.bbrc.2019.12.112. [PMID: 31928714]
  • Yanfeng Xue, Changzheng Guo, Fan Hu, Weiyun Zhu, Shengyong Mao. PPARA/RXRA signalling regulates the fate of hepatic non-esterified fatty acids in a sheep model of maternal undernutrition. Biochimica et biophysica acta. Molecular and cell biology of lipids. 2020 02; 1865(2):158548. doi: 10.1016/j.bbalip.2019.158548. [PMID: 31676441]
  • Almudena Bermejo, Aida Collado, Isabel Barrachina, Patrice Marqués, Noureddine El Aouad, Xavier Franck, Francisco Garibotto, Catherine Dacquet, Daniel H Caignard, Fernando D Suvire, Ricardo D Enriz, Laura Piqueras, Bruno Figadère, María-Jesús Sanz, Nuria Cabedo, Diego Cortes. Polycerasoidol, a Natural Prenylated Benzopyran with a Dual PPARα/PPARγ Agonist Activity and Anti-inflammatory Effect. Journal of natural products. 2019 07; 82(7):1802-1812. doi: 10.1021/acs.jnatprod.9b00003. [PMID: 31268307]
  • Deniz Kulaksiz, Cavit Kart, Suleyman Guven, Kubra Akbulut, Umit Cobanoglu, Orhan Deger. Comparison of the effect of isotretionin and alitretionin on endometriotic implants and serum vascular endothelial growth factor level: an experimental study. Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology. 2019 Apr; 35(4):301-304. doi: 10.1080/09513590.2018.1526275. [PMID: 30600729]
  • Hua Yang, Yue Tao, Mengli Zhang, Pengcheng Ma, Lingjun Li, Qingchun Diao. Effects of 9-cis-retinoic acid on the proliferation and apoptosis of cutaneous T-cell lymphoma cells. Anti-cancer drugs. 2019 01; 30(1):56-64. doi: 10.1097/cad.0000000000000692. [PMID: 30198914]
  • Zhiqing Yuan, Guiyang Wang, Junwen Qu, Xiaopeng Wang, Kewei Li. 9-cis-retinoic acid elevates MRP3 expression by inhibiting sumoylation of RXRα to alleviate cholestatic liver injury. Biochemical and biophysical research communications. 2018 09; 503(1):188-194. doi: 10.1016/j.bbrc.2018.06.001. [PMID: 29885283]
  • Lei Huang, Lei Zhang, Tong Li, Ying-Wu Liu, Yu Wang, Bo-Jiang Liu. Human Plasma Metabolomics Implicates Modified 9-cis-Retinoic Acid in the Phenotype of Left Main Artery Lesions in Acute ST-Segment Elevated Myocardial Infarction. Scientific reports. 2018 08; 8(1):12958. doi: 10.1038/s41598-018-30219-w. [PMID: 30154509]
  • Jing Wu, Rui Yang, Lei Zhang, YueGuo Li, BingBing Liu, Hua Kang, ZhiJuan Fan, YaQiong Tian, ShuYe Liu, Tong Li. Metabolomics research on potential role for 9-cis-retinoic acid in breast cancer progression. Cancer science. 2018 Jul; 109(7):2315-2326. doi: 10.1111/cas.13629. [PMID: 29737597]
  • Mengliu Zhang, Yang Wang, Qian Zhang, Changsheng Wang, Dawei Zhang, Jian-Bo Wan, Chunyan Yan. UPLC/Q-TOF-MS-based metabolomics study of the anti-osteoporosis effects of Achyranthes bidentata polysaccharides in ovariectomized rats. International journal of biological macromolecules. 2018 Jun; 112(?):433-441. doi: 10.1016/j.ijbiomac.2018.01.204. [PMID: 29410058]
  • Guido Heine, Tim Hollstein, Sandra Treptow, Andreas Radbruch, Margitta Worm. 9-cis retinoic acid modulates the type I allergic immune response. The Journal of allergy and clinical immunology. 2018 02; 141(2):650-658.e5. doi: 10.1016/j.jaci.2017.03.046. [PMID: 28526622]
  • Emilie Distel, Thomas Cadoudal, Martine Collinet, Edwards A Park, Chantal Benelli, Sylvie Bortoli. Early induction of pyruvate dehydrogenase kinase 4 by retinoic acids in adipocytes. Molecular nutrition & food research. 2017 05; 61(5):. doi: 10.1002/mnfr.201600920. [PMID: 27981737]
  • Pascal Heitel, Janosch Achenbach, Daniel Moser, Ewgenij Proschak, Daniel Merk. DrugBank screening revealed alitretinoin and bexarotene as liver X receptor modulators. Bioorganic & medicinal chemistry letters. 2017 03; 27(5):1193-1198. doi: 10.1016/j.bmcl.2017.01.066. [PMID: 28169169]
  • Tain-Junn Cheng, Shu-Wen Lin, Chih-Wei Chen, How-Ran Guo, Ying-Jang Wang. Arsenic trioxide suppresses liver X receptor β and enhances cholesteryl ester transfer protein expression without affecting the liver X receptor α in HepG2 cells. Chemico-biological interactions. 2016 Oct; 258(?):288-96. doi: 10.1016/j.cbi.2016.09.009. [PMID: 27622732]
  • Elina Shrestha, Maryem A Hussein, Jeffery N Savas, Mireille Ouimet, Tessa J Barrett, Sarah Leone, John R Yates, Kathryn J Moore, Edward A Fisher, Michael J Garabedian. Poly(ADP-ribose) Polymerase 1 Represses Liver X Receptor-mediated ABCA1 Expression and Cholesterol Efflux in Macrophages. The Journal of biological chemistry. 2016 May; 291(21):11172-84. doi: 10.1074/jbc.m116.726729. [PMID: 27026705]
  • Corina Roman, Elena V Fuior, Violeta G Trusca, Dimitris Kardassis, Maya Simionescu, Anca V Gafencu. Thyroid hormones upregulate apolipoprotein E gene expression in astrocytes. Biochemical and biophysical research communications. 2015 Dec; 468(1-2):190-5. doi: 10.1016/j.bbrc.2015.10.132. [PMID: 26519880]
  • Wenjing Zhou, Jiacheng Lin, Hongen Chen, Jingjing Wang, Yan Liu, Min Xia. Retinoic acid induces macrophage cholesterol efflux and inhibits atherosclerotic plaque formation in apoE-deficient mice. The British journal of nutrition. 2015 Aug; 114(4):509-18. doi: 10.1017/s0007114515002159. [PMID: 26201974]
  • Mengxia Xu, Chunxiao Huang, Nan Chen, Xinjie Wu, Kecheng Zhu, Weimin Wang, Huanling Wang. Sequence analysis and expression regulation of rbp4 by 9-cis-RA in Megalobrama amblycephala. Fish physiology and biochemistry. 2015 Apr; 41(2):437-47. doi: 10.1007/s10695-014-9995-7. [PMID: 25274419]
  • Carla M Teglia, María S Cámara, Héctor C Goicoechea. Rapid determination of retinoic acid and its main isomers in plasma by second-order high-performance liquid chromatography data modeling. Analytical and bioanalytical chemistry. 2014 Dec; 406(30):7989-98. doi: 10.1007/s00216-014-8268-8. [PMID: 25370161]
  • Jeyathevy Sukiban, Peter Bräunig, Jörg Mey, Katrin Bui-Göbbels. Retinoic acid as a survival factor in neuronal development of the grasshopper, Locusta migratoria. Cell and tissue research. 2014 Nov; 358(2):303-12. doi: 10.1007/s00441-014-1957-y. [PMID: 25107605]
  • Venkatram R Atigadda, Gang Xia, Anil Desphande, LeeAnn J Boerma, Susan Lobo-Ruppert, Clinton J Grubbs, Craig D Smith, Wayne J Brouillette, Donald D Muccio. Methyl substitution of a rexinoid agonist improves potency and reveals site of lipid toxicity. Journal of medicinal chemistry. 2014 Jun; 57(12):5370-80. doi: 10.1021/jm5004792. [PMID: 24801499]
  • M Lahfa. [Management of chronic hand eczema]. Annales de dermatologie et de venereologie. 2014 Jun; 141 Suppl 1(?):S143-50. doi: 10.1016/s0151-9638(14)70151-6. [PMID: 24953623]
  • Tetsuro Shimakami, Masao Honda, Takayoshi Shirasaki, Riuta Takabatake, Fanwei Liu, Kazuhisa Murai, Takayuki Shiomoto, Masaya Funaki, Daisuke Yamane, Seishi Murakami, Stanley M Lemon, Shuichi Kaneko. The acyclic retinoid Peretinoin inhibits hepatitis C virus replication and infectious virus release in vitro. Scientific reports. 2014 Apr; 4(?):4688. doi: 10.1038/srep04688. [PMID: 24732793]
  • J P Thyssen, L Vester, C Grønhøj Larsen, K Smidt, P Jakobsen, S H Hansen, D Vind-Kezunovic, L L Gluud, F Grønhøj Larsen. The single-dose pharmacokinetics of alitretinoin and its metabolites are not significantly altered in patients with cirrhosis. The British journal of dermatology. 2014 Feb; 170(2):408-14. doi: 10.1111/bjd.12546. [PMID: 23909409]
  • Mandana Schindler, Gennadiy Drozdenko, Anja Andrea Kühl, Margitta Worm. Immunomodulation in patients with chronic hand eczema treated with oral alitretinoin. International archives of allergy and immunology. 2014; 165(1):18-26. doi: 10.1159/000365659. [PMID: 25277487]
  • D Flodrova, D Benkovska, D Macejova, L Bialesova, J Bobalova, J Brtko. Effects of retinoic acid isomers on proteomic pattern in human breast cancer MCF-7 cell line. Endocrine regulations. 2013 Oct; 47(4):205-9. doi: 10.4149/endo_2013_04_205. [PMID: 24156709]
  • Yun Hu, Yaqi Yang, Yanjun Yu, Gesi Wen, Nana Shang, Wei Zhuang, Dihan Lu, Binhua Zhou, Baoxia Liang, Xin Yue, Feng Li, Jun Du, Xianzhang Bu. Synthesis and identification of new flavonoids targeting liver X receptor β involved pathway as potential facilitators of Aβ clearance with reduced lipid accumulation. Journal of medicinal chemistry. 2013 Aug; 56(15):6033-53. doi: 10.1021/jm301913k. [PMID: 23844653]
  • Chiaki Sagara, Katsuhiko Takahashi, Hiroyuki Kagechika, Noriko Takahashi. Molecular mechanism of 9-cis-retinoic acid inhibition of adipogenesis in 3T3-L1 cells. Biochemical and biophysical research communications. 2013 Mar; 433(1):102-7. doi: 10.1016/j.bbrc.2013.02.057. [PMID: 23485459]
  • Elyse K Paterson, Hsiang Ho, Rubina Kapadia, Anand K Ganesan. 9-cis retinoic acid is the ALDH1A1 product that stimulates melanogenesis. Experimental dermatology. 2013 Mar; 22(3):202-9. doi: 10.1111/exd.12099. [PMID: 23489423]
  • Efrat Sharvit, Shirley Abramovitch, Shimon Reif, Rafael Bruck. Amplified inhibition of stellate cell activation pathways by PPAR-γ, RAR and RXR agonists. PloS one. 2013; 8(10):e76541. doi: 10.1371/journal.pone.0076541. [PMID: 24098526]
  • Michiyasu Ishizawa, Hiroyuki Kagechika, Makoto Makishima. NR4A nuclear receptors mediate carnitine palmitoyltransferase 1A gene expression by the rexinoid HX600. Biochemical and biophysical research communications. 2012 Feb; 418(4):780-5. doi: 10.1016/j.bbrc.2012.01.102. [PMID: 22310716]
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  • I R Aguayo-Leiva, S Urrutia, P Jaén-Olasolo. [Response to treatment with oral alitretinoin in patients with chronic hand eczema that is refractory to treatment with potent topical corticosteroids: experience in 15 patients]. Actas dermo-sifiliograficas. 2011 Oct; 102(8):616-22. doi: 10.1016/j.ad.2010.10.012. [PMID: 21354545]
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  • A H Schmitt-Hoffmann, B Roos, J Sauer, M Schleimer, P Kovācs, K Stoeckel, J Maares. Influence of food on the pharmacokinetics of oral alitretinoin (9-cis retinoic acid). Clinical and experimental dermatology. 2011 Apr; 36 Suppl 2(?):18-23. doi: 10.1111/j.1365-2230.2011.04033.x. [PMID: 21443600]
  • A H Schmitt-Hoffmann, B Roos, J Sauer, J Spickermann, K Stoeckel, D Edwards, J van de Wetering, P J Coenraads, J Maares. Pharmacokinetics, efficacy and safety of alitretinoin in moderate or severe chronic hand eczema. Clinical and experimental dermatology. 2011 Apr; 36 Suppl 2(?):29-34. doi: 10.1111/j.1365-2230.2011.04035.x. [PMID: 21443602]
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  • A H Schmitt-Hoffmann, B Roos, J Sauer, J Spickermann, J Maares, A Schoetzau, I Meyer. Pharmacokinetic interactions between alitretinoin and ketoconazole or simvastatin or ciclosporin A. Clinical and experimental dermatology. 2011 Apr; 36 Suppl 2(?):24-8. doi: 10.1111/j.1365-2230.2011.04034.x. [PMID: 21443601]
  • A H Schmitt-Hoffmann, B Roos, J Sauer, M Schleimer, A Schoetzau, P T Leese, E Weidekamm, J Maares. Influence of alitretinoin on the pharmacokinetics of the oral contraceptive ethinyl estradiol/norgestimate. Clinical and experimental dermatology. 2011 Apr; 36 Suppl 2(?):4-11. doi: 10.1111/j.1365-2230.2011.04031.x. [PMID: 21443598]
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  • Maureen A Kane, Alexandra E Folias, Attilio Pingitore, Mariarita Perri, Kristin M Obrochta, Charles R Krois, Erika Cione, Joo Yeon Ryu, Joseph L Napoli. Identification of 9-cis-retinoic acid as a pancreas-specific autacoid that attenuates glucose-stimulated insulin secretion. Proceedings of the National Academy of Sciences of the United States of America. 2010 Dec; 107(50):21884-9. doi: 10.1073/pnas.1008859107. [PMID: 21115832]
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