
Citation: CHEN Meijun, LI Jinhai, ZHANG Zhijia, LIAO Siyan, HUANG Yan, TAN Yin. Synthesis and Anti-tumor Evaluation of Nitrile-Containing Gambogic Acid Derivatives[J]. Chinese Journal of Applied Chemistry, 2016, 33(8): 905-912. doi: 10.11944/j.issn.1000-0518.2016.08.150397

藤黄酸氰基衍生物的合成及抗肿瘤活性
English
Synthesis and Anti-tumor Evaluation of Nitrile-Containing Gambogic Acid Derivatives
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Key words:
- gambogic acid
- / cyano group
- / synthesis
- / antitumor
- / derivative
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[1] YANG Jing,DING Li,LIU Wenyuan,et al. Recent Advances in Chemistry and Biology of Gamboge[J]. China J Chinese Mater Med,2013,38(1):19-25(in Chinese).杨靖,丁黎,柳文嫒,等. 藤黄化学生物学研究进展[J]. 中国中药杂志,2013,38(1):19-25.[1] YANG Jing,DING Li,LIU Wenyuan,et al. Recent Advances in Chemistry and Biology of Gamboge[J]. China J Chinese Mater Med,2013,38(1):19-25(in Chinese).杨靖,丁黎,柳文嫒,等. 藤黄化学生物学研究进展[J]. 中国中药杂志,2013,38(1):19-25.
-
[2] Liesenklas W,Auterhoff H. The Constitution of Gambogic Acid and its Isomerization.4 Chemistry of Gum-resin[J]. Arch Pharm Ber Dtsch Pharm Ges,1966,299(9):797-798.[2] Liesenklas W,Auterhoff H. The Constitution of Gambogic Acid and its Isomerization.4 Chemistry of Gum-resin[J]. Arch Pharm Ber Dtsch Pharm Ges,1966,299(9):797-798.
-
[3] Wang X,Lu N,Yang Q,et al. Studies on Chemical Modification and Biology of a Natural Product, Gambogic Acid(Ⅲ):Determination of the Essential Pharmacophore for Biological Activity[J]. Eur J Med Chem,2011,46(4):1280-1290.[3] Wang X,Lu N,Yang Q,et al. Studies on Chemical Modification and Biology of a Natural Product, Gambogic Acid(Ⅲ):Determination of the Essential Pharmacophore for Biological Activity[J]. Eur J Med Chem,2011,46(4):1280-1290.
-
[4] Duan D,Zhang B,Yao J,et al. Gambogic Acid Induces Apoptosis in Hepatocellular Carcinoma SMMC-7721 Cells by Targeting Cytosolic Thioredoxin Reductase[J]. Free Radic Biol Med,2014,69(4):15-25.[4] Duan D,Zhang B,Yao J,et al. Gambogic Acid Induces Apoptosis in Hepatocellular Carcinoma SMMC-7721 Cells by Targeting Cytosolic Thioredoxin Reductase[J]. Free Radic Biol Med,2014,69(4):15-25.
-
[5] Shi X,Chen X,Li X,et al. Gambogic Acid Induces Apoptosis in Imatinib-resistant Chronic Myeloid Leukemia Cells via Inducing Proteasome Inhibition and Caspase-dependent Bcr-Abl downreg-ulation[J]. Clin Cancer Res,2014,20(1):151-163.[5] Shi X,Chen X,Li X,et al. Gambogic Acid Induces Apoptosis in Imatinib-resistant Chronic Myeloid Leukemia Cells via Inducing Proteasome Inhibition and Caspase-dependent Bcr-Abl downreg-ulation[J]. Clin Cancer Res,2014,20(1):151-163.
-
[6] Wang L H,Yang J Y,Yang S N,et al. Suppression of NF-κB Signaling and P-Glycoprotein Function by Gambogic Acid Synergistically Potentiates Adriamycin-induced Apoptosis in Lung Cancer[J]. Curr Cancer Drug Targets,2014,14(1):91-103.[6] Wang L H,Yang J Y,Yang S N,et al. Suppression of NF-κB Signaling and P-Glycoprotein Function by Gambogic Acid Synergistically Potentiates Adriamycin-induced Apoptosis in Lung Cancer[J]. Curr Cancer Drug Targets,2014,14(1):91-103.
-
[7] Chi Y,Zhan X K,Yu H,et al. An Open-labeled, Randomized, Multicenter PhaseⅡa Study of Gambogic Acid Injection for Advanced Malignant Tumors[J]. Chinese Med J(Engl),2013,126(9):1642-1646.[7] Chi Y,Zhan X K,Yu H,et al. An Open-labeled, Randomized, Multicenter PhaseⅡa Study of Gambogic Acid Injection for Advanced Malignant Tumors[J]. Chinese Med J(Engl),2013,126(9):1642-1646.
-
[8] A Krajarng,M Imoto,E Tashiro,et al. Apoptosis Induction Associated with the ER Stress Response through Up-regulation of JNK in Hela Cells by Gambogic Acid[J]. BMC Compl Alternat Med,2015,15(1):1-9.[8] A Krajarng,M Imoto,E Tashiro,et al. Apoptosis Induction Associated with the ER Stress Response through Up-regulation of JNK in Hela Cells by Gambogic Acid[J]. BMC Compl Alternat Med,2015,15(1):1-9.
-
[9] Mohammad Ishaq,Mohammad Aslam Khan,Kapil Sharma,et al. Gambogic Acid Induced Oxidative Stress Dependent Caspase Activation Regulates both Apoptosis and Autophagy by Targeting Various Key Molecules(NF-κB, Beclin-1, p62 and NBR1) in Human Bladder Cancer Cells[J]. Biochim Biophys Acta(BBA)-Gen Sub,2014,1840(12):3374-3384.[9] Mohammad Ishaq,Mohammad Aslam Khan,Kapil Sharma,et al. Gambogic Acid Induced Oxidative Stress Dependent Caspase Activation Regulates both Apoptosis and Autophagy by Targeting Various Key Molecules(NF-κB, Beclin-1, p62 and NBR1) in Human Bladder Cancer Cells[J]. Biochim Biophys Acta(BBA)-Gen Sub,2014,1840(12):3374-3384.
-
[10] Huang H,Chen D,Li S,et al. Gambogic Acid Enhances Proteasome Inhibitor-induced Anticancer Activity[J]. Cancer Lett,2011,301(2):221-228.[10] Huang H,Chen D,Li S,et al. Gambogic Acid Enhances Proteasome Inhibitor-induced Anticancer Activity[J]. Cancer Lett,2011,301(2):221-228.
-
[11] Zhao Q,Yang Y,Yu J,et al. Posttranscriptional Regulation of the Telomerase hTERT by Gambogic Acid in Human Gastric Carcinoma 823 Cells[J]. Cancer Lett,2008,262(2):223-231.[11] Zhao Q,Yang Y,Yu J,et al. Posttranscriptional Regulation of the Telomerase hTERT by Gambogic Acid in Human Gastric Carcinoma 823 Cells[J]. Cancer Lett,2008,262(2):223-231.
-
[12] Pandey M K,Sung B,Ahn K S,et al. Gambogic Acid, a Novel Ligand for Transferrin Receptor, Potentiates TNF-induced Apoptosis Through Modulation of the Nuclear Factor-κB Signaling Pathway[J]. Blood,2007,110(10):3517-3525.[12] Pandey M K,Sung B,Ahn K S,et al. Gambogic Acid, a Novel Ligand for Transferrin Receptor, Potentiates TNF-induced Apoptosis Through Modulation of the Nuclear Factor-κB Signaling Pathway[J]. Blood,2007,110(10):3517-3525.
-
[13] QIAN Jing,WANG Keming. Progress in the Effect of Anti-tumor Molecular Targets of Gambogic Acid[J]. China Cancer,2011,20(6):441-446(in Chinese).钱婧,王科明. 藤黄酸抗肿瘤作用靶点的研究进展[J]. 中国肿瘤,2011,20(6):441-446.[13] QIAN Jing,WANG Keming. Progress in the Effect of Anti-tumor Molecular Targets of Gambogic Acid[J]. China Cancer,2011,20(6):441-446(in Chinese).钱婧,王科明. 藤黄酸抗肿瘤作用靶点的研究进展[J]. 中国肿瘤,2011,20(6):441-446.
-
[14] Gupta S C,Kim J H,Prasad S,et al. Regulation of Survival, Proliferation, Invasion, Angiogenesis, and Metastasis of Tumor Cells through Modulation of Inflammatory Pathways by Nutraceuticals[J]. Cancer Metast Rev,2010,29(3):405-434.[14] Gupta S C,Kim J H,Prasad S,et al. Regulation of Survival, Proliferation, Invasion, Angiogenesis, and Metastasis of Tumor Cells through Modulation of Inflammatory Pathways by Nutraceuticals[J]. Cancer Metast Rev,2010,29(3):405-434.
-
[15] Fleming F F,Yao L H,Ravikumar P C,et al. Nitrile-Containing Pharmaceuticals:Efficacious Roles of the Nitrile Pharmacophore[J]. J Med Chem,2010,53(22):7902-7917.[15] Fleming F F,Yao L H,Ravikumar P C,et al. Nitrile-Containing Pharmaceuticals:Efficacious Roles of the Nitrile Pharmacophore[J]. J Med Chem,2010,53(22):7902-7917.
-
[16] WANG Jiang,LIU Hong. Application of Nitrile in Drug Design[J]. Chinese J Org Chem,2012,32(9):1643-1652(in Chinese).王江,柳红. 氰基在药物分子设计中的应用[J]. 有机化学,2012,32(9):1643-1652.[16] WANG Jiang,LIU Hong. Application of Nitrile in Drug Design[J]. Chinese J Org Chem,2012,32(9):1643-1652(in Chinese).王江,柳红. 氰基在药物分子设计中的应用[J]. 有机化学,2012,32(9):1643-1652.
-
[17] ZHAO Shengyin,HUANG Wenlong. Synthesis and Vasorelaxant Activity of Trans-3-hydroxy-4-aminobenzopyran Acetylated Derivatives as K+ Channel Openers[J]. Chinese J Appl Chem,2007,24(6):698-702(in Chinese).赵圣印,黄文龙. 反式-3-羟基-4-胺基苯并吡喃乙酰化物的合成及其血管舒张活性[J]. 应用化学,2007,24(6):698-702.[17] ZHAO Shengyin,HUANG Wenlong. Synthesis and Vasorelaxant Activity of Trans-3-hydroxy-4-aminobenzopyran Acetylated Derivatives as K+ Channel Openers[J]. Chinese J Appl Chem,2007,24(6):698-702(in Chinese).赵圣印,黄文龙. 反式-3-羟基-4-胺基苯并吡喃乙酰化物的合成及其血管舒张活性[J]. 应用化学,2007,24(6):698-702.
-
[18] Pascual E,Sivera F,Yasothan U,et al. Febuxostat [J]. Nat Rev Drug Discovery,2009,8(3):191-192.[18] Pascual E,Sivera F,Yasothan U,et al. Febuxostat [J]. Nat Rev Drug Discovery,2009,8(3):191-192.
-
[19] Fradet Y. Bicalutamide(Casodex) in the Treatment of Prostate Cancer[J]. Expert Rev Anticancer Ther,2004,4(1):37-48.[19] Fradet Y. Bicalutamide(Casodex) in the Treatment of Prostate Cancer[J]. Expert Rev Anticancer Ther,2004,4(1):37-48.
-
[20] ZHANG Shenglie,LI Qian,ZHANG Lei,et al. Synthesis and Bioevaluation of Gambogic Acid Derivatives as Antitumor Agents[J]. Chinese J Org Chem,2012,32(8):1450-1458(in Chinese).张生烈,李乾,张磊,等. 藤黄酸衍生物的合成及抗肿瘤活性研究[J]. 有机化学,2012,32(8):1450-1458.[20] ZHANG Shenglie,LI Qian,ZHANG Lei,et al. Synthesis and Bioevaluation of Gambogic Acid Derivatives as Antitumor Agents[J]. Chinese J Org Chem,2012,32(8):1450-1458(in Chinese).张生烈,李乾,张磊,等. 藤黄酸衍生物的合成及抗肿瘤活性研究[J]. 有机化学,2012,32(8):1450-1458.
-
[21] HE Liqin,WU Yaxian,FU Li,et al. Synthesis and Biological Evaluation of Aminoalcohol Gambogate as Anti-tumor Agents[J]. J China Pharm Univ,2013,44(5):394-400(in Chinese).何黎琴,吴亚先,付俐,等. 藤黄酸胺基醇酯的合成及其抗肿瘤活性[J]. 中国药科大学学报,2013,44(5):394-400.[21] HE Liqin,WU Yaxian,FU Li,et al. Synthesis and Biological Evaluation of Aminoalcohol Gambogate as Anti-tumor Agents[J]. J China Pharm Univ,2013,44(5):394-400(in Chinese).何黎琴,吴亚先,付俐,等. 藤黄酸胺基醇酯的合成及其抗肿瘤活性[J]. 中国药科大学学报,2013,44(5):394-400.
-
[22] Wang J X,Zhang B H,You Q D,et al. Synthesis and Anti-tumor Activity of NO-donating Derivatives of Gambogic Acid[J]. Chinese J Nat Med,2013,11(1):87-96.[22] Wang J X,Zhang B H,You Q D,et al. Synthesis and Anti-tumor Activity of NO-donating Derivatives of Gambogic Acid[J]. Chinese J Nat Med,2013,11(1):87-96.
-
[23] He L,Ling Y,Fu L,et al. Synthesis and Biological Evaluation of Novel Derivatives of Gambogic Acid as Anti-hepatocellular Carcinoma Agents[J]. Bioorg Med Chem Lett,2012,22(1):289-292.[23] He L,Ling Y,Fu L,et al. Synthesis and Biological Evaluation of Novel Derivatives of Gambogic Acid as Anti-hepatocellular Carcinoma Agents[J]. Bioorg Med Chem Lett,2012,22(1):289-292.
-
[24] Ahmad S A,Rigby W,Taylor R B. Gamboge. Part Ⅱ[J]. J Chem Soc C,1996:772-779.[24] Ahmad S A,Rigby W,Taylor R B. Gamboge. Part Ⅱ[J]. J Chem Soc C,1996:772-779.
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