Combretastatin (BioDeep_00000251836)

   

natural product


代谢物信息卡片


3,7-Dihydroxy-3,4,45-tetramethoxybibenzyl

化学式: C18H22O6 (334.1416312)
中文名称: 考布他汀
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: c1(c(c(cc(c1)[C@@H](Cc1ccc(c(c1)O)OC)O)OC)OC)OC
InChI: InChI=1S/C18H22O6/c1-21-15-6-5-11(8-14(15)20)7-13(19)12-9-16(22-2)18(24-4)17(10-12)23-3/h5-6,8-10,13,19-20H,7H2,1-4H3

描述信息

D050258 - Mitosis Modulators > D050256 - Antimitotic Agents > D050257 - Tubulin Modulators
D000970 - Antineoplastic Agents > D050256 - Antimitotic Agents

同义名列表

4 个代谢物同义名

Combretastatin; 3,7-Dihydroxy-3,4,45-tetramethoxybibenzyl; (R)-(-)-Combretastatin; Combretastatin, (+-)



数据库引用编号

8 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

11 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

  • Godshelp O Egharevba, Ahmed Kamal, Omotayo O Dosumu, Sunitha Routhu, Olatomide A Fadare, Stephen O Oguntoye, Stanislaus N Njinga, Abimbola P Oluyori. Synthesis and characterization of novel combretastatin analogues of 1,1-diaryl vinyl sulfones, with antiproliferative potential via in-silico and in-vitro studies. Scientific reports. 2022 02; 12(1):1901. doi: 10.1038/s41598-022-05958-6. [PMID: 35115623]
  • Kun Wang, Hui Zhong, Na Li, Nairong Yu, Yujin Wang, Li Chen, Jianbo Sun. Discovery of Novel Anti-Breast-Cancer Inhibitors by Synergistically Antagonizing Microtubule Polymerization and Aryl Hydrocarbon Receptor Expression. Journal of medicinal chemistry. 2021 09; 64(17):12964-12977. doi: 10.1021/acs.jmedchem.1c01099. [PMID: 34428056]
  • Sara El-Sahli, Khang Hua, Andrew Sulaiman, Jason Chambers, Li Li, Eliya Farah, Sarah McGarry, Dan Liu, Peiyong Zheng, Seung-Hwan Lee, Jiefeng Cui, Marc Ekker, Marceline Côté, Tommy Alain, Xuguang Li, Vanessa M D'Costa, Lisheng Wang, Suresh Gadde. A triple-drug nanotherapy to target breast cancer cells, cancer stem cells, and tumor vasculature. Cell death & disease. 2021 01; 12(1):8. doi: 10.1038/s41419-020-03308-w. [PMID: 33414428]
  • Hongjun Yuan, Xin Li, Jing Tang, Min Zhou, Fengyong Liu. Local application of doxorubicin- loaded Iron oxid nanoparticles and the vascular disrupting agent via the hepatic artery: chemoembolization-photothermal ablation treatment of hepatocellular carcinoma in rats. Cancer imaging : the official publication of the International Cancer Imaging Society. 2019 Nov; 19(1):71. doi: 10.1186/s40644-019-0257-x. [PMID: 31685015]
  • Syed Nasir Abbas Bukhari, Gajjela Bharath Kumar, Hrishikesh Mohan Revankar, Hua-Li Qin. Development of combretastatins as potent tubulin polymerization inhibitors. Bioorganic chemistry. 2017 06; 72(?):130-147. doi: 10.1016/j.bioorg.2017.04.007. [PMID: 28460355]
  • Merve Karacivi, Burcu Sumer Bolu, Rana Sanyal. Targeting to the Bone: Alendronate-Directed Combretastatin A-4 Bearing Antiangiogenic Polymer-Drug Conjugates. Molecular pharmaceutics. 2017 05; 14(5):1373-1383. doi: 10.1021/acs.molpharmaceut.6b01173. [PMID: 28358515]
  • Julienne K Muenzner, Bernhard Biersack, Hussein Kalie, Ion C Andronache, Leonard Kaps, Detlef Schuppan, Florenz Sasse, Rainer Schobert. Gold(I) biscarbene complexes derived from vascular-disrupting combretastatin A-4 address different targets and show antimetastatic potential. ChemMedChem. 2014 Jun; 9(6):1195-204. doi: 10.1002/cmdc.201400049. [PMID: 24648184]
  • Pierre P J Da Silva, Lyamin Z Bendjeddou, Laurent Meijer. [Search for natural substances with therapeutic activity: George R. Pettit]. Medecine sciences : M/S. 2014 Mar; 30(3):319-28. doi: 10.1051/medsci/20143003021. [PMID: 24685224]
  • Sandra Torijano-Gutiérrez, Santiago Díaz-Oltra, Eva Falomir, Juan Murga, Miguel Carda, J Alberto Marco. Synthesis of combretastatin A-4 O-alkyl derivatives and evaluation of their cytotoxic, antiangiogenic and antitelomerase activity. Bioorganic & medicinal chemistry. 2013 Dec; 21(23):7267-74. doi: 10.1016/j.bmc.2013.09.064. [PMID: 24145138]
  • Dmitry V Tsyganov, Leonid D Konyushkin, Irina B Karmanova, Sergei I Firgang, Yuri A Strelenko, Marina N Semenova, Alex S Kiselyov, Victor V Semenov. cis-Restricted 3-aminopyrazole analogues of combretastatins: synthesis from plant polyalkoxybenzenes and biological evaluation in the cytotoxicity and phenotypic sea urchin embryo assays. Journal of natural products. 2013 Aug; 76(8):1485-91. doi: 10.1021/np400310m. [PMID: 23924236]
  • Roger H Bisby, Stanley W Botchway, John A Hadfield, Alan T McGown, Anthony W Parker, Kathrin M Scherer. Fluorescence lifetime imaging of E-combretastatin uptake and distribution in live mammalian cells. European journal of cancer (Oxford, England : 1990). 2012 Aug; 48(12):1896-903. doi: 10.1016/j.ejca.2011.11.025. [PMID: 22209092]
  • Anja B Bohn, Rikke Nørregaard, Lene Stødkilde, Yan Wang, Lotte B Bertelsen, Robert A Fenton, Vladimir V Matchkov, Elena V Bouzinova, Michael R Horsman, Jørgen Frøkiær, Hans Stødkilde-Jørgensen. Treatment with the vascular disrupting agent combretastatin is associated with impaired AQP2 trafficking and increased urine output. American journal of physiology. Regulatory, integrative and comparative physiology. 2012 Jul; 303(2):R186-98. doi: 10.1152/ajpregu.00572.2011. [PMID: 22621967]
  • David R Katerere, Alexander I Gray, Robert J Nash, Roger D Waigh. Phytochemical and antimicrobial investigations of stilbenoids and flavonoids isolated from three species of Combretaceae. Fitoterapia. 2012 Jul; 83(5):932-40. doi: 10.1016/j.fitote.2012.04.011. [PMID: 22546149]
  • Xiao-Ping Xu, Xiao-Dong Wu, Gui-Lun Liang, Wen-Sheng Huang, Li Wang, Hai-Ying Jing, Shi-Long Zhong. Pharmacokinetics, excretion, and distribution of combretastatin A4 phosphate in rats. Die Pharmazie. 2012 Jun; 67(6):529-33. doi: NULL. [PMID: 22822542]
  • Michael R L Stratford, Lisa K Folkes. A validated HPLC method with fluorescence detection for the glucuronides of Combretastatin A1 in human plasma, and studies on their cis-trans isomerisation. Journal of pharmaceutical and biomedical analysis. 2012 Mar; 62(?):114-8. doi: 10.1016/j.jpba.2011.12.022. [PMID: 22251460]
  • M Gowri Ponnapalli, S Ch V A Rao Annam, Saidulu Ravirala, Sushma Sukki, Madhu Ankireddy, V Raju Tuniki. Unusual isomeric corniculatolides from mangrove, Aegiceras corniculatum. Journal of natural products. 2012 Feb; 75(2):275-9. doi: 10.1021/np200789s. [PMID: 22316191]
  • Jennifer S Carew, Juan A Esquivel, Claudia M Espitia, Christoph M Schultes, Marcel Mülbaier, Joe D Lewis, Bernd Janssen, Francis J Giles, Steffan T Nawrocki. ELR510444 inhibits tumor growth and angiogenesis by abrogating HIF activity and disrupting microtubules in renal cell carcinoma. PloS one. 2012; 7(1):e31120. doi: 10.1371/journal.pone.0031120. [PMID: 22295124]
  • Michael R L Stratford, Lisa K Folkes. Validation of a method for the determination of the anticancer agent Combretastatin A1 phosphate (CA1P, OXi4503) in human plasma by HPLC with post-column photolysis and fluorescence detection. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2011 Sep; 879(25):2673-6. doi: 10.1016/j.jchromb.2011.07.014. [PMID: 21820978]
  • Xuexin He, Su Li, He Huang, Zhiming Li, Likun Chen, Sheng Ye, Jiajia Huang, Jing Zhan, Tongyu Lin. A pharmacokinetic and safety study of single dose intravenous combretastatin A4 phosphate in Chinese patients with refractory solid tumours. British journal of clinical pharmacology. 2011 Jun; 71(6):860-70. doi: 10.1111/j.1365-2125.2011.03928.x. [PMID: 21276042]
  • Francesco Perri, Giuseppe Di Lorenzo, Giuseppina Della Vittoria Scarpati, Carlo Buonerba. Anaplastic thyroid carcinoma: A comprehensive review of current and future therapeutic options. World journal of clinical oncology. 2011 Mar; 2(3):150-7. doi: 10.5306/wjco.v2.i3.150. [PMID: 21611089]
  • Bruce C Baguley. Preclinical efficacy of vascular disrupting agents in non-small-cell lung cancer. Clinical lung cancer. 2011 Mar; 12(2):81-6. doi: 10.1016/j.cllc.2011.03.001. [PMID: 21550553]
  • Hamid-Reza Mohammadi-Motlagh, Ali Mostafaie, Kamran Mansouri. Anticancer and anti-inflammatory activities of shallot (Allium ascalonicum) extract. Archives of medical science : AMS. 2011 Feb; 7(1):38-44. doi: 10.5114/aoms.2011.20602. [PMID: 22291731]
  • Maluta S Mufamadi, Viness Pillay, Yahya E Choonara, Lisa C Du Toit, Girish Modi, Dinesh Naidoo, Valence M K Ndesendo. A review on composite liposomal technologies for specialized drug delivery. Journal of drug delivery. 2011; 2011(?):939851. doi: 10.1155/2011/939851. [PMID: 21490759]
  • Victor V Semenov, Alex S Kiselyov, Ilia Y Titov, Irina K Sagamanova, Natalie N Ikizalp, Natalia B Chernysheva, Dmitry V Tsyganov, Leonid D Konyushkin, Sergei I Firgang, Roman V Semenov, Irina B Karmanova, Mikhail M Raihstat, Marina N Semenova. Synthesis of antimitotic polyalkoxyphenyl derivatives of combretastatin using plant allylpolyalkoxybenzenes. Journal of natural products. 2010 Nov; 73(11):1796-802. doi: 10.1021/np1004278. [PMID: 21049975]
  • Zhe Wang, Paul C Ho. Self-assembled core-shell vascular-targeted nanocapsules for temporal antivasculature and anticancer activities. Small (Weinheim an der Bergstrasse, Germany). 2010 Nov; 6(22):2576-83. doi: 10.1002/smll.201001122. [PMID: 20976704]
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  • Xiao-yan Liu, Li-ming Ruan, Wei-wei Mao, Jin-qiang Wang, You-qing Shen, Mei-hua Sui. Preparation of RGD-modified long circulating liposome loading matrine, and its in vitro anti-cancer effects. International journal of medical sciences. 2010 Jun; 7(4):197-208. doi: 10.7150/ijms.7.197. [PMID: 20596360]
  • Astrid A M van der Veldt, Martijn R Meijerink, Alfons J M van den Eertwegh, Epie Boven. Targeted therapies in renal cell cancer: recent developments in imaging. Targeted oncology. 2010 Jun; 5(2):95-112. doi: 10.1007/s11523-010-0146-5. [PMID: 20625845]
  • Katsuyoshi Hori, Masamichi Nishihara, Kouichi Shiraishi, Masayuki Yokoyama. The combretastatin derivative (Cderiv), a vascular disrupting agent, enables polymeric nanomicelles to accumulate in microtumors. Journal of pharmaceutical sciences. 2010 Jun; 99(6):2914-25. doi: 10.1002/jps.22038. [PMID: 20039393]
  • April L Risinger, Susan L Mooberry. Taccalonolides: Novel microtubule stabilizers with clinical potential. Cancer letters. 2010 May; 291(1):14-9. doi: 10.1016/j.canlet.2009.09.020. [PMID: 19880245]
  • Supriya Baikar, Nutan Malpathak. Secondary metabolites as DNA topoisomerase inhibitors: A new era towards designing of anticancer drugs. Pharmacognosy reviews. 2010 Jan; 4(7):12-26. doi: 10.4103/0973-7847.65320. [PMID: 22228937]
  • C P Lee, G S Payne, A Oregioni, R Ruddle, S Tan, F I Raynaud, D Eaton, M J Campbell, K Cross, G Halbert, M Tracy, J McNamara, B Seddon, M O Leach, P Workman, I Judson. A phase I study of the nitroimidazole hypoxia marker SR4554 using 19F magnetic resonance spectroscopy. British journal of cancer. 2009 Dec; 101(11):1860-8. doi: 10.1038/sj.bjc.6605425. [PMID: 19935799]
  • Xiaojing Wang, Zhihang Chen, Jinjing Che, Qingfang Meng, Chengqi Shan, Yunan Hou, Xiaolei Liu, Yifeng Chai, Yuanguo Cheng. Development of a rapid and sensitive LC-MS/MS assay for the determination of combretastatin A4 phosphate, combretastatin A4 and combretastatin A4 glucuronide in beagle dog plasma and its application to a pharmacokinetic study. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2009 Nov; 877(30):3813-21. doi: 10.1016/j.jchromb.2009.09.027. [PMID: 19822461]
  • Yuval Shaked, Terence Tang, Jill Woloszynek, Laura G Daenen, Shan Man, Ping Xu, Shi-Rong Cai, Jeffrey M Arbeit, Emile E Voest, David J Chaplin, Jon Smythe, Adrian Harris, Paul Nathan, Ian Judson, Gordon Rustin, Francesco Bertolini, Daniel C Link, Robert S Kerbel. Contribution of granulocyte colony-stimulating factor to the acute mobilization of endothelial precursor cells by vascular disrupting agents. Cancer research. 2009 Oct; 69(19):7524-8. doi: 10.1158/0008-5472.can-09-0381. [PMID: 19738066]
  • Colin J Mooney, Govardhanan Nagaiah, Pingfu Fu, Jay K Wasman, Matthew M Cooney, Panos S Savvides, Joseph A Bokar, Afshin Dowlati, Ding Wang, Sanjiv S Agarwala, Susan M Flick, Paul H Hartman, Jose D Ortiz, Pierre N Lavertu, Scot C Remick. A phase II trial of fosbretabulin in advanced anaplastic thyroid carcinoma and correlation of baseline serum-soluble intracellular adhesion molecule-1 with outcome. Thyroid : official journal of the American Thyroid Association. 2009 Mar; 19(3):233-40. doi: 10.1089/thy.2008.0321. [PMID: 19265494]
  • S Aprile, E Del Grosso, G Grosa. In vitro and in vivo phase II metabolism of combretastatin A-4: evidence for the formation of a sulphate conjugate metabolite. Xenobiotica; the fate of foreign compounds in biological systems. 2009 Feb; 39(2):148-61. doi: 10.1080/00498250802566976. [PMID: 19255941]
  • M J McKeage, J Von Pawel, M Reck, M B Jameson, M A Rosenthal, R Sullivan, D Gibbs, P N Mainwaring, M Serke, J-J Lafitte, C Chouaid, L Freitag, E Quoix. Randomised phase II study of ASA404 combined with carboplatin and paclitaxel in previously untreated advanced non-small cell lung cancer. British journal of cancer. 2008 Dec; 99(12):2006-12. doi: 10.1038/sj.bjc.6604808. [PMID: 19078952]
  • Christian Billard, Faouzia Menasria, Claire Quiney, Anne-Marie Faussat, Jean-Pierre Finet, Sébastien Combes, Jean-Pierre Kolb. 4-arylcoumarin analogues of combretastatins stimulate apoptosis of leukemic cells from chronic lymphocytic leukemia patients. Experimental hematology. 2008 Dec; 36(12):1625-33. doi: 10.1016/j.exphem.2008.07.008. [PMID: 18922614]
  • Jun-Sung Kim, Kyeong Nam Yu, Mi Suk Noh, Min-Ah Woo, Sung-Jin Park, Jin Hong Park, Jin Hua, Hyun Sun Cho, Soon Kyung Hwang, Eun-Sun Lee, Youn-Sun Chung, In-Young Choi, Se-Chang Kwon, Myung-Haing Cho. Serum immunoglobulin fused interferon-alpha inhibited tumor growth in athymic mice bearing colon 26 adenocarcinoma cells. Journal of veterinary science. 2008 Mar; 9(1):45-50. doi: 10.4142/jvs.2008.9.1.45. [PMID: 18296888]
  • Thomas Nielsen, Kim Mouridsen, Ross J Maxwell, Hans Stødkilde-Jørgensen, Leif Østergaard, Michael R Horsman. Segmentation of dynamic contrast enhanced magnetic resonance imaging data. Acta oncologica (Stockholm, Sweden). 2008; 47(7):1265-70. doi: 10.1080/02841860802277489. [PMID: 18661437]
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  • Ramakrishna Nallamothu, George C Wood, Mohammad F Kiani, Bob M Moore, Frank P Horton, Laura A Thoma. A targeted liposome delivery system for combretastatin A4: formulation optimization through drug loading and in vitro release studies. PDA journal of pharmaceutical science and technology. 2006 May; 60(3):144-55. doi: ". [PMID: 17089683]
  • Ramakrishna Nallamothu, George C Wood, Christopher B Pattillo, Robert C Scott, Mohammad F Kiani, Bob M Moore, Laura A Thoma. A tumor vasculature targeted liposome delivery system for combretastatin A4: design, characterization, and in vitro evaluation. AAPS PharmSciTech. 2006 Apr; 7(2):E32. doi: 10.1208/pt070232. [PMID: 16796350]
  • Vandana Srivastava, Arvind Singh Negi, J K Kumar, M M Gupta, Suman P S Khanuja. Plant-based anticancer molecules: a chemical and biological profile of some important leads. Bioorganic & medicinal chemistry. 2005 Nov; 13(21):5892-908. doi: 10.1016/j.bmc.2005.05.066. [PMID: 16129603]
  • Beatrice Coggiola, Francesca Pagliai, Gianna Allegrone, Armando A Genazzani, Gian Cesare Tron. Synthesis and biological activity of mustard derivatives of combretastatins. Bioorganic & medicinal chemistry letters. 2005 Aug; 15(15):3551-4. doi: 10.1016/j.bmcl.2005.05.052. [PMID: 15963722]
  • Shiladitya Sengupta, David Eavarone, Ishan Capila, Ganlin Zhao, Nicki Watson, Tanyel Kiziltepe, Ram Sasisekharan. Temporal targeting of tumour cells and neovasculature with a nanoscale delivery system. Nature. 2005 Jul; 436(7050):568-72. doi: 10.1038/nature03794. [PMID: 16049491]
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  • Namphung Vongvanich, Prasat Kittakoop, Panarat Charoenchai, Sutichai Intamas, Kannawat Danwisetkanjana, Yodhathai Thebtaranonth. Combretastatins D-3 and D-4, new macrocyclic lactones from Getonia floribunda. Planta medica. 2005 Feb; 71(2):191-3. doi: 10.1055/s-2005-837791. [PMID: 15729632]
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  • Bronwyn G Siim, Alan E Lee, Sahar Shalal-Zwain, Frederik B Pruijn, Mark J McKeage, William R Wilson. Marked potentiation of the antitumour activity of chemotherapeutic drugs by the antivascular agent 5,6-dimethylxanthenone-4-acetic acid (DMXAA). Cancer chemotherapy and pharmacology. 2003 Jan; 51(1):43-52. doi: 10.1007/s00280-002-0529-0. [PMID: 12497205]
  • S E Holwell, P A Cooper, M J Thompson, G R Pettit, L W Lippert, S W Martin, M C Bibby. Anti-tumor and anti-vascular effects of the novel tubulin-binding agent combretastatin A-1 phosphate. Anticancer research. 2002 Nov; 22(6C):3933-40. doi: ". [PMID: 12553015]
  • Vivien E Prise, Davina J Honess, Michael R L Stratford, John Wilson, Gillian M Tozer. The vascular response of tumor and normal tissues in the rat to the vascular targeting agent, combretastatin A-4-phosphate, at clinically relevant doses. International journal of oncology. 2002 Oct; 21(4):717-26. doi: 10.3892/ijo.21.4.717. [PMID: 12239609]
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