(R)-(-)-Combretastatin (BioDeep_00000855640)
代谢物信息卡片
3-Hydroxy-4-methoxy-alpha-(3,4,5-trimethoxyphenyl)benzeneethanol
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: COC1=C(C=C(C=C1)CC(C2=CC(=C(C(=C2)OC)OC)OC)O)O
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/t13-/m1/s1
描述信息
C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C273 - Antimitotic Agent
D050258 - Mitosis Modulators > D050256 - Antimitotic Agents > D050257 - Tubulin Modulators
D000970 - Antineoplastic Agents > D050256 - Antimitotic Agents
同义名列表
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)
0 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] - 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] - 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] - 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] - 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] - Stewart Martin. New Agents in Clinical Oncology. 24 November 2006, London, UK.
IDrugs : the investigational drugs journal.
2007 Feb; 10(2):99-101. doi:
NULL. [PMID: 17285459] - 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] - 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] - Ian G Kirwan, Paul M Loadman, David J Swaine, D Alan Anthoney, George R Pettit, John W Lippert, Steve D Shnyder, Patricia A Cooper, Mike C Bibby. Comparative preclinical pharmacokinetic and metabolic studies of the combretastatin prodrugs combretastatin A4 phosphate and A1 phosphate.
Clinical cancer research : an official journal of the American Association for Cancer Research.
2004 Feb; 10(4):1446-53. doi:
10.1158/1078-0432.ccr-0518-03. [PMID: 14977848] - Alessandra Cirla, John Mann. Combretastatins: from natural products to drug discovery.
Natural product reports.
2003 Dec; 20(6):558-64. doi:
10.1039/b306797c. [PMID: 14700199] - Sara M Mariani. Anti-angiogenesis: the challenges ahead.
MedGenMed : Medscape general medicine.
2003 Apr; 5(2):22. doi:
NULL. [PMID: 14603121] - 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 Schwikkard, B N Zhou, T E Glass, J L Sharp, M R Mattern, R K Johnson, D G Kingston. Bioactive compounds from Combretum erythrophyllum.
Journal of natural products.
2000 Apr; 63(4):457-60. doi:
10.1021/np9904410. [PMID: 10785413] - D L Sackett. Podophyllotoxin, steganacin and combretastatin: natural products that bind at the colchicine site of tubulin.
Pharmacology & therapeutics.
1993 Aug; 59(2):163-228. doi:
10.1016/0163-7258(93)90044-e. [PMID: 8278462] - G R Pettit, G M Cragg, S B Singh. Antineoplastic agents, 122. Constituents of Combretum caffrum.
Journal of natural products.
1987 May; 50(3):386-91. doi:
10.1021/np50051a008. [PMID: 3668557] - E Hamel, C M Lin. Interactions of combretastatin, a new plant-derived antimitotic agent, with tubulin.
Biochemical pharmacology.
1983 Dec; 32(24):3864-7. doi:
10.1016/0006-2952(83)90163-6. [PMID: 6661259]