10-Hydroxycamptothecin (BioDeep_00000398762)

Main id: BioDeep_00000000240

 

natural product PANOMIX_OTCML-2023


代谢物信息卡片


10-Hydroxy camptothecin

化学式: C20H16N2O5 (364.1059166)
中文名称: 7-乙基-10-羟基喜树碱, (S)-10-羟基喜树碱, 10-羟基喜树碱
谱图信息: 最多检出来源 Ailuropoda melanoleuca(viridiplantae) 50%

分子结构信息

SMILES: CCC1(C2=C(COC1=O)C(=O)N3CC4=C(C3=C2)N=C5C=CC(=CC5=C4)O)O
InChI: InChI=1S/C20H16N2O5/c1-2-20(26)14-7-16-17-11(5-10-6-12(23)3-4-15(10)21-17)8-22(16)18(24)13(14)9-27-19(20)25/h3-7,23,26H,2,8-9H2,1H3

描述信息

SubCategory_DNP: : Alkaloids derived from anthranilic acid, Quinoline alkaloids
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.944
D000970 - Antineoplastic Agents
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.947
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.929
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.928
(S)-10-Hydroxycamptothecin (10-HCPT;10-Hydroxycamptothecin) is a DNA topoisomerase I inhibitor of isolated from the Chinese plant Camptotheca accuminata. (S)-10-Hydroxycamptothecin exhibits a remarkable apoptosis-inducing effect. (S)-10-Hydroxycamptothecin has the potential for hepatoma, gastric carcinoma, colon cancer and leukaemia treatment[1][2][3][4].
(S)-10-Hydroxycamptothecin (10-HCPT;10-Hydroxycamptothecin) is a DNA topoisomerase I inhibitor of isolated from the Chinese plant Camptotheca accuminata. (S)-10-Hydroxycamptothecin exhibits a remarkable apoptosis-inducing effect. (S)-10-Hydroxycamptothecin has the potential for hepatoma, gastric carcinoma, colon cancer and leukaemia treatment[1][2][3][4].

同义名列表

5 个代谢物同义名

10-Hydroxycamptothecin; 10-Hydroxy camptothecin; 10-Hydroxy-Camptothecin; 10-HCPT; (S)-10-Hydroxycamptothecin



数据库引用编号

32 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)

8 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

  • Yukun Chen, Zhenzhi Wang, Xiaofan Wang, Mingliang Su, Fan Xu, Lian Yang, Lijun Jia, Zhanxia Zhang. Advances in Antitumor Nano-Drug Delivery Systems of 10-Hydroxycamptothecin. International journal of nanomedicine. 2022; 17(?):4227-4259. doi: 10.2147/ijn.s377149. [PMID: 36134205]
  • Yingjie Qi, Guangxuan Liu. Berberine-10-hydroxy camptothecine-loaded lipid microsphere for the synergistic treatment of liver cancer by inhibiting topoisomerase and HIF-1α. Drug delivery. 2021 Dec; 28(1):171-182. doi: 10.1080/10717544.2020.1870020. [PMID: 33427515]
  • Lingqiang Meng, Jianmin Dai, Shengzhong Rong, Hongmin Gao, Ze Zhang, Yingcong Zhang, Dong Chang, Hongzhi Pan. One-step electrodeposition preparation of polyaniline/f-MWCNTs as electrochemical sensors for detection of 10-hydroxycamptothecine. Biotechnology and applied biochemistry. 2021 Dec; 68(6):1192-1201. doi: 10.1002/bab.2041. [PMID: 32970340]
  • Yanni Sun, Ning Zhang, Cuiling Wang, Xiao Bai, Yahui Wei, Jianli Liu. The biosynthesis of camptothecin derivatives by Camptotheca acuminata seedlings. Natural product research. 2021 Jul; 35(14):2403-2407. doi: 10.1080/14786419.2019.1678616. [PMID: 31631694]
  • Shu Fan, Yong-Xiao Cao, Guang-Yan Li, Hao Lei, Mawusse K I Attiogbe, Jing-Chun Yao, Xue-Yan Yang, Yan-Jie Liu, Yuan-Yuan Hei, Hao Zhang, Lei Cao, Xiao-Yan Zhang, Shuai-Shuai Du, Gui-Min Zhang, San-Qi Zhang. F10, a new camptothecin derivative, was identified as a new orally-bioavailable, potent antitumor agent. European journal of medicinal chemistry. 2020 Sep; 202(?):112528. doi: 10.1016/j.ejmech.2020.112528. [PMID: 32650182]
  • Sixi Huang, Di Ren, Xinrong Wu, Ming Li, Xuesong Yu, Xiaoling Nie, Ying Wang, Yan Wang. Glycyrrhetinic Acid and TAT Peptide Modified Dual-functional Liposomes for Treatment of Hepatocellular Cancer. Current topics in medicinal chemistry. 2020; 20(27):2493-2505. doi: 10.2174/1568026620666200722110244. [PMID: 32703132]
  • Ting Zhou, Xin Tang, Wei Zhang, Jianfang Feng, Wei Wu. Preparation and in vitro and in vivo evaluations of 10-hydroxycamptothecin liposomes modified with stearyl glycyrrhetinate. Drug delivery. 2019 Dec; 26(1):673-679. doi: 10.1080/10717544.2019.1636422. [PMID: 31266376]
  • Wugang Zhang, Mulan Li, Wendi Du, Wuliang Yang, Guofeng Li, Chen Zhang, Xinli Liang, Haifang Chen. Tissue Distribution and Anti-Lung Cancer Effect of 10-Hydroxycamptothecin Combined with Platycodonis Radix and Glycyrrhizae Radix ET Rhizoma. Molecules (Basel, Switzerland). 2019 May; 24(11):. doi: 10.3390/molecules24112068. [PMID: 31151274]
  • Huai-Qiu Li, Wei-Liang Ye, Meng-Lei Huan, Ying Cheng, Dao-Zhou Liu, Han Cui, Miao Liu, Bang-le Zhang, Qi-Bing Mei, Si-Yuan Zhou. Mitochondria and nucleus delivery of active form of 10-hydroxycamptothecin with dual shell to precisely treat colorectal cancer. Nanomedicine (London, England). 2019 04; 14(8):1011-1032. doi: 10.2217/nnm-2018-0227. [PMID: 30925116]
  • Yifei Guo, Ting Wang, Hanhong Qiu, Meihua Han, Zhengqi Dong, Xiangtao Wang, Yanhong Wang. Hydroxycamptothecin nanoparticles based on poly/oligo (ethylene glycol): Architecture effects of nanocarriers on antitumor efficacy. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V. 2019 Jan; 134(?):178-184. doi: 10.1016/j.ejpb.2018.12.003. [PMID: 30529294]
  • Yang Zhou, Tao Hong, Li Tong, Wei Liu, Xueting Yang, Jianghan Luo, Fuling Wang, Jian Li, Lijun Yan. Astragalus polysaccharide combined with 10-hydroxycamptothecin inhibits metastasis in non-small cell lung carcinoma cell lines via the MAP4K3/mTOR signaling pathway. International journal of molecular medicine. 2018 Dec; 42(6):3093-3104. doi: 10.3892/ijmm.2018.3868. [PMID: 30221690]
  • Yifei Guo, Ting Wang, Shuang Zhao, Hanhong Qiu, Meihua Han, Zhengqi Dong, Xiangtao Wang. Effect of alkyl chain on cellular uptake and antitumor activity of hydroxycamptothecin nanoparticles based on amphiphilic linear molecules. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2018 Nov; 124(?):266-272. doi: 10.1016/j.ejps.2018.08.043. [PMID: 30189259]
  • Chun-Gu Wang, Wei-Na Yao, Bin Zhang, Jing Hua, Dong Liang, Heng-Shan Wang. Lung cancer and matrix metalloproteinases inhibitors of polyphenols from Selaginella tamariscina with suppression activity of migration. Bioorganic & medicinal chemistry letters. 2018 08; 28(14):2413-2417. doi: 10.1016/j.bmcl.2018.06.024. [PMID: 29921475]
  • Yifei Guo, Ting Wang, Shuang Zhao, Meihua Han, Zhengqi Dong, Xiangtao Wang, Yanhong Wang. Amphiphilic Hybrid Dendritic-Linear Molecules as Nanocarriers for Shape-Dependent Antitumor Drug Delivery. Molecular pharmaceutics. 2018 07; 15(7):2665-2673. doi: 10.1021/acs.molpharmaceut.8b00190. [PMID: 29782803]
  • Vonny Salim, A Daniel Jones, Dean DellaPenna. Camptotheca acuminata 10-hydroxycamptothecin O-methyltransferase: an alkaloid biosynthetic enzyme co-opted from flavonoid metabolism. The Plant journal : for cell and molecular biology. 2018 07; 95(1):112-125. doi: 10.1111/tpj.13936. [PMID: 29681057]
  • Haiyang Wu, Tongya Yu, Ye Tian, Yinjie Wang, Ruizhi Zhao, Shirui Mao. Enhanced liver-targeting via coadministration of 10-Hydroxycamptothecin polymeric micelles with vinegar baked Radix Bupleuri. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2018 May; 44(?):1-8. doi: 10.1016/j.phymed.2018.04.022. [PMID: 29895488]
  • Jian Zheng, Yong Ji, Changmin Shao, Lijia Jing, Yang Wang. Pharmacokinetics and tissue distribution study of 10-methoxycamptothecin in rats following intragastric administration. Journal of pharmaceutical and biomedical analysis. 2018 Feb; 149(?):564-571. doi: 10.1016/j.jpba.2017.11.062. [PMID: 29197298]
  • Xiaoshuang Ren, Lan Zhang, Yanning Zhang, Liangang Mao, Hongyun Jiang. Mitochondria response to camptothecin and hydroxycamptothecine-induced apoptosis in Spodoptera exigua cells. Pesticide biochemistry and physiology. 2017 Aug; 140(?):97-104. doi: 10.1016/j.pestbp.2017.07.003. [PMID: 28755702]
  • Minjie Sun, Jing Li, Cuiting Zhang, Ying Xie, Hongzhi Qiao, Zhigui Su, David Oupický, Qineng Ping. Arginine-Modified Nanostructured Lipid Carriers with Charge-Reversal and pH-Sensitive Membranolytic Properties for Anticancer Drug Delivery. Advanced healthcare materials. 2017 Apr; 6(8):. doi: 10.1002/adhm.201600693. [PMID: 28187243]
  • Yifei Guo, Yanna Zhao, Ting Wang, Ran Li, Meihua Han, Zhengqi Dong, Chunyan Zhu, Xiangtao Wang. Hydroxycamptothecin Nanorods Prepared by Fluorescently Labeled Oligoethylene Glycols (OEG) Codendrimer: Antitumor Efficacy in Vitro and in Vivo. Bioconjugate chemistry. 2017 02; 28(2):390-399. doi: 10.1021/acs.bioconjchem.6b00536. [PMID: 27982573]
  • Linjie Yang, Jingyi Hong, Jing Di, Yifei Guo, Meihua Han, Meifeng Liu, Xiangtao Wang. 10-Hydroxycamptothecin (HCPT) nanosuspensions stabilized by mPEG1000-HCPT conjugate: high stabilizing efficiency and improved antitumor efficacy. International journal of nanomedicine. 2017; 12(?):3681-3695. doi: 10.2147/ijn.s134005. [PMID: 28553107]
  • Zhen Liu, Hongfa Li, Yaya Fan, Yuanxue Liu, Shuli Man, Peng Yu, Wenyuan Gao. Combination treatment with Rhizoma Paridis and Rhizoma Curcuma longa extracts and 10-hydroxycamptothecin enhances the antitumor effect in H22 tumor model by increasing the plasma concentration. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2016 Oct; 83(?):627-634. doi: 10.1016/j.biopha.2016.07.026. [PMID: 27459119]
  • Chun Pan, Yan-Fen Hu, Juan Song, Hua-Shan Yi, La Wang, Yi-Ying Yang, Yong-Ping Wang, Man Zhang, Min-Hui Pan, Cheng Lu. Effects of 10-hydroxycamptothecin on intrinsic mitochondrial pathway in silkworm BmN-SWU1 cells. Pesticide biochemistry and physiology. 2016 Feb; 127(?):15-20. doi: 10.1016/j.pestbp.2015.09.001. [PMID: 26821653]
  • Min Liu, Didi Chen, Jean Felix Mukerabigwi, Sha Chen, Yuannian Zhang, Shaojun Lei, Shiying Luo, Zhili Wen, Yu Cao, Xueying Huang, Hongxuan He. Intracellular delivery of 10-hydroxycamptothecin with targeted nanostructured lipid carriers against multidrug resistance. Journal of drug targeting. 2016; 24(5):433-40. doi: 10.3109/1061186x.2015.1086358. [PMID: 26422582]
  • Yue Yuan, Jian Wen, Jie Tang, Qiming Kan, Rose Ackermann, Karl Olsen, Anna Schwendeman. Synthetic high-density lipoproteins for delivery of 10-hydroxycamptothecin. International journal of nanomedicine. 2016 ; 11(?):6229-6238. doi: 10.2147/ijn.s112835. [PMID: 27920529]
  • Xiaofeng Yang, Yingying Liu, Yanna Zhao, Meihua Han, Yifei Guo, Haixue Kuang, Xiangtao Wang. A stabilizer-free and organic solvent-free method to prepare 10-hydroxycamptothecin nanocrystals: in vitro and in vivo evaluation. International journal of nanomedicine. 2016; 11(?):2979-94. doi: 10.2147/ijn.s102726. [PMID: 27382284]
  • Yang Li, Jinyan Lin, Yu Huang, Yanxiu Li, Xiangrui Yang, Hongjie Wu, Shichao Wu, Liya Xie, Lizong Dai, Zhenqing Hou. Self-Targeted, Shape-Assisted, and Controlled-Release Self-Delivery Nanodrug for Synergistic Targeting/Anticancer Effect of Cytoplasm and Nucleus of Cancer Cells. ACS applied materials & interfaces. 2015 Nov; 7(46):25553-9. doi: 10.1021/acsami.5b07348. [PMID: 26529185]
  • Peng Li, Qinhua Chen, Fei Yu, Xiaoyu Xie, Sicen Wang. Simultaneous determination of camptothecin and 10-hydroxycamptothecine in the Camptotheca acuminate, its medicinal preparation and in rat plasma by liquid chromatography with fluorescence detection. Biomedical chromatography : BMC. 2015 Oct; 29(10):1522-6. doi: 10.1002/bmc.3452. [PMID: 25728326]
  • Zhenbo Yang, Wei Gong, Zhiyuan Wang, Bingsheng Li, Mingyuan Li, Xiangyang Xie, Hui Zhang, Yang Yang, Zhiping Li, Ying Li, Fanglin Yu, Xingguo Mei. A novel drug-polyethylene glycol liquid compound method to prepare 10-hydroxycamptothecin loaded human serum albumin nanoparticle. International journal of pharmaceutics. 2015 Jul; 490(1-2):412-28. doi: 10.1016/j.ijpharm.2015.05.073. [PMID: 26027489]
  • Sheng-Jie Yang, Ming-Chuan Liu, Qi Zhao, De-Yu Hu, Wei Xue, Song Yang. Synthesis and biological evaluation of betulonic acid derivatives as antitumor agents. European journal of medicinal chemistry. 2015; 96(?):58-65. doi: 10.1016/j.ejmech.2015.04.006. [PMID: 25874331]
  • Min Liu, Didi Chen, Chenxu Wang, Xunhu Chen, Zhili Wen, Yu Cao, Hongxuan He. Intracellular target delivery of 10-hydroxycamptothecin with solid lipid nanoparticles against multidrug resistance. Journal of drug targeting. 2015; 23(9):800-5. doi: 10.3109/1061186x.2015.1020427. [PMID: 25766079]
  • Hui Luo, Shengjie Yang, Yongqiang Cai, Zhijun Peng, Tao Liu. Synthesis and biological evaluation of novel 6-chloro-quinazolin derivatives as potential antitumor agents. European journal of medicinal chemistry. 2014 Sep; 84(?):746-52. doi: 10.1016/j.ejmech.2014.07.053. [PMID: 25064351]
  • Guofei Li, Yan Li, Yilin Tang, Yu Zhang, Yan Zhang, Tian Yin, Hui Xu, Cuifang Cai, Xing Tang. Hydroxyethyl starch conjugates for improving the stability, pharmacokinetic behavior and antitumor activity of 10-hydroxy camptothecin. International journal of pharmaceutics. 2014 Aug; 471(1-2):234-44. doi: 10.1016/j.ijpharm.2014.05.038. [PMID: 24861941]
  • Qinhua Chen, Guangmin Pan, Lin Xiong, Hongsheng He, Hangdong Yang. Characterization and quantification of 10-hydroxycamptothecine in Camptotheca acuminate and its medicinal preparation by liquid chromatography-ion trap mass spectrometry. Biomedical chromatography : BMC. 2013 Dec; 27(12):1615-20. doi: 10.1002/bmc.2969. [PMID: 23813501]
  • Li Gan, Yi-Ping Gao, Chun-Liu Zhu, Xin-Xin Zhang, Yong Gan. Novel pH-sensitive lipid-polymer composite microspheres of 10-hydroxycamptothecin exhibiting colon-specific biodistribution and reduced systemic absorption. Journal of pharmaceutical sciences. 2013 Jun; 102(6):1752-1759. doi: 10.1002/jps.23499. [PMID: 23605625]
  • Zhe Yang, Xingen Luo, Xiaofang Zhang, Jie Liu, Qing Jiang. Targeted delivery of 10-hydroxycamptothecin to human breast cancers by cyclic RGD-modified lipid-polymer hybrid nanoparticles. Biomedical materials (Bristol, England). 2013 Apr; 8(2):025012. doi: 10.1088/1748-6041/8/2/025012. [PMID: 23507576]
  • Jian-Bo Qu, Hui-Hui Shao, Guang-Lun Jing, Fang Huang. PEG-chitosan-coated iron oxide nanoparticles with high saturated magnetization as carriers of 10-hydroxycamptothecin: preparation, characterization and cytotoxicity studies. Colloids and surfaces. B, Biointerfaces. 2013 Feb; 102(?):37-44. doi: 10.1016/j.colsurfb.2012.08.004. [PMID: 23000675]
  • Yuangang Zu, Li Meng, Xiuhua Zhao, Yunlong Ge, Xinyang Yu, Yin Zhang, Yiping Deng. Preparation of 10-hydroxycamptothecin-loaded glycyrrhizic acid-conjugated bovine serum albumin nanoparticles for hepatocellular carcinoma-targeted drug delivery. International journal of nanomedicine. 2013; 8(?):1207-22. doi: 10.2147/ijn.s40493. [PMID: 23569373]
  • Domenico Alloatti, Giuseppe Giannini, Loredana Vesci, Massimo Castorina, Claudio Pisano, Elena Badaloni, Walter Cabri. Camptothecins in tumor homing via an RGD sequence mimetic. Bioorganic & medicinal chemistry letters. 2012 Oct; 22(20):6509-12. doi: 10.1016/j.bmcl.2012.07.061. [PMID: 22959246]
  • Wei Hu, Chao Zhang, Wenjin Hu, Yun Fang, Wenjie Hou. Pharmacokinetics, tissue distribution, and the lactone/carboxylate equilibrium of hydroxycamptothecin delivered via aerosol in mice. Fitoterapia. 2012 Oct; 83(7):1291-8. doi: 10.1016/j.fitote.2011.12.005. [PMID: 22858157]
  • Jian Zheng, Rui Zhang, Changmin Shao, Zhiwei Hu, Di Wang, Tao Yu, Xiufeng Yan, Yang Wang. Development and validation of a RP-HPLC method with fluorescence detection for simultaneous determination of 10-methoxycamptothecin and its metabolite 10-hydroxycamptothecin in rat plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2012 Aug; 903(?):81-7. doi: 10.1016/j.jchromb.2012.07.001. [PMID: 22824730]
  • Jian Zheng, Honghong Guo, Na Guo, Wei Ma, Lijia Jing, Rui Zhang, Zhifei Dai, Xiufeng Yan, Yang Wang, Zhenyue Wang. A two-step pH-dependent liquid-liquid extraction combined with HPLC-fluorescence method for the determination of 10-hydroxycamptothecin in mouse liver tissue. Pharmaceutical biology. 2012 Aug; 50(8):954-61. doi: 10.3109/13880209.2011.654228. [PMID: 22486519]
  • Yong-Xing Zhao, Dan-Xing Liu, Wen-Quan Liang, Zhi-Wei Ye. In-vivo pharmacokinetics, tissue distribution and anti-tumour effect of hydroxycamptothecin delivered in oil-in-water submicron emulsions. The Journal of pharmacy and pharmacology. 2012 Jun; 64(6):783-91. doi: 10.1111/j.2042-7158.2012.01484.x. [PMID: 22571256]
  • Hui-Hui Sun, Jing Zhang, Ye-Zhong Zhang, Li-Yun Yang, Li-Li Yuan, Yi Liu. Interaction of human serum albumin with 10-hydroxycamptothecin: spectroscopic and molecular modeling studies. Molecular biology reports. 2012 May; 39(5):5115-23. doi: 10.1007/s11033-011-1307-z. [PMID: 22160573]
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  • Qingyong Li, Chen Liu, Xiuhua Zhao, Yuangang Zu, Ying Wang, Baoyou Zhang, Dongmei Zhao, Qi Zhao, Lin Su, Yang Gao, Baihe Sun. Preparation, characterization and targeting of micronized 10-hydroxycamptothecin-loaded folate-conjugated human serum albumin nanoparticles to cancer cells. International journal of nanomedicine. 2011; 6(?):397-405. doi: 10.2147/ijn.s16144. [PMID: 21499429]
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