Maytansine (BioDeep_00000008198)

 

Secondary id: BioDeep_00000395681

PANOMIX_OTCML-2023 Chemicals and Drugs


代谢物信息卡片


[(16Z,18E)-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10,12,14(26),16,18-pentaen-6-yl] 2-[acetyl(methyl)amino]propanoate

化学式: C34H46ClN3O10 (691.2871566)
中文名称: 美坦新, 美坦新
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 48.78%

分子结构信息

SMILES: CC1C2CC(C(C=CC=C(CC3=CC(=C(C(=C3)OC)Cl)N(C(=O)CC(C4(C1O4)C)OC(=O)C(C)N(C)C(=O)C)C)C)OC)(NC(=O)O2)O
InChI: InChI=1S/C34H46ClN3O10/c1-18-11-10-12-26(45-9)34(43)17-25(46-32(42)36-34)19(2)30-33(5,48-30)27(47-31(41)20(3)37(6)21(4)39)16-28(40)38(7)23-14-22(13-18)15-24(44-8)29(23)35/h10-12,14-15,19-20,25-27,30,43H,13,16-17H2,1-9H3,(H,36,42)/b12-10+,18-11-

描述信息

D050258 - Mitosis Modulators > D050256 - Antimitotic Agents > D050257 - Tubulin Modulators
D000970 - Antineoplastic Agents > D050256 - Antimitotic Agents
C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C273 - Antimitotic Agent
C274 - Antineoplastic Agent > C1931 - Antineoplastic Plant Product
C1907 - Drug, Natural Product
Same as: D04864
Maytansine is a highly potent microtubule-targeted compound that induces mitotic arrest and kills tumor cells at subnanomolar concentrations[1].

同义名列表

4 个代谢物同义名

[(16Z,18E)-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10,12,14(26),16,18-pentaen-6-yl] 2-[acetyl(methyl)amino]propanoate; Maytansine; Maitansine; NSC 153858



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(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)

7 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

  • Ryuto Tomabechi, Miki Miyasato, Taeka Sato, Tappei Takada, Kei Higuchi, Hisanao Kishimoto, Yoshiyuki Shirasaka, Katsuhisa Inoue. Identification of 5-Carboxyfluorescein as a Probe Substrate of SLC46A3 and Its Application in a Fluorescence-Based In Vitro Assay Evaluating the Interaction with SLC46A3. Molecular pharmaceutics. 2023 01; 20(1):491-499. doi: 10.1021/acs.molpharmaceut.2c00741. [PMID: 36458938]
  • Clemence Pouzin, Leonid Gibiansky, Nathalie Fagniez, Mustapha Chadjaa, Michel Tod, Laurent Nguyen. Integrated multiple analytes and semi-mechanistic population pharmacokinetic model of tusamitamab ravtansine, a DM4 anti-CEACAM5 antibody-drug conjugate. Journal of pharmacokinetics and pharmacodynamics. 2022 06; 49(3):381-394. doi: 10.1007/s10928-021-09799-0. [PMID: 35166967]
  • Hai-Na Xie, Yu-Yuan Chen, Guo-Biao Zhu, Hai-Hao Han, Xi-Le Hu, Zhi-Qiang Pan, Yi Zang, Dong-Hao Xie, Xiao-Peng He, Jia Li, Tony D James. Targeted delivery of maytansine to liver cancer cells via galactose-modified supramolecular two-dimensional glycomaterial. Chemical communications (Cambridge, England). 2022 Apr; 58(32):5029-5032. doi: 10.1039/d1cc06809a. [PMID: 35373789]
  • Yunlin Fu, Shashank Gorityala, Wenkui Li, David Humphries, Aaron Ledvina, Stephanie Cape, Franck Picard. Sensitive LC-MS/MS quantification of unconjugated maytansinoid DM4 and its metabolite S-methyl-DM4 in human plasma. Bioanalysis. 2022 Mar; 14(6):357-368. doi: 10.4155/bio-2021-0275. [PMID: 35234045]
  • Chao Xu, Shaojie Liu, Fa Yang, Keying Zhang, Yu Li, Xiaolong Zhao, Jiayu Zhang, Tong Lu, Shiqi Lu, Yao Jiang, Weijun Qin, Changhong Shi, Rui Zhang, An-Gang Yang, Aizhi Zhao, Donghui Han, Weihong Wen. Antibody-drug conjugates targeting CD248+ myofibroblasts effectively alleviate renal fibrosis in mice. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2022 02; 36(2):e22102. doi: 10.1096/fj.202101441r. [PMID: 34972243]
  • Yuan-Yuan Huang, Lu Chen, Guo-Xu Ma, Xu-Dong Xu, Xue-Gong Jia, Fu-Sheng Deng, Xue-Jian Li, Jing-Quan Yuan. A Review on Phytochemicals of the Genus Maytenus and Their Bioactive Studies. Molecules (Basel, Switzerland). 2021 Jul; 26(15):. doi: 10.3390/molecules26154563. [PMID: 34361712]
  • Li Li, Chanrui Wang, Yijue Wu, Lihou Dong, Fang Chen, Kelly Dong, Haifeng Song. Simple and Rapid LC-MS/MS Methods for Quantifying Catabolites of Antibody-Drug Conjugates with SMCC Linker. Journal of chromatographic science. 2021 Jun; 59(7):642-649. doi: 10.1093/chromsci/bmaa122. [PMID: 33420505]
  • Juan Li, Siyu Guo, Qiang Hua, Fengxian Hu. Improved AP-3 production through combined ARTP mutagenesis, fermentation optimization, and subsequent genome shuffling. Biotechnology letters. 2021 Jun; 43(6):1143-1154. doi: 10.1007/s10529-020-03034-5. [PMID: 33751317]
  • Pengcheng Xu, Ru Wang, Wenqian Yang, Yanyan Liu, Dongsheng He, Zixuan Ye, Daquan Chen, Yuan Ding, Jiasheng Tu, Yan Shen. A DM1-doped porous gold nanoshell system for NIR accelerated redox-responsive release and triple modal imaging guided photothermal synergistic chemotherapy. Journal of nanobiotechnology. 2021 Mar; 19(1):77. doi: 10.1186/s12951-021-00824-5. [PMID: 33741008]
  • Tengteng Yu, Bharat Chaganty, Liang Lin, Lijie Xing, Boopathy Ramakrishnan, Kenneth Wen, Phillip A Hsieh, Andrew Wollacott, Karthik Viswanathan, Hedy Adari, Shih-Feng Cho, Yuyin Li, Hailin Chen, Wenjuan Yang, Yan Xu, Gang An, Lugui Qiu, Nikhil Munshi, Gregory Babcock, Zachary Shriver, James R Myette, Kenneth C Anderson, Yu-Tzu Tai. VIS832, a novel CD138-targeting monoclonal antibody, potently induces killing of human multiple myeloma and further synergizes with IMiDs or bortezomib in vitro and in vivo. Blood cancer journal. 2020 11; 10(11):110. doi: 10.1038/s41408-020-00378-z. [PMID: 33149123]
  • Yu-Qing Wang, Meng-Ying Ji, Chang Wang. Endoplasmic reticulum-targeted glutathione and pH dual responsive vitamin lipid nanovesicles for tocopheryl DM1 delivery and cancer therapy. International journal of pharmaceutics. 2020 May; 582(?):119331. doi: 10.1016/j.ijpharm.2020.119331. [PMID: 32289484]
  • Vineesh Indira Chandran, Ann-Sofie Månsson, Magdalena Barbachowska, Myriam Cerezo-Magaña, Björn Nodin, Bharat Joshi, Neelima Koppada, Ola M Saad, Oleg Gluz, Karolin Isaksson, Signe Borgquist, Karin Jirström, Ivan Robert Nabi, Helena Jernström, Mattias Belting. Hypoxia Attenuates Trastuzumab Uptake and Trastuzumab-Emtansine (T-DM1) Cytotoxicity through Redistribution of Phosphorylated Caveolin-1. Molecular cancer research : MCR. 2020 04; 18(4):644-656. doi: 10.1158/1541-7786.mcr-19-0856. [PMID: 31900313]
  • Kerry A Whalen, Brian H White, James M Quinn, Kristina Kriksciukaite, Rossitza Alargova, Tsun P Au Yeung, Patrick Bazinet, Adam Brockman, Michelle M DuPont, Haley Oller, James Gifford, Charles-Andre Lemelin, Patrick Lim Soo, Samantha Perino, Benoît Moreau, Gitanjali Sharma, Rajesh Shinde, Beata Sweryda-Krawiec, Mark T Bilodeau, Richard Wooster. Targeting the Somatostatin Receptor 2 with the Miniaturized Drug Conjugate, PEN-221: A Potent and Novel Therapeutic for the Treatment of Small Cell Lung Cancer. Molecular cancer therapeutics. 2019 11; 18(11):1926-1936. doi: 10.1158/1535-7163.mct-19-0022. [PMID: 31649014]
  • Mark Rosenthal, Richard Curry, David A Reardon, Erik Rasmussen, Vijay V Upreti, Michael A Damore, Haby A Henary, John S Hill, Timothy Cloughesy. Safety, tolerability, and pharmacokinetics of anti-EGFRvIII antibody-drug conjugate AMG 595 in patients with recurrent malignant glioma expressing EGFRvIII. Cancer chemotherapy and pharmacology. 2019 08; 84(2):327-336. doi: 10.1007/s00280-019-03879-2. [PMID: 31154523]
  • David J Newman. Are Microbial Endophytes the 'Actual' Producers of Bioactive Antitumor Agents?. Trends in cancer. 2018 10; 4(10):662-670. doi: 10.1016/j.trecan.2018.08.002. [PMID: 30292350]
  • Hitomi Sakai, Junji Tsurutani, Tsutomu Iwasa, Yoshifumi Komoike, Kazuko Sakai, Kazuto Nishio, Kazuhiko Nakagawa. HER2 genomic amplification in circulating tumor DNA and estrogen receptor positivity predict primary resistance to trastuzumab emtansine (T-DM1) in patients with HER2-positive metastatic breast cancer. Breast cancer (Tokyo, Japan). 2018 Sep; 25(5):605-613. doi: 10.1007/s12282-018-0861-9. [PMID: 29700710]
  • Wen Jin, Lyle Burton, Ian Moore. LC-HRMS quantitation of intact antibody drug conjugate trastuzumab emtansine from rat plasma. Bioanalysis. 2018 Jun; 10(11):851-862. doi: 10.4155/bio-2018-0003. [PMID: 29863890]
  • Cornelius Cilliers, Bruna Menezes, Ian Nessler, Jennifer Linderman, Greg M Thurber. Improved Tumor Penetration and Single-Cell Targeting of Antibody-Drug Conjugates Increases Anticancer Efficacy and Host Survival. Cancer research. 2018 02; 78(3):758-768. doi: 10.1158/0008-5472.can-17-1638. [PMID: 29217763]
  • Antari Khot, Jay Tibbitts, Dan Rock, Dhaval K Shah. Development of a Translational Physiologically Based Pharmacokinetic Model for Antibody-Drug Conjugates: a Case Study with T-DM1. The AAPS journal. 2017 11; 19(6):1715-1734. doi: 10.1208/s12248-017-0131-3. [PMID: 28808917]
  • Noriko Iwamoto, Akihiko Shimomura, Kenji Tamura, Akinobu Hamada, Takashi Shimada. LC-MS bioanalysis of Trastuzumab and released emtansine using nano-surface and molecular-orientation limited (nSMOL) proteolysis and liquid-liquid partition in plasma of Trastuzumab emtansine-treated breast cancer patients. Journal of pharmaceutical and biomedical analysis. 2017 Oct; 145(?):33-39. doi: 10.1016/j.jpba.2017.06.032. [PMID: 28648785]
  • Chunze Li, Priya Agarwal, Ekaterina Gibiansky, Jin Yan Jin, Susan Dent, Anthony Gonçalves, Ihsan Nijem, Alexander Strasak, Marie-Laurence Harle-Yge, Nataliya Chernyukhin, Pat LoRusso, Sandhya Girish. A Phase I Pharmacokinetic Study of Trastuzumab Emtansine (T-DM1) in Patients with Human Epidermal Growth Factor Receptor 2-Positive Metastatic Breast Cancer and Normal or Reduced Hepatic Function. Clinical pharmacokinetics. 2017 09; 56(9):1069-1080. doi: 10.1007/s40262-016-0496-y. [PMID: 27995530]
  • Kathleen N Moore, Hossein Borghaei, David M O'Malley, Woondong Jeong, Shelly M Seward, Todd M Bauer, Raymond P Perez, Ursula A Matulonis, Kelli L Running, Xiaoyan Zhang, Jose F Ponte, Rodrigo Ruiz-Soto, Michael J Birrer. Phase 1 dose-escalation study of mirvetuximab soravtansine (IMGN853), a folate receptor α-targeting antibody-drug conjugate, in patients with solid tumors. Cancer. 2017 Aug; 123(16):3080-3087. doi: 10.1002/cncr.30736. [PMID: 28440955]
  • Ping Zhong, Hao Meng, Jie Qiu, Jian Zhang, Huanli Sun, Ru Cheng, Zhiyuan Zhong. αvβ3 Integrin-targeted reduction-sensitive micellar mertansine prodrug: Superb drug loading, enhanced stability, and effective inhibition of melanoma growth in vivo. Journal of controlled release : official journal of the Controlled Release Society. 2017 08; 259(?):176-186. doi: 10.1016/j.jconrel.2016.12.011. [PMID: 27986551]
  • Dennis Eckelmann, Souvik Kusari, Michael Spiteller. Spatial profiling of maytansine during the germination process of Maytenus senegalensis seeds. Fitoterapia. 2017 Jun; 119(?):51-56. doi: 10.1016/j.fitote.2017.03.014. [PMID: 28385670]
  • Li-Wei Yap, Jesper Brok, Kathy Pritchard-Jones. Role of CD56 in Normal Kidney Development and Wilms Tumorigenesis. Fetal and pediatric pathology. 2017 Feb; 36(1):62-75. doi: 10.1080/15513815.2016.1256358. [PMID: 27935326]
  • Yang Li, Yanhong Duo, Shiyun Bao, Lisheng He, Kai Ling, Jinfeng Luo, Yue Zhang, Hao Huang, Han Zhang, Xiaofang Yu. EpCAM aptamer-functionalized polydopamine-coated mesoporous silica nanoparticles loaded with DM1 for targeted therapy in colorectal cancer. International journal of nanomedicine. 2017; 12(?):6239-6257. doi: 10.2147/ijn.s143293. [PMID: 28894364]
  • Mark A Socinski, Frederic J Kaye, David R Spigel, Fred J Kudrik, Santiago Ponce, Peter M Ellis, Margarita Majem, Paul Lorigan, Leena Gandhi, Martin E Gutierrez, Dale Nepert, Jesus Corral, Luis Paz Ares. Phase 1/2 Study of the CD56-Targeting Antibody-Drug Conjugate Lorvotuzumab Mertansine (IMGN901) in Combination With Carboplatin/Etoposide in Small-Cell Lung Cancer Patients With Extensive-Stage Disease. Clinical lung cancer. 2017 01; 18(1):68-76.e2. doi: 10.1016/j.cllc.2016.09.002. [PMID: 28341109]
  • Dennis Eckelmann, Souvik Kusari, Michael Spiteller. Occurrence and spatial distribution of maytansinoids in Putterlickia pyracantha, an unexplored resource of anticancer compounds. Fitoterapia. 2016 Sep; 113(?):175-81. doi: 10.1016/j.fitote.2016.08.006. [PMID: 27521896]
  • Jose F Ponte, Xiuxia Sun, Nicholas C Yoder, Nathan Fishkin, Rassol Laleau, Jennifer Coccia, Leanne Lanieri, Megan Bogalhas, Lintao Wang, Sharon Wilhelm, Wayne Widdison, Jan Pinkas, Thomas A Keating, Ravi Chari, Hans K Erickson, John M Lambert. Understanding How the Stability of the Thiol-Maleimide Linkage Impacts the Pharmacokinetics of Lysine-Linked Antibody-Maytansinoid Conjugates. Bioconjugate chemistry. 2016 07; 27(7):1588-98. doi: 10.1021/acs.bioconjchem.6b00117. [PMID: 27174129]
  • Markus Walles, Bettina Rudolph, Thierry Wolf, Julien Bourgailh, Martina Suetterlin, Thomas Moenius, Gisela Peraus, Olivier Heudi, Walid Elbast, Christian Lanshoeft, Sanela Bilic. New Insights in Tissue Distribution, Metabolism, and Excretion of [3H]-Labeled Antibody Maytansinoid Conjugates in Female Tumor-Bearing Nude Rats. Drug metabolism and disposition: the biological fate of chemicals. 2016 07; 44(7):897-910. doi: 10.1124/dmd.115.069021. [PMID: 27122302]
  • Rachelle L Dillon, Shilpa Chooniedass, Arjune Premsukh, Gregory P Adams, Joycelyn Entwistle, Glen C MacDonald, Jeannick Cizeau. Trastuzumab-deBouganin Conjugate Overcomes Multiple Mechanisms of T-DM1 Drug Resistance. Journal of immunotherapy (Hagerstown, Md. : 1997). 2016 Apr; 39(3):117-26. doi: 10.1097/cji.0000000000000115. [PMID: 26938945]
  • Haoheng Yan, Yukinori Endo, Yi Shen, David Rotstein, Milos Dokmanovic, Nishant Mohan, Partha Mukhopadhyay, Bin Gao, Pal Pacher, Wen Jin Wu. Ado-Trastuzumab Emtansine Targets Hepatocytes Via Human Epidermal Growth Factor Receptor 2 to Induce Hepatotoxicity. Molecular cancer therapeutics. 2016 Mar; 15(3):480-90. doi: 10.1158/1535-7163.mct-15-0580. [PMID: 26712117]
  • Olivier Heudi, Samuel Barteau, Franck Picard, Olivier Kretz. Quantitative analysis of maytansinoid (DM1) in human serum by on-line solid phase extraction coupled with liquid chromatography tandem mass spectrometry - Method validation and its application to clinical samples. Journal of pharmaceutical and biomedical analysis. 2016 Feb; 120(?):322-32. doi: 10.1016/j.jpba.2015.12.026. [PMID: 26771131]
  • Yong-Guang Zhang, Qing Liu, Hong-Fei Wang, Dong-Jin Park, Jian-Wei Guo, Chang-Jin Kim, Yuan-Ming Zhang, Wen-Jun Li. Nocardiopsis ansamitocini sp. nov., a new producer of ansamitocin P-3 of the genus Nocardiopsis. International journal of systematic and evolutionary microbiology. 2016 Jan; 66(1):230-235. doi: 10.1099/ijsem.0.000703. [PMID: 26486850]
  • Laura Cosmai, Maurizio Gallieni, Camillo Porta. Renal toxicity of anticancer agents targeting HER2 and EGFR. Journal of nephrology. 2015 Dec; 28(6):647-57. doi: 10.1007/s40620-015-0226-9. [PMID: 26341657]
  • Rémy Gébleux, Sarah Wulhfard, Giulio Casi, Dario Neri. Antibody Format and Drug Release Rate Determine the Therapeutic Activity of Noninternalizing Antibody-Drug Conjugates. Molecular cancer therapeutics. 2015 Nov; 14(11):2606-12. doi: 10.1158/1535-7163.mct-15-0480. [PMID: 26294742]
  • Ben-Quan Shen, Daniela Bumbaca, Qin Yue, Ola Saad, Jay Tibbitts, S Cyrus Khojasteh, Sandhya Girish. Non-Clinical Disposition and Metabolism of DM1, a Component of Trastuzumab Emtansine (T-DM1), in Sprague Dawley Rats. Drug metabolism letters. 2015; 9(2):119-31. doi: 10.2174/1872312809666150602151922. [PMID: 26031461]
  • Hirdesh Uppal, Estelle Doudement, Kaushiki Mahapatra, Walter C Darbonne, Daniela Bumbaca, Ben-Quan Shen, Xiaoyan Du, Ola Saad, Kristin Bowles, Steve Olsen, Gail D Lewis Phillips, Dylan Hartley, Mark X Sliwkowski, Sandhya Girish, Donna Dambach, Vanitha Ramakrishnan. Potential mechanisms for thrombocytopenia development with trastuzumab emtansine (T-DM1). Clinical cancer research : an official journal of the American Association for Cancer Research. 2015 Jan; 21(1):123-33. doi: 10.1158/1078-0432.ccr-14-2093. [PMID: 25370470]
  • Souvik Kusari, Marc Lamshöft, Parijat Kusari, Sebastian Gottfried, Sebastian Zühlke, Kathrin Louven, Ute Hentschel, Oliver Kayser, Michael Spiteller. Endophytes are hidden producers of maytansine in Putterlickia roots. Journal of natural products. 2014 Dec; 77(12):2577-84. doi: 10.1021/np500219a. [PMID: 25478947]
  • Russ Wada, Hans K Erickson, Gail D Lewis Phillips, Carmela A Provenzano, Douglas D Leipold, Elaine Mai, Holly Johnson, Jay Tibbitts. Mechanistic pharmacokinetic/pharmacodynamic modeling of in vivo tumor uptake, catabolism, and tumor response of trastuzumab maytansinoid conjugates. Cancer chemotherapy and pharmacology. 2014 Nov; 74(5):969-80. doi: 10.1007/s00280-014-2561-2. [PMID: 25186956]
  • Thomas H Pillow, Janet Tien, Kathryn L Parsons-Reponte, Sunil Bhakta, Hao Li, Leanna R Staben, Guangmin Li, Josefa Chuh, Aimee Fourie-O'Donohue, Martine Darwish, Victor Yip, Luna Liu, Douglas D Leipold, Dian Su, Elmer Wu, Susan D Spencer, Ben-Quan Shen, Keyang Xu, Katherine R Kozak, Helga Raab, Richard Vandlen, Gail D Lewis Phillips, Richard H Scheller, Paul Polakis, Mark X Sliwkowski, John A Flygare, Jagath R Junutula. Site-specific trastuzumab maytansinoid antibody-drug conjugates with improved therapeutic activity through linker and antibody engineering. Journal of medicinal chemistry. 2014 Oct; 57(19):7890-9. doi: 10.1021/jm500552c. [PMID: 25191794]
  • Brendan Bender, Douglas D Leipold, Keyang Xu, Ben-Quan Shen, Jay Tibbitts, Lena E Friberg. A mechanistic pharmacokinetic model elucidating the disposition of trastuzumab emtansine (T-DM1), an antibody-drug conjugate (ADC) for treatment of metastatic breast cancer. The AAPS journal. 2014 Sep; 16(5):994-1008. doi: 10.1208/s12248-014-9618-3. [PMID: 24917179]
  • Vincent Ribrag, Jehan Dupuis, Herve Tilly, Franck Morschhauser, Fabrice Laine, Roch Houot, Corinne Haioun, Christiane Copie, Andrea Varga, John Lambert, Laurence Hatteville, Samira Ziti-Ljajic, Anne Caron, Sandrine Payrard, Bertrand Coiffier. A dose-escalation study of SAR3419, an anti-CD19 antibody maytansinoid conjugate, administered by intravenous infusion once weekly in patients with relapsed/refractory B-cell non-Hodgkin lymphoma. Clinical cancer research : an official journal of the American Association for Cancer Research. 2014 Jan; 20(1):213-20. doi: 10.1158/1078-0432.ccr-13-0580. [PMID: 24132920]
  • Dan Lu, Amita Joshi, Bei Wang, Steve Olsen, Joo-Hee Yi, Ian E Krop, Howard A Burris, Sandhya Girish. An integrated multiple-analyte pharmacokinetic model to characterize trastuzumab emtansine (T-DM1) clearance pathways and to evaluate reduced pharmacokinetic sampling in patients with HER2-positive metastatic breast cancer. Clinical pharmacokinetics. 2013 Aug; 52(8):657-72. doi: 10.1007/s40262-013-0060-y. [PMID: 23553425]
  • Susanne Wings, Henry Müller, Gabriele Berg, Marc Lamshöft, Eckhard Leistner. A study of the bacterial community in the root system of the maytansine containing plant Putterlickia verrucosa. Phytochemistry. 2013 Jul; 91(?):158-64. doi: 10.1016/j.phytochem.2012.06.016. [PMID: 22795602]
  • Naomi Pode-Shakked, Rachel Shukrun, Michal Mark-Danieli, Peter Tsvetkov, Sarit Bahar, Sara Pri-Chen, Ronald S Goldstein, Eithan Rom-Gross, Yoram Mor, Edward Fridman, Karen Meir, Amos Simon, Marcus Magister, Naftali Kaminski, Victor S Goldmacher, Orit Harari-Steinberg, Benjamin Dekel. The isolation and characterization of renal cancer initiating cells from human Wilms' tumour xenografts unveils new therapeutic targets. EMBO molecular medicine. 2013 01; 5(1):18-37. doi: 10.1002/emmm.201201516. [PMID: 23239665]
  • Hans K Erickson, John M Lambert. ADME of antibody-maytansinoid conjugates. The AAPS journal. 2012 Dec; 14(4):799-805. doi: 10.1208/s12248-012-9386-x. [PMID: 22875610]
  • John A Davis, Dan A Rock, Larry C Wienkers, Josh T Pearson. In vitro characterization of the drug-drug interaction potential of catabolites of antibody-maytansinoid conjugates. Drug metabolism and disposition: the biological fate of chemicals. 2012 Oct; 40(10):1927-34. doi: 10.1124/dmd.112.046169. [PMID: 22752008]
  • P D Garzone, A J Atkinson. In search of physiologically based distribution volume estimates for macromolecules. Clinical pharmacology and therapeutics. 2012 Oct; 92(4):419-21. doi: 10.1038/clpt.2012.156. [PMID: 22992670]
  • Ben-Quan Shen, Daniela Bumbaca, Ola Saad, Qin Yue, Cinthia V Pastuskovas, S Cyrus Khojasteh, Jay Tibbitts, Surinder Kaur, Bei Wang, Yu-Waye Chu, Patricia M LoRusso, Sandhya Girish. Catabolic fate and pharmacokinetic characterization of trastuzumab emtansine (T-DM1): an emphasis on preclinical and clinical catabolism. Current drug metabolism. 2012 Sep; 13(7):901-10. doi: 10.2174/138920012802138598. [PMID: 22475269]
  • Simona Lapusan, Maria B Vidriales, Xavier Thomas, Stephane de Botton, Anne Vekhoff, Ruoping Tang, Charles Dumontet, Rodica Morariu-Zamfir, John M Lambert, Marie-Laure Ozoux, Philippe Poncelet, Jesus F San Miguel, Ollivier Legrand, Daniel J DeAngelo, Francis J Giles, Jean-Pierre Marie. Phase I studies of AVE9633, an anti-CD33 antibody-maytansinoid conjugate, in adult patients with relapsed/refractory acute myeloid leukemia. Investigational new drugs. 2012 Jun; 30(3):1121-31. doi: 10.1007/s10637-011-9670-0. [PMID: 21519855]
  • Manish Gupta, Patricia M Lorusso, Bei Wang, Joo-Hee Yi, Howard A Burris, Muralidhar Beeram, Shanu Modi, Yu-Waye Chu, Samuel Agresta, Barbara Klencke, Amita Joshi, Sandhya Girish. Clinical implications of pathophysiological and demographic covariates on the population pharmacokinetics of trastuzumab emtansine, a HER2-targeted antibody-drug conjugate, in patients with HER2-positive metastatic breast cancer. Journal of clinical pharmacology. 2012 May; 52(5):691-703. doi: 10.1177/0091270011403742. [PMID: 21953571]
  • Hans K Erickson, Gail D Lewis Phillips, Douglas D Leipold, Carmela A Provenzano, Elaine Mai, Holly A Johnson, Bert Gunter, Charlene A Audette, Manish Gupta, Jan Pinkas, Jay Tibbitts. The effect of different linkers on target cell catabolism and pharmacokinetics/pharmacodynamics of trastuzumab maytansinoid conjugates. Molecular cancer therapeutics. 2012 May; 11(5):1133-42. doi: 10.1158/1535-7163.mct-11-0727. [PMID: 22408268]
  • Ben-Quan Shen, Keyang Xu, Luna Liu, Helga Raab, Sunil Bhakta, Margaret Kenrick, Kathryn L Parsons-Reponte, Janet Tien, Shang-Fan Yu, Elaine Mai, Dongwei Li, Jay Tibbitts, Jakub Baudys, Ola M Saad, Suzie J Scales, Paul J McDonald, Philip E Hass, Charles Eigenbrot, Trung Nguyen, Willy A Solis, Reina N Fuji, Kelly M Flagella, Darshana Patel, Susan D Spencer, Leslie A Khawli, Allen Ebens, Wai Lee Wong, Richard Vandlen, Surinder Kaur, Mark X Sliwkowski, Richard H Scheller, Paul Polakis, Jagath R Junutula. Conjugation site modulates the in vivo stability and therapeutic activity of antibody-drug conjugates. Nature biotechnology. 2012 Jan; 30(2):184-9. doi: 10.1038/nbt.2108. [PMID: 22267010]
  • Nathan Fishkin, Erin K Maloney, Ravi V J Chari, Rajeeva Singh. A novel pathway for maytansinoid release from thioether linked antibody-drug conjugates (ADCs) under oxidative conditions. Chemical communications (Cambridge, England). 2011 Oct; 47(38):10752-4. doi: 10.1039/c1cc14164c. [PMID: 21874179]
  • Brenda A Kellogg, Lisa Garrett, Yelena Kovtun, Katharine C Lai, Barbara Leece, Michael Miller, Gillian Payne, Rita Steeves, Kathleen R Whiteman, Wayne Widdison, Hongsheng Xie, Rajeeva Singh, Ravi V J Chari, John M Lambert, Robert J Lutz. Disulfide-linked antibody-maytansinoid conjugates: optimization of in vivo activity by varying the steric hindrance at carbon atoms adjacent to the disulfide linkage. Bioconjugate chemistry. 2011 Apr; 22(4):717-27. doi: 10.1021/bc100480a. [PMID: 21425776]
  • Guo-Zhu Wei, Lin-Quan Bai, Tao Yang, Juan Ma, Ying Zeng, Yue-Mao Shen, Pei-Ji Zhao. A new antitumour ansamitocin from Actinosynnema pretiosum. Natural product research. 2010 Jul; 24(12):1146-50. doi: 10.1080/14786410902916552. [PMID: 20582809]
  • Yelena V Kovtun, Charlene A Audette, Michele F Mayo, Gregory E Jones, Heather Doherty, Erin K Maloney, Hans K Erickson, Xiuxia Sun, Sharon Wilhelm, Olga Ab, Katharine C Lai, Wayne C Widdison, Brenda Kellogg, Holly Johnson, Jan Pinkas, Robert J Lutz, Rajeeva Singh, Victor S Goldmacher, Ravi V J Chari. Antibody-maytansinoid conjugates designed to bypass multidrug resistance. Cancer research. 2010 Mar; 70(6):2528-37. doi: 10.1158/0008-5472.can-09-3546. [PMID: 20197459]
  • Gail D Lewis Phillips, Guangmin Li, Debra L Dugger, Lisa M Crocker, Kathryn L Parsons, Elaine Mai, Walter A Blättler, John M Lambert, Ravi V J Chari, Robert J Lutz, Wai Lee T Wong, Frederic S Jacobson, Hartmut Koeppen, Ralph H Schwall, Sara R Kenkare-Mitra, Susan D Spencer, Mark X Sliwkowski. Targeting HER2-positive breast cancer with trastuzumab-DM1, an antibody-cytotoxic drug conjugate. Cancer research. 2008 Nov; 68(22):9280-90. doi: 10.1158/0008-5472.can-08-1776. [PMID: 19010901]
  • Midori A Arai, Chikashi Tateno, Takahiro Hosoya, Takashi Koyano, Thaworn Kowithayakorn, Masami Ishibashi. Hedgehog/GLI-mediated transcriptional inhibitors from Zizyphus cambodiana. Bioorganic & medicinal chemistry. 2008 Nov; 16(21):9420-4. doi: 10.1016/j.bmc.2008.09.053. [PMID: 18842418]
  • Jordi Rodon, Mitchell Garrison, Lisa A Hammond, Johann de Bono, Lon Smith, Leonardo Forero, Desirée Hao, Chris Takimoto, John M Lambert, Lini Pandite, Maria Howard, Hongsheng Xie, Anthony W Tolcher. Cantuzumab mertansine in a three-times a week schedule: a phase I and pharmacokinetic study. Cancer chemotherapy and pharmacology. 2008 Oct; 62(5):911-9. doi: 10.1007/s00280-007-0672-8. [PMID: 18301896]
  • Peiji Zhao, Linquan Bai, Juan Ma, Ying Zeng, Lei Li, Yirong Zhang, Chunhua Lu, Huanqin Dai, Zhaoxian Wu, Yaoyao Li, Xuan Wu, Gang Chen, Xiaojiang Hao, Yuemao Shen, Zixin Deng, Heinz G Floss. Amide N-glycosylation by Asm25, an N-glycosyltransferase of ansamitocins. Chemistry & biology. 2008 Aug; 15(8):863-74. doi: 10.1016/j.chembiol.2008.06.007. [PMID: 18721757]
  • Joseph A Reddy, Elaine Westrick, Hari K R Santhapuram, Stephen J Howard, Michael L Miller, Marilynn Vetzel, Iontcho Vlahov, Ravi V J Chari, Victor S Goldmacher, Christopher P Leamon. Folate receptor-specific antitumor activity of EC131, a folate-maytansinoid conjugate. Cancer research. 2007 Jul; 67(13):6376-82. doi: 10.1158/0008-5472.can-06-3894. [PMID: 17616697]
  • Juan Ma, Pei-Ji Zhao, Yue-Mao Shen. New amide N-glycosides of ansamitocins identified from Actinosynnema pretiosum. Archives of pharmacal research. 2007 Jun; 30(6):670-3. doi: 10.1007/bf02977625. [PMID: 17679541]
  • Alexander Sauter, Charlotte Kloft, Silke Gronau, Felix Bogeschdorfer, Thomas Erhardt, Wolfram Golze, Carsten Schroen, Alexander Staab, Herbert Riechelmann, Karl Hoermann. Pharmacokinetics, immunogenicity and safety of bivatuzumab mertansine, a novel CD44v6-targeting immunoconjugate, in patients with squamous cell carcinoma of the head and neck. International journal of oncology. 2007 Apr; 30(4):927-35. doi: 10.3892/ijo.30.4.927. [PMID: 17332932]
  • Nathalie Griffon, Elaine C Budreck, Christopher J Long, Uli C Broedl, Dawn H L Marchadier, Jane M Glick, Daniel J Rader. Substrate specificity of lipoprotein lipase and endothelial lipase: studies of lid chimeras. Journal of lipid research. 2006 Aug; 47(8):1803-11. doi: 10.1194/jlr.m500552-jlr200. [PMID: 16682746]
  • Sharon X Lu, Edward J Takach, Marjorie Solomon, Qing Zhu, Say-Jong Law, Frank Y Hsieh. Mass spectral analyses of labile DOTA-NHS and heterogeneity determination of DOTA or DM1 conjugated anti-PSMA antibody for prostate cancer therapy. Journal of pharmaceutical sciences. 2005 Apr; 94(4):788-97. doi: 10.1002/jps.20289. [PMID: 15729708]
  • Zhongfa Liu, Heinz G Floss, John M Cassady, Kenneth K Chan. Metabolism studies of the anti-tumor agent maytansine and its analog ansamitocin P-3 using liquid chromatography/tandem mass spectrometry. Journal of mass spectrometry : JMS. 2005 Mar; 40(3):389-99. doi: 10.1002/jms.800. [PMID: 15674857]
  • Zhongfa Liu, Heinz G Floss, John M Cassady, Jim Xiao, Kenneth K Chan. An API LC/MS/MS quantitation method for ansamitocin P-3 (AP3) and its preclinical pharmacokinetics. Journal of pharmaceutical and biomedical analysis. 2004 Nov; 36(4):815-21. doi: 10.1016/j.jpba.2004.07.045. [PMID: 15533675]
  • Pierfrancesco Tassone, Antonella Gozzini, Victor Goldmacher, Masood A Shammas, Kathleen R Whiteman, Daniel R Carrasco, Cheng Li, Charles K Allam, Salvatore Venuta, Kenneth C Anderson, Nikhil C Munshi. In vitro and in vivo activity of the maytansinoid immunoconjugate huN901-N2'-deacetyl-N2'-(3-mercapto-1-oxopropyl)-maytansine against CD56+ multiple myeloma cells. Cancer research. 2004 Jul; 64(13):4629-36. doi: 10.1158/0008-5472.can-04-0142. [PMID: 15231675]
  • Paul R Helft, Richard L Schilsky, Frank J Hoke, Daphne Williams, Hedy L Kindler, Evie Sprague, Mark DeWitte, Helen K Martino, John Erickson, Lini Pandite, Mark Russo, John M Lambert, Maria Howard, Mark J Ratain. A phase I study of cantuzumab mertansine administered as a single intravenous infusion once weekly in patients with advanced solid tumors. Clinical cancer research : an official journal of the American Association for Cancer Research. 2004 Jul; 10(13):4363-8. doi: 10.1158/1078-0432.ccr-04-0088. [PMID: 15240523]
  • Chunhua Lu, Linquan Bai, Yuemao Shen. A novel amide N-glycoside of ansamitocins from Actinosynnema pretiosum. The Journal of antibiotics. 2004 May; 57(5):348-50. doi: 10.7164/antibiotics.57.348. [PMID: 15303496]
  • Hongsheng Xie, Charlene Audette, Mary Hoffee, John M Lambert, Walter A Blättler. Pharmacokinetics and biodistribution of the antitumor immunoconjugate, cantuzumab mertansine (huC242-DM1), and its two components in mice. The Journal of pharmacology and experimental therapeutics. 2004 Mar; 308(3):1073-82. doi: 10.1124/jpet.103.060533. [PMID: 14634038]
  • Christian B Pullen, Petra Schmitz, Dietmar Hoffmann, Kristina Meurer, Theresa Boettcher, Daniel von Bamberg, Ana Maria Pereira, Suzelei de Castro França, Manfred Hauser, Henk Geertsema, Abraam van Wyk, Taifo Mahmud, Heinz G Floss, Eckhard Leistner. Occurrence and non-detectability of maytansinoids in individual plants of the genera Maytenus and Putterlickia. Phytochemistry. 2003 Feb; 62(3):377-87. doi: 10.1016/s0031-9422(02)00550-2. [PMID: 12620351]
  • Anthony W Tolcher, Leonel Ochoa, Lisa A Hammond, Amita Patnaik, Tam Edwards, Chris Takimoto, Lon Smith, Johann de Bono, Garry Schwartz, Theresa Mays, Zdenka L Jonak, Randall Johnson, Mark DeWitte, Helen Martino, Charlene Audette, Kate Maes, Ravi V J Chari, John M Lambert, Eric K Rowinsky. Cantuzumab mertansine, a maytansinoid immunoconjugate directed to the CanAg antigen: a phase I, pharmacokinetic, and biologic correlative study. Journal of clinical oncology : official journal of the American Society of Clinical Oncology. 2003 Jan; 21(2):211-22. doi: 10.1200/jco.2003.05.137. [PMID: 12525512]
  • S S Rai, J Wolff. The C terminus of beta-tubulin regulates vinblastine-induced tubulin polymerization. Proceedings of the National Academy of Sciences of the United States of America. 1998 Apr; 95(8):4253-7. doi: 10.1073/pnas.95.8.4253. [PMID: 9539723]
  • M Novelo, J G Cruz, L Hernández, R Pereda-Miranda, H Chai, W Mar, J M Pezzuto. Cytotoxic constituents from Hyptis verticillata. Journal of natural products. 1993 Oct; 56(10):1728-36. doi: 10.1021/np50100a011. [PMID: 8277312]
  • G T Tan, J M Pezzuto, A D Kinghorn, S H Hughes. Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. Journal of natural products. 1991 Jan; 54(1):143-54. doi: 10.1021/np50073a012. [PMID: 1710653]
  • W Dymowski, M Furmanowa. [Investigating cytostatic substances in tissue of plants Maytenus Molina in in-vitro cultures. II. chromatographic test of extracts from callus of Maytenus wallichiana R. et B]. Acta poloniae pharmaceutica. 1990; 47(5-6):51-4. doi: . [PMID: 1669332]
  • T Tsuruo, T Oh-hara, H Iida, S Tsukagoshi, Z Sato, I Matsuda, S Iwasaki, S Okuda, F Shimizu, K Sasagawa. Rhizoxin, a macrocyclic lactone antibiotic, as a new antitumor agent against human and murine tumor cells and their vincristine-resistant sublines. Cancer research. 1986 Jan; 46(1):381-5. doi: . [PMID: 3753552]
  • R E Perdue. KB cell culture I. Role in discovery of antitumor agents from higher plants. Journal of natural products. 1982 Jul; 45(4):418-26. doi: 10.1021/np50022a010. [PMID: 7130986]
  • S U Kim, M Tomonaga, B Ghetti. Neurofibrillary degeneration in cultured adult mouse neurons induced by maytansine. Acta neuropathologica. 1980; 52(2):161-4. doi: 10.1007/bf00688016. [PMID: 7435167]
  • S M Sieber, J Whang-Peng, C Botkin, T Knutsen. Teratogenic and cytogenetic effects of some plant-derived antitumor agents (vincristine, colchicine, maytansine, VP-16-213 and VM-26) in mice. Teratology. 1978 Aug; 18(1):31-47. doi: 10.1002/tera.1420180107. [PMID: 694777]
  • R H Blum, T Kahlert. Maytansine: a phase I study of an ansa macrolide with antitumor activity. Cancer treatment reports. 1978 Mar; 62(3):435-8. doi: . [PMID: 348312]
  • B A Chabner, A S Levine, B L Johnson, R C Young. Initial clinical trials of maytansine, an antitumor plant alkaloid. Cancer treatment reports. 1978 Mar; 62(3):429-33. doi: . [PMID: 348311]
  • R T Eagan, J N Ingle, J Rubin, S Frytak, C G Moertel. Early clinical study of an intermittent schedule for maytansine (NSC-153858): brief communication. Journal of the National Cancer Institute. 1978 Jan; 60(1):93-6. doi: 10.1093/jnci/60.1.93. [PMID: 628025]