Bibliographies thématiques / Maytansinoids

Littérature scientifique sur le sujet « Maytansinoids »

Auteur : Grafiati
Publié le 14 mars 2023

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Articles de revues sur le sujet "Maytansinoids"

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Giles, Francis, Rodica Morariu-Zamfir, John Lambert, Srdan Verstovsek, Deborah Thomas, Farhad Ravandi et Dan Deangelo. « Phase I Study of AVE9633, an AntiCD33-Maytansinoid Immunoconjugate, Administered as an Intravenous Infusion in Patients with Refractory/Relapsed CD33-Positive Acute Myeloid Leukemia (AML). » Blood 108, no 11 (16 novembre 2006) : 4548. http://dx.doi.org/10.1182/blood.v108.11.4548.4548.

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Abstract AVE9633 is an immunoconjugate created by conjugation of the cytotoxic maytansinoid, DM4, to the monoclonal IgG1 antibody, huMy9-6 (average of 3.5 molecules of DM4 per antibody). The huMy9-6 antibody is a humanized version of a murine monoclonal antibody, My9-6, which is specific for the CD33 antigen expressed on the surface of myeloid cells, including the majority of cases of AML. Because CD33 has little expression outside the hematopoietic system, it represents an attractive target for antibody-based therapy in patients with AML. The humanized antibody, huMy9-6, binds to the CD33 antigen with an apparent KD in the range of 10−10 M. Maytansinoids are anti-mitotics that inhibit tubulin polymerization and microtubule assembly, inhibiting cells during the G2/M phase of the mitotic cycle. In order to link maytansinoids to antibodies via disulfide bonds, a new thiol-containing maytansinoid (DM4) was synthesized. Attachment of potent maytansinoids to an antibody via disulfide bonds provides a satisfactory stability in the bloodstream. After the conjugate is bound at the specific tumor site it is internalized and the cytotoxic agent is released within the target cell. A phase I study of AVE9633 is being conducted in patients with refractory/relapsed CD33+ AML. The study regimen consists of AVE9633 IV infusion on Day 1 of a 3 weeks cycle. To date dose levels of 15 (N=3), 30 (N=5), 50 (N=4), 75 (N=4), 105 (N=2), 200 (N=3) and 260 (N=1) mg/m2 have been investigated. Hypersensitivity reactions during perfusion were noted, requiring prophylaxis with steroids. No other AVE9633- attributable extramedullary Grade 3 AE has been observed to date. Free DM4, measured by LC/MS/MS was detectable from the 75 mg/m2 dose level; its Cmax (at the end of infusion) increased from 10 ng/mL at the 75 mg/m2 dose level to 70 ng/mL at 200 mg/m2. Neither AVE9633-associated myelosuppression nor responses have been noted. Using Flow Cytometry Assay on peripheral blasts and monocytes, total saturation and down regulation of CD33 were observed following administration of doses ≥ 30 mg/m2. AVE9633 exposure (measuring, by ELISA method, all antibodies containing at lease one molecule of DM4) increased proportionally with the administered dose in the dose range 15 to 200 mg/m2. Updated PK results and potential explanations for the lack of efficacy using this treatment schedule will be presented.
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Plattner, Ronald D., et Richard G. Powell. « Tandem Mass Spectrometry of Maytansinoids ». Journal of Natural Products 49, no 3 (mai 1986) : 475–82. http://dx.doi.org/10.1021/np50045a016.

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Larson, Gretchen M., Brian T. Schaneberg et Albert T. Sneden. « Two New Maytansinoids fromMaytenus buchananii ». Journal of Natural Products 62, no 2 (février 1999) : 361–63. http://dx.doi.org/10.1021/np9803732.

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Lo, Chen-Fu, Tai-Yu Chiu, Yu-Tzu Liu, Li-Rung Huang, Teng-Kuang Yeh, Kuan-Hsun Huang, Kuan-Liang Liu et al. « Synthesis and Evaluation of Small Molecule Drug Conjugates Harnessing Thioester-Linked Maytansinoids ». Pharmaceutics 14, no 7 (21 juin 2022) : 1316. http://dx.doi.org/10.3390/pharmaceutics14071316.

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Ligand-targeting drug conjugates are a class of clinically validated biopharmaceutical drugs constructed by conjugating cytotoxic drugs with specific disease antigen targeting ligands through appropriate linkers. The integrated linker-drug motif embedded within such a system can prevent the premature release during systemic circulation, thereby allowing the targeting ligand to engage with the disease antigen and selective accumulation. We have designed and synthesized new thioester-linked maytansinoid conjugates. By performing in vitro cytotoxicity, targeting ligand binding assay, and in vivo pharmacokinetic studies, we investigated the utility of this new linker-drug moiety in the small molecule drug conjugate (SMDC) system. In particular, we conjugated the thioester-linked maytansinoids to the phosphatidylserine-targeting small molecule zinc dipicolylamine and showed that Zn8_DM1 induced tumor regression in the HCC1806 triple-negative breast cancer xenograft model. Moreover, in a spontaneous sorafenib-resistant liver cancer model, Zn8_DM1 exhibited potent antitumor growth efficacy. From quantitative mRNA analysis of Zn8_DM1 treated-tumor tissues, we observed the elevation of gene expressions associated with a “hot inflamed tumor” state. With the identification and validation of a plethora of cancer-associated antigens in the “omics” era, this work provided the insight that antibody- or small molecule-based targeting ligands can be conjugated similarly to generate new ligand-targeting drug conjugates.
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Nittoli, Thomas, Frank Delfino, Marcus Kelly, Serena Carosso, Thomas Markotan, Arthur Kunz, Zhaoyuan Chen et al. « Antibody drug conjugates of cleavable amino-benzoyl-maytansinoids ». Bioorganic & ; Medicinal Chemistry 28, no 23 (décembre 2020) : 115785. http://dx.doi.org/10.1016/j.bmc.2020.115785.

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Suchocki, John A., et Albert T. Sneden. « New maytansinoids : reduction products of the C(9)-carbinolamide ». Journal of Organic Chemistry 53, no 17 (août 1988) : 4116–18. http://dx.doi.org/10.1021/jo00252a047.

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Ladino, Cynthia A., Ravi V. J. Chari, Lizabeth A. Bourret, Nancy L. Kedersha et Victor S. Goldmacher. « Folate-maytansinoids : Target-selective drugs of low molecular weight ». International Journal of Cancer 73, no 6 (10 décembre 1997) : 859–64. http://dx.doi.org/10.1002/(sici)1097-0215(19971210)73:6<859 ::aid-ijc16>3.0.co;2-#.

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Perrino, Elena, Martina Steiner, Nikolaus Krall, Gonçalo J. L. Bernardes, Francesca Pretto, Giulio Casi et Dario Neri. « Curative Properties of Noninternalizing Antibody–Drug Conjugates Based on Maytansinoids ». Cancer Research 74, no 9 (11 février 2014) : 2569–78. http://dx.doi.org/10.1158/0008-5472.can-13-2990.

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Nittoli, Thomas, Marcus P. Kelly, Frank Delfino, John Rudge, Arthur Kunz, Thomas Markotan, Jan Spink et al. « Antibody drug conjugates of cleavable amino-alkyl and aryl maytansinoids ». Bioorganic & ; Medicinal Chemistry 26, no 9 (mai 2018) : 2271–79. http://dx.doi.org/10.1016/j.bmc.2018.02.025.

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Liu, C., B. M. Tadayoni, L. A. Bourret, K. M. Mattocks, S. M. Derr, W. C. Widdison, N. L. Kedersha et al. « Eradication of large colon tumor xenografts by targeted delivery of maytansinoids. » Proceedings of the National Academy of Sciences 93, no 16 (6 août 1996) : 8618–23. http://dx.doi.org/10.1073/pnas.93.16.8618.

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Thèses sur le sujet "Maytansinoids"

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Hodgson, D. M. « Synthetic studies towards the maytansinoids ». Thesis, University of Southampton, 1989. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.330146.

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Princiotto, S. « Synthesis of intermediates for the preparation of Active Pharmaceutical Ingredients (APIs) ». Doctoral thesis, Università di Siena, 2020. http://hdl.handle.net/11365/1095607.

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Maytansinoids are ansa macrocycles extracted from shrubs of Maytenus ovatus. Their anticancer activity is known since the 1970s, but it could be possible to be exploited only recently, as conjugated to different antibody in the context of antibody drug conjugates (ADCs). This kind of approach allowed to drive the pharmacologically active compound (payload) selectively towards the target cancer cells, avoiding to exert the cytotoxicity also in healthy cells. Ansamitocin P3, isolated from fermentation of Actinosynnema pretiosum, is a useful precursor for the preparation of DM1, the payload present within ado-trastuzumab emtansine, commercially available as Kadcyla® for the treatment of metastatic breast cancer. To date, several methods for the synthesis of DM1 have been described in literature, all of them based on the reductive hydrolysis of ansamitocin P3 ester to the corresponding secondary alcohol maytansinol and its further functionalization. In the first section of this thesis it was described a new method to perform the reductive hydrolysis, using different methodologies with respect to the traditional in batch reaction. Moreover, a new, unprecedently reported method for the synthesis of the methyl disulfide derivative of DM1 (DM1-SMe) was developed, so that it was possible to achieve prepare the payload in a complete diastereoselective manner.
Inositols are a class of 9 compounds characterized by the presence of the cyclohexan-hex-ol moiety, with different stereochemical configuration of the carbons present upon the structure. In particular, myo-inositol is widely present in nature (plants and mammals), mostly in form of phytate (as phosphorus reservoir within the plants) and as important components of cellular membrane (phosphatidyl inositol phosphates) or second messengers of intracellular signaling cascades (inositol triphosphate, IP3). Due to its very important role within different physiological conditions, in the second section of this thesis the performed reactivity studies about myo-inositol were described. In particular, the different regio- and stereoselectivities in presence of different reaction conditions were reported. Different protection protocols for the myo-inositol orthoformate were established and the results were rationalized and applied for the total synthesis of a natural origin compound, with particular attention to the desymmetrization process, necessary for the obtainment of optically pure derivatives.
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Meurer, Kristina. « Untersuchungen zum Vorkommen von Maytansinoiden in Höheren Pflanzen : ein Beitrag zur Suche nach einem maytansinproduzierenden Mikroorganismus / ». [S.l. : s.n.], 2002. http://www.gbv.de/dms/bs/toc/356980243.pdf.

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Brünjes, Marco. « Studien zur chemoenzymatischen Synthese und Biosynthese von Maytansinoid-Analoga ». [S.l.] : [s.n.], 2006. http://deposit.ddb.de/cgi-bin/dokserv?idn=98052542X.

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Frenzel, Thomas. « Studien zur chemoenzymatischen Synthese von Maytansinoid-Analoga Synthese von seco-Proansamitocin / ». [S.l.] : [s.n.], 2005. http://deposit.ddb.de/cgi-bin/dokserv?idn=977228118.

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Brünjes, Marco [Verfasser]. « Studien zur chemoenzymatischen Synthese und Biosynthese von Maytansinoid-Analoga / von Marco Brünjes ». 2006. http://d-nb.info/98052542X/34.

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MERLINO, GIUSEPPE. « Characterization of MEN1309/OBT076, a new antibody conjugated to the DM4 maytansinoide toxin ». Doctoral thesis, 2020. http://hdl.handle.net/11573/1341225.

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CD205 is a type I transmembrane glycoprotein, member of C-type lectin receptor family. Analysis by mass spectrometry revealed that CD205 antigen was robustly expressed and highly prevalent in a variety of solid malignancies of different histotypes. Immunohistochemistry (IHC) confirmed the increased expression of CD205 antigen in pancreatic, bladder and triple negative breast cancer (TNBC) malignancies compared to corresponding normal tissues. Using immunofluorescence microscopy, rapid internalization of the CD205 antigen was observed. These results supported the development of MEN1309/OBT076, a fully human CD205-targeting monoclonal antibody conjugated to DM4, a potent maytansinoid derivate, via a cleavable N-succinimidyl-4-(2-pyridyldithio) butanoate linker. MEN1309/OBT076 was characterized in vitro for target binding affinity, mechanism of action (MoA) and cytotoxic activity against a panel of cancer cell lines demonstrating selective and potent cytotoxic effects against tumor cells with strong and low to moderate CD205 antigen expression. In addition, MEN1309/OBT076 showed potent antitumor activity resulting in durable responses and complete tumor regressions in many xenografts of TNBC, pancreatic, bladder cancer cell-lines as well as in patient-derived xenograft (PDX) models. Finally, the pharmacokinetics (PK) and pharmacodynamics (PD) profile of MEN1309/OBT076 was characterized in a mouse model harboring a pancreatic tumor. Overall, these data demonstrate that MEN1309/OBT076 is a novel and selective antibody-drug conjugate (ADC) with potent activity against CD205 antigen positive tumors. These data supported the clinical development of MEN1309/OBT076 in the phase I of “SHUTTLE” clinical trial, currently ongoing.
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Frenzel, Thomas [Verfasser]. « Studien zur chemoenzymatischen Synthese von Maytansinoid-Analoga : Synthese von seco-Proansamitocin / von Thomas Frenzel ». 2005. http://d-nb.info/977228118/34.

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Chapitres de livres sur le sujet "Maytansinoids"

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Erickson, Hans. « Antibody-Maytansinoid Conjugates : From the Bench to the Clinic ». Dans Drug Delivery in Oncology, 375–94. Weinheim, Germany : Wiley-VCH Verlag GmbH & Co. KGaA, 2011. http://dx.doi.org/10.1002/9783527634057.ch13.

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Widdison, Wayne C. « CHAPTER 5. Maytansinoid Payloads for Antibody–Drug Conjugates (ADCs) ». Dans Cytotoxic Payloads for Antibody–Drug Conjugates, 100–116. Cambridge : Royal Society of Chemistry, 2019. http://dx.doi.org/10.1039/9781788012898-00100.

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Lambert, John M., Veronique Blanc, Nathalie Le Bail et Anne Bousseau. « Targeting CD19 with SAR3419, an anti-CD19-Maytansinoid Conjugate for the Treatment of B Cell Malignancies ». Dans Antibody-Drug Conjugates and Immunotoxins, 149–60. New York, NY : Springer New York, 2012. http://dx.doi.org/10.1007/978-1-4614-5456-4_9.

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« Maytansinoids ». Dans Encyclopedia of Genetics, Genomics, Proteomics and Informatics, 1166. Dordrecht : Springer Netherlands, 2008. http://dx.doi.org/10.1007/978-1-4020-6754-9_9986.

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« Ansamitocins (Maytansinoids) ». Dans Anticancer Agents from Natural Products, 423–44. CRC Press, 2011. http://dx.doi.org/10.1201/b11185-21.

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« Ansamitocins (Maytansinoids) ». Dans Anticancer Agents from Natural Products, 337–54. CRC Press, 2005. http://dx.doi.org/10.1201/9781420039658-21.

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Actes de conférences sur le sujet "Maytansinoids"

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Sala, Gianluca, Emily Capone, Enza Piccolo, Sara Ponziani, Roberta Gentile, Rodolfo Ippoliti, Francesco Giansanti et Stefano Iacobelli. « Abstract 748 : Non-internalizing site-specific antibody-drug conjugates based on maytansinoids display curative properties ». Dans Proceedings : AACR Annual Meeting 2018 ; April 14-18, 2018 ; Chicago, IL. American Association for Cancer Research, 2018. http://dx.doi.org/10.1158/1538-7445.am2018-748.

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Nollmann, Friederike I., Patricia Perez Galan, Javier Garcia Fernandez, Heidi K. Walter, Johannes P. Magnusson, Federico Medda, Felix Kratz et al. « Abstract 1657 : Structure-activity relationship studies and biological evaluation of novel maytansinoids, a class of highly selective tubulin inhibitors ». Dans Proceedings : AACR Annual Meeting 2018 ; April 14-18, 2018 ; Chicago, IL. American Association for Cancer Research, 2018. http://dx.doi.org/10.1158/1538-7445.am2018-1657.

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Nollmann, Friederike I., Patricia Perez Galan, Javier Garcia Fernandez, Heidi K. Walter, Johannes P. Magnusson, Federico Medda, Felix Kratz et al. « Abstract 2661 : Novel albumin-binding maytansinoids inducing long-term partial and complete tumor regressions in several human cancer xenograft models in nude mice ». Dans Proceedings : AACR Annual Meeting 2018 ; April 14-18, 2018 ; Chicago, IL. American Association for Cancer Research, 2018. http://dx.doi.org/10.1158/1538-7445.am2018-2661.

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Whiteman, Kathleen R., Holly A. Johnson, Xiuxia Sun, Robert Mastico, Susan Emrich, Lauren Clancy, Hans Erickson et Jan Pinkas. « Abstract 4628 : Anti-tumor activity and pharmacokinetics of the anti-FOLR1-maytansinoid conjugate IMGN853 is maintained over a wide range of maytansinoid-to-antibody ratios ». Dans Proceedings : AACR 103rd Annual Meeting 2012‐‐ Mar 31‐Apr 4, 2012 ; Chicago, IL. American Association for Cancer Research, 2012. http://dx.doi.org/10.1158/1538-7445.am2012-4628.

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Widdison, Wayne C., Sharon Wilhelm, Karen Veale, Yelena Kovtun, Hans Erickson, Charlene Audette, Barbara Leeca, Gregory Jones et Ravi Chari. « Abstract 2668 : Detoxification of metabolites from antibody-maytansinoid conjugates by human liver microsomes ». Dans Proceedings : AACR 101st Annual Meeting 2010‐‐ Apr 17‐21, 2010 ; Washington, DC. American Association for Cancer Research, 2010. http://dx.doi.org/10.1158/1538-7445.am10-2668.

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Sun, Xiuxia, Jose F. Ponte, Nicholas C. Yoder, Jennifer Coccia, Leanne Lanieri, Rassol Laleau, Qifeng Qiu et al. « Abstract 4531 : Effects of drug load on therapeutic index for antibody-maytansinoid conjugates ». Dans Proceedings : AACR 106th Annual Meeting 2015 ; April 18-22, 2015 ; Philadelphia, PA. American Association for Cancer Research, 2015. http://dx.doi.org/10.1158/1538-7445.am2015-4531.

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Kellogg, Brenda, Charlene Audette, Hans Erickson, Michelle Mayo, Michael Okamoto, Jan Pinkas, Xiuxia Sun et al. « Abstract 4404 : Comparativein vivopharmacokinetic properties of antibody-maytansinoid conjugates with alternative non-cleavable linkers ». Dans Proceedings : AACR 101st Annual Meeting 2010‐‐ Apr 17‐21, 2010 ; Washington, DC. American Association for Cancer Research, 2010. http://dx.doi.org/10.1158/1538-7445.am10-4404.

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Singh, Rajeeva, Nathan Fishkin, Yelena Kovtun, Gregory Jones, Jose Ponte, Hans Erickson, Erica Hong et al. « Abstract C164 : New tri-glycyl peptide linker offers advantages for maytansinoid antibody-drug conjugates (ADCs). » Dans Abstracts : AACR-NCI-EORTC International Conference : Molecular Targets and Cancer Therapeutics--Oct 19-23, 2013 ; Boston, MA. American Association for Cancer Research, 2013. http://dx.doi.org/10.1158/1535-7163.targ-13-c164.

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Ab, Olga, Laura M. Bartle, Lingyun Rui, Jennifer Coccia, Holly A. Johnson, Kathleen R. Whiteman, Brenda Kellogg, Lauren Clancy, Xiuxia Sun et Victor S. Goldmacher. « Abstract 4576 : IMGN853, an anti-Folate Receptor I antibody-maytansinoid conjugate for targeted cancer therapy ». Dans Proceedings : AACR 102nd Annual Meeting 2011‐‐ Apr 2‐6, 2011 ; Orlando, FL. American Association for Cancer Research, 2011. http://dx.doi.org/10.1158/1538-7445.am2011-4576.

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Widdison, Wayne C., Joe Ponte, Jennifer Coccia, Yulius Setiady, Ling Dong, Anja Skaletskaya, Nathan Fishkin et al. « Abstract 1618 : New peptide-linked anilino-maytansinoid antibody-drug conjugates (ADCs) for the treatment of cancer ». Dans Proceedings : AACR Annual Meeting 2014 ; April 5-9, 2014 ; San Diego, CA. American Association for Cancer Research, 2014. http://dx.doi.org/10.1158/1538-7445.am2014-1618.

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