Supporting Information
Supporting Information File 1: Experimental details, characterization data and copies of spectra. | ||
Format: PDF | Size: 2.5 MB | Download |
Cite the Following Article
Synthesis and biological evaluation of RGD and isoDGR peptidomimetic-α-amanitin conjugates for tumor-targeting
Lizeth Bodero, Paula López Rivas, Barbara Korsak, Torsten Hechler, Andreas Pahl, Christoph Müller, Daniela Arosio, Luca Pignataro, Cesare Gennari and Umberto Piarulli
Beilstein J. Org. Chem. 2018, 14, 407–415.
https://doi.org/10.3762/bjoc.14.29
How to Cite
Bodero, L.; López Rivas, P.; Korsak, B.; Hechler, T.; Pahl, A.; Müller, C.; Arosio, D.; Pignataro, L.; Gennari, C.; Piarulli, U. Beilstein J. Org. Chem. 2018, 14, 407–415. doi:10.3762/bjoc.14.29
Download Citation
Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window
below.
Citation data in RIS format can be imported by all major citation management software, including EndNote,
ProCite, RefWorks, and Zotero.
Presentation Graphic
Picture with graphical abstract, title and authors for social media postings and presentations. | ||
Format: PNG | Size: 1.1 MB | Download |
Citations to This Article
Up to 20 of the most recent references are displayed here.
Scholarly Works
- Paulus, J.; Sewald, N. Small molecule- and peptide-drug conjugates addressing integrins: A story of targeted cancer treatment. Journal of peptide science : an official publication of the European Peptide Society 2024, 30, e3561. doi:10.1002/psc.3561
- Zambra, M.; Ranđelović, I.; Talarico, F.; Borbély, A.; Svajda, L.; Tóvári, J.; Mező, G.; Bodero, L.; Colombo, S.; Arrigoni, F.; Fasola, E.; Gazzola, S.; Piarulli, U. Optimizing the enzymatic release of MMAE from isoDGR-based small molecule drug conjugate by incorporation of a GPLG-PABC enzymatically cleavable linker. Frontiers in pharmacology 2023, 14, 1215694. doi:10.3389/fphar.2023.1215694
- Davis, R. A.; Ganguly, T.; Harris, R.; Hausner, S. H.; Kovacs, L.; Sutcliffe, J. L. Synthesis and Evaluation of a Monomethyl Auristatin E─Integrin αvβ6 Binding Peptide-Drug Conjugate for Tumor Targeted Drug Delivery. Journal of medicinal chemistry 2023, 66, 9842–9852. doi:10.1021/acs.jmedchem.3c00631
- Cossu, J.; Thoreau, F.; Boturyn, D. Multimeric RGD-Based Strategies for Selective Drug Delivery to Tumor Tissues. Pharmaceutics 2023, 15, 525. doi:10.3390/pharmaceutics15020525
- Paulus, J.; Nachtigall, B.; Meyer, P.; Sewald, N. RGD Peptidomimetic MMAE-Conjugate Addressing Integrin αVβ3-Expressing Cells with High Targeting Index. Chemistry (Weinheim an der Bergstrasse, Germany) 2023, 29, e202203476. doi:10.1002/chem.202203476
- Gomari, M. M.; Abkhiz, S.; Pour, T. G.; Lotfi, E.; Rostami, N.; Monfared, F. N.; Ghobari, B.; Mosavi, M.; Alipour, B.; Dokholyan, N. V. Peptidomimetics in cancer targeting. Molecular medicine (Cambridge, Mass.) 2022, 28, 146. doi:10.1186/s10020-022-00577-3
- Zhu, W.; Wang, Y.; Lv, L.; Wang, H.; Shi, W.; Liu, Z.; Yang, W.; Zhu, J.; Lu, H. SHTXTHHly, an extracellular secretion platform for the preparation of bioactive peptides and proteins in Escherichia coli. Microbial cell factories 2022, 21, 128. doi:10.1186/s12934-022-01856-8
- Todorovic, M.; Rivollier, P.; Wong, A. A. W. L.; Wang, Z.; Pryyma, A.; Nguyen, T. T.; Newell, K. C.; Froelich, J.; Perrin, D. M. Rationally Designed Amanitins Achieve Enhanced Cytotoxicity. Journal of medicinal chemistry 2022, 65, 10357–10376. doi:10.1021/acs.jmedchem.1c02226
- Zuppone, S.; Assalini, C.; Minici, C.; Botrugno, O. A.; Curnis, F.; Degano, M.; Corti, A.; Montorsi, F.; Salonia, A.; Vago, R. A Novel RGD-4C-Saporin Conjugate Inhibits Tumor Growth in Mouse Models of Bladder Cancer. Frontiers in oncology 2022, 12, 846958. doi:10.3389/fonc.2022.846958
- Pryyma, A.; Matinkhoo, K.; Bu, Y. J.; Merkens, H.; Zhang, Z.; Bénard, F.; Perrin, D. M. Synthesis and preliminary evaluation of octreotate conjugates of bioactive synthetic amatoxins for targeting somatostatin receptor (sstr2) expressing cells. RSC chemical biology 2022, 3, 69–78. doi:10.1039/d1cb00036e
- Vakhrushev, A. V.; Demin, A. M.; Krasnov, V. P. Synthesis of fluorescent GRGD peptide derivatives. In AIP Conference Proceedings, AIP Publishing, 2022; pp 20083 ff. doi:10.1063/5.0069274
- Pryyma, A.; Matinkhoo, K.; Bu, Y. J.; Merkens, H.; Zhang, Z.; Benard, F.; Perrin, D. M.
- Matinkhoo, K.; Wong, A. A. W. L.; Hambira, C. M.; Kato, B.; Wei, C.; Müller, C.; Hechler, T.; Braun, A.; Gallo, F.; Pahl, A.; Perrin, D. M. Design, Synthesis, and Biochemical Evaluation of Alpha-Amanitin Derivatives Containing Analogs of the trans-Hydroxyproline Residue for Potential Use in Antibody-Drug Conjugates. Chemistry (Weinheim an der Bergstrasse, Germany) 2021, 27, 10282–10292. doi:10.1002/chem.202101373
- Balachandra, C.; Padhi, D.; Govindaraju, T. Cyclic Dipeptide: A Privileged Molecular Scaffold to Derive Structural Diversity and Functional Utility. ChemMedChem 2021, 16, 2558–2587. doi:10.1002/cmdc.202100149
- Bodero, L.; Parente, S.; Arrigoni, F.; Klimpel, A.; Neundorf, I.; Gazzola, S.; Piarulli, U. Synthesis and Biological Evaluation of an isoDGR-Paclitaxel Conjugate Containing a Cell-Penetrating Peptide to Promote Cellular Uptake. European Journal of Organic Chemistry 2021, 2021, 2383–2387. doi:10.1002/ejoc.202100241
- Battistini, L.; Bugatti, K.; Sartori, A.; Curti, C.; Zanardi, F. RGD Peptide-Drug Conjugates as Effective Dual Targeting Platforms: Recent Advances. European Journal of Organic Chemistry 2021, 2021, 2506–2528. doi:10.1002/ejoc.202100240
- Gallo, F.; Korsak, B.; Müller, C.; Hechler, T.; Yanakieva, D.; Avrutina, O.; Kolmar, H.; Pahl, A. Enhancing the Pharmacokinetics and Antitumor Activity of an α-Amanitin-Based Small-Molecule Drug Conjugate via Conjugation with an Fc Domain. Journal of medicinal chemistry 2021, 64, 4117–4129. doi:10.1021/acs.jmedchem.1c00003
- Panzeri, S.; Arosio, D.; Gazzola, S.; Belvisi, L.; Civera, M.; Potenza, D.; Vasile, F.; Kemker, I.; Ertl, T.; Sewald, N.; Reiser, O.; Piarulli, U. Cyclic RGD and isoDGR Integrin Ligands Containing cis-2-amino-1-cyclopentanecarboxylic (cis-β-ACPC) Scaffolds. Molecules (Basel, Switzerland) 2020, 25, 5966–5980. doi:10.3390/molecules25245966
- Pryyma, A.; Matinkhoo, K.; Wong, A. A. W. L.; Perrin, D. M. Meeting key synthetic challenges in amanitin synthesis with a new cytotoxic analog: 5'-hydroxy-6'-deoxy-amanitin. Chemical science 2020, 11, 11927–11935. doi:10.1039/d0sc04150e
- Dordoni, F.; Scarpi, D.; Bianchini, F.; Contini, A.; Occhiato, E. G. Enantioselective Synthesis of cis and trans 4-Aminopipecolic Acids as γ-Amino Acids for the Construction of Cyclic RGD-Containing Peptidomimetics Antagonists of αVβ3 Integrin. European Journal of Organic Chemistry 2020, 2020, 4371–4383. doi:10.1002/ejoc.202000634
Patents
- VAGO RICCARDO. FUSION PROTEINS AND USES THEREOF. WO 2023170209 A1, Sept 14, 2023.
- BERTRAND ROMAIN; ATTINGER-TOLLER ISABELLA; FAY RACHAEL; GRABULOVSKI DRAGAN; SPYCHER PHILIPP. PEPTIDE LINKERS COMPRISING TWO OR MORE PAYLOADS. WO 2023161291 A1, Aug 31, 2023.
- ATTINGER-TOLLER ISABELLA; BERTRAND ROMAIN; STARK RAMONA; GRABULOVSKI DRAGAN; SPYCHER PHILIPP. METHODS FOR PRODUCING ANTIBODY-LINKER CONJUGATES. WO 2023072934 A1, May 4, 2023.
- SPYCHER PHILIPP; PROBST PHILIPP; ATTINGER-TOLLER ISABELLA; BERTRAND ROMAIN; STARK RAMONA; GRABULOVSKI DRAGAN. MEANS AND METHODS FOR PRODUCING ANTIBODY-LINKER CONJUGATES. WO 2022084560 A1, April 28, 2022.
- BERTRAND ROMAIN; ATTINGER-TOLLER ISABELLA; GRABULOVSKI DRAGAN; SPYCHER PHILIPP. TRANSGLUTAMINASE CONJUGATION METHOD WITH AMINO ACID-BASED LINKERS. WO 2022058594 A1, March 24, 2022.
- SCHIBLI ROGER; BEHE ROGER; SPYCHER PHILIPP; FREI JULIA; WEHRMÜLLER JÖRI. TRANSGLUTAMINASE CONJUGATION METHOD WITH A GLYCINE BASED LINKER. WO 2020188061 A1, Sept 24, 2020.