Synthesis and biological evaluation of novel mono- and bivalent ASGP-R-targeted drug-conjugates
[Display omitted] Asialoglycoprotein receptor (ASGP-R) is a promising biological target for drug delivery into hepatoma cells. Nevertheless, there are only few examples of small-molecule conjugates of ASGP-R selective ligand equipped by a therapeutic agent for the treatment of hepatocellular carcino...
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| Published in | Bioorganic & medicinal chemistry letters Vol. 28; no. 3; pp. 382 - 387 |
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| Main Authors | , , , , , , , , , , , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
OXFORD
Elsevier Ltd
01.02.2018
Elsevier |
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| Online Access | Get full text |
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| Abstract | [Display omitted]
Asialoglycoprotein receptor (ASGP-R) is a promising biological target for drug delivery into hepatoma cells. Nevertheless, there are only few examples of small-molecule conjugates of ASGP-R selective ligand equipped by a therapeutic agent for the treatment of hepatocellular carcinoma (HCC). In the present work, we describe a convenient and versatile synthetic approach to novel mono- and multivalent drug-conjugates containing N-acetyl-2-deoxy-2-aminogalactopyranose and anticancer drug – paclitaxel (PTX). Several molecules have demonstrated high affinity towards ASGP-R and good stability under physiological conditions, significant in vitro anticancer activity comparable to PTX, as well as good internalization via ASGP-R-mediated endocytosis. Therefore, the conjugates with the highest potency can be regarded as a promising therapeutic option against HCC. |
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| AbstractList | [Display omitted]
Asialoglycoprotein receptor (ASGP-R) is a promising biological target for drug delivery into hepatoma cells. Nevertheless, there are only few examples of small-molecule conjugates of ASGP-R selective ligand equipped by a therapeutic agent for the treatment of hepatocellular carcinoma (HCC). In the present work, we describe a convenient and versatile synthetic approach to novel mono- and multivalent drug-conjugates containing N-acetyl-2-deoxy-2-aminogalactopyranose and anticancer drug – paclitaxel (PTX). Several molecules have demonstrated high affinity towards ASGP-R and good stability under physiological conditions, significant in vitro anticancer activity comparable to PTX, as well as good internalization via ASGP-R-mediated endocytosis. Therefore, the conjugates with the highest potency can be regarded as a promising therapeutic option against HCC. Asialoglycoprotein receptor (ASGP-R) is a promising biological target for drug delivery into hepatoma cells. Nevertheless, there are only few examples of small-molecule conjugates of ASGP-R selective ligand equipped by a therapeutic agent for the treatment of hepatocellular carcinoma (HCC). In the present work, we describe a convenient and versatile synthetic approach to novel mono- and multivalent drug-conjugates containing N-acetyl-2-deoxy-2-aminogalactopyranose and anticancer drug - paclitaxel (PTX). Several molecules have demonstrated high affinity towards ASGP-R and good stability under physiological conditions, significant in vitro anticancer activity comparable to PTX, as well as good internalization via ASGP-R-mediated endocytosis. Therefore, the conjugates with the highest potency can be regarded as a promising therapeutic option against HCC. Asialoglycoprotein receptor (ASGP-R) is a promising biological target for drug delivery into hepatoma cells. Nevertheless, there are only few examples of small-molecule conjugates of ASGP-R selective ligand equipped by a therapeutic agent for the treatment of hepatocellular carcinoma (HCC). In the present work, we describe a convenient and versatile synthetic approach to novel mono- and multivalent drug-conjugates containing N-acetyl-2-deoxy-2-aminogalactopyranose and anticancer drug - paclitaxel (PTX). Several molecules have demonstrated high affinity towards ASGP-R and good stability under physiological conditions, significant in vitro anticancer activity comparable to PTX, as well as good internalization via ASGP-R-mediated endocytosis. Therefore, the conjugates with the highest potency can be regarded as a promising therapeutic option against HCC.Asialoglycoprotein receptor (ASGP-R) is a promising biological target for drug delivery into hepatoma cells. Nevertheless, there are only few examples of small-molecule conjugates of ASGP-R selective ligand equipped by a therapeutic agent for the treatment of hepatocellular carcinoma (HCC). In the present work, we describe a convenient and versatile synthetic approach to novel mono- and multivalent drug-conjugates containing N-acetyl-2-deoxy-2-aminogalactopyranose and anticancer drug - paclitaxel (PTX). Several molecules have demonstrated high affinity towards ASGP-R and good stability under physiological conditions, significant in vitro anticancer activity comparable to PTX, as well as good internalization via ASGP-R-mediated endocytosis. Therefore, the conjugates with the highest potency can be regarded as a promising therapeutic option against HCC. Asialoglycoprotein receptor (ASGP-R) is a promising biological target for drug delivery into hepatoma cells. Nevertheless, there are only few examples of small-molecule conjugates of ASGP-R selective ligand equipped by a therapeutic agent for the treatment of hepatocellular carcinoma (HCC). In the present work, we describe a convenient and versatile synthetic approach to novel mono- and multivalent drug-conjugates containing N-acetyl-2-deoxy-2-aminogalactopyranose and anticancer drug - paclitaxel (PTX). Several molecules have demonstrated high affinity towards ASGP-R and good stability under physiological conditions, significant in vitro anticancer activity comparable to PTX, as well as good internalization via ASGP-R-mediated endocytosis. Therefore, the conjugates with the highest potency can be regarded as a promising therapeutic option against HCC. (C) 2017 Elsevier Ltd. All rights reserved. |
| Author | Alieva, Irina B. Kovalev, Sergey V. Kireev, Igor I. Kotelianski, Victor E. Majouga, Alexander G. Ivanenkov, Yan A. Sofronova, Alina A. Petrov, Stanislav A. Trofimenko, Alexandre V. Saltykova, Irina V. Sergeeva, Olga V. Aladinskaia, Anastasiia V. Beloglazkina, Elena K. Maklakova, Svetlana Yu Yamansarov, Emil Yu Zatsepin, Timofey S. Yamidanov, Renat S. Petrov, Rostislav A. Deyneka, Ekaterina V. |
| Author_xml | – sequence: 1 givenname: Rostislav A. surname: Petrov fullname: Petrov, Rostislav A. organization: Lomonosov Moscow State University, Chemistry Dept, Leninskie Gory, Building 1/3, GSP-1, Moscow 119991, Russian Federation – sequence: 2 givenname: Svetlana Yu surname: Maklakova fullname: Maklakova, Svetlana Yu organization: Lomonosov Moscow State University, Chemistry Dept, Leninskie Gory, Building 1/3, GSP-1, Moscow 119991, Russian Federation – sequence: 3 givenname: Yan A. surname: Ivanenkov fullname: Ivanenkov, Yan A. email: yai@chemdiv.com organization: Lomonosov Moscow State University, Chemistry Dept, Leninskie Gory, Building 1/3, GSP-1, Moscow 119991, Russian Federation – sequence: 4 givenname: Stanislav A. surname: Petrov fullname: Petrov, Stanislav A. organization: Lomonosov Moscow State University, Chemistry Dept, Leninskie Gory, Building 1/3, GSP-1, Moscow 119991, Russian Federation – sequence: 5 givenname: Olga V. surname: Sergeeva fullname: Sergeeva, Olga V. organization: Lomonosov Moscow State University, Chemistry Dept, Leninskie Gory, Building 1/3, GSP-1, Moscow 119991, Russian Federation – sequence: 6 givenname: Emil Yu surname: Yamansarov fullname: Yamansarov, Emil Yu organization: Lomonosov Moscow State University, Chemistry Dept, Leninskie Gory, Building 1/3, GSP-1, Moscow 119991, Russian Federation – sequence: 7 givenname: Irina V. surname: Saltykova fullname: Saltykova, Irina V. organization: Lomonosov Moscow State University, Chemistry Dept, Leninskie Gory, Building 1/3, GSP-1, Moscow 119991, Russian Federation – sequence: 8 givenname: Igor I. surname: Kireev fullname: Kireev, Igor I. organization: Lomonosov Moscow State University, A.N. Belozersky Institute of Physico-Chemical Biology, Leninskye Gory, House 1, Building 40, Moscow 119992, Russian Federation – sequence: 9 givenname: Irina B. surname: Alieva fullname: Alieva, Irina B. organization: Lomonosov Moscow State University, A.N. Belozersky Institute of Physico-Chemical Biology, Leninskye Gory, House 1, Building 40, Moscow 119992, Russian Federation – sequence: 10 givenname: Ekaterina V. surname: Deyneka fullname: Deyneka, Ekaterina V. organization: Moscow Institute of Physics and Technology (State University), 9 Institutskiy Lane, Dolgoprudny City, Moscow Region 141700, Russian Federation – sequence: 11 givenname: Alina A. surname: Sofronova fullname: Sofronova, Alina A. organization: Lomonosov Moscow State University, Faculty of Bioengineering and Bioinformatics, Moscow, Russia – sequence: 12 givenname: Anastasiia V. surname: Aladinskaia fullname: Aladinskaia, Anastasiia V. organization: Moscow Institute of Physics and Technology (State University), 9 Institutskiy Lane, Dolgoprudny City, Moscow Region 141700, Russian Federation – sequence: 13 givenname: Alexandre V. surname: Trofimenko fullname: Trofimenko, Alexandre V. organization: Moscow Institute of Physics and Technology (State University), 9 Institutskiy Lane, Dolgoprudny City, Moscow Region 141700, Russian Federation – sequence: 14 givenname: Renat S. surname: Yamidanov fullname: Yamidanov, Renat S. organization: Institute of Biochemistry and Genetics Ufa Science Centre Russian Academy of Sciences (IBG RAS), Prosp. Oktybrya 71, Ufa, Bashkortostan 450054, Russian Federation – sequence: 15 givenname: Sergey V. surname: Kovalev fullname: Kovalev, Sergey V. organization: Lomonosov Moscow State University, Chemistry Dept, Leninskie Gory, Building 1/3, GSP-1, Moscow 119991, Russian Federation – sequence: 16 givenname: Victor E. surname: Kotelianski fullname: Kotelianski, Victor E. organization: Skolkovo Institute of Science and Technology, 100 Novaya St., 143025 Skolkovo, Russian Federation – sequence: 17 givenname: Timofey S. surname: Zatsepin fullname: Zatsepin, Timofey S. organization: Lomonosov Moscow State University, Chemistry Dept, Leninskie Gory, Building 1/3, GSP-1, Moscow 119991, Russian Federation – sequence: 18 givenname: Elena K. surname: Beloglazkina fullname: Beloglazkina, Elena K. organization: Lomonosov Moscow State University, Chemistry Dept, Leninskie Gory, Building 1/3, GSP-1, Moscow 119991, Russian Federation – sequence: 19 givenname: Alexander G. surname: Majouga fullname: Majouga, Alexander G. organization: Lomonosov Moscow State University, Chemistry Dept, Leninskie Gory, Building 1/3, GSP-1, Moscow 119991, Russian Federation |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/29269214$$D View this record in MEDLINE/PubMed |
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| Keywords | Targeted drug delivery ASGP-R Paclitaxel Cancer FUNCTIONAL RESERVE HIGH-AFFINITY CLUSTER GALACTOSIDES HEPATIC ASIALOGLYCOPROTEIN RECEPTOR OLIGONUCLEOTIDES POSTOPERATIVE LIVER-FUNCTION DELIVERY SYSTEM LIGANDS PREOPERATIVE ESTIMATION CARBOHYDRATE-RECOGNITION DOMAIN |
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Asialoglycoprotein receptor (ASGP-R) is a promising biological target for drug delivery into hepatoma cells. Nevertheless, there are only few... Asialoglycoprotein receptor (ASGP-R) is a promising biological target for drug delivery into hepatoma cells. Nevertheless, there are only few examples of... |
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| SubjectTerms | Antineoplastic Agents, Phytogenic - chemical synthesis Antineoplastic Agents, Phytogenic - chemistry Antineoplastic Agents, Phytogenic - pharmacology ASGP-R Asialoglycoprotein Receptor - antagonists & inhibitors Asialoglycoprotein Receptor - metabolism Cancer Carcinoma, Hepatocellular - drug therapy Carcinoma, Hepatocellular - metabolism Carcinoma, Hepatocellular - pathology Cell Proliferation - drug effects Chemistry Chemistry, Medicinal Chemistry, Organic Dose-Response Relationship, Drug Drug Delivery Systems Drug Screening Assays, Antitumor Galactose - analogs & derivatives Galactose - chemistry Galactose - pharmacology Hep G2 Cells Humans Life Sciences & Biomedicine Liver Neoplasms - drug therapy Liver Neoplasms - metabolism Liver Neoplasms - pathology Molecular Structure Paclitaxel Paclitaxel - chemical synthesis Paclitaxel - chemistry Paclitaxel - pharmacology Pharmacology & Pharmacy Physical Sciences Science & Technology Small Molecule Libraries - chemical synthesis Small Molecule Libraries - chemistry Small Molecule Libraries - pharmacology Structure-Activity Relationship Targeted drug delivery |
| Title | Synthesis and biological evaluation of novel mono- and bivalent ASGP-R-targeted drug-conjugates |
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