Selective Inhibitors of Human Neuraminidase 3
Human neuraminidases (NEU) are associated with human diseases including cancer, atherosclerosis, and diabetes. To obtain small molecule inhibitors as research tools for the study of their biological functions, we designed a library of 2-deoxy-2,3-didehydro-N-acetylneuraminic acid (DANA) analogues wi...
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| Published in: | Journal of medicinal chemistry Vol. 61; no. 5; pp. 1990 - 2008 |
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| Main Authors: | , , , , , , , , , , |
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American Chemical Society
08-03-2018
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| Abstract | Human neuraminidases (NEU) are associated with human diseases including cancer, atherosclerosis, and diabetes. To obtain small molecule inhibitors as research tools for the study of their biological functions, we designed a library of 2-deoxy-2,3-didehydro-N-acetylneuraminic acid (DANA) analogues with modifications at C4 and C9 positions. This library allowed us to discover selective inhibitors targeting the human NEU3 isoenzyme. Our most selective inhibitor for NEU3 has a K i of 320 ± 40 nM and a 15-fold selectivity over other human neuraminidase isoenzymes. This inhibitor blocks glycolipid processing by NEU3 in vitro. To improve their pharmacokinetic properties, various esters of the best inhibitors were synthesized and evaluated. Finally, we confirmed that our best compounds exhibited selective inhibition of NEU orthologues from murine brain. |
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| AbstractList | Human neuraminidases (NEU) are associated with human diseases including cancer, atherosclerosis, and diabetes. To obtain small molecule inhibitors as research tools for the study of their biological functions, we designed a library of 2-deoxy-2,3-didehydro- N-acetylneuraminic acid (DANA) analogues with modifications at C4 and C9 positions. This library allowed us to discover selective inhibitors targeting the human NEU3 isoenzyme. Our most selective inhibitor for NEU3 has a Ki of 320 ± 40 nM and a 15-fold selectivity over other human neuraminidase isoenzymes. This inhibitor blocks glycolipid processing by NEU3 in vitro. To improve their pharmacokinetic properties, various esters of the best inhibitors were synthesized and evaluated. Finally, we confirmed that our best compounds exhibited selective inhibition of NEU orthologues from murine brain. Human neuraminidases (NEU) are associated with human diseases including cancer, atherosclerosis, and diabetes. To obtain small molecule inhibitors as research tools for the study of their biological functions, we designed a library of 2-deoxy-2,3-didehydro- N-acetylneuraminic acid (DANA) analogues with modifications at C4 and C9 positions. This library allowed us to discover selective inhibitors targeting the human NEU3 isoenzyme. Our most selective inhibitor for NEU3 has a K of 320 ± 40 nM and a 15-fold selectivity over other human neuraminidase isoenzymes. This inhibitor blocks glycolipid processing by NEU3 in vitro. To improve their pharmacokinetic properties, various esters of the best inhibitors were synthesized and evaluated. Finally, we confirmed that our best compounds exhibited selective inhibition of NEU orthologues from murine brain. Human neuraminidases (NEU) are associated with human diseases including cancer, atherosclerosis, and diabetes. To obtain small molecule inhibitors as research tools for the study of their biological functions, we designed a library of 2-deoxy-2,3-didehydro-N-acetylneuraminic acid (DANA) analogues with modifications at C4 and C9 positions. This library allowed us to discover selective inhibitors targeting the human NEU3 isoenzyme. Our most selective inhibitor for NEU3 has a K i of 320 ± 40 nM and a 15-fold selectivity over other human neuraminidase isoenzymes. This inhibitor blocks glycolipid processing by NEU3 in vitro. To improve their pharmacokinetic properties, various esters of the best inhibitors were synthesized and evaluated. Finally, we confirmed that our best compounds exhibited selective inhibition of NEU orthologues from murine brain. |
| Author | Richards, Michele R Zheng, Ruixiang Cairo, Christopher W Guo, Tianlin Ge, Peng Demina, Ekaterina Dätwyler, Philipp Zou, Chunxia Fougerat, Anne Ernst, Beat Pshezhetsky, Alexey V |
| AuthorAffiliation | Department of Pharmaceutical Sciences, Pharmacenter University of Basel Alberta Glycomics Centre and Department of Chemistry University of Alberta Division of Medical Genetics, Sainte-Justine University Hospital Research Center University of Montreal |
| AuthorAffiliation_xml | – name: University of Alberta – name: Division of Medical Genetics, Sainte-Justine University Hospital Research Center – name: University of Basel – name: Department of Pharmaceutical Sciences, Pharmacenter – name: University of Montreal – name: Alberta Glycomics Centre and Department of Chemistry |
| Author_xml | – sequence: 1 givenname: Tianlin surname: Guo fullname: Guo, Tianlin organization: University of Alberta – sequence: 2 givenname: Philipp surname: Dätwyler fullname: Dätwyler, Philipp organization: University of Basel – sequence: 3 givenname: Ekaterina surname: Demina fullname: Demina, Ekaterina organization: University of Montreal – sequence: 4 givenname: Michele R surname: Richards fullname: Richards, Michele R organization: University of Alberta – sequence: 5 givenname: Peng surname: Ge fullname: Ge, Peng organization: University of Alberta – sequence: 6 givenname: Chunxia surname: Zou fullname: Zou, Chunxia organization: University of Alberta – sequence: 7 givenname: Ruixiang surname: Zheng fullname: Zheng, Ruixiang organization: University of Alberta – sequence: 8 givenname: Anne surname: Fougerat fullname: Fougerat, Anne organization: University of Montreal – sequence: 9 givenname: Alexey V surname: Pshezhetsky fullname: Pshezhetsky, Alexey V organization: University of Montreal – sequence: 10 givenname: Beat orcidid: 0000-0001-5787-2297 surname: Ernst fullname: Ernst, Beat organization: University of Basel – sequence: 11 givenname: Christopher W orcidid: 0000-0003-3363-8708 surname: Cairo fullname: Cairo, Christopher W email: ccairo@ualberta.ca organization: University of Alberta |
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| Snippet | Human neuraminidases (NEU) are associated with human diseases including cancer, atherosclerosis, and diabetes. To obtain small molecule inhibitors as research... |
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| SubjectTerms | Animals Enzyme Inhibitors - pharmacology Humans Isoenzymes Life Sciences Mice N-Acetylneuraminic Acid - analogs & derivatives Neuraminidase - antagonists & inhibitors Small Molecule Libraries |
| Title | Selective Inhibitors of Human Neuraminidase 3 |
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