Harnessing natural-product-inspired combinatorial chemistry and computation-guided synthesis to develop N -glycan modulators as anticancer agents

Modulation of N -glycosylation using human Golgi α-mannosidase II (α-hGMII) inhibitors is a potential anticancer approach, but the clinical utility of current α-hGMII inhibitors is limited by their co-inhibition of human lysosomal α-mannosidase (α-hLM), resulting in abnormal storage of oligomannoses...

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Published inChemical science (Cambridge) Vol. 13; no. 21; pp. 6233 - 6243
Main Authors Chen, Wei-An, Chen, Yu-Hsin, Hsieh, Chiao-Yun, Hung, Pi-Fang, Chen, Chiao-Wen, Chen, Chien-Hung, Lin, Jung-Lee, Cheng, Ting-Jen R., Hsu, Tsui-Ling, Wu, Ying-Ta, Shen, Chia-Ning, Cheng, Wei-Chieh
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.06.2022
Royal Society of Chemistry
The Royal Society of Chemistry
Subjects
Anticancer properties
Cancer
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Combinatorial analysis
Combinatorial chemistry
Computation
Glycan
In vivo methods and tests
Inhibitors
Modulation
Modulators
Natural products
Physical Sciences
Science & Technology
Selectivity
5-SUBSTITUTED SWAINSONINE ANALOGS
SELECTIVE INHIBITORS
MECHANISMS
GLYCOSYLATION
SCAFFOLDS
ALPHA-MANNOSIDASE-II
CANCER
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Abstract Modulation of N -glycosylation using human Golgi α-mannosidase II (α-hGMII) inhibitors is a potential anticancer approach, but the clinical utility of current α-hGMII inhibitors is limited by their co-inhibition of human lysosomal α-mannosidase (α-hLM), resulting in abnormal storage of oligomannoses. We describe the synthesis and screening of a small library of novel bicyclic iminosugar-based scaffolds, prepared via natural product-inspired combinatorial chemistry (NPICC), which resulted in the identification of a primary α-hGMII inhibitor with 13.5-fold selectivity over α-hLM. Derivatization of this primary inhibitor using computation-guided synthesis (CGS) yielded an advanced α-hGMII inhibitor with nanomolar potency and 106-fold selectivity over α-hLM. In vitro studies demonstrated its N -glycan modulation and inhibitory effect on hepatocellular carcinoma (HCC) cells. In vivo studies confirmed its encouraging anti-HCC activity, without evidence of oligomannose accumulation.
AbstractList Modulation of N -glycosylation using human Golgi α-mannosidase II (α-hGMII) inhibitors is a potential anticancer approach, but the clinical utility of current α-hGMII inhibitors is limited by their co-inhibition of human lysosomal α-mannosidase (α-hLM), resulting in abnormal storage of oligomannoses. We describe the synthesis and screening of a small library of novel bicyclic iminosugar-based scaffolds, prepared via natural product-inspired combinatorial chemistry (NPICC), which resulted in the identification of a primary α-hGMII inhibitor with 13.5-fold selectivity over α-hLM. Derivatization of this primary inhibitor using computation-guided synthesis (CGS) yielded an advanced α-hGMII inhibitor with nanomolar potency and 106-fold selectivity over α-hLM. In vitro studies demonstrated its N -glycan modulation and inhibitory effect on hepatocellular carcinoma (HCC) cells. In vivo studies confirmed its encouraging anti-HCC activity, without evidence of oligomannose accumulation. An integrated strategy of Natural-Product-Inspired Combinatorial Chemistry (NPICC) and Computation-Guided Synthesis is used to develop an α-hGMII inhibitor with 106-fold selectivity over α-hLM, with inhibitory effect on hepatocellular carcinoma.
Modulation of N-glycosylation using human Golgi α-mannosidase II (α-hGMII) inhibitors is a potential anticancer approach, but the clinical utility of current α-hGMII inhibitors is limited by their co-inhibition of human lysosomal α-mannosidase (α-hLM), resulting in abnormal storage of oligomannoses. We describe the synthesis and screening of a small library of novel bicyclic iminosugar-based scaffolds, prepared via natural product-inspired combinatorial chemistry (NPICC), which resulted in the identification of a primary α-hGMII inhibitor with 13.5-fold selectivity over α-hLM. Derivatization of this primary inhibitor using computation-guided synthesis (CGS) yielded an advanced α-hGMII inhibitor with nanomolar potency and 106-fold selectivity over α-hLM. In vitro studies demonstrated its N-glycan modulation and inhibitory effect on hepatocellular carcinoma (HCC) cells. In vivo studies confirmed its encouraging anti-HCC activity, without evidence of oligomannose accumulation.Modulation of N-glycosylation using human Golgi α-mannosidase II (α-hGMII) inhibitors is a potential anticancer approach, but the clinical utility of current α-hGMII inhibitors is limited by their co-inhibition of human lysosomal α-mannosidase (α-hLM), resulting in abnormal storage of oligomannoses. We describe the synthesis and screening of a small library of novel bicyclic iminosugar-based scaffolds, prepared via natural product-inspired combinatorial chemistry (NPICC), which resulted in the identification of a primary α-hGMII inhibitor with 13.5-fold selectivity over α-hLM. Derivatization of this primary inhibitor using computation-guided synthesis (CGS) yielded an advanced α-hGMII inhibitor with nanomolar potency and 106-fold selectivity over α-hLM. In vitro studies demonstrated its N-glycan modulation and inhibitory effect on hepatocellular carcinoma (HCC) cells. In vivo studies confirmed its encouraging anti-HCC activity, without evidence of oligomannose accumulation.
Modulation of N-glycosylation using human Golgi α-mannosidase II (α-hGMII) inhibitors is a potential anticancer approach, but the clinical utility of current α-hGMII inhibitors is limited by their co-inhibition of human lysosomal α-mannosidase (α-hLM), resulting in abnormal storage of oligomannoses. We describe the synthesis and screening of a small library of novel bicyclic iminosugar-based scaffolds, prepared via natural product-inspired combinatorial chemistry (NPICC), which resulted in the identification of a primary α-hGMII inhibitor with 13.5-fold selectivity over α-hLM. Derivatization of this primary inhibitor using computation-guided synthesis (CGS) yielded an advanced α-hGMII inhibitor with nanomolar potency and 106-fold selectivity over α-hLM. In vitro studies demonstrated its N-glycan modulation and inhibitory effect on hepatocellular carcinoma (HCC) cells. In vivo studies confirmed its encouraging anti-HCC activity, without evidence of oligomannose accumulation.
Modulation of N -glycosylation using human Golgi α-mannosidase II (α-hGMII) inhibitors is a potential anticancer approach, but the clinical utility of current α-hGMII inhibitors is limited by their co-inhibition of human lysosomal α-mannosidase (α-hLM), resulting in abnormal storage of oligomannoses. We describe the synthesis and screening of a small library of novel bicyclic iminosugar-based scaffolds, prepared via natural product-inspired combinatorial chemistry (NPICC), which resulted in the identification of a primary α-hGMII inhibitor with 13.5-fold selectivity over α-hLM. Derivatization of this primary inhibitor using computation-guided synthesis (CGS) yielded an advanced α-hGMII inhibitor with nanomolar potency and 106-fold selectivity over α-hLM. In vitro studies demonstrated its N -glycan modulation and inhibitory effect on hepatocellular carcinoma (HCC) cells. In vivo studies confirmed its encouraging anti-HCC activity, without evidence of oligomannose accumulation.
Modulation of N-glycosylation using human Golgi alpha-mannosidase II (alpha-hGMII) inhibitors is a potential anticancer approach, but the clinical utility of current alpha-hGMII inhibitors is limited by their co-inhibition of human lysosomal alpha-mannosidase (alpha-hLM), resulting in abnormal storage of oligomannoses. We describe the synthesis and screening of a small library of novel bicyclic iminosugar-based scaffolds, prepared via natural product-inspired combinatorial chemistry (NPICC), which resulted in the identification of a primary alpha-hGMII inhibitor with 13.5-fold selectivity over alpha-hLM. Derivatization of this primary inhibitor using computation-guided synthesis (CGS) yielded an advanced alpha-hGMII inhibitor with nanomolar potency and 106-fold selectivity over alpha-hLM. In vitro studies demonstrated its N-glycan modulation and inhibitory effect on hepatocellular carcinoma (HCC) cells. In vivo studies confirmed its encouraging anti-HCC activity, without evidence of oligomannose accumulation.
Author Hsieh, Chiao-Yun
Chen, Chiao-Wen
Hung, Pi-Fang
Lin, Jung-Lee
Shen, Chia-Ning
Wu, Ying-Ta
Chen, Wei-An
Chen, Yu-Hsin
Hsu, Tsui-Ling
Chen, Chien-Hung
Cheng, Ting-Jen R.
Cheng, Wei-Chieh
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Keywords 5-SUBSTITUTED SWAINSONINE ANALOGS
SELECTIVE INHIBITORS
MECHANISMS
GLYCOSYLATION
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CANCER
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SSID ssj0000331527
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Snippet Modulation of N -glycosylation using human Golgi α-mannosidase II (α-hGMII) inhibitors is a potential anticancer approach, but the clinical utility of current...
Modulation of N-glycosylation using human Golgi alpha-mannosidase II (alpha-hGMII) inhibitors is a potential anticancer approach, but the clinical utility of...
Modulation of N-glycosylation using human Golgi α-mannosidase II (α-hGMII) inhibitors is a potential anticancer approach, but the clinical utility of current...
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StartPage 6233
SubjectTerms Anticancer properties
Cancer
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Combinatorial analysis
Combinatorial chemistry
Computation
Glycan
In vivo methods and tests
Inhibitors
Modulation
Modulators
Natural products
Physical Sciences
Science & Technology
Selectivity
Title Harnessing natural-product-inspired combinatorial chemistry and computation-guided synthesis to develop N -glycan modulators as anticancer agents
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https://www.proquest.com/docview/2672066455
https://www.proquest.com/docview/2680241785
https://pubmed.ncbi.nlm.nih.gov/PMC9159088
Volume 13
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