Aglycone mimics for tuning of glycosidase inhibition: design, synthesis and biological evaluation of bicyclic pyrrolidotriazole iminosugars

RSC Advances ◽  
2016 ◽  
Vol 6 (16) ◽  
pp. 13014-13026 ◽  
Author(s):  
Inderpreet Arora ◽  
Sandeep K. Sharma ◽  
Arun K. Shaw
Keyword(s):  
Click Reaction ◽  
Biological Evaluation ◽  
Terminal Alkynes ◽  
Design Synthesis ◽  
Synthesis And Biological Evaluation ◽  
Glycosidase Inhibition

Various fuco-configured bicyclic pyrrolidotriazole aglycone mimics were synthesised using copper-catalysed coupling of allyl bromides with terminal alkynes and Sonogashira–Hagihara reaction followed by intramolecular azide-alkyne ‘click’ reaction.

scholarly journals Synthetic Integrin-Targeting Dextran-Fc Hybrids Efficiently Inhibit Tumor Proliferation In Vitro

2021 ◽  
Vol 9 ◽  
Author(s):  
Hendrik Schneider ◽  
Simon Englert ◽  
Arturo Macarrón Palacios ◽  
Jorge Alberto Lerma Romero ◽  
Ataurehman Ali ◽  
...  
Keyword(s):  
Click Reaction ◽  
Biological Evaluation ◽  
Rgd Peptides ◽  
Design Synthesis ◽  
Antitumor Potential ◽  
Molecular Hybrids ◽  
The Stability ◽  
Proliferation In Vitro ◽  
Synthesis And Biological Evaluation

Herein, we present the design, synthesis, and biological evaluation of novel integrin-targeting molecular hybrids combining RGD peptides and a potent cytotoxin presented on dextran polysaccharides. Based on an aglycosylated Fc as a centerpiece, endosomal-cleavable cytotoxic agent monomethyl auristatin E (MMAE) and dextran as multimerization site were covalently connected by two bioorthogonal enzyme-mediated reactions site-specifically. Decoration of dextran with cyclic RGD peptides, introduced by copper “click” reaction, resulted in the final constructs with the potential to kill integrin-overexpressing tumor cells. We found that these modifications had little impact on the stability of the Fc scaffold and the RGD-bearing construct showed good binding properties of αvβ3-expressing U87MG cells. Furthermore, the construct showed a remarkable antiproliferative activity. These results demonstrate the general capability of our design to provoke receptor-mediated endocytosis upon binding to the cellular surface, followed by endosomal cleavage of the linkage between Fc-dextran and MMAE and its subsequent release. Our approach opens new avenues to transcribe small molecule binders into tailor-made multimeric molecular hybrids with antitumor potential.

scholarly journals Correction: Aglycone mimics for tuning of glycosidase inhibition: design, synthesis and biological evaluation of bicyclic pyrrolidotriazole iminosugars

RSC Advances ◽  
2016 ◽  
Vol 6 (29) ◽  
pp. 24683-24683
Author(s):  
Inderpreet Arora ◽  
Sandeep K. Sharma ◽  
Arun K. Shaw
Keyword(s):  
Biological Evaluation ◽  
Design Synthesis ◽  
Synthesis And Biological Evaluation ◽  
Glycosidase Inhibition

Correction for ‘Aglycone mimics for tuning of glycosidase inhibition: design, synthesis and biological evaluation of bicyclic pyrrolidotriazole iminosugars’ by Inderpreet Arora et al., RSC Adv., 2016, 6, 13014–13026.

Design, Synthesis and Biological Evaluation of Hybrid Molecules Containing Conjugated Styryl Ketone and α-Bromoacryloyl Moieties

2012 ◽  
Vol 9 (2) ◽  
pp. 140-152 ◽  
Author(s):  
Romeo Romagnoli ◽  
Pier Giovanni Baraldi ◽  
Olga Cruz-Lopez ◽  
Maria Kimatrai Salvador ◽  
Delia Preti ◽  
...  
Keyword(s):  
Biological Evaluation ◽  
Design Synthesis ◽  
Hybrid Molecules ◽  
Synthesis And Biological Evaluation

Design, Synthesis and Biological Evaluation of Novel Aminosaccharide Derivatives of Combretastatin A-4

2013 ◽  
Vol 10 (10) ◽  
pp. 935-941
Author(s):  
Yan Tang ◽  
Zhewei Tu ◽  
Jing Sun ◽  
Xiong Zhu ◽  
Kun Liu ◽  
...  
Keyword(s):  
Biological Evaluation ◽  
Design Synthesis ◽  
Synthesis And Biological Evaluation ◽  
Derivatives Of

Design, Synthesis and Biological Evaluation of Benzopyran Derivatives as KATP Channel Openers

2010 ◽  
Vol 7 (6) ◽  
pp. 415-420 ◽  
Author(s):  
Jinpei Zhou ◽  
Hai Qian ◽  
Huibin Zhang ◽  
Hui Gao ◽  
Wenlong Huang ◽  
...  
Keyword(s):  
Katp Channel ◽  
Biological Evaluation ◽  
Design Synthesis ◽  
Synthesis And Biological Evaluation ◽  
Katp Channel Openers
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