Insights into the structure–activity relationship of the anticancer compound ZJ-101: A critical role played by the cyclohexene ring

2016 ◽  
Vol 26 (12) ◽  
pp. 2890-2892 ◽  
Author(s):  
Aashay K. Shah ◽  
Shan Qian ◽  
Dawei Zhang ◽  
Sarah A. Head ◽  
Jun O. Liu ◽  
...  
Keyword(s):  
Critical Role ◽  
Structure Activity Relationship ◽  
Activity Relationship ◽  
Structure Activity ◽  
Cyclohexene Ring ◽  
Relationship Of ◽  
Anticancer Compound

scholarly journals Exploring the structure-activity relationship of Mincle ligands

2021 ◽  
Author(s):  
◽  
M. Rhia L. Stone
Keyword(s):  
Critical Role ◽  
Structure Activity Relationship ◽  
Biological Evaluation ◽  
Activity Relationship ◽  
Trehalose Dimycolate ◽  
Structure Activity ◽  
Ligand Interactions ◽  
Regioselective Modification ◽  
Bacteria And Fungi ◽  
Relationship Of

<p>Mincle is a C-type lectin that plays a critical role in the body’s innate immune response to bacteria and fungi. Compounds identified as ligands for Mincle include trehalose and glycerol esters of complex long chain fatty acids. Harnessing its ability to activate the immune system, trehalose dimycolate has been used as a vaccine adjuvant and for anti-cancer treatment, highlighting the potential use of Mincle immunomodulators in a medical context. To further understand the receptor-ligand interactions and optimise biological activity, the structure-activity relationship of Mincle ligands was investigated through the synthesis and biological evaluation of a series of modified ligands. The preparation of carbohydrate modified trehalose dibehenates was attempted in order to assess the importance of hydroxylprotein interactions, and despite the syntheses being incomplete, improvements on literature methodologies for the regioselective modification of α,α′-D-trehalose were developed. Simplified analogues of the glycerol based natural products identified as Mincle ligands containing straight chain and iso-branched lipids were prepared to evaluate the significance of the branch and establish whether there is a relationship between lipid length and Mincle activation. The corresponding trehalose diester analogues were also synthesised to gauge the capacity of the protein to tolerate changes in the carbohydrate portion of ligands.</p>

scholarly journals Exploring the structure-activity relationship of Mincle ligands

2021 ◽  
Author(s):  
◽  
M. Rhia L. Stone
Keyword(s):  
Critical Role ◽  
Structure Activity Relationship ◽  
Biological Evaluation ◽  
Activity Relationship ◽  
Trehalose Dimycolate ◽  
Structure Activity ◽  
Ligand Interactions ◽  
Regioselective Modification ◽  
Bacteria And Fungi ◽  
Relationship Of

<p>Mincle is a C-type lectin that plays a critical role in the body’s innate immune response to bacteria and fungi. Compounds identified as ligands for Mincle include trehalose and glycerol esters of complex long chain fatty acids. Harnessing its ability to activate the immune system, trehalose dimycolate has been used as a vaccine adjuvant and for anti-cancer treatment, highlighting the potential use of Mincle immunomodulators in a medical context. To further understand the receptor-ligand interactions and optimise biological activity, the structure-activity relationship of Mincle ligands was investigated through the synthesis and biological evaluation of a series of modified ligands. The preparation of carbohydrate modified trehalose dibehenates was attempted in order to assess the importance of hydroxylprotein interactions, and despite the syntheses being incomplete, improvements on literature methodologies for the regioselective modification of α,α′-D-trehalose were developed. Simplified analogues of the glycerol based natural products identified as Mincle ligands containing straight chain and iso-branched lipids were prepared to evaluate the significance of the branch and establish whether there is a relationship between lipid length and Mincle activation. The corresponding trehalose diester analogues were also synthesised to gauge the capacity of the protein to tolerate changes in the carbohydrate portion of ligands.</p>

Structure-activity relationship of (-) mammea A/BB derivatives against Leishmania amazonensis

Planta Medica ◽  
2008 ◽  
Vol 74 (09) ◽  
Author(s):  
MA Brenzan ◽  
CV Nakamura ◽  
BPD Filho ◽  
T Ueda-Nakamura ◽  
MCM Young ◽  
...  
Keyword(s):  
Structure Activity Relationship ◽  
Leishmania Amazonensis ◽  
Activity Relationship ◽  
Structure Activity ◽  
Relationship Of

Antineoplastic Activity, Structural Modification, Synthesis and Structure-activity Relationship of Dammarane-type Ginsenosides: An Overview

2019 ◽  
Vol 23 (5) ◽  
pp. 503-516 ◽  
Author(s):  
Qiang Zhang ◽  
Xude Wang ◽  
Liyan Lv ◽  
Guangyue Su ◽  
Yuqing Zhao
Keyword(s):  
Structural Modification ◽  
Gastrointestinal Disease ◽  
Structure Activity Relationship ◽  
Cerebrovascular Diseases ◽  
Activity Relationship ◽  
Cycle Arrest ◽  
Structure Activity ◽  
Wide Range ◽  
Structural Association ◽  
Relationship Of

Dammarane-type ginsenosides are a class of tetracyclic triterpenoids with the same dammarane skeleton. These compounds have a wide range of pharmaceutical applications for neoplasms, diabetes mellitus and other metabolic syndromes, hyperlipidemia, cardiovascular and cerebrovascular diseases, aging, neurodegenerative disease, bone disease, liver disease, kidney disease, gastrointestinal disease and other conditions. In order to develop new antineoplastic drugs, it is necessary to improve the bioactivity, solubility and bioavailability, and illuminate the mechanism of action of these compounds. A large number of ginsenosides and their derivatives have been separated from certain herbs or synthesized, and tested in various experiments, such as anti-proliferation, induction of apoptosis, cell cycle arrest and cancer-involved signaling pathways. In this review, we have summarized the progress in structural modification, shed light on the structure-activity relationship (SAR), and offered insights into biosynthesis-structural association. This review is expected to provide a preliminary guide for the modification and synthesis of ginsenosides.

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