Structure-activity relationships in the hydrophobic interactions of polyphenols with cellulose and collagen

Biopolymers ◽  
2003 ◽  
Vol 70 (3) ◽  
pp. 403-413 ◽  
Author(s):  
H. R. Tang ◽  
A. D. Covington ◽  
R. A. Hancock
Keyword(s):  
Hydrophobic Interactions ◽  
Structure Activity Relationships ◽  
Structure Activity

scholarly journals Structure-Activity Relationships of Holothuroid’s Triterpene Glycosides and Some In Silico Insights Obtained by Molecular Dynamics Study on the Mechanisms of Their Membranolytic Action

Marine Drugs ◽  
2021 ◽  
Vol 19 (11) ◽  
pp. 604
Author(s):  
Elena A. Zelepuga ◽  
Alexandra S. Silchenko ◽  
Sergey A. Avilov ◽  
Vladimir I. Kalinin
Keyword(s):  
Molecular Dynamics ◽  
Hemolytic Activity ◽  
In Silico ◽  
Sea Cucumber ◽  
Hydrophobic Interactions ◽  
Membrane Surface ◽  
Erythrocyte Membranes ◽  
Inner Membrane ◽  
Structure Activity Relationships ◽  
Structure Activity

The article describes the structure-activity relationships (SAR) for a broad series of sea cucumber glycosides on different tumor cell lines and erythrocytes, and an in silico modulation of the interaction of selected glycosides from the sea cucumber Eupentacta fraudatrix with model erythrocyte membranes using full-atom molecular dynamics (MD) simulations. The in silico approach revealed that the glycosides bound to the membrane surface mainly through hydrophobic interactions and hydrogen bonds. The mode of such interactions depends on the aglycone structure, including the side chain structural peculiarities, and varies to a great extent. Two different mechanisms of glycoside/membrane interactions were discovered. The first one was realized through the pore formation (by cucumariosides A1 (40) and A8 (44)), preceded by bonding of the glycosides with membrane sphingomyelin, phospholipids, and cholesterol. Noncovalent intermolecular interactions inside multimolecular membrane complexes and their stoichiometry differed for 40 and 44. The second mechanism was realized by cucumarioside A2 (59) through the formation of phospholipid and cholesterol clusters in the outer and inner membrane leaflets, correspondingly. Noticeably, the glycoside/phospholipid interactions were more favorable compared to the glycoside/cholesterol interactions, but the glycoside possessed an agglomerating action towards the cholesterol molecules from the inner membrane leaflet. In silico simulations of the interactions of cucumarioside A7 (45) with model membrane demonstrated only slight interactions with phospholipid polar heads and the absence of glycoside/cholesterol interactions. This fact correlated well with very low experimental hemolytic activity of this substance. The observed peculiarities of membranotropic action are in good agreement with the corresponding experimental data on hemolytic activity of the investigated compounds in vitro.

Structure-activity relationships in the acronycine and benzo[b]acronycine series: Role of the pyran ring

Planta Medica ◽  
2008 ◽  
Vol 74 (09) ◽  
Author(s):  
Q Do ◽  
H Doan Thi Mai ◽  
T Gaslonde ◽  
B Pfeiffer ◽  
S Léonce ◽  
...  
Keyword(s):  
Pyran Ring ◽  
Structure Activity Relationships ◽  
Structure Activity

Structure activity-relationships of P-Glycoprotein modulation using a small library of macrocyclic lathyrane diterpenes

Planta Medica ◽  
2012 ◽  
Vol 78 (11) ◽  
Author(s):  
M Reis ◽  
RJ Ferreira ◽  
MMM Santos ◽  
DJVA dos Santos ◽  
J Molnár ◽  
...  
Keyword(s):  
Structure Activity Relationships ◽  
Structure Activity ◽  
P Glycoprotein
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