Functional foldamers that target bacterial membranes: The effect of charge, amphiphilicity and conformation

Abstract

Snape, Timothy James, Dennison, Sarah Rachel and Patil sen, Yogita (2016) Functional foldamers that target bacterial membranes: the effect of charge, amphiphilicity and conformation. Bioorganic & Medicinal Chemistry, 24 (18) AbstractBy varying the molecular charge, shape and amphiphilicity of a series of conformationally distinct diarylureas it is possible to control the levels of phospholipid membrane lysis using membranes composed of bacterial lipid extracts. From the data obtained, it appears as though the lysis activity observed is not due to charge, conformation or amphiphilicity in isolation, but that surface aggregation, H-bonding and other factors may also play a part. The work provides evidence that this class of foldamer possesses potential for optimisation into new antibacterial agents.

Stoichiometric Reactions of CO2 and Indium‐Silylamides and Catalytic Synthesis of Ureas

“…The series of compounds In(N(SiMe 3 ) 2 ) 3 ( 1 ), In(N(SiMe 3 ) 2 ) 2 Cl⋅THF ( 2 ) and In(N(SiMe 3 ) 2 )Cl 2 ⋅(THF) n ( 3 ) were prepared by minor modifications of the literature method involving a salt metathesis reaction of Na(N(SiMe 3 ) 2 ) and InCl 3 –. In the case of compounds 2 and 3 crystallographic studies confirmed the formulations (Figure ).…”

Synthesis of chiral 3,5-bis(l-phenylalaninyl-l-leucinyl)pyridine Schiff base and their macrocyclic carboxaimide derivatives using 3,5-bis(l-phenylalaninyl)-pyridine methyl ester

“…The higher obtained activities of these compounds can be attributed to the presence of macrocyclic octapeptide ring, the Schiff base of 3-pyridine carbaldehyde and the hydrazide bond in compounds 9, 4b and 2, respectively. Generally, the antimicrobial activity of the synthesized peptides can be due to the interaction of the peptides with microbial cell membranes, and thus affecting the integrity of the cell walls [33,34]. Furthermore, peptides have been reported to effect microbial cells intracellularly by interacting with cellular DNA or enzyme machinery [35].…”

Novel diarylamides and diarylureas with N-substitution dependent activity against medulloblastoma

“…(4) (5)We have an on-going interest in the established phenomenon that diarylamides and diarylureas adopt discrete three-dimensional conformations that place the aromatic rings in either a stacked or unstacked arrangement dependent on their N-substitution pattern, (6)(7)(8)(9)(10) and within the context of cancer therapy, we have previously exploited this through the synthesis of a range of diarylurea-based combretastatin A4 analogues (e.g. 1, Figure 1).…”