A symbiotic supramolecular approach to the design of novel amphiphiles with antibacterial properties against MSRA

Abstract

The co-formulation of supramolecular self-associating amphiphiles (SSAs) enhances solution state physicochemical properties and increases efficacy against methicillin-resistant Staphylococcus aureus.

Towards the Prediction of Antimicrobial Efficacy for Hydrogen Bonded, Self‐Associating Amphiphiles

“…[14][15][16][17][18] Members from this class of compound have also been identified as antimicrobial agents against both Grampositive and Gram-negative bacteria. [19][20][21] In this work, we now expand our initial SSA library and combine low-level computational modelling and physicochemical self-associative property determination towards the elucidation of SSA structure-physicochemical property-antimicrobial activity relationships against Gram-positive (MRSA) and/or Gram-negative (E. coli) bacteria of clinical interest. [22] This has resulted in the production of predictive models to drive the intelligent design of ever more effective, next generation SSA technologies.…”

Towards the Application of Supramolecular Self-Associating Amphiphiles as Next-Generation Delivery Vehicles

“…Previously published high resolution electrospray ionisation (ESI) mass spectrometry studies have shown the anionic portion of most SSAs to exist as dimeric species [ 16 , 17 , 18 , 19 , 20 , 21 , 22 ]. Data previously obtained for SSAs 1 [ 16 ], 2 [ 21 ] and 4 [ 18 ] confirmed the presence of SSA anionic dimers under these experimental conditions. Supporting these previous observations, the presence of anionic SSA dimers were also observed for SSAs 3 , 10 and 11 , see Table 2 .…”

“…To date, a library of >50 SSAs and structurally related compounds have been synthesized. The self-associative properties of this compound library and any resultant aggregate structure have also been characterised, using a variety of complementary experimental techniques ( Figure 1 ) [ 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 ]. A series of solid state, single crystal X-ray diffraction studies have shown the intermolecular binding mode adopted by the anionic component of an SSA to be cation dependent [ 17 ].…”

“…Interestingly, examples from this SSA library have been shown to act as antimicrobial agents against both clinically relevant model Gram-positive (methicillin resistant Staphylococcus aureus —MRSA) and Gram-negative ( Escherichia coli ) bacteria [ 21 , 22 , 23 ]. Within the scope of our studies we have also hypothesised that SSA antimicrobial activity is related to both molecular self-association [ 23 ] and selective SSA:phospholipid complexation [ 24 ].…”

Ionicity-dependent proton-coupled electron transfer of supramolecular self-assembled electroactive heterocycles

“…22 In 1 : 19 EtOH : H 2 O solutions these SSAs have shown the propensity towards the formation of spherical aggregates E150-350 nm in hydrodynamic diameter. [23][24][25] Herein, we explore the use of the SSA construct to produce switchable electroactive quinone containing species (Fig. 2).…”