Pendant ionic groups of conjugated oligoelectrolytes govern their ability to intercalate into microbial membranes

Abstract

Conjugated oligoelectrolytes (COEs) bearing pyridinium and carboxylate groups are synthesized, characterized, and compared to the trimethylammonium analogue from which they are derived. All COEs are able to spontaneously intercalate into liposomes, whereas only positively charged COEs intercalate into E. coli membranes. Membrane intercalation is determined necessary for performance enhancement in microbial fuel cells.

The photobioelectrochemical activity of thylakoid bioanodes is increased via photocurrent generation and improved contacts by membrane-intercalating conjugated oligoelectrolytes

“…8 Indeed, in this present work, COE3-4C does not increase the thylakoid dark current (while COE1-4C does), and yet both COE1-4C and COE3-4C increase photocurrent. COE1-4C and COE3-4C will therefore have opposite coulombic interactions with charged surfaces, while keeping the conjugated segment constant.…”

“…2B). [1][2][3][4][5][6][7][8] Therefore, this study is an essential conceptual steppingstone towards understanding practical utility of COEs in light-driven systems. 2 schematic, the twocompartment design of the bio-solar cells allows use of two solutions so that COEs are prevented by the PEM from interacting with the cathode.…”

A Membrane‐Intercalating Conjugated Oligoelectrolyte with High‐Efficiency Photodynamic Antimicrobial Activity

“…[1] Certain MICOEs lead to increases in the current generation of bioelectrochemical systems, [2] serve as cell staining methods, [3] and provide the molecular basis for membrane permeation and antimicrobial function. [1] Certain MICOEs lead to increases in the current generation of bioelectrochemical systems, [2] serve as cell staining methods, [3] and provide the molecular basis for membrane permeation and antimicrobial function.…”

“…It is also worth considering that the light penetration increases and light toxicity decreases with longer wavelengths. Key structural elements include a) electronrich (thieno[3,2-b]thiophene) and electron-poor ( [1,2,5]thiadiazolo [3,4-c]pyridine) subunits that give rise to red shifted charge transfer excited states, [5d, 11] b) at opology and molecular length that are commensurate for insertion into lipid membranes, [4d, 11a] and c) six cationic pendant groups for solubility in aqueous media. [1a, 4b,d] We thus designed PTTP, see Scheme 1.…”

Membrane permeabilization by conjugated oligoelectrolytes accelerates whole-cell catalysis

“…13 To add to mechanistic complexity, recent results suggest that COEs may interact with other components in the cell envelope, such as lipopolysaccharides and cholic acid. [31][32][33] The degree to which such processes dominate bioelectrochemical changes, relative to electron transfer mechanisms, is not entirely known. Regardless, it is generally acknowledged that the ability of COEs to spontaneously intercalate in the membrane underlies their ability to increase charge transfer in bioelectrochemical devices.…”