Conjugated Oligoelectrolytes: Materials for Acceleration of Whole Cell Biocatalysis

Wang, Bing; Fronk, Stephanie L.; Rengert, Zachary D.; Limwongyut, Jakkarin; Bazan, Guillermo C.

doi:10.1021/acs.chemmater.8b02848

Cited by 10 publications

(10 citation statements)

References 44 publications

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“…238−241 The shorter DSB derivatives (DSBN+) are less well tolerated because of a pinching effect that damages the membrane and causes leakage of the cell. 238,240 At higher concentrations (40 μM) DSBN+ associates with the cells in a ratio higher than 2.5 × 10 7 molecules per cell. Given the estimated number of lipids per E. coli cell of ∼2.2 × 10 7 , the COE:lipid ratio is higher than 1:1 in this case, which points to association not being limited only to membrane intercalation.…”

Section: Intercalation Into Cell Walls or Cell Membranesmentioning

confidence: 99%

“…It is also worth mentioning that the nature of the cationic pendant charged groups, in this case quaternary ammonium versus pyridinium, does not largely affect intercalation. However, the length of the DSB core affects intercalation and cell viability. − The shorter DSB derivatives (DSBN+) are less well tolerated because of a pinching effect that damages the membrane and causes leakage of the cell. , At higher concentrations (40 μM) DSBN+ associates with the cells in a ratio higher than 2.5 × 10 7 molecules per cell. Given the estimated number of lipids per E.…”

Section: Design Of Organic Materials For Interfacing Into Microbial E...mentioning

confidence: 99%

“…For example, the emission maxima of DSSN+ shifts from 594 to 532 nm and quantum efficiency increases from 0.06% to 0.85% when going from water to a lipid bilayer. Polarized confocal microscopy can be used to identify the orientation of COEs in a membrane because the primary transition dipole moment (μ) of the molecules is along the direction of the conjugated core (Figure c,d). , During polarized confocal microscopy, , multilamellar vesicles with DSSN+ and DSBN+ showed an equatorial region with decreased fluorescence intensity perpendicular to the plane of polarization. These data are consistent with the COEs’ structure aligning in the membrane with the cationic pendant groups interacting with the polar lipid heads while the hydrophobic core resides in the nonpolar lipid tails.…”

Section: Characterization Techniquesmentioning

confidence: 99%

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Current Progress of Interfacing Organic Semiconducting Materials with Bacteria

et al. 2021

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Microbial bioelectronics require interfacing microorganisms with electrodes. The resulting abiotic/biotic platforms provide the basis of a range of technologies, including energy conversion and diagnostic assays. Organic semiconductors (OSCs) provide a unique strategy to modulate the interfaces between microbial systems and external electrodes, thereby improving the performance of these incipient technologies. In this review, we explore recent progress in the field on how OSCs, and related materials capable of charge transport, are being used within the context of microbial systems, and more specifically bacteria. We begin by examining the electrochemical communication modes in bacteria and the biological basis for charge transport. Different types of synthetic organic materials that have been designed and synthesized for interfacing and interrogating bacteria are discussed next, followed by the most commonly used characterization techniques for evaluating transport in microbial, synthetic, and hybrid systems. A range of applications is subsequently examined, including biological sensors and energy conversion systems. The review concludes by summarizing what has been accomplished so far and suggests future design approaches for OSC bioelectronics materials and technologies that hybridize characteristic properties of microbial and OSC systems. CONTENTS 5.1. Biosensors 4806 5.2. Energy Conversion Applications 4810 6. Future Directions 4813 Author Information 4814 Corresponding Authors 4814 Authors 4814 Notes 4814 Biographies 4814 Acknowledgments 4815 References 4815

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Section: Intercalation Into Cell Walls or Cell Membranesmentioning

confidence: 99%

Section: Design Of Organic Materials For Interfacing Into Microbial E...mentioning

confidence: 99%

Section: Characterization Techniquesmentioning

confidence: 99%

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Current Progress of Interfacing Organic Semiconducting Materials with Bacteria

et al. 2021

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“…1). For example, by simply regulating their molecular lengths, MICOEs can be tuned to serve a range of functions from being antimicrobial agents (through bacterial membrane disruption), 6 to biocatalysts (through promoting electron transport across membranes), 14 to chemical fortifiers (through stabilising membranes against environmental stresses). 11 The conjugated backbone of MICOEs also allows them to be utilized as membrane-specific fluorescent probes for cellular or vesicle detection ( i.e.…”

Section: Introductionmentioning

confidence: 99%

Membrane-intercalating conjugated oligoelectrolytes

2022

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“…22,23 The extent of membrane perturbation can be ne-tuned via molecular design approaches. 24,25 A general guiding principle is that the mismatch between the bilayer thickness and length of the COE leads to membrane disruption. 26,27 In particular, the distyrylbenzene derivative COE2-3C-C6 (previously referred to as COE2-3C, see Scheme 1) was reported to have the lowest minimum inhibitory concentration (MIC) against E. coli K12 among a homologous series of structures that differed in the number of phenylenevinylene units.…”

Section: Introductionmentioning

confidence: 99%