Porphyrins for Probing Electrical Potential Across Lipid Bilayer Membranes by Second Harmonic Generation

Reeve, James E.; Corbett, Alexander D.; Boczarow, Igor; Kaluza, Wojciech; Barford, William; Bayley, Hagan; Wilson, Tony; Anderson, Harry L.

doi:10.1002/anie.201304515

Cited by 36 publications

(32 citation statements)

References 54 publications

(71 reference statements)

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“…These include small molecule fluorescent approaches like merocyanines 2 , oxonols, and rhodamines, 3 charge-shift electrochromic dyes, 4–6 lipophilic anions, 7–10 second-harmonic generation 11,12 and nanoparticles. 13,14 Genetically encoded voltage indicators are also known and make use of fluorescent protein fusions to endogenous voltage-sensing domains 15–20 or microbial opsins 21,22 to transduce voltage changes into photons.…”

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confidence: 99%

Improved PeT Molecules for Optically Sensing Voltage in Neurons

Woodford¹,

Frady²,

et al. 2015

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VoltageFluor (VF) dyes have the potential to optically measure voltage in excitable membranes with the combination of high spatial and temporal resolution essential to better characterize the voltage dynamics of large groups of excitable cells. VF dyes sense voltage with high speed and sensitivity using photoinduced electron transfer (PeT) through a conjugated molecular wire. We show that tuning the driving force for PeT (ΔGPeT + w) through systematic chemical substitution modulates voltage sensitivity, estimate (ΔGPeT + w) values from experimentally measured redox potentials, and validate the voltage sensitivities in patch-clamped HEK cells for 10 new VF dyes. VF2.1(OMe).H, with a 48% ΔF/F per 100 mV, shows approximately 2-fold improvement over previous dyes in HEK cells, dissociated rat cortical neurons, and medicinal leech ganglia. Additionally, VF2.1(OMe).H faithfully reports pharmacological effects and circuit activity in mouse olfactory bulb slices, thus opening a wide range of previously inaccessible applications for voltage sensitive dyes.

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confidence: 99%

Improved PeT Molecules for Optically Sensing Voltage in Neurons

Woodford¹,

Frady²,

et al. 2015

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“…The double jeopardy of fast biological events and small volumes requires bright, photostable, highly sensitive, and non-disruptive voltage-sensitive dyes. There have been a number of promising approaches put forward for optical voltage sensing, including, more recently, the use of fluorescent proteins[5, 6], opsins[7, 8], second-harmonic generation[9], and nanomaterials [10, 11]. This review will focus on recent[12–14] developments in small molecule fluorescent voltage indicators.…”

Section: Voltage Indicator Challengesmentioning

confidence: 99%

Small molecule fluorescent voltage indicators for studying membrane potential

Miller¹

2016

Current Opinion in Chemical Biology

110

121

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Voltage imaging has the potential to unravel the contributions that rapid changes in membrane voltage make to cellular physiology, especially in the context of neuroscience. In particular, small molecule fluorophores are especially attractive because they can, in theory, provide fast and sensitive measurements of membrane potential dynamics. A number of classes of small molecule voltage indicators will be discussed, including dyes with improved two-photon voltage sensing, near infrared optical profiles for use in in vivo applications, and newly developed electron-transfer based indicators, or VoltageFluors, that can be tuned across a range of wavelengths to enable all-optical voltage manipulation and measurement. Limitations and a “wish-list” for voltage indicators will also be discussed.

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“…Anderson and coworkers also introduced pyridyl substituents to the meso -position of trans -AB porphyrins by Sonogashira coupling of meso -alkynyl porphyrin with 4-iodopyridine. The pyridyl groups were then quarternized with the electrophiles CH 3 I, 1,4-butane sultone or 5-iodo- N , N , N -tri-methylpentan-1-ammonium [ 92 , 93 , 94 ].…”

Section: Water-soluble Porphyrins Bearing Cationic Substituentsmentioning

confidence: 99%

Modifications of Porphyrins and Hydroporphyrins for Their Solubilization in Aqueous Media

Luciano

Brückner

2017

Molecules

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The increasing popularity of porphyrins and hydroporphyrins for use in a variety of biomedical (photodynamic therapy, fluorescence tagging and imaging, photoacoustic imaging) and technical (chemosensing, catalysis, light harvesting) applications is also associated with the growing number of methodologies that enable their solubilization in aqueous media. Natively, the vast majority of synthetic porphyrinic compounds are not water-soluble. Moreover, any water-solubility imposes several restrictions on the synthetic chemist on when to install solubilizing groups in the synthetic sequence, and how to isolate and purify these compounds. This review summarizes the chemical modifications to render synthetic porphyrins water-soluble, with a focus on the work disclosed since 2000. Where available, practical data such as solubility, indicators for the degree of aggregation, and special notes for the practitioner are listed. We hope that this review will guide synthetic chemists through the many strategies known to make porphyrins and hydroporphyrins water soluble.

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Porphyrins for Probing Electrical Potential Across Lipid Bilayer Membranes by Second Harmonic Generation

Cited by 36 publications

References 54 publications

Improved PeT Molecules for Optically Sensing Voltage in Neurons

Improved PeT Molecules for Optically Sensing Voltage in Neurons

Small molecule fluorescent voltage indicators for studying membrane potential

Modifications of Porphyrins and Hydroporphyrins for Their Solubilization in Aqueous Media

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