2016
DOI: 10.1021/jacs.6b05672
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Isomerically Pure Tetramethylrhodamine Voltage Reporters

Abstract: We present the design, synthesis, and application of a new family of fluorescent voltage indicators based on isomerically pure tetramethylrhodamines. These new Rhodamine Voltage Reporters, or RhoVRs, use photoinduced electron transfer (PeT) as a trigger for voltage sensing, display excitation and emission profiles in the green to orange region of the visible spectrum, demonstrate high sensitivity to membrane potential changes (up to 47% ΔF/F per 100 mV), and employ a tertiary amide derived from sarcosine, whic… Show more

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Cited by 66 publications
(123 citation statements)
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“…The N,N-diethyl-3-methoxyaniline was used in place of the previously described N,N-dimethyl-3-methoxyaniline wire because the diethyl derivative can be simply prepared from commercially available N,N-diethylsalicylaldehyde. (38) Heck coupling between the styrene molecular wires and corresponding mono- or di-sulfonated fluoresceins provided the ms- and dsVF dyes after purification via crystallization. Small amounts of dye were purified by semi-preparative HPLC for further analysis.…”
Section: Resultsmentioning
confidence: 99%
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“…The N,N-diethyl-3-methoxyaniline was used in place of the previously described N,N-dimethyl-3-methoxyaniline wire because the diethyl derivative can be simply prepared from commercially available N,N-diethylsalicylaldehyde. (38) Heck coupling between the styrene molecular wires and corresponding mono- or di-sulfonated fluoresceins provided the ms- and dsVF dyes after purification via crystallization. Small amounts of dye were purified by semi-preparative HPLC for further analysis.…”
Section: Resultsmentioning
confidence: 99%
“…Finally, the disulfonated VoltageFluor dyes represent one possible solution for designing future dyes with higher voltage sensitivity than first generation VF dyes. Efforts are currently underway in our lab to generalize this scaffold to other xanthene chromophores, such as rhodamines(38) and silicon-rhodamines(13), and integrate it with our understanding of the contributions electron affinities make to voltage sensing(23). …”
Section: Discussionmentioning
confidence: 99%
“…14 Because the reporter (fluorescent dye) is chemically orthogonal to the voltage sensing domain (molecular wire/aniline) the VF scaffold enables ready exchange the fluorophore acceptor to access a wide range of the visible and near-infrared portions of the electromagnetic spectrum, 12, 15 as well as optimized VoltageFluors for two-photon voltage imaging. 16 Although VoltageFluors are bright, sensitive, and employ a fast and non-disruptive mechanism of voltage sensing, their pan-membrane localization introduces a source of background noise in heterogeneous samples, limiting sensitivity.…”
Section: Small-molecule Fluorescent Voltage Indicatorsmentioning
confidence: 99%
“…For example, the red voltage indicator developed in our lab, RhoVR 1 shows excellent signal to noise and good ΔF/F, in addition to far superior kinetics for single action potentials when compared to the genetically encoded Ca 2+ indicator GCaMP (Figure 3). 12 …”
Section: Universal Challenges For Voltage Imagingmentioning
confidence: 99%
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