Convergent synthesis and optical properties of near-infrared emitting bioluminescent infra-luciferins

Anderson, James C.; Grounds, Helen; Jathoul, Amit P.; Murray, James A. H.; Pacman, Steven J.; Tisi, Laurence

doi:10.1039/c6ra19541e

Cited by 24 publications

(31 citation statements)

References 26 publications

(22 reference statements)

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“…The syntheses of luciferin and infraluciferin used in this work have been described fully in previous publications. 29,30 Photoelectron spectra were recorded using our anion photoelectron imaging spectrometer which combines an electrospray anion source with collinear velocity-map imaging detection of electrons. The electrospray anion photodetachment spectroscopy method was pioneered by LS Wang 31 and used by XB Wang 32 and photoelectron imaging spectroscopy of anions is employed by a number of groups [33][34][35][36][37] as well as our own.…”

Section: Anion Photoelectron Spectroscopymentioning

confidence: 99%

Photoelectron spectroscopy of isolated luciferin and infraluciferin anions in vacuo: competing photodetachment, photofragmentation and internal conversion

Woodhouse

Aßmann

Parkes

et al. 2017

Phys. Chem. Chem. Phys.

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The electronic structure and excited-state dynamics of the ubiquitous bioluminescent probe luciferin and its furthest red-shifted analogue infraluciferin have been investigated using photoelectron spectroscopy and quantum chemistry calculations. In our electrospray ionization source, the deprotonated anions are formed predominantly in their phenolate forms and are directly relevant to studies of luciferin and infraluciferin as models for their unstable oxyluciferin and oxyinfraluciferin emitters. Following photoexcitation in the range 357-230 nm, we find that internal conversion from high-lying excited states to the S(1ππ*) state competes efficiently with electron detachment. In infraluciferin, we find that decarboxylation also competes with direct electron detachment and internal conversion. This detailed spectroscopic and computational study defines the electronic structure and electronic relaxation processes of luciferin and infraluciferin and will inform the design of new bioluminescent systems and applications.

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Section: Anion Photoelectron Spectroscopymentioning

confidence: 99%

Photoelectron spectroscopy of isolated luciferin and infraluciferin anions in vacuo: competing photodetachment, photofragmentation and internal conversion

Woodhouse

Aßmann

Parkes

et al. 2017

Phys. Chem. Chem. Phys.

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“…This small molecule is the effective light emitter; thus, modifications to the scaffold can, in principle, impact both pharmacokinetic and spectral properties. There have been many notable successes in engineering unique luciferins in recent years . However, many of the scaffolds exhibit reduced photon outputs with luciferase, limiting their use in some cellular and tissue environments.…”

Section: Introductionmentioning

confidence: 99%

Pyridone Luciferins and Mutant Luciferases for Bioluminescence Imaging

2018

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New applications for bioluminescence imaging require an expanded set of luciferase enzymes and luciferin substrates. Here, we report two novel luciferins for use in vitro and in cells. These molecules comprise regioisomeric pyridone cores that can be accessed from a common synthetic route. The analogues exhibited unique emission spectra with firefly luciferase, although photon intensities remained weak. Enhanced light outputs were achieved by using mutant luciferase enzymes. One of the luciferin-luciferase pairs produced light on par with native probes in live cells. The pyridone analogues and complementary luciferases add to a growing set of designer probes for bioluminescence imaging.

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“…For example, extending the conjugation of the luciferin pi system or altering heteroatom substituents can alter emission wavelengths. [26–28] Both blue- and red-shifted analogs have been synthesized in recent years, although most remain weak emitters with native luciferases. [26,27,29] Engineering enzymes to better process the modified analogs—and thus recover light intensity—has been successful in some cases.…”

Section: Generating a Palette Of Bioluminescent Probesmentioning

confidence: 99%

“…[26–28] Both blue- and red-shifted analogs have been synthesized in recent years, although most remain weak emitters with native luciferases. [26,27,29] Engineering enzymes to better process the modified analogs—and thus recover light intensity—has been successful in some cases. [27,29,30]…”

Section: Generating a Palette Of Bioluminescent Probesmentioning

confidence: 99%

Advances in bioluminescence imaging: new probes from old recipes

Yao

Zhang

Prescher

2018

Current Opinion in Chemical Biology

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Bioluminescent probes are powerful tools for visualizing biology in live tissues and whole animals. Recent years have seen a surge in the number of new luciferases, luciferins, and related tools available for bioluminescence imaging. Many were crafted using classic methods of optical probe design and engineering. Here we highlight recent advances in bioluminescent tool discovery and development, along with applications of the probes in cells, tissues, and organisms. Collectively, these tools are improving in vivo imaging capabilities and bolstering new research directions.

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Convergent synthesis and optical properties of near-infrared emitting bioluminescent infra-luciferins

Abstract: A high yielding, scalable and convergent synthesis of infra-luciferins and investigation of their potential for near-infrared bioluminescence imaging.

Cited by 24 publications

References 26 publications

Photoelectron spectroscopy of isolated luciferin and infraluciferin anions in vacuo: competing photodetachment, photofragmentation and internal conversion

Photoelectron spectroscopy of isolated luciferin and infraluciferin anions in vacuo: competing photodetachment, photofragmentation and internal conversion

Pyridone Luciferins and Mutant Luciferases for Bioluminescence Imaging

Advances in bioluminescence imaging: new probes from old recipes

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