Brominated Luciferins Are Versatile Bioluminescent Probes

Steinhardt, Rachel C.; Rathbun, Colin M.; Krull, Brandon T.; Yu, Jason M.; Yang, Yuhang; Nguyen, Brian D.; Kwon, Jake; McCutcheon, David C.; Jones, Krysten A.; Furche, Filipp; Prescher, Jennifer A.

doi:10.1002/cbic.201600564

Title: Brominated Luciferins Are Versatile Bioluminescent Probes

Abstract

Here, we report a set of brominated luciferins for bioluminescence imaging. These regioisomeric scaffolds were accessed by using a common synthetic route. All analogues produced light with firefly luciferase, although varying levels of emission were observed. Differences in photon output were analyzed by computation and photophysical measurements. The brightest brominated luciferin was further evaluated in cell and animal models. At low doses, the analogue outperformed the native substrate in cells. The remaining luciferins, although weak emitters with firefly luciferase, were inherently capable of light production and thus potential substrates for orthogonal mutant enzymes.

Authors:

Steinhardt, Rachel C. ^[1]; Rathbun, Colin M. ^[1]; Krull, Brandon T. ^[1]; Yu, Jason M. ^[1]; Yang, Yuhang ^[1]; Nguyen, Brian D. ^[1]; Kwon, Jake ^[1]; McCutcheon, David C. ^[1]; Jones, Krysten A. ^[2]; Furche, Filipp ^[1];

^[3]

Univ. of California, Irvine, CA (United States). Dept. of Chemistry
Univ. of California, Irvine, CA (United States). Dept. of Molecular Biology and Biochemistry
Univ. of California, Irvine, CA (United States). Dept. of Chemistry; Univ. of California, Irvine, CA (United States). Dept. of Pharmaceutical Sciences

Publication Date:: Thu Dec 08 00:00:00 EST 2016

Research Org.:: Univ. of California, Irvine, CA (United States)

Sponsoring Org.:: USDOE Office of Science (SC), Basic Energy Sciences (BES); National Institutes of Health (NIH)

OSTI Identifier:: 1423816

Grant/Contract Number:: SC0008694

Resource Type:: Accepted Manuscript

Journal Name:: ChemBioChem: a European journal of chemical biology

Additional Journal Information:: Journal Volume: 18; Journal Issue: 1; Journal ID: ISSN 1439-4227

Publisher:: ChemPubSoc Europe

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats


                    Steinhardt, Rachel C., Rathbun, Colin M., Krull, Brandon T., Yu, Jason M., Yang, Yuhang, Nguyen, Brian D., Kwon, Jake, McCutcheon, David C., Jones, Krysten A., Furche, Filipp, and Prescher, Jennifer A. Brominated Luciferins Are Versatile Bioluminescent Probes.  United States: N. p., 2016. 
Web.  doi:10.1002/cbic.201600564.

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                    Steinhardt, Rachel C., Rathbun, Colin M., Krull, Brandon T., Yu, Jason M., Yang, Yuhang, Nguyen, Brian D., Kwon, Jake, McCutcheon, David C., Jones, Krysten A., Furche, Filipp, & Prescher, Jennifer A. Brominated Luciferins Are Versatile Bioluminescent Probes.  United States.  https://doi.org/10.1002/cbic.201600564

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                    Steinhardt, Rachel C., Rathbun, Colin M., Krull, Brandon T., Yu, Jason M., Yang, Yuhang, Nguyen, Brian D., Kwon, Jake, McCutcheon, David C., Jones, Krysten A., Furche, Filipp, and Prescher, Jennifer A. Thu .  
"Brominated Luciferins Are Versatile Bioluminescent Probes".  United States.  https://doi.org/10.1002/cbic.201600564.  https://www.osti.gov/servlets/purl/1423816.

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@article{osti_1423816,

  title        = {Brominated Luciferins Are Versatile Bioluminescent Probes},

  author       = {Steinhardt, Rachel C. and Rathbun, Colin M. and Krull, Brandon T. and Yu, Jason M. and Yang, Yuhang and Nguyen, Brian D. and Kwon, Jake and McCutcheon, David C. and Jones, Krysten A. and Furche, Filipp and Prescher, Jennifer A.},

  abstractNote = {Here, we report a set of brominated luciferins for bioluminescence imaging. These regioisomeric scaffolds were accessed by using a common synthetic route. All analogues produced light with firefly luciferase, although varying levels of emission were observed. Differences in photon output were analyzed by computation and photophysical measurements. The brightest brominated luciferin was further evaluated in cell and animal models. At low doses, the analogue outperformed the native substrate in cells. The remaining luciferins, although weak emitters with firefly luciferase, were inherently capable of light production and thus potential substrates for orthogonal mutant enzymes.},

  doi          = {10.1002/cbic.201600564},

  journal      = {ChemBioChem: a European journal of chemical biology},

  number       = 1,

  volume       = 18,

  place        = {United States},

  year         = {Thu Dec 08 00:00:00 EST 2016},

  month        = {Thu Dec 08 00:00:00 EST 2016}

}

Copy to clipboard

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Works referenced in this record:

Analogs of Firefly Luciferin
journal, July 1965

White, Emil H.; Wörther, Helmut; Field, George F.
The Journal of Organic Chemistry, Vol. 30, Issue 7
DOI: 10.1021/jo01018a054

Crystal Structure of Firefly Luciferase in a Second Catalytic Conformation Supports a Domain Alternation Mechanism
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Sundlov, Jesse A.; Fontaine, Danielle M.; Southworth, Tara L.
Biochemistry, Vol. 51, Issue 33
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Nicolaou, K. C.; Bulger, Paul G.; Sarlah, David
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Synthesis and bioluminescence of difluoroluciferin
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Pirrung, Michael C.; Biswas, Goutam; De Howitt, Natalie
Bioorganic & Medicinal Chemistry Letters, Vol. 24, Issue 20
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Firefly Luciferase Mutants Allow Substrate-Selective Bioluminescence Imaging in the Mouse Brain
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Adams, Spencer T.; Mofford, David M.; Reddy, G. S. Kiran Kumar
Angewandte Chemie International Edition, Vol. 55, Issue 16
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Chemi- and bioluminescence of firefly luciferin
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White, Emil Henry; Rapaport, Eliezer; Hopkins, Thomas A.
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Chemi- and bioluminescence of firefly luciferin
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Kojima, Ryosuke; Takakura, Hideo; Ozawa, Takeaki
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A Dual-Color Far-Red to Near-Infrared Firefly Luciferin Analogue Designed for Multiparametric Bioluminescence Imaging
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Jathoul, Amit P.; Grounds, Helen; Anderson, James C.
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Aminoluciferins Extend Firefly Luciferase Bioluminescence into the Near-Infrared and Can Be Preferred Substrates over d -Luciferin
journal, September 2014

Mofford, David M.; Reddy, Gadarla Randheer; Miller, Stephen C.
Journal of the American Chemical Society, Vol. 136, Issue 38
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In vivo imaging of hydrogen peroxide production in a murine tumor model with a chemoselective bioluminescent reporter
journal, November 2010

Van de Bittner, G. C.; Dubikovskaya, E. A.; Bertozzi, C. R.
Proceedings of the National Academy of Sciences, Vol. 107, Issue 50
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Nicolaou, K. C.; Bulger, Paul G.; Sarlah, David
Angewandte Chemie, Vol. 117, Issue 29
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Photoinduced Intramolecular Charge Transfer in 4-(Dimethyl)aminobenzonitrile − A Theoretical Perspective
journal, February 2004

Rappoport, Dmitrij; Furche, Filipp
Journal of the American Chemical Society, Vol. 126, Issue 4
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A synthetic luciferin improves bioluminescence imaging in live mice
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Evans, Melanie S.; Chaurette, Joanna P.; Adams, Spencer T.
Nature Methods, Vol. 11, Issue 4
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Cage the firefly luciferin! – a strategy for developing bioluminescent probes
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Li, Jing; Chen, Laizhong; Du, Lupei
Chem. Soc. Rev., Vol. 42, Issue 2
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Pd/P( t -Bu) ₃ : A Mild and General Catalyst for Stille Reactions of Aryl Chlorides and Aryl Bromides
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Littke, Adam F.; Schwarz, Lothar; Fu, Gregory C.
Journal of the American Chemical Society, Vol. 124, Issue 22
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Robust Light Emission from Cyclic Alkylaminoluciferin Substrates for Firefly Luciferase
journal, October 2010

Reddy, Gadarla Randheer; Thompson, Walter C.; Miller, Stephen C.
Journal of the American Chemical Society, Vol. 132, Issue 39
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Excited-State Intramolecular Proton Transfer: A Survey of TDDFT and RI-CC2 Excited-State Potential Energy Surfaces
journal, April 2005

Aquino, Adelia J. A.; Lischka, Hans; Hättig, Christof
The Journal of Physical Chemistry A, Vol. 109, Issue 14
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Expedient Synthesis of Electronically Modified Luciferins for Bioluminescence Imaging
journal, April 2012

McCutcheon, David C.; Paley, Miranda A.; Steinhardt, Rachel C.
Journal of the American Chemical Society, Vol. 134, Issue 18
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Development of 5′- and 7′-Substituted Luciferin Analogues as Acid-Tolerant Substrates of Firefly Luciferase
journal, June 2012

Takakura, Hideo; Kojima, Ryosuke; Ozawa, Takeaki
ChemBioChem, Vol. 13, Issue 10
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A “Caged” Luciferin for Imaging Cell–Cell Contacts
journal, July 2015

Porterfield, William B.; Jones, Krysten A.; McCutcheon, David C.
Journal of the American Chemical Society, Vol. 137, Issue 27
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Bauernschmitt, Rüdiger; Ahlrichs, Reinhart
Chemical Physics Letters, Vol. 256, Issue 4-5
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Source of oxygen in the CO2 produced in the bioluminescent oxidation of firefly luciferin
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Shimomura, O.; Goto, T.; Johnson, F. H.
Proceedings of the National Academy of Sciences, Vol. 74, Issue 7
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Firefly luminescence: A historical perspective and recent developments
journal, January 2008

Fraga, Hugo
Photochemical & Photobiological Sciences, Vol. 7, Issue 2
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Beyond D-luciferin: expanding the scope of bioluminescence imaging in vivo
journal, August 2014

Adams, Spencer T.; Miller, Stephen C.
Current Opinion in Chemical Biology, Vol. 21
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Analogs of Firefly Luciferin. III ¹
journal, May 1966

White, Emil H.; Wörther, Helmut
The Journal of Organic Chemistry, Vol. 31, Issue 5
DOI: 10.1021/jo01343a039

A Selenium Analogue of Firefly D-Luciferin with Red-Shifted Bioluminescence Emission
journal, February 2012

Conley, Nicholas R.; Dragulescu-Andrasi, Anca; Rao, Jianghong
Angewandte Chemie, Vol. 124, Issue 14
DOI: 10.1002/ange.201105653

A Dual-Color Far-Red to Near-Infrared Firefly Luciferin Analogue Designed for Multiparametric Bioluminescence Imaging
journal, September 2014

Jathoul, Amit P.; Grounds, Helen; Anderson, James C.
Angewandte Chemie, Vol. 126, Issue 48
DOI: 10.1002/ange.201405955

A Selenium Analogue of Firefly D-Luciferin with Red-Shifted Bioluminescence Emission
journal, February 2012

Conley, Nicholas R.; Dragulescu-Andrasi, Anca; Rao, Jianghong
Angewandte Chemie International Edition, Vol. 51, Issue 14
DOI: 10.1002/anie.201105653

A luciferin analogue generating near-infrared bioluminescence achieves highly sensitive deep-tissue imaging
journal, June 2016

Kuchimaru, Takahiro; Iwano, Satoshi; Kiyama, Masahiro
Nature Communications, Vol. 7, Issue 1
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Rapid and scalable assembly of firefly luciferase substrates
journal, January 2015

McCutcheon, David C.; Porterfield, William B.; Prescher, Jennifer A.
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Chemiluminescence of Firefly Luciferin without Enzyme
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Seliger, H. H.; McElroy, W. D.
Science, Vol. 138, Issue 3541
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Firefly Luciferase Mutants Allow Substrate-Selective Bioluminescence Imaging in the Mouse Brain
journal, March 2016

Adams, Spencer T.; Mofford, David M.; Reddy, G. S. Kiran Kumar
Angewandte Chemie, Vol. 128, Issue 16
DOI: 10.1002/ange.201511350

Rational Design and Development of Near-Infrared-Emitting Firefly Luciferins Available In Vivo
journal, December 2012

Kojima, Ryosuke; Takakura, Hideo; Ozawa, Takeaki
Angewandte Chemie, Vol. 125, Issue 4
DOI: 10.1002/ange.201205151

Bioluminescence: a versatile technique for imaging cellular and molecular features
journal, January 2014

Paley, Miranda A.; Prescher, Jennifer A.
Med. Chem. Commun., Vol. 5, Issue 3
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Identification of Mutant Firefly Luciferases that Efficiently Utilize Aminoluciferins
journal, December 2011

Harwood, Katryn R.; Mofford, David M.; Reddy, Gadarla R.
Chemistry & Biology, Vol. 18, Issue 12
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Works referencing / citing this record:

Pyridone Luciferins and Mutant Luciferases for Bioluminescence Imaging
journal, January 2018

Zhang, Brendan S.; Jones, Krysten A.; McCutcheon, David C.
ChemBioChem, Vol. 19, Issue 5
DOI: 10.1002/cbic.201700542

Computational investigation into the fluorescence of luciferin analogues
journal, December 2018

Vreven, Thom; Miller, Stephen C.
Journal of Computational Chemistry, Vol. 40, Issue 2
DOI: 10.1002/jcc.25745

An allylated firefly luciferin analogue with luciferase specific response in living cells
journal, January 2018

Ikeda, Yuma; Saitoh, Tsuyoshi; Niwa, Kazuki
Chemical Communications, Vol. 54, Issue 14
DOI: 10.1039/c7cc09720d

Opening a Gateway for Chemiluminescence Cell Imaging: Distinctive Methodology for Design of Bright Chemiluminescent Dioxetane Probes
journal, March 2017

Green, Ori; Eilon, Tal; Hananya, Nir
ACS Central Science, Vol. 3, Issue 4
DOI: 10.1021/acscentsci.7b00058

Parallel Screening for Rapid Identification of Orthogonal Bioluminescent Tools
journal, November 2017

Rathbun, Colin M.; Porterfield, William B.; Jones, Krysten A.
ACS Central Science, Vol. 3, Issue 12
DOI: 10.1021/acscentsci.7b00394

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Title: Brominated Luciferins Are Versatile Bioluminescent Probes

Abstract

Citation Formats

Analogs of Firefly Luciferin journal, July 1965

Crystal Structure of Firefly Luciferase in a Second Catalytic Conformation Supports a Domain Alternation Mechanism journal, August 2012

Palladium-Catalyzed Cross-Coupling Reactions in Total Synthesis journal, July 2005

Synthesis and bioluminescence of difluoroluciferin journal, October 2014

Firefly Luciferase Mutants Allow Substrate-Selective Bioluminescence Imaging in the Mouse Brain journal, March 2016

Chemi- and bioluminescence of firefly luciferin journal, April 1969

Chemi- and bioluminescence of firefly luciferin journal, April 1980

Rational Design and Development of Near-Infrared-Emitting Firefly Luciferins Available In Vivo journal, December 2012

A Dual-Color Far-Red to Near-Infrared Firefly Luciferin Analogue Designed for Multiparametric Bioluminescence Imaging journal, September 2014

Aminoluciferins Extend Firefly Luciferase Bioluminescence into the Near-Infrared and Can Be Preferred Substrates over d -Luciferin journal, September 2014

In vivo imaging of hydrogen peroxide production in a murine tumor model with a chemoselective bioluminescent reporter journal, November 2010

Palladiumkatalysierte Kreuzkupplungen in der Totalsynthese journal, July 2005

Photoinduced Intramolecular Charge Transfer in 4-(Dimethyl)aminobenzonitrile − A Theoretical Perspective journal, February 2004

A synthetic luciferin improves bioluminescence imaging in live mice journal, February 2014

Cage the firefly luciferin! – a strategy for developing bioluminescent probes journal, January 2013

Pd/P( t -Bu) 3 : A Mild and General Catalyst for Stille Reactions of Aryl Chlorides and Aryl Bromides journal, June 2002

Robust Light Emission from Cyclic Alkylaminoluciferin Substrates for Firefly Luciferase journal, October 2010

Excited-State Intramolecular Proton Transfer: A Survey of TDDFT and RI-CC2 Excited-State Potential Energy Surfaces journal, April 2005

Expedient Synthesis of Electronically Modified Luciferins for Bioluminescence Imaging journal, April 2012

Development of 5′- and 7′-Substituted Luciferin Analogues as Acid-Tolerant Substrates of Firefly Luciferase journal, June 2012

A “Caged” Luciferin for Imaging Cell–Cell Contacts journal, July 2015

Treatment of electronic excitations within the adiabatic approximation of time dependent density functional theory journal, July 1996

Source of oxygen in the CO2 produced in the bioluminescent oxidation of firefly luciferin journal, July 1977

Firefly luminescence: A historical perspective and recent developments journal, January 2008

Beyond D-luciferin: expanding the scope of bioluminescence imaging in vivo journal, August 2014

Analogs of Firefly Luciferin. III 1 journal, May 1966

A Selenium Analogue of Firefly D-Luciferin with Red-Shifted Bioluminescence Emission journal, February 2012

A Dual-Color Far-Red to Near-Infrared Firefly Luciferin Analogue Designed for Multiparametric Bioluminescence Imaging journal, September 2014

A Selenium Analogue of Firefly D-Luciferin with Red-Shifted Bioluminescence Emission journal, February 2012

A luciferin analogue generating near-infrared bioluminescence achieves highly sensitive deep-tissue imaging journal, June 2016

Rapid and scalable assembly of firefly luciferase substrates journal, January 2015

Chemiluminescence of Firefly Luciferin without Enzyme journal, November 1962

Firefly Luciferase Mutants Allow Substrate-Selective Bioluminescence Imaging in the Mouse Brain journal, March 2016

Rational Design and Development of Near-Infrared-Emitting Firefly Luciferins Available In Vivo journal, December 2012

Bioluminescence: a versatile technique for imaging cellular and molecular features journal, January 2014

Identification of Mutant Firefly Luciferases that Efficiently Utilize Aminoluciferins journal, December 2011

Pyridone Luciferins and Mutant Luciferases for Bioluminescence Imaging journal, January 2018

Computational investigation into the fluorescence of luciferin analogues journal, December 2018

An allylated firefly luciferin analogue with luciferase specific response in living cells journal, January 2018

Opening a Gateway for Chemiluminescence Cell Imaging: Distinctive Methodology for Design of Bright Chemiluminescent Dioxetane Probes journal, March 2017

Parallel Screening for Rapid Identification of Orthogonal Bioluminescent Tools journal, November 2017

Analogs of Firefly Luciferin
journal, July 1965

Crystal Structure of Firefly Luciferase in a Second Catalytic Conformation Supports a Domain Alternation Mechanism
journal, August 2012

Palladium-Catalyzed Cross-Coupling Reactions in Total Synthesis
journal, July 2005

Synthesis and bioluminescence of difluoroluciferin
journal, October 2014

Firefly Luciferase Mutants Allow Substrate-Selective Bioluminescence Imaging in the Mouse Brain
journal, March 2016

Chemi- and bioluminescence of firefly luciferin
journal, April 1969

Chemi- and bioluminescence of firefly luciferin
journal, April 1980

Rational Design and Development of Near-Infrared-Emitting Firefly Luciferins Available In Vivo
journal, December 2012

A Dual-Color Far-Red to Near-Infrared Firefly Luciferin Analogue Designed for Multiparametric Bioluminescence Imaging
journal, September 2014

Aminoluciferins Extend Firefly Luciferase Bioluminescence into the Near-Infrared and Can Be Preferred Substrates over d -Luciferin
journal, September 2014

In vivo imaging of hydrogen peroxide production in a murine tumor model with a chemoselective bioluminescent reporter
journal, November 2010

Palladiumkatalysierte Kreuzkupplungen in der Totalsynthese
journal, July 2005

Photoinduced Intramolecular Charge Transfer in 4-(Dimethyl)aminobenzonitrile − A Theoretical Perspective
journal, February 2004

A synthetic luciferin improves bioluminescence imaging in live mice
journal, February 2014

Cage the firefly luciferin! – a strategy for developing bioluminescent probes
journal, January 2013

Pd/P( t -Bu) ₃ : A Mild and General Catalyst for Stille Reactions of Aryl Chlorides and Aryl Bromides
journal, June 2002

Robust Light Emission from Cyclic Alkylaminoluciferin Substrates for Firefly Luciferase
journal, October 2010

Excited-State Intramolecular Proton Transfer: A Survey of TDDFT and RI-CC2 Excited-State Potential Energy Surfaces
journal, April 2005

Expedient Synthesis of Electronically Modified Luciferins for Bioluminescence Imaging
journal, April 2012

Development of 5′- and 7′-Substituted Luciferin Analogues as Acid-Tolerant Substrates of Firefly Luciferase
journal, June 2012

A “Caged” Luciferin for Imaging Cell–Cell Contacts
journal, July 2015

Treatment of electronic excitations within the adiabatic approximation of time dependent density functional theory
journal, July 1996

Source of oxygen in the CO2 produced in the bioluminescent oxidation of firefly luciferin
journal, July 1977

Firefly luminescence: A historical perspective and recent developments
journal, January 2008

Beyond D-luciferin: expanding the scope of bioluminescence imaging in vivo
journal, August 2014

Analogs of Firefly Luciferin. III ¹
journal, May 1966

A Selenium Analogue of Firefly D-Luciferin with Red-Shifted Bioluminescence Emission
journal, February 2012

A Dual-Color Far-Red to Near-Infrared Firefly Luciferin Analogue Designed for Multiparametric Bioluminescence Imaging
journal, September 2014

A Selenium Analogue of Firefly D-Luciferin with Red-Shifted Bioluminescence Emission
journal, February 2012

A luciferin analogue generating near-infrared bioluminescence achieves highly sensitive deep-tissue imaging
journal, June 2016

Rapid and scalable assembly of firefly luciferase substrates
journal, January 2015

Chemiluminescence of Firefly Luciferin without Enzyme
journal, November 1962

Firefly Luciferase Mutants Allow Substrate-Selective Bioluminescence Imaging in the Mouse Brain
journal, March 2016

Rational Design and Development of Near-Infrared-Emitting Firefly Luciferins Available In Vivo
journal, December 2012

Bioluminescence: a versatile technique for imaging cellular and molecular features
journal, January 2014

Identification of Mutant Firefly Luciferases that Efficiently Utilize Aminoluciferins
journal, December 2011

Pyridone Luciferins and Mutant Luciferases for Bioluminescence Imaging
journal, January 2018

Computational investigation into the fluorescence of luciferin analogues
journal, December 2018

An allylated firefly luciferin analogue with luciferase specific response in living cells
journal, January 2018

Opening a Gateway for Chemiluminescence Cell Imaging: Distinctive Methodology for Design of Bright Chemiluminescent Dioxetane Probes
journal, March 2017

Parallel Screening for Rapid Identification of Orthogonal Bioluminescent Tools
journal, November 2017