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Literature DB >> 26784889

Design and Synthesis of an Alkynyl Luciferin Analogue for Bioluminescence Imaging.

Rachel C Steinhardt¹, Jessica M O'Neill¹, Colin M Rathbun¹, David C McCutcheon¹, Miranda A Paley¹, Jennifer A Prescher^2,3,4.

Abstract

Herein, the synthesis and characterization of an alkyne-modified luciferin is reported. This bioluminescent probe was accessed using C-H activation methodology and was found to be stable in solution and capable of light production with firefly luciferase. The luciferin analogue was also cell permeant and emitted more redshifted light than d-luciferin, the native luciferase substrate. Based on these features, the alkynyl luciferin will be useful for a variety of imaging applications.

Entities: CellLine Chemical Disease Gene Species

Keywords: C−H activation; Sonogashira coupling; bioluminescence imaging; luciferase; luciferin

Mesh：

Substances：

Year: 2016 PMID： 26784889 PMCID： PMC4868354 DOI： 10.1002/chem.201503944

Source DB: PubMed Journal: Chemistry ISSN： 0947-6539 Impact factor: 5.236

50 in total

1. Cancer stem cells from human breast tumors are involved in spontaneous metastases in orthotopic mouse models.

Authors: Huiping Liu; Manishkumar R Patel; Jennifer A Prescher; Antonia Patsialou; Dalong Qian; Jiahui Lin; Susanna Wen; Ya-Fang Chang; Michael H Bachmann; Yohei Shimono; Piero Dalerba; Maddalena Adorno; Neethan Lobo; Janet Bueno; Frederick M Dirbas; Sumanta Goswami; George Somlo; John Condeelis; Christopher H Contag; Sanjiv Sam Gambhir; Michael F Clarke
Journal: Proc Natl Acad Sci U S A Date: 2010-10-04 Impact factor: 11.205

2. A bioluminogenic substrate for in vivo imaging of beta-lactamase activity.

Authors: Hequan Yao; Min-kyung So; Jianghong Rao
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

3. Self-renewal and expansion of single transplanted muscle stem cells.

Authors: Alessandra Sacco; Regis Doyonnas; Peggy Kraft; Stefan Vitorovic; Helen M Blau
Journal: Nature Date: 2008-09-17 Impact factor: 49.962

Review 4. Finding the right (bioorthogonal) chemistry.

Authors: David M Patterson; Lidia A Nazarova; Jennifer A Prescher
Journal: ACS Chem Biol Date: 2014-01-30 Impact factor: 5.100

5. Identification of mutant firefly luciferases that efficiently utilize aminoluciferins.

Authors: Katryn R Harwood; David M Mofford; Gadarla R Reddy; Stephen C Miller
Journal: Chem Biol Date: 2011-12-23

6. Robust light emission from cyclic alkylaminoluciferin substrates for firefly luciferase.

Authors: Gadarla Randheer Reddy; Walter C Thompson; Stephen C Miller
Journal: J Am Chem Soc Date: 2010-10-06 Impact factor: 15.419

7. The conversion of [(4-chloro-5H-1,2,3-dithiazol-5-ylidene)amino]azines into azine fused thiazole-2-carbonitriles.

Authors: Panayiotis A Koutentis; Maria Koyioni; Sophia S Michaelidou
Journal: Org Biomol Chem Date: 2012-12-04 Impact factor: 3.876

8. Tissue-specific homing and expansion of donor NK cells in allogeneic bone marrow transplantation.

Authors: Janelle A Olson; Robert Zeiser; Andreas Beilhack; Joshua J Goldman; Robert S Negrin
Journal: J Immunol Date: 2009-08-05 Impact factor: 5.422

9. Forkhead box O1 (FOXO1) protein, but not p53, contributes to robust induction of p21 expression in fasted mice.

Authors: Kelsey L Tinkum; Lynn S White; Luciano Marpegan; Erik Herzog; David Piwnica-Worms; Helen Piwnica-Worms
Journal: J Biol Chem Date: 2013-08-05 Impact factor: 5.157

10. Aminoluciferins extend firefly luciferase bioluminescence into the near-infrared and can be preferred substrates over D-luciferin.

Authors: David M Mofford; Gadarla Randheer Reddy; Stephen C Miller
Journal: J Am Chem Soc Date: 2014-09-11 Impact factor: 15.419

9 in total

Design and Synthesis of an Alkynyl Luciferin Analogue for Bioluminescence Imaging.

1. Cancer stem cells from human breast tumors are involved in spontaneous metastases in orthotopic mouse models.

2. A bioluminogenic substrate for in vivo imaging of beta-lactamase activity.

3. Self-renewal and expansion of single transplanted muscle stem cells.

Review 4. Finding the right (bioorthogonal) chemistry.

5. Identification of mutant firefly luciferases that efficiently utilize aminoluciferins.

6. Robust light emission from cyclic alkylaminoluciferin substrates for firefly luciferase.

7. The conversion of [(4-chloro-5H-1,2,3-dithiazol-5-ylidene)amino]azines into azine fused thiazole-2-carbonitriles.

8. Tissue-specific homing and expansion of donor NK cells in allogeneic bone marrow transplantation.

9. Forkhead box O1 (FOXO1) protein, but not p53, contributes to robust induction of p21 expression in fasted mice.

10. Aminoluciferins extend firefly luciferase bioluminescence into the near-infrared and can be preferred substrates over D-luciferin.

Review 1. Lessons Learned from Luminous Luciferins and Latent Luciferases.

2. Building Biological Flashlights: Orthogonal Luciferases and Luciferins for in Vivo Imaging.

3. Pyridone Luciferins and Mutant Luciferases for Bioluminescence Imaging.

4. Luciferase Activity of Insect Fatty Acyl-CoA Synthetases with Synthetic Luciferins.

Review 5. New imaging probes to track cell fate: reporter genes in stem cell research.

Review 6. Seeing (and Using) the Light: Recent Developments in Bioluminescence Technology.

7. Economical and scalable synthesis of 6-amino-2-cyanobenzothiazole.

Review 8. Chemiluminescence and Bioluminescence Imaging for Biosensing and Therapy: In Vitro and In Vivo Perspectives.

9. Novel caged luciferin derivatives can prolong bioluminescence imaging in vitro and in vivo.