5,5-Dialkylluciferins are thermal stable substrates for bioluminescence-based detection systems

PLoS One. 2020 Dec 14;15(12):e0243747. doi: 10.1371/journal.pone.0243747. eCollection 2020.

Abstract

Firefly luciferase-based ATP detection assays are frequently used as a sensitive, cost-efficient method for monitoring hygiene in many industrial settings. Solutions of detection reagent, containing a mixture of a substrate and luciferase enzyme that produces photons in the presence of ATP, are relatively unstable and maintain only a limited shelf life even under refrigerated conditions. It is therefore common for the individual performing a hygiene test to manually prepare fresh reagent at the time of monitoring. To simplify sample processing, a liquid detection reagent with improved thermal stability is needed. The engineered firefly luciferase, Ultra-Glo™, fulfills one aspect of this need and has been valuable for hygiene monitoring because of its high resistance to chemical and thermal inactivation. However, solutions containing both Ultra-Glo™ luciferase and its substrate luciferin gradually lose the ability to effectively detect ATP over time. We demonstrate here that dehydroluciferin, a prevalent oxidative breakdown product of luciferin, is a potent inhibitor of Ultra-Glo™ luciferase and that its formation in the detection reagent is responsible for the decreased ability to detect ATP. We subsequently found that dialkylation at the 5-position of luciferin (e.g., 5,5-dimethylluciferin) prevents degradation to dehydroluciferin and improves substrate thermostability in solution. However, since 5,5-dialkylluciferins are poorly utilized by Ultra-Glo™ luciferase as substrates, we used structural optimization of the luciferin dialkyl modification and protein engineering of Ultra-Glo™ to develop a luciferase/luciferin pair that shows improved total reagent stability in solution at ambient temperature. The results of our studies outline a novel luciferase/luciferin system that could serve as foundations for the next generation of bioluminescence ATP detection assays with desirable reagent stability.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine Triphosphate / chemistry
  • Alkylation
  • Firefly Luciferin / chemistry*
  • Indicators and Reagents
  • Luciferases, Firefly / chemistry
  • Luminescent Agents / chemistry*
  • Luminescent Measurements / methods*
  • Substrate Specificity
  • Temperature

Substances

  • Indicators and Reagents
  • Luminescent Agents
  • Firefly Luciferin
  • Adenosine Triphosphate
  • Luciferases, Firefly

Grants and funding

Funding was provided by Promega Corporation. The funder provided support in the form of salaries and laboratory resources for authors. The funders had no role in study design, data collection and analysis, decision to publish, or preparation of the manuscript.