Theoretical Insight into the Emission Properties of the Luciferin and Oxyluciferin of <i>Latia</i>

Luciferin analogues that display bioluminescence at specific wavelengths can broaden the scope of imaging and biological assays, but the need to design and synthesize many new analogues can be time-consuming. Employing a collection of previously synthesized and characterized aminoluciferin analogues, we demonstrate that computational TD-DFT methods can accurately reproduce and further explain the experimentally measured fluorescence wavelengths. The best computational approach yields a correlation with experiment of r = 0.98, which we expect to guide and accelerate the further development of luciferin analogues.

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“…The 6–31 + G(d) basis sets were used throughout. These approaches were shown successful in other studies on similar systems …”

Section: Methodsmentioning

confidence: 78%

Computational investigation into the fluorescence of luciferin analogues

Vreven

Miller

2018

J Comput Chem

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“…The Coulomb‐attenuated hybrid exchange‐correlation functional CAM‐B3LYP is employed in the present calculations. As a long–range‐corrected hybrid exchange‐correlation functional, CAM‐B3LYP performs well in predicting charge‐transfer excitations and has been widely used to study the mechanism and spectral properties of many bioluminescence and chemiluminescence phenomena . The effect of the size of basis set on geometries, absorption maxima ( λ max ) and fluorescence wavelengths ( λ F ) was tested.…”

Section: Computational Detailsmentioning

confidence: 99%

“…CAM-B3LYP performs well in predicting charge-transfer excitations and has been widely used to study the mechanism and spectral properties of many bioluminescence and chemiluminescence phenomena (35)(36)(37)(38)(39)(40)(41). The effect of the size of basis set on geometries, absorption maxima (k max ) and fluorescence wavelengths (k F ) was tested.…”

Section: Introductionmentioning

confidence: 99%

Photoluminescence Rainbow from Coelenteramide—A Theoretical Study

Gao

Liu

2018

Photochem & Photobiology

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A wide variety of marine bioluminescent organisms emit light via the excited-state coelenteramide, which is produced from the coelenterazine oxidation via a series of complicated chemical reactions in protein. Photoluminescence of coelenteramide is a simple way to produce light without experiencing the intricate reactions starting from coelenterazine. To extend the color range of light emission, many coelenterazine analogues were synthesized, but mostly only produce blue and cyan fluorescence. Based on the 42 synthesized coelenterazine analogues, we theoretically studied the absorption and fluorescence properties of the corresponding coelenteramide analogues. The electronic effect, steric effect, conjugated effect and solvated effect were considered. The results indicated that conjugated effect has great influence on the strength and wavelength of fluorescence and large electron transfer is beneficial to redshift. Based on the regularities, we theoretically designed six coelenteramide analogues, and together with the original coelenteramide, the seven-ones emit the seven colors of rainbow via their photoluminescences. This study expands the coelenteramide fluorescence to the whole visible light region and could inspire new application.

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“…There are exceptions to this base reaction, for example, in some luminous earthworms [5] and acorn worms [21], the bioluminescent event is triggered by H 2 O 2 and not for O 2 . Besides, the electronic structures, absorption and fluorescence spectra of luciferin, its six analogues and its oxidized form, oxyluciferin showed clear evidence of the lack of fluorescence in Latia neritoides [22].…”

Section: Introductionmentioning

confidence: 98%

New Perspectives Related to the Bioluminescent System in Dinoflagellates: Pyrocystis lunula, a Case Study

Fajardo

Donato

Rodulfo

et al. 2020

IJMS

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Pyrocystis lunula is considered a model organism due to its bioluminescence capacity linked to circadian rhythms. The mechanisms underlying the bioluminescent phenomenon have been well characterized in dinoflagellates; however, there are still some aspects that remain an enigma. Such is the case of the presence and diversity of the luciferin-binding protein (LBP), as well as the synthesis process of luciferin. Here we carry out a review of the literature in relation to the molecular players responsible for bioluminescence in dinoflagellates, with particular interest in P. lunula. We also carried out a phylogenetic analysis of the conservation of protein sequence, structure and evolutionary pattern of these key players. The basic structure of the luciferase (LCF) is quite conserved among the sequences reported to date for dinoflagellate species, but not in the case of the LBP, which has proven to be more variable in terms of sequence and structure. In the case of luciferin, its synthesis has been shown to be complex process with more than one metabolic pathway involved. The glutathione S-transferase (GST) and the P630 or blue compound, seem to be involved in this process. In the same way, various hypotheses regarding the role of bioluminescence in dinoflagellates are exposed.

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Theoretical Insight into the Emission Properties of the Luciferin and Oxyluciferin of Latia

Cited by 11 publications

References 46 publications

Computational investigation into the fluorescence of luciferin analogues

Computational investigation into the fluorescence of luciferin analogues

Photoluminescence Rainbow from Coelenteramide—A Theoretical Study

New Perspectives Related to the Bioluminescent System in Dinoflagellates: Pyrocystis lunula, a Case Study

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