Understanding the complete bioluminescence cycle from a multiscale computational perspective: A review

Liu, Yajun

doi:10.1016/j.jphotochemrev.2022.100537

Cited by 15 publications

(16 citation statements)

References 432 publications

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“…The differences between these two mechanisms were deeply discussed in the two reviews. 53,54 We calculated the CIEEL reaction process using the PCM model with a dielectric of 4 at the UCAM-B3LYP/6-31G** level. We made an initial guess on the structure of IM-2c-2 from the structure of IM-2d-1 in our previous CTIL mechanistic calculations.…”

Section: Resultsmentioning

confidence: 99%

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Thorough Understanding of Bioluminophore Production in Bacterial Bioluminescence

Luo

Liu

2022

J. Phys. Chem. A

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Bioluminophore of bioluminescence (BL) comes from the decomposition of peroxide, which is an intermediate produced in the complicated chemical reactions of BL. The peroxide is a dioxetanone in most BL cases and an endoperoxide in fungal BL. The decomposition mechanisms of these two types of peroxides have been exclusively studied. However, the peroxide is a linear organic peroxide in bacterial BL, whose decomposition explanations are quite controversial, and seven mechanisms have been proposed. To thoroughly understand the mechanism of bioluminophore production in bacterial BL, this paper systematically discusses the seven proposed mechanisms via the present computational results and previous experimental and theoretical results. Our research results indicate that the bioluminophore in bacterial BL is produced through the charge-transfer initiated luminescence (CTIL) mechanism. The decomposition mechanism of linear organic peroxide was compared with the decomposition mechanisms of the other two types of peroxides, dioxetanone and endoperoxide. This study is also helpful in understanding the bioluminophore production in other BLs via the decomposition of an organic peroxide, such as dinoflagellate BL.

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Section: Resultsmentioning

confidence: 99%

“…The CTIL mechanism occurs via a molecular CT complex, but the CIEEL one assumes the generation of the cation and anion radical pair. The differences between these two mechanisms were deeply discussed in the two reviews. , …”

Section: Resultsmentioning

confidence: 99%

Thorough Understanding of Bioluminophore Production in Bacterial Bioluminescence

Luo

Liu

2022

J. Phys. Chem. A

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“…The ETcatalyzed decomposition of 1,2-dioxetanones was shown to provide a high singlet chemiexcitation. 13,32,81 The firefly dioxetanone anion (FDO − , Scheme 2) which is an HEI formed in the oxidation of firefly luciferin, 5,6,14,95 is probably one of the most successful instances of highly efficient intramolecular ETcatalyzed CL. In ET-catalyzed CL, 10,13,15 Moreover, the optimized MECI can be regarded as a sloped CI with the quasi-(N int − 1)-dimensional IS (Figure 6B), 96 as the S 0 and S 1 surfaces along the GDV are almost degenerate.…”

Section: ■ Conical Intersectionsmentioning

confidence: 99%

“…The ET-catalyzed decomposition of 1,2-dioxetanones was shown to provide a high singlet chemiexcitation. ,, The firefly dioxetanone anion ( FDO – , Scheme ) which is an HEI formed in the oxidation of firefly luciferin, ,,, is probably one of the most successful instances of highly efficient intramolecular ET-catalyzed CL. In ET-catalyzed CL, ,, an intermolecular or intramolecular ET from a donor orbital (e.g., conjugated π orbital on aromatic substitution) of the activator to the σ* orbital of O–O bond occurs and leads to the donor π orbital of the activator and the σ* orbital of O–O being nearly singly occupied, resulting in a new ET-state, 1 (π, σ*), whose energy depends on the O–O and C–C distances.…”

Section: Conical Intersectionsmentioning

confidence: 99%

“…In this respect, CL can be seen as the reversed processes of photoinduced excited-state reactions (photochemistry and photophysics). Nowadays, CL not only is acknowledged to be one of most useful analytical techniques, based on its simplicity and high sensitivity, but also is often utilized in chemical lights due to the versatility for energy transformation. − Its sibling, bioluminescence (BL), − which can be seen as an enzymatic CL occurring in living organisms such as fireflies, has aroused the interest of mankind for centuries . Of all the discovered CL species, high-energy peroxides, especially some strained cyclic peroxides produced in chemical reactions, − have constituted almost the basis of organic CL .…”

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Conical Intersection in Chemiluminescence of Cyclic Peroxides

Yue

Liu

2022

J. Phys. Chem. Lett.

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Chemiluminescence (CL) utilizing chemiexcitation for energy transformation is one of the most highly sensitive and useful analytical techniques. The chemiexcitation is a chemical process of a ground-state reactant producing an excited-state product, in which a nonadiabatic event is facilitated by conical intersections (CIs), the specific molecular geometries where electronic states are degenerated. Cyclic peroxides, especially 1,2-dioxetane/dioxetanone derivatives, are the iconic chemiluminescent substances. In this Perspective, we concentrated on the CIs in the CL of cyclic peroxides. We first present a computational overview on the role of CIs between the ground (S 0 ) state and the lowest singlet excited (S 1 ) state in the thermolysis of cyclic peroxides. Subsequently, we discuss the role of the S 0 /S 1 CI in the CL efficiency and point out misunderstandings in some theoretical studies on the singlet chemiexcitations of cyclic peroxides. Finally, we address the challenges and future prospects in theoretically calculating S 0 /S 1 CIs and simulating the dynamics and chemiexcitation efficiency in the CL of cyclic peroxides.

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Mechanistic Insights into the Bacterial Luciferase‐based Bioluminescence Resonance Energy Transfer Luminescence: The Role of Protein Complex Dimer

Luo,

Pi,

Liu

2024

ChemPhysChem

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Bacterial bioluminescence holds significant potential in the realm of optical imaging due to the inherent advantages of bioluminescence and ease of operation. However, its practical utility is hindered by its low light intensity. The fusion of bacterial luciferase with a highly fluorescent protein has been demonstrated to significantly enhance autonomous luminescence. Nevertheless, the underlying mechanism behind this enhancement remains unclear, and there is a dearth of research investigating the mechanistic aspects of bioluminescence resonance energy transfer (BRET) luminescence, whether it occurs naturally or can be achieved through experimental means. In this study, we investigated the phenomenon of bacterial luciferase‐based BRET luminescence employing a range of computational techniques, including structural modeling, molecular docking, molecular dynamics simulations, as well as combined quantum mechanics and molecular mechanics calculations. The theoretical findings suggest that the BRET luminescence occurs through resonance energy transfer between the excited bioluminophore and the ground chromophore within the protein complex dimer. The proposed mechanism of the protein complex dimer offers a microscopic understanding of the intriguing BRET phenomenon and has the potential to inspire further practical applications in the field of optical imaging.

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Understanding the complete bioluminescence cycle from a multiscale computational perspective: A review

Cited by 15 publications

References 432 publications

Thorough Understanding of Bioluminophore Production in Bacterial Bioluminescence

Thorough Understanding of Bioluminophore Production in Bacterial Bioluminescence

Conical Intersection in Chemiluminescence of Cyclic Peroxides

Mechanistic Insights into the Bacterial Luciferase‐based Bioluminescence Resonance Energy Transfer Luminescence: The Role of Protein Complex Dimer

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