Substituent effects on the kinetics for the chemiluminescence reaction of 6-arylimidazo[1,2-a]pyrazin-3(7H)-ones (Cypridina luciferin analogues): support for the single electron transfer (SET)–oxygenation mechanism with triplet molecular oxygen

Kondo, Hiroyuki; Igarashi, Takayuki; Maki, Shôjirô; Niwa, Haruki; Ikeda, Hiroshi; Hirano, Takashi

doi:10.1016/j.tetlet.2005.09.014

Cited by 45 publications

(51 citation statements)

References 30 publications

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“…Coupling of the coelenterazine radical and superoxide anion gives a peroxide anion of coelenterazine. In the case of bioluminescent reactions catalysed by luciferases, cyclization of the coelenterazine peroxide anion then takes place, giving dioxetanone, which decomposes with a loss of CO 2 , generating the singlet excited state of coelenteramide [54]. Thus, the 2‐hydroperoxycoelenterazine intermediate, which is most likely destroyed by light in the berovin photoprotein complex, is not generated during the luciferase‐type reaction and so light does not influence luciferase activity.…”

Section: Resultsmentioning

confidence: 99%

The light‐sensitive photoprotein berovin from the bioluminescent ctenophore Beroe abyssicola: a novel type of Ca²⁺‐regulated photoprotein

Markova¹,

Burakova²,

Gölz³

et al. 2012

The FEBS Journal

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Light-sensitive Ca 2+ -regulated photoproteins are responsible for the bright bioluminescence of ctenophores. Using functional screening, four full-size cDNA genes encoding the same 208-amino-acid polypeptide were isolated from two independent cDNA libraries prepared from two Beroe abyssicola specimens. Sequence analysis revealed three canonical EF-hand calciumbinding sites characteristic of Ca 2+ -regulated photoproteins, but a very low degree of sequence identity (27-29%) with aequorin-type photoproteins, despite functional similarities. Recombinant berovin was expressed in Escherichia coli cells, purified, converted to active photoprotein and characterized. Active berovin has absorption maxima at 280 and 437 nm. The Ca 2+ -discharged protein loses visible absorption, but exhibits a new absorption maximum at 335 nm. The berovin bioluminescence is blue (k max = 491 nm) and a change in pH over the range 6.0-9.5 has no significant effect on the light emission spectrum. By contrast, the fluorescence of Ca 2+ -discharged protein (k ex = 350 nm) is pH sensitive: at neutral pH the maximum is at 420 nm and at alkaline pH there are two maxima at 410 and 485 nm. Like native ctenophore photoproteins, recombinant berovin is also inactivated by light. The Ca 2+ concentration-effect curve is a sigmoid with a slope on a log-log plot of 2.5. Although this curve for berovin is very similar to those obtained for obelin and aequorin, there are evident distinctions: berovin responds to calcium changes at lower concentrations than jellyfish photoproteins and its Ca 2+

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Section: Resultsmentioning

confidence: 99%

The light‐sensitive photoprotein berovin from the bioluminescent ctenophore Beroe abyssicola: a novel type of Ca²⁺‐regulated photoprotein

Markova¹,

Burakova²,

Gölz³

et al. 2012

The FEBS Journal

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“…This molecule is involved in reactions catalyzed by many luciferases, such as Renilla reniformis (Rluc) and Gaussia luciferases, and even photoproteins . As well as being functional in BL, coelenterazine can also be used as a CL substrate in reactions involving molecular oxygen or ROS such as superoxide anion and singlet oxygen . As such, coelenterazine and derivatives are now used routinely as probe for ROS …”

Section: Molecular Mechanisms Of Chemiluminescent and Bioluminescentmentioning

confidence: 99%

Chemiluminescence and Bioluminescence as an Excitation Source in the Photodynamic Therapy of Cancer: A Critical Review

2016

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Photodynamic therapy (PDT) of cancer is known for its limited number of side effects, and requires light, oxygen and photosensitizer. However, PDT is limited by poor penetration of light into deeply localized tissues, and the use of external light sources is required. Thus, researchers have been studying ways to improve the effectiveness of this phototherapy and expand it for the treatment of the deepest cancers, by using chemiluminescent or bioluminescent formulations to excite the photosensitizer by intracellular generation of light. The aim of this Minireview is to give a précis of the most important general chemi-/bioluminescence mechanisms and to analyze several studies that apply them for PDT. These studies have demonstrated the potential of utilizing chemi-/bioluminescence as excitation source in the PDT of cancer, besides combining new approaches to overcome the limitations of this mode of treatment.

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“…) in the bioluminescence reaction catalyzed by copepod luciferases. The studies on chemiluminescence of various imidazopyrazinone compounds in solvents of different polarity allowed suggesting a credible mechanism of bioluminescence reaction catalyzed by luciferases and photoproteins using coelenterazine as a substrate . According to the proposed mechanism, the deprotonation of N7 of coelenterazine with a base yielding C2(−) anion is the first step of the reaction.…”

Section: Bioluminescent Reaction and Primary Structuresmentioning

confidence: 99%

Shining Light on the Secreted Luciferases of Marine Copepods: Current Knowledge and Applications

Markova

Larionova

Vysotski

2019

Photochem & Photobiology

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Copepod luciferases—a family of small secretory proteins of 18.4–24.3 kDa, including a signal peptide—are responsible for bright secreted bioluminescence of some marine copepods. The copepod luciferases use coelenterazine as a substrate to produce blue light in a simple oxidation reaction without any additional cofactors. They do not share sequence or structural similarity with other identified bioluminescent proteins including coelenterazine‐dependent Renilla and Oplophorus luciferases. The small size, strong luminescence activity and high stability, including thermostability, make secreted copepod luciferases very attractive candidates as reporter proteins which are particularly useful for nondisruptive reporter assays and for high‐throughput format. The most known and extensively investigated representatives of this family are the first cloned GpLuc and MLuc luciferases from copepods Gaussia princeps and Metridia longa, respectively. Immediately after cloning, these homologous luciferases were successfully applied as bioluminescent reporters in vivo and in vitro, and since then, the scope of their applications continues to grow. This review is an attempt to systemize and critically evaluate the data scattered through numerous articles regarding the main structural features of copepod luciferases, their luminescent and physicochemical properties. We also review the main trends of their application as bioluminescent reporters in cell and molecular biology.

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Substituent effects on the kinetics for the chemiluminescence reaction of 6-arylimidazo[1,2-a]pyrazin-3(7H)-ones (Cypridina luciferin analogues): support for the single electron transfer (SET)–oxygenation mechanism with triplet molecular oxygen

Cited by 45 publications

References 30 publications

The light‐sensitive photoprotein berovin from the bioluminescent ctenophore Beroe abyssicola: a novel type of Ca²⁺‐regulated photoprotein

The light‐sensitive photoprotein berovin from the bioluminescent ctenophore Beroe abyssicola: a novel type of Ca²⁺‐regulated photoprotein

Chemiluminescence and Bioluminescence as an Excitation Source in the Photodynamic Therapy of Cancer: A Critical Review

Shining Light on the Secreted Luciferases of Marine Copepods: Current Knowledge and Applications

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Substituent effects on the kinetics for the chemiluminescence reaction of 6-arylimidazo[1,2-a]pyrazin-3(7H)-ones (Cypridina luciferin analogues): support for the single electron transfer (SET)–oxygenation mechanism with triplet molecular oxygen

Cited by 45 publications

References 30 publications

The light‐sensitive photoprotein berovin from the bioluminescent ctenophore Beroe abyssicola: a novel type of Ca2+‐regulated photoprotein

The light‐sensitive photoprotein berovin from the bioluminescent ctenophore Beroe abyssicola: a novel type of Ca2+‐regulated photoprotein

Chemiluminescence and Bioluminescence as an Excitation Source in the Photodynamic Therapy of Cancer: A Critical Review

Shining Light on the Secreted Luciferases of Marine Copepods: Current Knowledge and Applications

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Product

Resources

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The light‐sensitive photoprotein berovin from the bioluminescent ctenophore Beroe abyssicola: a novel type of Ca²⁺‐regulated photoprotein

The light‐sensitive photoprotein berovin from the bioluminescent ctenophore Beroe abyssicola: a novel type of Ca²⁺‐regulated photoprotein