Amino Analogs of Firefly Luciferin and Biological Activity Thereof<sup>1</sup>

White, Emil H.; Wörther, Helmut; Seliger, H. H.; McElroy, W. D.

doi:10.1021/ja00961a030

Cited by 126 publications

(111 citation statements)

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“…Luciferin analogues for luciferase substrate White et al first synthesized the luciferin analogues in the 1960s [73][74][75][76] and showed narrow substrate specificity for luciferase. A convenient method of firefly luciferin synthesis was reported by Seto et al [77].…”

Section: Biosynthesis Of Firefly Luciferin In Vivomentioning

confidence: 99%

Firefly luciferase: an adenylate-forming enzyme for multicatalytic functions

Inouye

2009

Cell. Mol. Life Sci.

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Firefly luciferase is a member of the acyl-adenylate/thioester-forming superfamily of enzymes and catalyzes the oxidation of firefly luciferin with molecular oxygen to emit light. Knowledge of the luminescence mechanism catalyzed by firefly luciferase has been gathered, leading to the discovery of a novel catalytic function of luciferase. Recently, we demonstrated that firefly luciferase has a catalytic function of fatty acyl-CoA synthesis from fatty acids in the presence of ATP, Mg(2+) and coenzyme A. Based on identification of fatty acyl-CoA genes in firefly, Drosophila, and non-luminous click beetles, we then proposed that the evolutionary origin of firefly luciferase is a fatty acyl-CoA synthetase in insects. Further, we succeeded in converting the fatty acyl-CoA synthetase of non-luminous insects into functional luciferase showing luminescence activity by site-directed mutagenesis.

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Section: Biosynthesis Of Firefly Luciferin In Vivomentioning

confidence: 99%

Firefly luciferase: an adenylate-forming enzyme for multicatalytic functions

Inouye

2009

Cell. Mol. Life Sci.

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“…Some luciferin analogs that produce different bioluminescence colors have also been synthesized. The 6¢aminoluciferin emits red light with firefly luciferase [70]. The naphthyl and quinolyl analogs produce blue and red bioluminescence, respectively [71].…”

Section: Substrates and Products Of The Firefly Luciferase Reactionmentioning

confidence: 99%

The origin, diversity, and structure function relationships of insect luciferases

Viviani

2002

CMLS, Cell. Mol. Life Sci.

294

295

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Luciferases are the enzymes that catalyze the reactions that produce light in bioluminescence. Whereas the oxidative mechanism which leads to light emission is similar for most luciferases, these enzymes and their substrates are evolutionarily unrelated. Among all bioluminescent groups, insects constitute one of the most diverse in terms of biochemistry. In the fungus-gnats (Mycetophilidae: Diptera), for example, bioluminescence is generated by two biochemically distinct systems. Despite the diversity, investigations on insect luciferases and biochemistry have been conducted mostly with fireflies. The luciferases from the related phengodid beetles, which can produce green to red bioluminescence using the same chemistry as firefly luciferases, have been recently investigated. Beetle luciferases originated from ancestral acyl-CoA ligases. Present data suggest that conserved motifs among this class of ligases are involved in substrate adenylation. The three-dimensional structure of firefly luciferase was recently solved and mutagenesis studies have been performed identifying putative residues involved in luciferin binding and bioluminescence color determination in several beetle luciferases. The knowledge gained through these studies is helping in the development of useful reporter gene tools for biotechnological and biomedical purposes.

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“…Approximately one photon is produced for every molecule of luciferin (14)(15)(16)(17)(18); that is, the quantum yield of the donor, OD, is unity. Comparable values of RO are observed for the pigments that constitute donor-acceptor pairs for energy transfer in photosynthesis (22).…”

Section: Resultsmentioning

confidence: 99%

Chemiluminescent activation of the antiviral activity of hypericin: a molecular flashlight.

Carpenter

Fehr

Kraus

et al. 1994

Proc. Natl. Acad. Sci. U.S.A.

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Hypericin is a naturally occurring photosensitizer that displays potent antiviral activity in the presence of light. The absence of light in many regions of the body may preclude the use of hypericin and other photosensitizers as therapeutic compounds for the treatment of viral infections in vivo. The chemiluminescent oxidation of luciferin by the luciferase from the North American firefly Photinus pyralis was found to generate sufficiently intense and long-lived emission to induce antiviral activity of hypericin. Light-induced virucidal activity of hypericin was demonstrated against equine infectious anemia virus, a lentivirus structurally, genetically, and antigenically related to the human immunodeficiency virus. The implications for exploiting chemiluminescence as a "molecular flashlight" for effecting photodynamic therapy against virus-infected cells and tumor cells are discussed.

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Amino Analogs of Firefly Luciferin and Biological Activity Thereof¹

Cited by 126 publications

References 0 publications

Firefly luciferase: an adenylate-forming enzyme for multicatalytic functions

Firefly luciferase: an adenylate-forming enzyme for multicatalytic functions

The origin, diversity, and structure function relationships of insect luciferases

Chemiluminescent activation of the antiviral activity of hypericin: a molecular flashlight.

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Amino Analogs of Firefly Luciferin and Biological Activity Thereof1

Cited by 126 publications

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Firefly luciferase: an adenylate-forming enzyme for multicatalytic functions

Firefly luciferase: an adenylate-forming enzyme for multicatalytic functions

The origin, diversity, and structure function relationships of insect luciferases

Chemiluminescent activation of the antiviral activity of hypericin: a molecular flashlight.

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Amino Analogs of Firefly Luciferin and Biological Activity Thereof¹