firefly luciferin

Firefly luciferin
Names
	IUPAC name (4S)-2-(6-hydroxy-1,3-benzothiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid
	Other names D-(−)-Luciferin
Identifiers
CAS Number	2591-17-5
3D model (Jmol)	Interactive image
ChemSpider	4588411; 16735812 One of the other tautomeric representations
ECHA InfoCard	100.018.166
PubChem	5484207
	InChI One of the other tautomeric representations: InChI=1S/C11H8N2O3S2/c14-5-1-2-6-8(3-5)18-10(12-6)9-13-7(4-17-9)11(15)16/h1-3,7,13H,4H2,(H,15,16)/b10-9+/t7-/m1/s1 ; InChI=1S/C11H8N2O3S2/c14-5-1-2-6-8(3-5)18-10(12-6)9-13-7(4-17-9)11(15)16/h1-3,7,14H,4H2,(H,15,16)/t7-/m1/s1 ;
	SMILES O=C(O)[C@@H]1/N=C(\SC1)c2sc3cc(O)ccc3n2 ;
Properties
Chemical formula	C11H8N2O3S2
Molar mass	280.32 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

ホタルルシフェリン

WordNet

tropical American click beetle having bright luminous spots (同)fire beetle, Pyrophorus noctiluca
nocturnal beetle common in warm regions having luminescent abdominal organs (同)lightning_bug
pigment occurring in luminescent organisms (as fireflies); emits heatless light when undergoing oxidation

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/01/17 14:58:50」(JST)

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Firefly luciferin is the luciferin, or light-emitting compound, found in many firefly (Lampyridae) species. It is the substrate of luciferase (EC 1.13.12.7), which is responsible for the characteristic yellow light emission from many firefly species.

As with all other luciferins, oxygen is required to elicit light; however, it has also been found adenosine triphosphate (ATP) and magnesium are required for light emission.^[1]^[2]

History

Much of the early work on the chemistry of the firefly luminescence was done in the lab of William D. McElroy at Johns Hopkins University. The luciferin was first isolated and purified in 1949, though it would be several years until a procedure was developed to crystallize the compound in high yield. This, along with the synthesis and structure elucidation, was accomplished by Dr. Emil H. White at the Johns Hopkins University, Department of Chemistry.^[3] The procedure was an acid-base extraction, given the carboxylic acid group on the luciferin. The luciferin could be effectively extracted using ethyl acetate at low pH from powder of approximately 15,000 firefly lanterns.^[4] The structure was later confirmed by combined use of infrared spectroscopy, UV-vis spectroscopy and synthetic methods to degrade the compound into identifiable fragments.^[5]

Properties

Crystal luciferin was found to be fluorescent, absorbing ultraviolet light with a peak at 327 nm and emitting light with a peak at 530 nm. Visible emission occurs upon relaxation of the oxyluciferin from a singlet excited state down to its ground state.^[6]Alkaline solutions caused a redshift of the absorption likely due to deprotonation of the hydroxyl group on the benzothiazole, but did not affect the fluorescence emission. It was found that the luciferyl adenylate (the AMP ester of luciferin) spontaneously emits light in solution.^[7] Different species of fireflies all use the same luciferin, however the color of the light emitted can differ greatly. The light from Photuris pennsylvanica was measured to be 552 nm (green-yellow) while Pyrophorus plagiophthalamus was measured to emit light at 582 nm (orange) in the ventral organ. Such differences are likely due to pH changes or differences in primary structure of the luciferase.^[8] Modification of the firefly luciferin substrate has led to "red-shifted" emissions (up to emission wavelength of 675 nm).^[9]

Biological Activity

The in vivo synthesis of firefly luciferin is not completely understood. Only the final step of the enzymatic pathway has been studied, which is the condensation reaction of D-cysteine with 2-cyano-6-hydroxybenzothiazole, and is the same reaction used to produce the compound synthetically.^[10] This was confirmed by radiolabeling of atoms in the two compounds and by identification of a luciferin-regenerating enzyme.^[11]

In firefly, oxidation of luciferins, which is catalyzed by luciferases, yields a peroxy compound 1,2-dioxetane. The dioxetane is unstable and decays spontaneously to carbon dioxide and excited ketones, which release excess energy by emitting light (bioluminescence).^[12]

Loss of CO₂ of a dioxetane, giving rise to an excited ketone, which relaxes by emitting light.

Firefly luciferin and modified substrates are fatty acid mimics and have been used to localize fatty acid amide hydrolase (FAAH) in vivo.^[13] Firefly luciferin is a substrate of the ABCG2 transporter and has been used as part of a bioluminescence imaging high thoroughput assay to screen for inhibitors of the transporter.^[14]

References

^ McElroy WD (1947). "The Energy Source for Bioluminescence in an Isolated System.". Proc Natl Acad Sci USA. 33 (11): 342–345. doi:10.1073/pnas.33.11.342. PMC 1079070. PMID 16588763.
^ Green A, McElroy WD (1956). "Function of adenosine triphosphate in the activation of luciferin.". Arch Biochem Biophys. 64 (2): 257–271. doi:10.1016/0003-9861(56)90268-5. PMID 13363432.
^ Strehler BL, McElroy WD (1949). "Purification of firefly luciferin.". J Cell Physiol. 34 (3): 457–466. doi:10.1002/jcp.1030340310. PMID 15406363.
^ Bitler B, McElroy WD (1957). "The Preparation and Properties of Crystalline Firely Luciferin". Arch Biochem Biophys. 72 (2): 358–368. doi:10.1016/0003-9861(57)90212-6. PMID 13479120.
^ White EH, McCapra F, Field GF, McElroy WD (1961). "The Structure and Synthesis of Firefly Luciferin". J Am Chem Soc. 83 (10): 2402–2403. doi:10.1021/ja01471a051.
^ "Firefly Bioluminescence: A Mechanistic Approach of Luciferase Catalyzed Reactions". IUBMB Life. 61.
^ Rhodes WC, McElroy WD (1958). "The synthesis and function of luciferyl-adenylate and oxyluciferyl-adenylate.". J Biol Chem. 233 (6): 1528–1537. PMID 13610868.
^ Seliger HH, Buck JB, Fastie WG, McElroy WD (1964). "The Spectral Distribution of Firefly Light.". J Gen Physiol. 48 (1): 95–104. doi:10.1085/jgp.48.1.95. PMC 2195396. PMID 14212153.
^ "Multicolor Bioluminescence Obtained Using Firefly Luciferin". Current Topics in Medicinal Chemistry. 16.
^ White EH, Worther H, Field GF, McElroy WD (1965). "Analogs of Firefly Luciferin.". J. Org. Chem. 30 (7): 2344–2348. doi:10.1021/jo01018a054.
^ Gomi K, Kajiyama N (2001). "Oxyluciferin, a Luminescence Product of Firefly Luciferase, Is Enzymatically Regenerated into Luciferin.". J Biol Chem. 276 (39): 36508–36513. doi:10.1074/jbc.M105528200. PMID 11457857.
^ Aldo Roda Chemiluminescence and Bioluminescence: Past, Present and Future, p. 57, Royal Society of Chemistry, 2010, ISBN 1-84755-812-7
^ "Luciferin Amides Enable in Vivo Bioluminescence Detection of Endogenous Fatty Acid Amide Hydrolase Activity". J. Am. Chem. Soc.
^ "Identification of Inhibitors of ABCG2 by a Bioluminescence Imaging-Based High-Throughput Assay.". Cancer Res. 69.

External links

Bioluminescence Page showing major luciferin types

UpToDate Contents

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Structural and functional effects of circular permutation on firefly luciferase: In vitro assay of caspase 3/7.

Cheraghi R, Hosseinkhani S, Davoodi J, Nazari M, Bayat ZA, Karimi H, Shamseddin M, Gheydary F.SourceDepartment of Biochemistry, Faculty of Biological Sciences, Tarbiat Modares University, Tehran 14115-175, Iran; Tranplant Research center, Shiraz university of Medical Sciences, Shiraz, Iran.
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Bioluminescence reaction, which uses luciferin, Mg2+-ATP and molecular oxygen to yield an electronically excited oxyluciferin, is carried out by the luciferase and emit visible light. One of the most promising applications of firefly luciferase is biosensors. In order to develop an apoptosis biosens
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Bioluminescent microcapsules: applications in activating a photosensitizer.

Zhao J, Fei J, Gao L, Cui W, Yang Y, Wang A, Li J.SourceBeijing National Laboratory for Molecular Sciences (BNLMS), Key Lab of Colloid and Interface Science, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190 (P.R. China).
Chemistry (Weinheim an der Bergstrasse, Germany).Chemistry.2013 Apr 2;19(14):4548-55. doi: 10.1002/chem.201203922. Epub 2013 Feb 21.
Bioluminescent microcapsules uploading D-luciferin have been fabricated by using the covalent assembly of firefly luciferase and alginate dialdehyde through a layer-by-layer technique. Such assembled microcapsules can produce visible light in the region of 520-680 nm, which can activate the photos
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Development of a novel telomerase assay using the PPDK-luciferin-luciferase detection system.

Karasawa K, Sano Y, Arakawa H.SourceDepartment of Analytical Biochemistry, School of Pharmacy, Showa University, Tokyo, Japan.
Luminescence : the journal of biological and chemical luminescence.Luminescence.2013 Apr 2. doi: 10.1002/bio.2501. [Epub ahead of print]
Telomerase participates in malignant transformation or immortalization of cells, and has attracted attention as an anticancer drug screening and diagnostic tumor marker. We developed a novel telomerase assay called the PPDK-luciferin-luciferase system bioluminescence assay (PLLBA) using pyruvate pho
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Japanese Journal

1P-094 L-ルシフェリンを用いたホタル発光システム(酵素学,酵素工学,一般講演)

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日本生物工学会大会講演要旨集 66, 40, 2014-08-05
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Identification of 3-enol sulfate of Cypridina luciferin, Cypridina luciferyl sulfate, in the sea-firefly Cypridina (Vargula) hilgendorfii

Nakamura M,Suzuki T,Ishizaka N,Sato J,Inouye S
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日本生物工学会大会講演要旨集 65, 119, 2013-08-25
NAID 110009737730

Related Pictures

[1] McElroy WD (1947). "The Energy Source for Bioluminescence in an Isolated System.". Proc Natl Acad Sci USA. 33 (11): 342–345. doi:10.1073/pnas.33.11.342. PMC 1079070. PMID 16588763.

[2] Green A, McElroy WD (1956). "Function of adenosine triphosphate in the activation of luciferin.". Arch Biochem Biophys. 64 (2): 257–271. doi:10.1016/0003-9861(56)90268-5. PMID 13363432.

[3] Strehler BL, McElroy WD (1949). "Purification of firefly luciferin.". J Cell Physiol. 34 (3): 457–466. doi:10.1002/jcp.1030340310. PMID 15406363.

[4] Bitler B, McElroy WD (1957). "The Preparation and Properties of Crystalline Firely Luciferin". Arch Biochem Biophys. 72 (2): 358–368. doi:10.1016/0003-9861(57)90212-6. PMID 13479120.

[5] White EH, McCapra F, Field GF, McElroy WD (1961). "The Structure and Synthesis of Firefly Luciferin". J Am Chem Soc. 83 (10): 2402–2403. doi:10.1021/ja01471a051.

[6] "Firefly Bioluminescence: A Mechanistic Approach of Luciferase Catalyzed Reactions". IUBMB Life. 61.

[7] Rhodes WC, McElroy WD (1958). "The synthesis and function of luciferyl-adenylate and oxyluciferyl-adenylate.". J Biol Chem. 233 (6): 1528–1537. PMID 13610868.

[8] Seliger HH, Buck JB, Fastie WG, McElroy WD (1964). "The Spectral Distribution of Firefly Light.". J Gen Physiol. 48 (1): 95–104. doi:10.1085/jgp.48.1.95. PMC 2195396. PMID 14212153.

[9] "Multicolor Bioluminescence Obtained Using Firefly Luciferin". Current Topics in Medicinal Chemistry. 16.

[10] White EH, Worther H, Field GF, McElroy WD (1965). "Analogs of Firefly Luciferin.". J. Org. Chem. 30 (7): 2344–2348. doi:10.1021/jo01018a054.

[11] Gomi K, Kajiyama N (2001). "Oxyluciferin, a Luminescence Product of Firefly Luciferase, Is Enzymatically Regenerated into Luciferin.". J Biol Chem. 276 (39): 36508–36513. doi:10.1074/jbc.M105528200. PMID 11457857.

[12] Aldo Roda Chemiluminescence and Bioluminescence: Past, Present and Future, p. 57, Royal Society of Chemistry, 2010, ISBN 1-84755-812-7

[13] "Luciferin Amides Enable in Vivo Bioluminescence Detection of Endogenous Fatty Acid Amide Hydrolase Activity". J. Am. Chem. Soc.

[14] "Identification of Inhibitors of ABCG2 by a Bioluminescence Imaging-Based High-Throughput Assay.". Cancer Res. 69.

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