Firefly luciferin

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Firefly luciferin
Names
IUPAC name
(4S)-2-(6-hydroxy-1,3-benzothiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid
Other names
D-(−)-Luciferin, beetle luciferin
Identifiers
3D model (
JSmol
)
ChemSpider
ECHA InfoCard
 100.018.166 Edit this at Wikidata
EC Number
  • 219-981-3
UNII
  • 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
    Key: BJGNCJDXODQBOB-SSDOTTSWSA-N
  • 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
  • O=C(O)[C@@H]1/N=C(\SC1)c2sc3cc(O)ccc3n2
Properties
C11H8N2O3S2
Molar mass 280.32 g·mol−1
UV-vis (λmax) 330 nm (neutral and somewhat acidic aqueous solutions) [1]
Absorbance
ε330 = 18.2 mM−1 cm−1 [1]
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Firefly luciferin (also known as beetle luciferin) is the

Lampyridae), railroad worm (Phengodidae), starworm (Rhagophthalmidae), and click-beetle (Pyrophorini) bioluminescent systems. 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.[2][3]

History

Much of the early work on the chemistry of the firefly luminescence was done in the lab of

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.[5] The structure was later confirmed by combined use of infrared spectroscopy, UV–vis spectroscopy and synthetic methods to degrade the compound into identifiable fragments.[6]

Properties

Crystal luciferin was found to be

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.[8]
Different species of fireflies all use the same luciferin, however the
primary structure of the luciferase.[9] Modification of the firefly luciferin substrate has led to "red-shifted" emissions (up to emission wavelength of 675 nm).[10]

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.[11] This was confirmed by radiolabeling of atoms in the two compounds and by identification of a luciferin-regenerating enzyme.[12]

In

1,2-dioxetane. The dioxetane is unstable and decays spontaneously to carbon dioxide and excited ketones, which release excess energy by emitting light (bioluminescence).[13]

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.[14] Firefly luciferin is a substrate of the ABCG2 transporter and has been used as part of a bioluminescence imaging high throughput assay to screen for inhibitors of the transporter.[15]

References

  1. ^ a b "D-luciferin product information" (PDF). Sigma Aldrich.
  2. PMID 16588763
    .
  3. PMID 13363432
    .
  4. PMID 15406363
    .
  5. PMID 13479120
    .
  6. doi:10.1021/ja01471a051
    .
  7. S2CID 21583225
    .
  8. PMID 13610868
    .
  9. PMID 14212153
    .
  10. PMID 27072707
    .
  11. doi:10.1021/jo01018a054
    .
  12. PMID 11457857
    .
  13. ISBN 1-84755-812-7
  14. PMID 26120870
    .
  15. ^ "Identification of Inhibitors of ABCG2 by a Bioluminescence Imaging-Based High-Throughput Assay". Cancer Res. 69.

External links

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