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Details

Stereochemistry ABSOLUTE
Molecular Formula C11H8N2O3S2
Molecular Weight 280.323
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FIREFLY LUCIFERIN

SMILES

OC(=O)[C@H]1CSC(=N1)C2=NC3=C(S2)C=C(O)C=C3

InChI

InChIKey=BJGNCJDXODQBOB-SSDOTTSWSA-N
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

HIDE SMILES / InChI

Molecular Formula C11H8N2O3S2
Molecular Weight 280.323
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/3072882 | https://www.ncbi.nlm.nih.gov/pubmed/24738957 | https://www.ncbi.nlm.nih.gov/pubmed/12702568 | https://www.ncbi.nlm.nih.gov/pubmed/27424909

Firefly luciferin (D-luciferin) is the luciferin, or light-emitting compound, found in many firefly (Lampyridae) species. D-luciferin is the substrate for firefly luciferase (Photinus pyralis). Luciferase catalyzes the oxidation of Firefly luciferin to oxyluciferin in the presence of ATP and magnesium, resulting in bioluminescence. This bioluminescent reaction is the most efficient known in nature, with about 90% of the energy released being converted to light. The luciferin/luciferase system is used as a very sensitive reporter assay for gene expression. It can also be used for ATP assays in research applications or to detect bacterial contamination. A luciferase-based ATP-TCA (ATP-tumour chemosensitivity test) to measure ATP levels was designed in the 1990s. This method permits the effects of different medicines and their combinations to be assessed in tumour biopsy specimens and has been used for chemotherapy drug selection for the treatment of ovarian cancer, cervical cancer, and breast cancer as well as melanoma and hepatoma.

Originator

Sources: Orig. Com. 8th Intern. Congr. Appl. Chem. (1912), 19, 83-9.

Approval Year

PubMed

PubMed

TitleDatePubMed
Firefly luciferin-activated rose bengal: in vitro photodynamic therapy by intracellular chemiluminescence in transgenic NIH 3T3 cells.
2003 Apr 15
Patents

Patents

Sample Use Guides

Mice: 75 mg/kg
Route of Administration: Other
NIH 3T3 cells (10^4/well) were plated in a 96-well plate and were used the following day. Cells, when appropriate, were treated with RB in serum-free media for 3 h. Control groups were treated in an identical fashion without rose bengal (RB). A D-luciferin and RB-lycopene control group was included as well as a non-PDT-RB group. After this time, cells were washed once in serum containing medium and then were incubated for 24 h in the same medium in the presence or absence of 500 mkM D-luciferin. The fluorescence of luciferin was excited using the 351-nm laser line. MTT assays were performed to determine the cell survival rate. Each well was incubated with medium containing MTT (1 mg/ml) for 3 h. The medium was then removed and 100 mkl of DMSO (Sigma) were added per well. After 20 min at room temperature with agitation, samples were read in a microplate reader (Titertek Multiskan MCC), using a 540-nm filter.
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:59:31 UTC 2023
Edited
by admin
on Fri Dec 15 17:59:31 UTC 2023
Record UNII
5TBB02N29K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FIREFLY LUCIFERIN
MI  
Common Name English
D-(-)-LUCIFERIN
Common Name English
FIREFLY LUCIFERIN [MI]
Common Name English
(4S)-4,5-DIHYDRO-2-(6-HYDROXY-2-BENZOTHIAZOLYL)-4-THIAZOLECARBOXYLIC ACID
Systematic Name English
Code System Code Type Description
FDA UNII
5TBB02N29K
Created by admin on Fri Dec 15 17:59:31 UTC 2023 , Edited by admin on Fri Dec 15 17:59:31 UTC 2023
PRIMARY
CAS
2591-17-5
Created by admin on Fri Dec 15 17:59:31 UTC 2023 , Edited by admin on Fri Dec 15 17:59:31 UTC 2023
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CHEBI
17165
Created by admin on Fri Dec 15 17:59:31 UTC 2023 , Edited by admin on Fri Dec 15 17:59:31 UTC 2023
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PUBCHEM
92934
Created by admin on Fri Dec 15 17:59:31 UTC 2023 , Edited by admin on Fri Dec 15 17:59:31 UTC 2023
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WIKIPEDIA
FIREFLY LUCIFERIN
Created by admin on Fri Dec 15 17:59:31 UTC 2023 , Edited by admin on Fri Dec 15 17:59:31 UTC 2023
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MERCK INDEX
m5387
Created by admin on Fri Dec 15 17:59:31 UTC 2023 , Edited by admin on Fri Dec 15 17:59:31 UTC 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
219-981-3
Created by admin on Fri Dec 15 17:59:31 UTC 2023 , Edited by admin on Fri Dec 15 17:59:31 UTC 2023
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EPA CompTox
DTXSID00894865
Created by admin on Fri Dec 15 17:59:31 UTC 2023 , Edited by admin on Fri Dec 15 17:59:31 UTC 2023
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