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
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
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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/27711774Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27711774
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.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1293267 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23888932 |
12.9 µM [EC50] | ||
Target ID: CHEMBL2292 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25768698 |
|||
Target ID: CHEMBL4575 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25768698 |
|||
Target ID: CHEMBL4376 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25768698 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Diagnostic | CellTiter-Glo Approved UseUnknown |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19096841
Mice: 75 mg/kg
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12702568
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
Edited
Fri Dec 15 17:59:31 GMT 2023
by
admin
on
Fri Dec 15 17:59:31 GMT 2023
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Record UNII |
5TBB02N29K
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Record Status |
Validated (UNII)
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Record Version |
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5TBB02N29K
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2591-17-5
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17165
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92934
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FIREFLY LUCIFERIN
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m5387
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219-981-3
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DTXSID00894865
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