| Identification | Back Directory | [Name]
scytonemin | [CAS]
152075-98-4 | [Synonyms]
scytonemin
[1,1'-Bicyclopent[b]indole]-2,2'(3H,3'H)-dione, 3,3'-bis[(4-hydroxyphenyl)methylene]- | [Molecular Formula]
C36H20N2O4 | [MOL File]
152075-98-4.mol | [Molecular Weight]
544.55 |
| Chemical Properties | Back Directory | [Boiling point ]
813.5±65.0 °C(Predicted) | [density ]
1.42±0.1 g/cm3(Predicted) | [form ]
Solid | [pka]
8.83±0.30(Predicted) | [color ]
Brown to black |
| Hazard Information | Back Directory | [Uses]
Scytonemin is a hydrophobic alkaloid pigment that can be isolated from the outer sheath of cyanobacteria. Scytonemin has protective function against short-wave solar ultraviolet (UV) radiation, which can reduce the generation of reactive oxygen species (ROS) and the formation of DNA damage. Scytonemin also has anti-inflammatory and anti-proliferative activities, produces concentration-dependent inhibition (IC50=2.0 μM) of polo-like kinase 1 (PLK1)-mediated cdc25C phosphorylation, and plays an important role in regulating the G2/M transition in the cell cycle. It can be used in the research of cancer, acute inflammation and sunscreen cosmetics[1][2][3][4][5]. | [Definition]
ChEBI: A ring assembly obtained by 1,1'-coupling of two molecules of (3E)-3-[(4-hydroxyphenyl)methylidene]cyclopenta[b]indol-2(3H)-one. A UV-screening molecule produced by many strains of cyanobacteria. | [in vivo]
Scytonemin has a highly effective inhibitory effect (ED50=10 mg/kg) on Phorbol 12-myristate 13-acetate (HY-18739) induced ear inflammation in mice when administered parenterally[3]. | [References]
[1] Proteau PJ, et al. The structure of scytonemin, an ultraviolet sunscreen pigment from the sheaths of cyanobacteria. Experientia. 1993 Sep 15;49(9):825-9. DOI:10.1007/BF01923559
[2] Rastogi RP, et al. Cyanobacterial Sunscreen Scytonemin: Role in Photoprotection and Biomedical Research. Appl Biochem Biotechnol. 2015 Jul;176(6):1551-63. DOI:10.1007/s12010-015-1676-1
[3] Gerwick, et al. "Antimutagenic, antiinflammatory, and potential anticancer substances from marine algae." Food Factors for Cancer Prevention. Springer Japan, 1997.
[4] Stevenson, et al. "The identification and characterization of the marine natural product scytonemin as a novel antiproliferative pharmacophore." Journal of Pharmacology and Experimental Therapeutics 303.2 (2002): 858-866. DOI:10.1124/jpet.102.036350
[5] Degenhardt, et al. "Targeting Polo-like kinase in cancer therapy." Clinical cancer research 16.2 (2010): 384-389. DOI:10.1158/1078-0432.CCR-09-1380 |
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