scytonemin

• CAT Number: M095418
• CAS Number: 152075-98-4
• Molecular Formula: C36H20N2O4
• Molecular Weight: 544.566
• Purity: ≥95%
• Synonyms: scytonemin
• Target: PLK1 inhibitor
• Storage: -20°C
• IUPAC Name: 3-[(4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-1-[2-oxo-3-[(4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-4H-cyclopenta[b]indol-1-yl]-4H-cyclopenta[b]indol-2-one
• InChI: InChI=1S/C36H20N2O4/c39-21-13-9-19(10-14-21)17-25-33-29(23-5-1-3-7-27(23)37-33)31(35(25)41)32-30-24-6-2-4-8-28(24)38-34(30)26(36(32)42)18-20-11-15-22(40)16-12-20/h1-18,37-38H
• InChIKey: UKHVKOPXBMEBTD-UHFFFAOYSA-N
• SMILES: C1=CC=C2C(=C1)C3=C(C(=O)C(=C3N2)C=C4C=CC(=O)C=C4)C5=C6C7=CC=CC=C7NC6=C(C5=O)C=C8C=CC(=O)C=C8

Scytonemin is a biological pigment synthesized by many strains of cyanobacteria, including Calothrix sp., Lyngbya aestuarii, and others. Scytonemin is also a potent PKL1 inhibitor, which inhibits cell proliferation and arrests cell cycle through downregulating Plk1 activity in many cancel cells. Scytonemin was able to inhibit the proliferation of three myeloma cells in a dose-dependent manner, while U266 was the most sensitive one to scytonemin. Scytonemin , representing a novel Plk1 inhibitor, induced the inhibition of cell growth and cell cycle arrest in multiple myeloma cells by specifically decreasing Plk1 activity.

Reference

1:Scytonemin Plays a Potential Role in Stabilizing the Exopolysaccharidic Matrix in Terrestrial Cyanobacteria. Gao X.Microb Ecol. 2017 Feb;73(2):255-258. doi: 10.1007/s00248-016-0851-4. Epub 2016 Sep 13. PMID: 27623964 2:A comparison of scytonemin and its carbon analogue in terms of antioxidant properties through free radical mechanisms and conformational analysis: a DFT investigation. Varnali T.J Mol Model. 2016 Sep;22(9):213. doi: 10.1007/s00894-016-3094-x. Epub 2016 Aug 20. PMID: 27544141 3:Extracellular Polysaccharide Production in a Scytonemin-Deficient Mutant of Nostoc punctiforme Under UVA and Oxidative Stress. Soule T, Shipe D, Lothamer J.Curr Microbiol. 2016 Oct;73(4):455-62. doi: 10.1007/s00284-016-1084-y. Epub 2016 Jun 15. PMID: 27301251 4:Mutational Studies of Putative Biosynthetic Genes for the Cyanobacterial Sunscreen Scytonemin in Nostoc punctiforme ATCC 29133. Ferreira D, Garcia-Pichel F.Front Microbiol. 2016 May 18;7:735. doi: 10.3389/fmicb.2016.00735. eCollection 2016. PMID: 27242750 Free PMC Article5:The response regulator Npun_F1278 is essential for scytonemin biosynthesis in the cyanobacterium Nostoc punctiforme ATCC 29133. Naurin S, Bennett J, Videau P, Philmus B, Soule T.J Phycol. 2016 Aug;52(4):564-71. doi: 10.1111/jpy.12414. Epub 2016 May 11. PMID: 27020740 6:The total synthesis and stereochemical assignment of scytonemin A. Liu J, Wang L, Zhang J, Xu Z, Ye T.Chem Commun (Camb). 2016 Jan 18;52(5):1002-5. doi: 10.1039/c5cc08324a. PMID: 26593048 7:On the photostability of scytonemin, analogues thereof and their monomeric counterparts. Ekebergh A, Sandin P, Mårtensson J.Photochem Photobiol Sci. 2015 Dec;14(12):2179-86. doi: 10.1039/c5pp00215j. PMID: 26452010 8:Cyanobacterial Sunscreen Scytonemin: Role in Photoprotection and Biomedical Research. Rastogi RP, Sonani RR, Madamwar D.Appl Biochem Biotechnol. 2015 Jul;176(6):1551-63. doi: 10.1007/s12010-015-1676-1. Epub 2015 May 27. Review. PMID: 26013282 9:Synthesis of a carbon analogue of scytonemin. Mukai C, Arima K, Hirata S, Yasuda S.Chem Pharm Bull (Tokyo). 2015;63(4):273-7. doi: 10.1248/cpb.c14-00838. PMID: 25832021 Free Article10:Raman spectroscopic fingerprints of scytonemin-imine: density functional theory calculations of a novel potential biomarker. Varnali T, Edwards HG.Philos Trans A Math Phys Eng Sci. 2014 Dec 13;372(2030). pii: 20140201. doi: 10.1098/rsta.2014.0201. PMID: 25368353 Free Article