IUPAC/Chemical Name
(3E,3'E)-3,3'-bis(4-hydroxybenzylidene)-[1,1'-bi(cyclopenta[b]indole)]-2,2'(3H,3'H)-dione.
InChi Key
CGZKSPLDUIRCIO-RPCRKUJJSA-N
InChi Code
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/h1-18,39-40H/b25-17+,26-18+
SMILES Code
O=C(/C1=C/C2=CC=C(O)C=C2)C(C(C(/C3=C/C4=CC=C(O)C=C4)=O)=C5C3=NC6=C5C=CC=C6)=C7C1=NC8=C7C=CC=C8
Appearance
Yellow solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Scytonemin is a small hydrophobic alkaloid, and a yellow-brown pigment present in the polysaccharide extracellular sheaths of genera Peltula, Collema, and Gonohymenia. This pigment was observed in more than 300 species of cyanobacteria, including genera Scytonema, Stigonema, Chlorogloeopsis, Anabaena, Calothrix, Nostoc, Lyngbya, Chroococcidiopsis, Chroococcus, Rivularia, Hyella, or Tolypothrix.
Scytonemin (C36H22N2O4) is constituted by indolic and phenolic subunits and their binding resorts to an olefin carbon atom that is unique among natural products.
It is considered a secondary metabolite but gains relevance with regard to adaption to harsh environments.9,139,140 This pigment absorbs within a broad UV range across the violet-blue spectral region (UV-A, UV-B, and UV-C); it absorbs most strongly within the UV-A spectral region (λ=315–400 nm), as well as in the UV-B (λ=280–320 nm), and UV-C (λ=190–280 nm) regions.9,141,142 Scytonemin has an absorption maximum of 370 nm (in tetrahydrofuran) in vivo, whereas purified scytonemin absorbs at 386 nm; however, it also absorbs at 252, 278, and 300 nm. Despite not playing a direct role in photosynthesis, it conveys the correct absorption of wavelengths by light-harvesting pigments and protecting chl a in cyanobacteria, against photobleaching or damage alike.
Source: https://www.sciencedirect.com/topics/agricultural-and-biological-sciences/scytonemin
Scytonemin was originally discovered in 1849, although the structure remained unsolved until 1993. Scytonemin is believed to act as a bacterial sunscreen with a broad absorption from 325-425 nm and a separate maxima at 250 nm,[4] and its biosynthesis triggered by exposure to UV light. (http://en.wikipedia.org/wiki/Scytonemin)
Preparing Stock Solutions
The following data is based on the
product
molecular weight
544.56
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Zhang G, Zhang Z, Liu Z. Scytonemin inhibits cell proliferation and arrests cell cycle through downregulating Plk1 activity in multiple myeloma cells. Tumour Biol. 2013 Aug;34(4):2241-7. doi: 10.1007/s13277-013-0764-5. Epub 2013 Apr 13. PubMed PMID: 23584897.
2: Zhang G, Zhang Z, Liu Z. Polo-like kinase 1 is overexpressed in renal cancer and participates in the proliferation and invasion of renal cancer cells. Tumour Biol. 2013 Jun;34(3):1887-94. doi: 10.1007/s13277-013-0732-0. Epub 2013 Mar 14. PubMed PMID: 23494182.
3: Zhang Z, Zhang G, Kong C. High expression of polo-like kinase 1 is associated with the metastasis and recurrence in urothelial carcinoma of bladder. Urol Oncol. 2013 Oct;31(7):1222-30. doi: 10.1016/j.urolonc.2011.11.028. Epub 2011 Dec 20. PubMed PMID: 22192978.
4: Duan Z, Ji D, Weinstein EJ, Liu X, Susa M, Choy E, Yang C, Mankin H, Hornicek FJ. Lentiviral shRNA screen of human kinases identifies PLK1 as a potential therapeutic target for osteosarcoma. Cancer Lett. 2010 Jul 28;293(2):220-9. doi: 10.1016/j.canlet.2010.01.014. Epub 2010 Feb 9. PubMed PMID: 20144850.
5: Zhang Z, Su WH, Feng C, Yu DH, Cui C, Xu XY, Yu BZ. Polo-like kinase 1 may regulate G2/M transition of mouse fertilized eggs by means of inhibiting the phosphorylation of Tyr 15 of Cdc2. Mol Reprod Dev. 2007 Oct;74(10):1247-54. PubMed PMID: 17342725.
6: McInnes C, Mezna M, Fischer PM. Progress in the discovery of polo-like kinase inhibitors. Curr Top Med Chem. 2005;5(2):181-97. Review. PubMed PMID: 15853646.
