Scytonemin

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MedKoo CAT#: 406446

CAS#: 152075-98-4

Description: 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.

Chemical Structure

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Scytonemin
CAS# 152075-98-4
Instruction

Theoretical Analysis

MedKoo Cat#: 406446
Name: Scytonemin
CAS#: 152075-98-4
Chemical Formula: C36H20N2O4
Exact Mass: 544.14
Molecular Weight: 544.555
Elemental Analysis: C, 79.40; H, 3.70; N, 5.14; O, 11.75

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Scytonemin;

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)         

Biological target:
In vitro activity:
In vivo activity:

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.

Recalculate based on batch purity %
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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.