Cercosporin

Names

[ Name ]:
Cercosporin

[Synonym ]:
cercosporin from cercospora hayii
cercosporin

Biological Activity

[Description]:

Cercosporin is produced by a plant pathogen, Cercosporakikuchii, and the elsinochromes, pigments of the elsinoe family of fungi. Cercosporin is a potent photosensitizer with a short activation wavelength, mostly suitable for superficial photodynamic therapy (PDT) treatments, especially when it is necessary to avoid perforations[1].Cercosporin contains the perylenequinone structural features necessary to PKC activity with an IC50 of 0.6-1.3 μM[2].

[Related Catalog]:

Signaling Pathways >> Epigenetics >> PKC

Research Areas >> Cancer

Signaling Pathways >> TGF-beta/Smad >> PKC

[Target]

IC50: 0.6-1.3 μM (PKC)[2]

[In Vitro]

Cercosporin (0.8-8.0 μM; 30 s, 60 s, 90 s, 120 s) photodynamic therapy (PDT) effect is stronger in T98G cells than in U87 or MCF7 cells, the LD50 value for the T98G cells (0.14 J cm2) is much less than the LD50 value for MCF-7 and U87 cell lines (0.26 and 0.24 J cm2, respectively)[1]. Cercosporin (0-3 μΜ; 24 hours) interplays with copper results in a synergistic cytotoxicity in MCF7 and T98G cells, that is, S(CuSO4 + Cerco) ≪ S(CuSO4) x S(Cerco), barely has an additive effect in U87 cells[1]. Cell Viability Assay[1] Cell Line: Human GBM cell lines, T98G and U87; Breast carcinoma cell line, MCF-7 Concentration: 0 μM, 1 μM, 2 μM, 3 μM Incubation Time: 24 hours Result: Exhibited a synergistic cytotoxicity with copper only in the most respiratory cell lines (MCF-7 and T98G).

[References]

[1]. Mastrangelopoulou M, et al. Cytotoxic and Photocytotoxic Effects of Cercosporin on Human Tumor Cell Lines. Photochem Photobiol. 2019 Jan;95(1):387-396.

[2]. Morgan BJ, et al. Design, synthesis, and investigation of protein kinase C inhibitors: total syntheses of (+)-calphostin D, (+)-phleichrome, cercosporin, and new photoactive perylenequinones. J Am Chem Soc. 2009 Jul 8;131(26):9413-25.

Chemical & Physical Properties

[ Density]:
1.59g/cm3

[ Boiling Point ]:
886.9ºC at 760mmHg

[ Molecular Formula ]:
C₂₉H₂₆O₁₀

[ Molecular Weight ]:
534.51100

[ Flash Point ]:
299ºC

[ Exact Mass ]:
534.15300

[ PSA ]:
151.98000

[ LogP ]:
3.56450

[ Index of Refraction ]:
1.754

MSDS

Click to get detail MSDS

Safety Information

[ Hazard Codes ]:
Xn: Harmful;

[ RIDADR ]:
NONH for all modes of transport

Articles

CbCTB2, an O-methyltransferase is essential for biosynthesis of the phytotoxin cercosporin and infection of sugar beet by Cercospora beticola.

BMC Plant Biol. 13 , 50, (2013)

Cercospora leaf spot disease, caused by the fungus Cercospora beticola, is the most destructive foliar disease of sugar beets (Beta vulgaris) worldwide. Cercosporin, a light-inducible toxin, is essent...

Antiproliferative activity of epi-cercosporin in human solid tumor cell lines.

Nat. Prod. Commun. 8(2) , 187-9, (2013)

From cultures of Cercospora piaropi, a phytopathogenic fungus isolated from symptomatic leaves of water hyacinth was obtained a red compound, which, according to the spectroscopic data, was epi-cercos...

Reactive oxygen species in plant pathogenesis: the role of perylenequinone photosensitizers.

Antioxid. Redox Signal. 19(9) , 970-89, (2013)

Reactive oxygen species (ROS) play multiple roles in interactions between plants and microbes, both as host defense mechanisms and as mediators of pathogenic and symbiotic associations. One source of ...

Related Compounds

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