Cercosporin

[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.

[ 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

Click to get detail MSDS

[ Hazard Codes ]:
Xn: Harmful;

[ RIDADR ]:
NONH for all modes of transport

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 ...

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