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MedKoo Cat#: 593156 | Name: Cercosporin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Cercosporin, also known as CGP049090 and NSC 153111, is a phytotoxin isolated from the fungus C. kikuchii that produces reactive oxygen species in plant hosts leading to cellular damage. It exhibits light-activated cytotoxic effects in vitro with cytotoxic concentration (CC50) values of 241, 282, and 174 nM in HeLa, A432, and MCF-7 cells, respectively. Cercosporin is a potent photosensitizer, but with a short activation wavelength, mostly suitable for superficial PDT treatments, especially when it is necessary to avoid perforations.

Chemical Structure

Cercosporin
CAS#35082-49-6

Theoretical Analysis

MedKoo Cat#: 593156

Name: Cercosporin

CAS#: 35082-49-6

Chemical Formula: C29H26O10

Exact Mass: 534.1526

Molecular Weight: 534.52

Elemental Analysis: C, 65.17; H, 4.90; O, 29.93

Price and Availability

Size Price Availability Quantity
1mg USD 285.00 2 Weeks
5mg USD 650.00 2 Weeks
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Related CAS #
No Data
Synonym
CGP049090; CGP 049090; CGP-049090; NSC 153111; NSC-153111; NSC153111; Cercosporin; (+)-Cercosporin
IUPAC/Chemical Name
Perylo[1,​12-​def]​-​1,​3-​dioxepin-​5,​11-​dione, 6,​12-​dihydroxy-​8,​9-​bis[(2R)​-​2-​hydroxypropyl]​-​7,​10-​dimethoxy-​, (13bR)​-
InChi Key
DGAZLNHJYDOWLG-UHFFFAOYSA-N
InChi Code
InChI=1S/C29H26O10/c1-10(30)5-12-18-19-13(6-11(2)31)29(37-4)27(35)21-15(33)8-17-23(25(19)21)22-16(38-9-39-17)7-14(32)20(24(18)22)26(34)28(12)36-3/h7-8,10-11,30-33H,5-6,9H2,1-4H3
SMILES Code
O=C(C(OC)=C1CC(O)C)C2=C(O)C=C(C(C3=C45)=C2C1=C5C(CC(O)C)=C6OC)OCOC3=CC(O)=C4C6=O
Appearance
Solid powder
Purity
>95% (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
Shelf Life
>3 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

Preparing Stock Solutions

The following data is based on the product molecular weight 534.52 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
1: Koh E, Chaturvedi AK, Javitt G, Brandis A, Fluhr R. Multiple paths of plant host toxicity are associated with the fungal toxin cercosporin. Plant Cell Environ. 2023 Aug;46(8):2542-2557. doi: 10.1111/pce.14613. Epub 2023 May 22. PMID: 37212197. 2: Liu M, Zhang Y, Yuan Z, Lu L, Liu X, Zhu X, Wang L, Liu C, Rao Y. Cercosporin-bioinspired photoinactivation of harmful cyanobacteria under natural sunlight via bifunctional mechanisms. Water Res. 2022 May 15;215:118242. doi: 10.1016/j.watres.2022.118242. Epub 2022 Mar 2. PMID: 35259559. 3: Wu Y, Lu L, Zhang Y, Yuan Z, Yang L, Wang L, Rao Y. A bioinspired cercosporin/polymethylmethacrylate photocatalyst with high efficiency for decontamination of pharmaceuticals and pathogens. J Hazard Mater. 2021 Oct 5;419:126555. doi: 10.1016/j.jhazmat.2021.126555. Epub 2021 Jul 1. PMID: 34323722. 4: Zhou T, Yu S, Hu Y, Zhang Y, Song Y, Chu J, Liu C, Rao Y. Enhanced cercosporin production by co-culturing Cercospora sp. JNU001 with leaf-spot- disease-related endophytic bacteria. Microb Cell Fact. 2021 May 15;20(1):100. doi: 10.1186/s12934-021-01587-2. PMID: 33992112; PMCID: PMC8126151. 5: Zivanovic M, Chen ZY. In Vitro Screening of Various Bacterially Produced Double-Stranded RNAs for Silencing Cercospora cf. flagellaris Target Genes and Suppressing Cercosporin Production. Phytopathology. 2021 Jul;111(7):1228-1237. doi: 10.1094/PHYTO-09-20-0409-R. Epub 2021 Sep 7. PMID: 33289403. 6: Icyishaka P, Li C, Lu L, Bao W, Li J, Zhang Y, Rao Y. Cercosporin- Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions. J Vis Exp. 2020 Jul 17;(161). doi: 10.3791/60786. PMID: 32744529. 7: Thomas E, Herrero S, Eng H, Gomaa N, Gillikin J, Noar R, Beseli A, Daub ME. Engineering Cercospora disease resistance via expression of Cercospora nicotianae cercosporin-resistance genes and silencing of cercosporin production in tobacco. PLoS One. 2020 Mar 16;15(3):e0230362. doi: 10.1371/journal.pone.0230362. PMID: 32176712; PMCID: PMC7075572. 8: Grigalavicius M, Mastrangelopoulou M, Arous D, Juzeniene A, Ménard M, Skarpen E, Berg K, Theodossiou TA. Photodynamic Efficacy of Cercosporin in 3D Tumor Cell Cultures. Photochem Photobiol. 2020 May;96(3):699-707. doi: 10.1111/php.13257. Epub 2020 Apr 23. PMID: 32125700. 9: Santos Rezende J, Zivanovic M, Costa de Novaes MI, Chen ZY. The AVR4 effector is involved in cercosporin biosynthesis and likely affects the virulence of Cercospora cf. flagellaris on soybean. Mol Plant Pathol. 2020 Jan;21(1):53-65. doi: 10.1111/mpp.12879. Epub 2019 Oct 23. PMID: 31642594; PMCID: PMC6913201. 10: Li J, Bao W, Zhang Y, Rao Y. Cercosporin-photocatalyzed sp3 (C-H) activation for the synthesis of pyrrolo[3,4-c]quinolones. Org Biomol Chem. 2019 Oct 28;17(40):8958-8962. doi: 10.1039/c9ob01946d. Epub 2019 Oct 3. PMID: 31580376. 11: Correction for de Jonge et al., Gene cluster conservation provides insight into cercosporin biosynthesis and extends production to the genus Colletotrichum. Proc Natl Acad Sci U S A. 2018 Aug 28;115(35):E8324. doi: 10.1073/pnas.1812828115. Epub 2018 Aug 20. Erratum for: Proc Natl Acad Sci U S A. 2018 Jun 12;115(24):E5459-E5466. PMID: 30126995; PMCID: PMC6126760. 12: Mastrangelopoulou M, Grigalavicius M, Berg K, Ménard M, Theodossiou TA. Cytotoxic and Photocytotoxic Effects of Cercosporin on Human Tumor Cell Lines. Photochem Photobiol. 2019 Jan;95(1):387-396. doi: 10.1111/php.12997. Epub 2018 Sep 27. PMID: 30107033. 13: de Jonge R, Ebert MK, Huitt-Roehl CR, Pal P, Suttle JC, Spanner RE, Neubauer JD, Jurick WM 2nd, Stott KA, Secor GA, Thomma BPHJ, Van de Peer Y, Townsend CA, Bolton MD. Gene cluster conservation provides insight into cercosporin biosynthesis and extends production to the genus Colletotrichum. Proc Natl Acad Sci U S A. 2018 Jun 12;115(24):E5459-E5466. doi: 10.1073/pnas.1712798115. Epub 2018 May 29. Erratum in: Proc Natl Acad Sci U S A. 2018 Aug 28;115(35):E8324. PMID: 29844193; PMCID: PMC6004482. 14: Swart V, Crampton BG, Ridenour JB, Bluhm BH, Olivier NA, Meyer JJM, Berger DK. Complementation of CTB7 in the Maize Pathogen Cercospora zeina Overcomes the Lack of In Vitro Cercosporin Production. Mol Plant Microbe Interact. 2017 Sep;30(9):710-724. doi: 10.1094/MPMI-03-17-0054-R. Epub 2017 Jul 7. PMID: 28535078. 15: Kumar P, Chand R, Singh V, Pal C. In vitro screening of calli of mungbean to cercosporin, a photoactivated toxin. Indian J Exp Biol. 2017 Feb;55(2):113-21. PMID: 30184412. 16: Gunasinghe N, You MP, Cawthray GR, Barbetti MJ. Cercosporin From Pseudocercosporella capsellae and its Critical Role in White Leaf Spot Development. Plant Dis. 2016 Aug;100(8):1521-1531. doi: 10.1094/PDIS-10-15-1192-RE. Epub 2016 May 19. PMID: 30686233. 17: Newman AG, Townsend CA. Molecular Characterization of the Cercosporin Biosynthetic Pathway in the Fungal Plant Pathogen Cercospora nicotianae. J Am Chem Soc. 2016 Mar 30;138(12):4219-28. doi: 10.1021/jacs.6b00633. Epub 2016 Mar 16. PMID: 26938470; PMCID: PMC5129747. 18: Beseli A, Noar R, Daub ME. Characterization of Cercospora nicotianae Hypothetical Proteins in Cercosporin Resistance. PLoS One. 2015 Oct 16;10(10):e0140676. doi: 10.1371/journal.pone.0140676. PMID: 26474162; PMCID: PMC4608573. 19: Beseli A, Amnuaykanjanasin A, Herrero S, Thomas E, Daub ME. Membrane transporters in self resistance of Cercospora nicotianae to the photoactivated toxin cercosporin. Curr Genet. 2015 Nov;61(4):601-20. doi: 10.1007/s00294-015-0486-x. Epub 2015 Apr 11. PMID: 25862648. 20: Beseli A, Goulart da Silva M, Daub ME. The role of Cercospora zeae-maydis homologs of Rhodobacter sphaeroides 1O2-resistance genes in resistance to the photoactivated toxin cercosporin. FEMS Microbiol Lett. 2015 Jan;362(2):1-7. doi: 10.1093/femsle/fnu036. Epub 2014 Dec 4. PMID: 25670706.