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MedKoo Cat#: 584217 | Name: Bikaverin
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Description:

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

Bikaverin, also known as Lycopersin, is a reddish pigment produced by different fungal species, most of them from the genus Fusarium, with antibiotic properties against certain protozoa and fungi. The biological properties of bikaverin include antitumoral activity against different cancer cell lines.

Chemical Structure

Bikaverin
Bikaverin
CAS#33390-21-5

Theoretical Analysis

MedKoo Cat#: 584217

Name: Bikaverin

CAS#: 33390-21-5

Chemical Formula: C20H14O8

Exact Mass: 382.0689

Molecular Weight: 382.32

Elemental Analysis: C, 62.83; H, 3.69; O, 33.48

Price and Availability

Size Price Availability Quantity
1mg USD 450.00 2 Weeks
5mg USD 1,350.00 2 Weeks
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Related CAS #
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Synonym
Bikaverin; Lycopersin; BRN 0358013; BRN0358013; BRN-0358013; NSC 215139; NSC215139; NSC-215139;
IUPAC/Chemical Name
10H-Benzo(b)xanthene-7,10,12-trione, 6,11-dihydroxy-3,8-dimethoxy-1-methyl-
InChi Key
ZOQMSOSJEWBMHP-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H14O8/c1-7-4-8(26-2)5-10-12(7)17(23)15-18(24)13-9(21)6-11(27-3)16(22)14(13)19(25)20(15)28-10/h4-6,24-25H,1-3H3
SMILES Code
O=C1C(OC)=CC(C2=C(O)C(C3=O)=C(OC4=C3C(C)=CC(OC)=C4)C(O)=C21)=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
>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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Bikaverin shows antibiotic properties against certain protozoa and fungi.
In vitro activity:
Bikaverin pretreatment efficiently potentiated the H2O2-induced neuronal markers, such as BDNF, TH, and AADC expression, which orchestrate the neuronal damage of the cell. The H2O2-induced damage to cells, nuclear, and mitochondrial integrity was also restored by bikaverin. Reference: Cell Mol Neurobiol. 2014 Oct;34(7):973-85. https://pubmed.ncbi.nlm.nih.gov/24848007/
In vivo activity:
TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 382.32 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:
1. Haidar S, Aichele D, Birus R, Hielscher J, Laitinen T, Poso A, Jose J. In Vitro and in Silico Evaluation of Bikaverin as a Potent Inhibitor of Human Protein Kinase CK2. Molecules. 2019 Apr 8;24(7):1380. doi: 10.3390/molecules24071380. PMID: 30965682; PMCID: PMC6479664. 2. Nirmaladevi D, Venkataramana M, Chandranayaka S, Ramesha A, Jameel NM, Srinivas C. Neuroprotective effects of bikaverin on H2O2-induced oxidative stress mediated neuronal damage in SH-SY5Y cell line. Cell Mol Neurobiol. 2014 Oct;34(7):973-85. doi: 10.1007/s10571-014-0073-6. Epub 2014 May 22. PMID: 24848007.
In vitro protocol:
1. Haidar S, Aichele D, Birus R, Hielscher J, Laitinen T, Poso A, Jose J. In Vitro and in Silico Evaluation of Bikaverin as a Potent Inhibitor of Human Protein Kinase CK2. Molecules. 2019 Apr 8;24(7):1380. doi: 10.3390/molecules24071380. PMID: 30965682; PMCID: PMC6479664. 2. Nirmaladevi D, Venkataramana M, Chandranayaka S, Ramesha A, Jameel NM, Srinivas C. Neuroprotective effects of bikaverin on H2O2-induced oxidative stress mediated neuronal damage in SH-SY5Y cell line. Cell Mol Neurobiol. 2014 Oct;34(7):973-85. doi: 10.1007/s10571-014-0073-6. Epub 2014 May 22. PMID: 24848007.
In vivo protocol:
TBD
1: Sørensen JL, Nielsen KF, Sondergaard TE. Redirection of pigment biosynthesis to isocoumarins in Fusarium. Fungal Genet Biol. 2012 Aug;49(8):613-8. doi: 10.1016/j.fgb.2012.06.004. Epub 2012 Jun 17. PubMed PMID: 22713716. 2: Chelkowski J, Zajkowski P, Visconti A. Bikaverin production by Fusarium species. Mycotoxin Res. 1992 Sep;8(2):73-6. doi: 10.1007/BF03192219. PubMed PMID: 23606002. 3: Limón MC, Rodríguez-Ortiz R, Avalos J. Bikaverin production and applications. Appl Microbiol Biotechnol. 2010 Jun;87(1):21-9. doi: 10.1007/s00253-010-2551-1. Epub 2010 Apr 8. Review. PubMed PMID: 20376635. 4: Rodríguez-Ortiz R, Mehta BJ, Avalos J, Limón MC. Stimulation of bikaverin production by sucrose and by salt starvation in Fusarium fujikuroi. Appl Microbiol Biotechnol. 2010 Feb;85(6):1991-2000. doi: 10.1007/s00253-009-2282-3. Epub 2009 Oct 17. PubMed PMID: 19838698. 5: Kovác L, Böhmerová E, Fuska J. Inhibition of mitochondrial functions by the antibiotics, bikaverin and duclauxine. J Antibiot (Tokyo). 1978 Jun;31(6):616-20. PubMed PMID: 681242. 6: Betina V, Janstová D, Spisiaková J. Effects of antibiotics on the life cycle of Neurospora crassa. Folia Microbiol (Praha). 1975;20(4):340-5. PubMed PMID: 51812. 7: Cornforth JW, Ryback G, Robinson PM, Park D. Isolation and characterization of a fungal vacuolation factor (bikaverin). J Chem Soc Perkin 1. 1971;16:2786-8. PubMed PMID: 5168483. 8: McInnes AG, Walter JA, Smith DG, Wright JL, Vining LC. Biosynthesis of bikaverin in Fusarium oxysporum. Use of 13C nuclear magnetic resonance with homonuclear 13C decoupling to locate adjacent 13C labels. J Antibiot (Tokyo). 1976 Oct;29(10):1050-7. PubMed PMID: 994324. 9: Goliński P, Chełkowski J, Zajkowski P, Kostecki M. Do the pigments differ chemotaxonomically fungi belonging to genusFusarium? Mycotoxin Res. 1991 Sep;7 Suppl 2:165-71. doi: 10.1007/BF03192204. PubMed PMID: 23605899. 10: Lale GJ, Gadre RV. Production of bikaverin by a Fusarium fujikuroi mutant in submerged cultures. AMB Express. 2016 Dec;6(1):34. doi: 10.1186/s13568-016-0205-0. Epub 2016 May 3. PubMed PMID: 27142994; PubMed Central PMCID: PMC4854849. 11: Wiemann P, Willmann A, Straeten M, Kleigrewe K, Beyer M, Humpf HU, Tudzynski B. Biosynthesis of the red pigment bikaverin in Fusarium fujikuroi: genes, their function and regulation. Mol Microbiol. 2009 May;72(4):931-46. doi: 10.1111/j.1365-2958.2009.06695.x. Epub 2009 Apr 14. PubMed PMID: 19400779. 12: Kjaer D, Kjaer A, Pedersen C, Bu'lock JD, Smith JR. Bikaverin and norbikaverin, benzoxanthentrione pigments of Gibberella fujikuroi. J Chem Soc Perkin 1. 1971;16:2792-7. PubMed PMID: 5168485. 13: Campbell MA, Staats M, van Kan JA, Rokas A, Slot JC. Repeated loss of an anciently horizontally transferred gene cluster in Botrytis. Mycologia. 2013 Sep-Oct;105(5):1126-34. doi: 10.3852/12-390. Epub 2013 Aug 6. PubMed PMID: 23921237. 14: Fuska J, Proksa B, Fusková A. New potential cytotoxic and antitumor substances I. In vitro effect of bikaverin and its derivatives on cells of certain tumors. Neoplasma. 1975;22(3):335-8. PubMed PMID: 1172201. 15: Nirmaladevi D, Venkataramana M, Chandranayaka S, Ramesha A, Jameel NM, Srinivas C. Neuroprotective effects of bikaverin on H2O2-induced oxidative stress mediated neuronal damage in SH-SY5Y cell line. Cell Mol Neurobiol. 2014 Oct;34(7):973-85. doi: 10.1007/s10571-014-0073-6. Epub 2014 May 22. PubMed PMID: 24848007. 16: Suzuki T, Kitagawa A, Kawai K, Hamasaki T. Reexamination of respiration-impairing effect of bikaverin on isolated mitochondria. Mycotoxin Res. 1998 Mar;14(1):19-27. doi: 10.1007/BF02945089. PubMed PMID: 23604958. 17: Lazzaro I, Busman M, Battilani P, Butchko RA. FUM and BIK gene expression contribute to describe fumonisin and bikaverin synthesis in Fusarium verticillioides. Int J Food Microbiol. 2012 Nov 15;160(2):94-8. doi: 10.1016/j.ijfoodmicro.2012.10.004. Epub 2012 Oct 13. PubMed PMID: 23177047. 18: Henderson JF, Battell ML, Zombor G, Fuska J, Nemec P. Effects of bikaverin on purine nucleotide synthesis and catabolism in Ehrlich ascites tumor cells in vitro. Biochem Pharmacol. 1977 Nov 1;26(21):1973-7. PubMed PMID: 562668. 19: Balan J, Fuska J, Kuhr I, Kuhrová V. Bikaverin, an antibiotic from ibberella fujikoi, effective against Leishmania brasiliensis. Folia Microbiol (Praha). 1970;15(6):479-84. PubMed PMID: 5497222. 20: Campbell MA, Rokas A, Slot JC. Horizontal transfer and death of a fungal secondary metabolic gene cluster. Genome Biol Evol. 2012;4(3):289-93. doi: 10.1093/gbe/evs011. Epub 2012 Jan 31. PubMed PMID: 22294497; PubMed Central PMCID: PMC3318441.