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Cyclopenin (CAS 19553-26-5)

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Application:
Cyclopenin is an intermediate in the biosynthesis of the viridicatins
CAS Number:
19553-26-5
Purity:
≥95%
Molecular Weight:
294.3
Molecular Formula:
C17H14N2O3
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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Cyclopenin is a distinctive member of the benzodiazepine metabolite family, produced by several species of the Penicillium genus. Despite being occasionally misidentified as a mycotoxin, cyclopenin exhibits minimal toxicity when tested against mammalian cells, bacteria, or fungi in vitro. Notably, it serves as an intermediary compound in the biosynthesis of the viridicatins, potent inhibitors of tumor necrosis factor α (TNFα)-induced replication of human immunodeficiency virus (HIV). Additionally, cyclopenin acts as an inhibitor of AChE. As a synthetic molecule, cyclopenin has been designed to target specific biological pathways and facilitate research in the realms of biochemistry and physiology. This small molecule finds utility in laboratory and clinical studies to investigate the impact of diverse biological pathways and their associated processes, including signal transduction, gene regulation, and metabolic pathways. Furthermore, cyclopenin has been employed to examine how various drugs affect biological pathways, particularly their effects on the immune system. Laboratory experiments involving cyclopenin encompass the exploration of its mechanism of action, biochemical and physiological effects, as well as its advantages and limitations. The precise mechanism of action of cyclopenin remains incompletely understood. Nonetheless, it is postulated to engage specific cellular molecules, such as proteins, leading to either the activation or inhibition of their respective activities.


Cyclopenin (CAS 19553-26-5) References

  1. [Mycotoxins from the fungi Penicillium vulpinum (Cooke & Massee) Seifert & Samson].  |  Kozlovskiĭ, AG., et al. 2000. Mikrobiologiia. 69: 45-8. PMID: 10808488
  2. Mixed functional oxygenations during the biosynthesis of cyclopenin and cyclopenol, benzodiazepine alkaloids of penicillium cyclopium westling. Incorporation of molecular oxygen and NIH-shift.  |  Nover, L. and Luckner, M. 1969. FEBS Lett. 3: 292-296. PMID: 11947032
  3. Studies in the biochemistry of microorganisms. 93. Cyclopenin, a nitrogen-containing metabolic product of Penicillium cyclopium Westling.  |  BRACKEN, A., et al. 1954. Biochem J. 57: 587-95. PMID: 13198807
  4. Design and synthesis of novel 1,4-benzodiazepine derivatives and their biological evaluation as cholinesterase inhibitors.  |  Mohamed, LW. and El-Yamany, MF. 2012. Arch Pharm Res. 35: 1369-77. PMID: 22941479
  5. Penicillium strains isolated from Slovak grape berries taxonomy assessment by secondary metabolite profile.  |  Santini, A., et al. 2014. Mycotoxin Res. 30: 213-20. PMID: 25109845
  6. Penicyrones A and B, an epimeric pair of α-pyrone-type polyketides produced by the marine-derived Penicillium sp.  |  Bu, YY., et al. 2016. J Antibiot (Tokyo). 69: 57-61. PMID: 26243556
  7. Inhibition of cellular inflammatory mediator production and amelioration of learning deficit in flies by deep sea Aspergillus-derived cyclopenin.  |  Wang, L., et al. 2020. J Antibiot (Tokyo). 73: 622-629. PMID: 32210361
  8. HPLC-MS/MS Method for the Detection of Selected Toxic Metabolites Produced by Penicillium spp. in Nuts.  |  Spadaro, D., et al. 2020. Toxins (Basel). 12: PMID: 32397224
  9. Bioactive compounds derived from the marine-derived fungus MCCC3A00951 and their influenza neuraminidase inhibition activity in vitro and in silico.  |  Liu, SZ., et al. 2021. Nat Prod Res. 35: 5621-5628. PMID: 32927980
  10. Biosynthesis of Viridicatol in Penicillium palitans Implies a Cytochrome P450-Mediated meta Hydroxylation at a Monoalkylated Benzene Ring.  |  Zhang, ZX., et al. 2022. Org Lett. 24: 262-267. PMID: 34928155
  11. Effect of different storage conditions on the stability and safety of almonds.  |  Rodrigues, P., et al. 2023. J Food Sci. 88: 848-859. PMID: 36633227
  12. Synthesis of cyclopenin and glycosminine from phenylpyruvic acid.  |  Rhee, RP. and White, JD. 1977. J Org Chem. 42: 3650-3. PMID: 915586
  13. Stereochemical studies on the biosynthesis of the alpha beta-didehydro-amino-acid units of mycelianamide, cyclopenin, and cyclopenol.  |  Kirby, GW. and Narayanaswami, S. 1976. J Chem Soc Perkin 1. 1564-7. PMID: 987053

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

Cyclopenin, 5 mg

sc-202115
5 mg
$263.00