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MedKoo Cat#: 540303 | Name: Moniliformin

Description:

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

Moniliformin is a mycotoxin and potential dehydrogenase inhibitor found in Fusarium. It decreases collage synthesis, suppresses endocytosis, and may damage myocardial tissue.

Chemical Structure

Moniliformin
Moniliformin
CAS#31876-38-7

Theoretical Analysis

MedKoo Cat#: 540303

Name: Moniliformin

CAS#: 31876-38-7

Chemical Formula: C4H2O3

Exact Mass: 98.0004

Molecular Weight: 98.06

Elemental Analysis: C, 49.00; H, 2.06; O, 48.95

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Synonym
Moniliformin; Hydroxycyclobutenedione; NSC 292896; NSC292896; NSC-292896
IUPAC/Chemical Name
3-hydroxycyclobut-3-ene-1,2-dione
InChi Key
KGPQKNJSZNXOPV-UHFFFAOYSA-N
InChi Code
InChI=1S/C4H2O3/c5-2-1-3(6)4(2)7/h1,5H
SMILES Code
O=C1C=C(O)C1=O
Appearance
Solid powder
Purity
>98% (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:
Moniliformin is a mycotoxin and potential dehydrogenase inhibitor found in Fusarium.
In vitro activity:
Here, this study describes that a moniliformin derivative (IUPAC name: 3-(naphthalen-2-ylsulfanyl)-4-{[(2Z)-1,3,3-trimethyl-2,3-dihydro-1H-indol-2-ylidene]methyl}cyclobut-3-ene-1,2-dione; code: MCC1381) bypasses P-gp-mediated MDR. MCC1381 decreased the expression of HDAC6, inversely correlated with the increase of acetylated HDAC6 substrates, acetylation p53 and α-tubulin. Furthermore, MCC1381 arrested the cell cycle at the G2/M phase, induced the generation of reactive oxygen species and collapse of the mitochondrial membrane potential. Reference: Biochem Pharmacol. 2021 Dec;194:114677. https://pubmed.ncbi.nlm.nih.gov/34265280/
In vivo activity:
MCC1381 (moniliformin) exhibited in vivo anti-cancer activity in xenografted zebrafish. Collectively, MCC1381 extended cytotoxicity towards P-gp-resistant leukemia cancer cells and may act as a pan-HDACs inhibitor, indicating that MCC1381 is a novel candidate for cancer therapy. Reference: Biochem Pharmacol. 2021 Dec;194:114677. https://pubmed.ncbi.nlm.nih.gov/34265280/

Preparing Stock Solutions

The following data is based on the product molecular weight 98.06 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:
Lu X, Yan G, Dawood M, Klauck SM, Sugimoto Y, Klinger A, Fleischer E, Shan L, Efferth T. A novel moniliformin derivative as pan-inhibitor of histone deacetylases triggering apoptosis of leukemia cells. Biochem Pharmacol. 2021 Dec;194:114677. doi: 10.1016/j.bcp.2021.114677. Epub 2021 Jul 13. PMID: 34265280.
In vitro protocol:
Lu X, Yan G, Dawood M, Klauck SM, Sugimoto Y, Klinger A, Fleischer E, Shan L, Efferth T. A novel moniliformin derivative as pan-inhibitor of histone deacetylases triggering apoptosis of leukemia cells. Biochem Pharmacol. 2021 Dec;194:114677. doi: 10.1016/j.bcp.2021.114677. Epub 2021 Jul 13. PMID: 34265280.
In vivo protocol:
Lu X, Yan G, Dawood M, Klauck SM, Sugimoto Y, Klinger A, Fleischer E, Shan L, Efferth T. A novel moniliformin derivative as pan-inhibitor of histone deacetylases triggering apoptosis of leukemia cells. Biochem Pharmacol. 2021 Dec;194:114677. doi: 10.1016/j.bcp.2021.114677. Epub 2021 Jul 13. PMID: 34265280.
1: Jonsson M, Atosuo J, Jestoi M, Nathanail AV, Kokkonen UM, Anttila M, Koivisto P, Lilius EM, Peltonen K. Repeated dose 28-day oral toxicity study of moniliformin in rats. Toxicol Lett. 2015 Feb 17;233(1):38-44. doi: 10.1016/j.toxlet.2014.11.006. Epub 2014 Dec 4. PubMed PMID: 25482064. 2: Jonsson M, Jestoi M, Nathanail AV, Kokkonen UM, Anttila M, Koivisto P, Karhunen P, Peltonen K. Application of OECD Guideline 423 in assessing the acute oral toxicity of moniliformin. Food Chem Toxicol. 2013 Mar;53:27-32. doi: 10.1016/j.fct.2012.11.023. Epub 2012 Nov 28. PubMed PMID: 23201451. 3: Lim CW, Lai KY, Yeo JF, Tai SH, Chan SH. Quantitative assessment of moniliformin in cereals via alternative precipitation pathways, aided by LC-LIT-MS and LC-Q-TOF-MS. Food Chem. 2015 May 1;174:372-9. doi: 10.1016/j.foodchem.2014.11.069. Epub 2014 Nov 15. PubMed PMID: 25529694. 4: Hallas-Møller M, Nielsen KF, Frisvad JC. Production of the Fusarium Mycotoxin Moniliformin by Penicillium melanoconidium. J Agric Food Chem. 2016 Jun 8;64(22):4505-10. doi: 10.1021/acs.jafc.6b00298. Epub 2016 May 31. PubMed PMID: 27195914. 5: Gräfenhan T, Patrick SK, Roscoe M, Trelka R, Gaba D, Chan JM, McKendry T, Clear RM, Tittlemier SA. Fusarium damage in cereal grains from Western Canada. 1. Phylogenetic analysis of moniliformin-producing fusarium species and their natural occurrence in mycotoxin-contaminated wheat, oats, and rye. J Agric Food Chem. 2013 Jun 12;61(23):5425-37. doi: 10.1021/jf400651p. Epub 2013 May 31. PubMed PMID: 23683177. 6: von Bargen KW, Lohrey L, Cramer B, Humpf HU. Analysis of the Fusarium mycotoxin moniliformin in cereal samples using 13C2-moniliformin and high-resolution mass spectrometry. J Agric Food Chem. 2012 Apr 11;60(14):3586-91. doi: 10.1021/jf300323d. Epub 2012 Mar 28. PubMed PMID: 22428531. 7: Nazari F, Sulyok M, Kobarfard F, Yazdanpanah H, Krska R. Evaluation of Emerging Fusarium mycotoxins beauvericin, Enniatins, Fusaproliferin and Moniliformin in Domestic Rice in Iran. Iran J Pharm Res. 2015 Spring;14(2):505-12. PubMed PMID: 25901158; PubMed Central PMCID: PMC4403067. 8: Behrens M, Hüwel S, Galla HJ, Humpf HU. Blood-Brain Barrier Effects of the Fusarium Mycotoxins Deoxynivalenol, 3 Acetyldeoxynivalenol, and Moniliformin and Their Transfer to the Brain. PLoS One. 2015 Nov 23;10(11):e0143640. doi: 10.1371/journal.pone.0143640. eCollection 2015. PubMed PMID: 26600019; PubMed Central PMCID: PMC4658139. 9: Ficheux AS, Sibiril Y, Parent-Massin D. Effects of beauvericin, enniatin b and moniliformin on human dendritic cells and macrophages: an in vitro study. Toxicon. 2013 Sep;71:1-10. doi: 10.1016/j.toxicon.2013.04.024. Epub 2013 May 17. PubMed PMID: 23685117. 10: Scarpino V, Blandino M, Negre M, Reyneri A, Vanara F. Moniliformin analysis in maize samples from North-West Italy using multifunctional clean-up columns and the LC-MS/MS detection method. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2013;30(5):876-84. doi: 10.1080/19440049.2013.793825. Epub 2013 Jun 3. PubMed PMID: 23731218. 11: Morgan MK, Fitzgerald SD, Rottinghaus GE, Bursian SJ, Aulerich RJ. Toxic effects to mink of moniliformin extracted from Fusarium fujikuroi culture material. Vet Hum Toxicol. 1999 Feb;41(1):1-5. PubMed PMID: 9949474. 12: Gathercole PS, Thiel PG, Hofmeyr JH. Inhibition of pyruvate dehydrogenase complex by moniliformin. Biochem J. 1986 Feb 1;233(3):719-23. PubMed PMID: 3707519; PubMed Central PMCID: PMC1153090. 13: Rabie CJ, Marasas WF, Thiel PG, Lübben A, Vleggaar R. Moniliformin production and toxicity of different Fusarium species from Southern Africa. Appl Environ Microbiol. 1982 Mar;43(3):517-21. PubMed PMID: 7073272; PubMed Central PMCID: PMC241867. 14: Appell M, Kendra DF, Kim EK, Maragos CM. Synthesis and evaluation of molecularly imprinted polymers as sorbents of moniliformin. Food Addit Contam. 2007 Jan;24(1):43-52. PubMed PMID: 17164216. 15: Thiel PG. Determination of moniliformin by high-performance liquid chromatography. J Environ Pathol Toxicol Oncol. 1990 May-Jun;10(3):162-5. PubMed PMID: 2254865. 16: Nagaraj RY, Wu W, Will JA, Vesonder RF. Acute cardiotoxicity of moniliformin in broiler chickens as measured by electrocardiography. Avian Dis. 1996 Jan-Mar;40(1):223-7. PubMed PMID: 8713038. 17: Zhang H, Li JL. [Study on toxicological mechanism of moniliformin]. Wei Sheng Wu Xue Bao. 1989 Apr;29(2):93-100. Chinese. PubMed PMID: 2800548. 18: Herrera M, van Dam R, Spanjer M, de Stoppelaar J, Mol H, de Nijs M, López P. Survey of moniliformin in wheat- and corn-based products using a straightforward analytical method. Mycotoxin Res. 2017 Aug 8. doi: 10.1007/s12550-017-0287-9. [Epub ahead of print] PubMed PMID: 28791630. 19: Zhao D, Feng Q, Yan X, Li C, Pan Y, Cui Q. Ultrastructural study of moniliformin induced lesions of myocardium in rats and mice. Biomed Environ Sci. 1993 Mar;6(1):37-44. PubMed PMID: 8476531. 20: Reams R, Thacker HL, Novilla M, Laska D, Horn J, Harrington D, Greenlee W, Vesonder R. Development of an L6 myoblast in vitro model of moniliformin toxicosis. Mycopathologia. 1996;133(2):105-14. PubMed PMID: 8751829.