Monorden E
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Others |
| Catalog number | BBF-01961 |
| CAS | |
| Molecular Weight | 352.81 |
| Molecular Formula | C18H21ClO5 |
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Description
Monorden E is a metabolite of Humicola sp. FO-2942. It has the effect of arresting the cell cycle of Jurket cells in G1 and G2/M phases. It has anti-Aspergillus niger activity.
Specification
| IUPAC Name | (6E)-15-chloro-16,18-dihydroxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),6,15,17-tetraene-2,12-dione |
| Canonical SMILES | CC1CC=CCCCCC(=O)CC2=C(C(=CC(=C2Cl)O)O)C(=O)O1 |
| InChI | InChI=1S/C18H21ClO5/c1-11-7-5-3-2-4-6-8-12(20)9-13-16(18(23)24-11)14(21)10-15(22)17(13)19/h3,5,10-11,21-22H,2,4,6-9H2,1H3/b5-3+ |
| InChI Key | MAIXLHSZNVDUIV-HWKANZROSA-N |
Properties
| Appearance | Yellow Oil |
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 594.7±50.0°C at 760 mmHg |
| Melting Point | 89°C |
| Density | 1.2±0.1 g/cm3 |
Reference Reading
1. Antimicrobial Natural Products from Plant Pathogenic Fungi
Melissa M Cadelis, Steven A Li, Shara J van de Pas, Alex Grey, Daniel Mulholland, Bevan S Weir, Brent R Copp, Siouxsie Wiles Molecules. 2023 Jan 23;28(3):1142. doi: 10.3390/molecules28031142.
Isolates of a variety of fungal plant pathogens (Alternaria radicina ICMP 5619, Cercospora beticola ICMP 15907, Dactylonectria macrodidyma ICMP 16789, D. torresensis ICMP 20542, Ilyonectria europaea ICMP 16794, and I. liriodendra ICMP 16795) were screened for antimicrobial activity against the human pathogenic bacteria Acinetobacter baumannii, Pseudomonas aeruginosa, Escherichia coli, Mycobacterium abscessus, and M. marinum and were found to have some activity. Investigation of the secondary metabolites of these fungal isolates led to the isolation of ten natural products (1-10) of which one was novel, (E)-4,7-dihydroxyoct-2-enoic acid (1). Structure elucidation of all natural products was achieved by a combination of NMR spectroscopy and mass spectrometry. We also investigated the antimicrobial activity of a number of the isolated natural products. While we did not find (E)-4,7-dihydroxyoct-2-enoic acid (1) to have any activity against the bacteria and fungi in our assays, we did find that cercosporin (7) exhibited potent activity against Methicillin resistant Staphylococcus aureus (MRSA), dehydro-curvularin (6) and radicicol (10) exhibited antimycobacterial activity against M. marinum, and brefeldin A (8) and radicicol (10) exhibited antifungal activity against Candida albicans. Investigation of the cytotoxicity and haemolytic activities of these natural products (6-8 and 10) found that only one of the four active compounds, radicicol (10), was non-cytotoxic and non-haemolytic.
2. Kinome expression profiling of human neuroblastoma tumors identifies potential drug targets for ultra high-risk patients
Roberta Russo, Flora Cimmino, Lucia Pezone, Francesco Manna, Marianna Avitabile, Concetta Langella, Jan Koster, Fiorina Casale, Maddalena Raia, Giampietro Viola, Matthias Fischer, Achille Iolascon, Mario Capasso Carcinogenesis. 2017 Oct 1;38(10):1011-1020. doi: 10.1093/carcin/bgx077.
Neuroblastoma (NBL) accounts for >7% of malignancies in patients younger than 15 years. Low- and intermediate-risk patients exhibit excellent or good prognosis after treatment, whereas for high-risk (HR) patients, the estimated 5-year survival rates is still <40%. The ability to stratify HR patients that will not respond to standard treatment strategies is critical for informed treatment decisions. In this study, we have generated a specific kinome gene signature, named Kinome-27, which is able to identify a subset of HR-NBL tumors, named ultra-HR NBL, with highly aggressive clinical behavior that not adequately respond to standard treatments. We have demonstrated that NBL cell lines expressing the same kinome signature of ultra-HR tumors (ultra-HR-like cell lines) may be selectively targeted by the use of two drugs [suberoylanilide hydroxamic acid (SAHA) and Radicicol], and that the synergic combination of these drugs is able to block the ultra-HR-like cells in G2/M phase of cell cycle. The use of our signature in clinical practice will allow identifying patients with negative outcome, which would benefit from new and more personalized treatments. Preclinical in vivo studies are needed to consolidate the SAHA and Radicicol treatment in ultra-HR NBL patients.
3. Design, Synthesis and In Vitro Investigation of Novel Basic Celastrol Carboxamides as Bio-Inspired Leishmanicidal Agents Endowed with Inhibitory Activity against Leishmania Hsp90
Ivan Bassanini, Silvia Parapini, Erica E Ferrandi, Elena Gabriele, Nicoletta Basilico, Donatella Taramelli, Anna Sparatore Biomolecules. 2021 Jan 5;11(1):56. doi: 10.3390/biom11010056.
The natural triterpene celastrol (CE) is here used as lead compound for the design and synthesis of a panel of eleven CE carboxamides that were tested in vitro for their growth inhibitory activity against Leishmania infantum and L.tropica parasites. Among them, in vitro screening identified four basic CE carboxamides endowed with nanomolar leishmanicidal activity, against both the promastigotes and the intramacrophage Leishmania amastigotes forms. These compounds also showed low toxicity toward two human (HMEC-1 and THP-1) and one murine (BMDM) cell lines. Interestingly, the most selective CE analogue (compound 3) was also endowed with the ability to inhibit the ATPase activity of the Leishmania protein chaperone Hsp90 as demonstrated by the in vitro assay conducted on a purified, full-length recombinant protein. Preliminary investigations by comparing it with the naturally occurring Hsp90 active site inhibitor Geldanamycin (GA) in two different in vitro experiments were performed. These promising results set the basis for a future biochemical investigation of the mode of interaction of celastrol and CE-inspired compounds with Leishmania Hsp90.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
