Monorden A
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| Category | Others |
| Catalog number | BBF-02561 |
| CAS | 12772-57-5 |
| Molecular Weight | 364.78 |
| Molecular Formula | C18H17ClO6 |
| Purity | >98% |
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Description
Monorden A 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. It inhibits Hsp90 activity by binding to the ATP-binding pocket, thus suppressing cell transformation induced by src, ras and mos.
Specification
| Synonyms | radicicol |
| Storage | Desiccate at -20°C |
| IUPAC Name | (4R,6R,8R,9Z,11E)-16-chloro-17,19-dihydroxy-4-methyl-3,7-dioxatricyclo[13.4.0.06,8]nonadeca-1(15),9,11,16,18-pentaene-2,13-dione |
| Canonical SMILES | CC1CC2C(O2)C=CC=CC(=O)CC3=C(C(=CC(=C3Cl)O)O)C(=O)O1 |
| InChI | InChI=1S/C18H17ClO6/c1-9-6-15-14(25-15)5-3-2-4-10(20)7-11-16(18(23)24-9)12(21)8-13(22)17(11)19/h2-5,8-9,14-15,21-22H,6-7H2,1H3/b4-2+,5-3-/t9-,14-,15-/m1/s1 |
| InChI Key | WYZWZEOGROVVHK-GTMNPGAYSA-N |
| Source | Unidentified fungus |
Properties
| Appearance | Yellow Powder |
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 656.2°C at 760 mmHg |
| Melting Point | 191°C |
| Density | 1.364 g/cm3 |
| Solubility | Ethanol: 25 mg/mL |
Reference Reading
1.The epigenetic regulator Smchd1 contains a functional GHKL-type ATPase domain.
Chen K1, Dobson RC2, Lucet I3, Young SN4, Pearce FG5, Blewitt ME1, Murphy JM6. Biochem J. 2016 Apr 8. pii: BCJ20160189. [Epub ahead of print]
Structural maintenance of chromosomes flexible hinge domain containing 1 (Smchd1) is an epigenetic regulator that plays critical roles in gene regulation during development. Mutations in SMCHD1 were recently implicated in the pathogenesis of facioscapulohumeral muscular dystrophy (FSHD), although the mechanistic basis remains of outstanding interest. We have previously shown that Smchd1 associates with chromatin via its homodimeric C-terminal hinge domain, yet little is known about the function of the putative GHKL (gyrase, Hsp90, histidine kinase, MutL)-type ATPase domain at its N-terminus. To formally assess the structure and function of Smchd1's ATPase domain, we have generated recombinant proteins encompassing the predicted ATPase domain and the adjacent region. Here, we show that the Smchd1 N-terminal region exists as a monomer and adopts a conformation resembling that of monomeric full-length Hsp90 protein in solution, even though the two proteins share only ~8% overall sequence identity.
2.Role of connexin 43 in cardiovascular diseases.
Michela P1, Velia V1, Aldo P1, Ada P2. Eur J Pharmacol. 2015 Dec 5;768:71-6. doi: 10.1016/j.ejphar.2015.10.030. Epub 2015 Oct 20.
Gap junctions (GJs) channels provide the basis for intercellular communication in the cardiovascular system for maintenance of the normal cardiac rhythm, regulation of vascular tone and endothelial function as well as metabolic interchange between the cells. They allow the transfer of small molecules and may enable slow calcium wave spreading, transfer of "death" or of "survival" signals. In the cardiomyocytes the most abundant isoform is Connexin 43 (Cx43). Alterations in Cx43 expression and distribution were observed in myocardium disease; i.e. in hypertrophic cardiomyopathy, heart failure and ischemia. Recent reports suggest the presence of Cx43 in the mitochondria as well, at least in the inner mitochondrial membrane, where it plays a central role in ischemic preconditioning. In this review, the current knowledge on the relationship between the remodeling of cardiac gap junctions and cardiac diseases are summarized.
3.PU-H71: An improvement on nature's solutions to oncogenic Hsp90 addiction.
Trendowski M1. Pharmacol Res. 2015 Sep;99:202-16. doi: 10.1016/j.phrs.2015.06.007. Epub 2015 Jun 25.
Despite recent advances in precision medicine, many molecular-based antineoplastic agents do not potentiate sustainable long term remissions, warranting the investigation of novel therapeutic strategies. Heat shock protein 90 (Hsp90) is a molecular chaperone that not only has oncogenic properties, but also has distinct expression profiles in malignant and normal cells, providing a rational strategy to attain preferential damage. Prior attempts to target Hsp90 with natural product-based compounds have been hampered by their associated off target toxicities, suggesting that novel, fully synthetic inhibitors may be required to achieve the specificity necessary for therapeutic efficacy. Therefore, this review highlights the antineoplastic potential of PU-H71 (8-[(6-iodo-1,3-benzodioxol-5-yl)sulfanyl]-9-[3-(propan-2-ylamino)propyl]purin-6-amine), a novel purine based analog that has shown efficacy in many preclinical models of malignancy, and is now under clinical examination.
4.Rubratoxin-B-induced secretion of chemokine ligands of cysteine-cysteine motif chemokine receptor 5 (CCR5) and its dependence on heat shock protein 90 in HL60 cells.
Nagashima H1. Environ Toxicol Pharmacol. 2015 Nov;40(3):997-1000. doi: 10.1016/j.etap.2015.10.012. Epub 2015 Nov 2.
To elucidate the mechanism underlying rubratoxin B toxicity, the effects of rubratoxin B on the secretion of CCR5 chemokines, CCL3, CCL4, and CCL5, in a human promyelocytic leukemia cell line, HL60, were investigated. In addition, to examine whether the molecular chaperone 90-kDa heat shock protein (Hsp90) contributes to rubratoxin B toxicity, the effects of Hsp90-specific inhibitors, radicicol and geldanamycin, were investigated. Exposure to rubratoxin B for 24h induced secretion of each CCR5 chemokine, although the effect on CCL5 secretion was modest, and it enhanced secretion of proinflammatory cytokines tumor necrosis factor-α, CXCL8, and CCL2. Concomitant treatment with radicicol abolished the rubratoxin-induced secretion of all cytokines investigated. Geldanamycin antagonized the rubratoxin B-induced effects on CCL3 and CCL5, but not CCL4; the effects of geldanamycin were less than that of radicicol. Taken together, the results suggest that rubratoxin B, with the contribution of Hsp90, induces secretion of CCR5 chemokines.
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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 ╳
