Cyclophostin
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01116 |
| CAS | 144773-26-2 |
| Molecular Weight | 234.14 |
| Molecular Formula | C8H11O6P |
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Description
It is produced by the strain of Streptomyces lavendulae NK901093. It strongly inhibits AChE activity, it inhibits the AchE of houseflies with IC50 of 7.6 X 10-10 mol/L.
Specification
| Synonyms | Rac-Cyclophostin; 1H,6H-Furo(3,4-e)(1,3,2)dioxaphosphepin-6-one,8,8a-dihydro-3-methoxy-5-methyl-, 3-oxide, (3R-cis)- |
| IUPAC Name | (3R,8aR)-3-methoxy-5-methyl-3-oxo-8,8a-dihydro-1H-furo[3,4-e][1,3,2]dioxaphosphepin-6-one |
| Canonical SMILES | CC1=C2C(COC2=O)COP(=O)(O1)OC |
| InChI | InChI=1S/C8H11O6P/c1-5-7-6(3-12-8(7)9)4-13-15(10,11-2)14-5/h6H,3-4H2,1-2H3/t6-,15-/m1/s1 |
| InChI Key | OMPQJMDGDAAXPE-NPMWZIQKSA-N |
Properties
| Appearance | Crystal |
| Boiling Point | 338.1 °C at 760 mmHg |
| Melting Point | 113-114 °C |
| Density | 1.41 g/cm3 |
| Solubility | Soluble in Ethanol |
Reference Reading
1. Synthesis and Biological Characterization of Fluorescent Cyclipostins and Cyclophostin Analogues: New Insights for the Diagnosis of Mycobacterial-Related Diseases
Morgane Sarrazin, Benjamin P Martin, Romain Avellan, Giri Raj Gnawali, Isabelle Poncin, Hugo Le Guenno, Christopher D Spilling, Jean-François Cavalier, Stéphane Canaan ACS Infect Dis. 2022 Dec 9;8(12):2564-2578. doi: 10.1021/acsinfecdis.2c00448. Epub 2022 Nov 15.
Patients with cystic fibrosis (CF) have a significantly higher risk of acquiring nontuberculous mycobacteria infections, predominantly due to Mycobacterium abscessus, than the healthy population. Because M. abscessus infections are a major cause of clinical decline and morbidity in CF patients, improving treatment and the detection of this mycobacterium in the context of a polymicrobial culture represents a critical component to better manage patient care. We report here the synthesis of fluorescent Dansyl derivatives of four active cyclipostins and cyclophostin analogues (CyCs) and provide new insights regarding the CyC's lack of activity against Gram-negative and Gram-positive bacteria, and above all into their mode of action against intramacrophagic M. abscessus cells. Our results pointed out that the intracellularly active CyC accumulate in acidic compartments within macrophage cells, that this accumulation appears to be essential for their delivery to mycobacteria-containing phagosomes, and consequently, for their antimicrobial effect against intracellular replicating M. abscessus, and that modification of such intracellular localization via disruption of endolysosomal pH strongly affects the CyC accumulation and efficacy. Moreover, we discovered that these fluorescent compounds could become efficient probes to specifically label mycobacterial species with high sensitivity, including M. abscessus in the presence several other pathogens like Pseudomonas aeruginosa and Staphylococcus aureus. Collectively, all present and previous data emphasized the therapeutic potential of unlabeled CyCs and the attractiveness of the fluorescent CyC as a potential new efficient diagnostic tool to be exploited in future diagnostic developments against mycobacterial-related infections, especially against M. abscessus.
2. The Chemistry and Biology of Cyclophostin, the Cyclipostins and Related Compounds
Christopher D Spilling Molecules. 2019 Jul 16;24(14):2579. doi: 10.3390/molecules24142579.
Cyclophostin, the cyclipostins and the salinipostins are structurally related cyclic enolphosphate natural products. This mini review describes their isolation, synthesis and biological activities. In addition, the synthesis and biological activities of monocyclic enolphosphate and mono and bicyclic enolphosphonate analogs are presented.
3. Cyclipostins and Cyclophostin Analogues as Multitarget Inhibitors That Impair Growth of Mycobacterium abscessus
Abdeldjalil Madani, Jeremy N Ridenour, Benjamin P Martin, Rishi R Paudel, Anosha Abdul Basir, Vincent Le Moigne, Jean-Louis Herrmann, Stéphane Audebert, Luc Camoin, Laurent Kremer, Christopher D Spilling, Stéphane Canaan, Jean-François Cavalier ACS Infect Dis. 2019 Sep 13;5(9):1597-1608. doi: 10.1021/acsinfecdis.9b00172. Epub 2019 Jul 25.
Twelve new Cyclophostin and Cyclipostins analogues (CyC19-30) were synthesized, thus extending our series to 38 CyCs. Their antibacterial activities were evaluated against four pathogenic mycobacteria (Mycobacterium abscessus, Mycobacterium marinum, Mycobacterium bovis BCG, and Mycobacterium tuberculosis) and two Gram negative bacteria. The CyCs displayed very low toxicity toward host cells and were only active against mycobacteria. Importantly, several CyCs were active against extracellular M. abscessus (CyC17/CyC18β/CyC25/CyC26) or intramacrophage residing mycobacteria (CyC7(α,β)/CyC8(α,β)) with minimal inhibitory concentrations (MIC50) values comparable to or better than those of amikacin or imipenem, respectively. An activity-based protein profiling combined with mass spectrometry allowed identification of the potential target enzymes of CyC17/CyC26, mostly being involved in lipid metabolism and/or in cell wall biosynthesis. Overall, these results strengthen the selective activity of the CyCs against mycobacteria, including the most drug-resistant M. abscessus, through the cumulative inhibition of a large number of Ser- and Cys-enzymes participating in key physiological processes.
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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 ╳
