Aphidicolin-17-monoacetate
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| Category | Enzyme inhibitors |
| Catalog number | BBF-00057 |
| CAS | |
| Molecular Weight | 380.52 |
| Molecular Formula | C22H36O5 |
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Description
Aphidicolin-17-monoacetate is an antibiotic produced by Phoma betae PS-13, which inhibits DNA polymerase and interferes with root growth.
Properties
| Appearance | White Crystals |
| Melting Point | 196-199°C |
| Solubility | Soluble in DMSO, Methanol, Pyridine |
Reference Reading
1. Isolation and Characterization of Aphidicolin Derivatives from Tolypocladium inflatum
Jie Lin, Shubin Niu, Zhengfeng Ding, Renlei Wang, Qun Dai, Wei Wei, Rongrong Luo, Ling Liu Molecules. 2017 Jul 12;22(7):1168. doi: 10.3390/molecules22071168.
Inflatin G (1), a new aphidicolin analogue, together with seven known compounds inflatin A (2), inflatin B (3), aphidicolin (4), aphidicolin-17-monoacetate (5), gulypyrone A (6), pyridoxatin rotamers A (7) and B (8), were isolated from the ascomycete fungus Tolypocladium inflatum. Their structures were determined through NMR analyses and the circular dichroism data of the in situ formed [Rh₂(OCOCF₃)₄] complexes. Compounds 1, 4, 5, 7, and 8 showed modest cytotoxicity against four human cancer cell lines A549, CNE1-MP1, A375, and MCF-7.
2. Specific inhibitors of eukaryotic DNA synthesis and DNA polymerase alpha, 3-deoxyaphidicolin and aphidicolin-17-monoacetate
T Haraguchi, M Oguro, H Nagano, A Ichihara, S Sakamura Nucleic Acids Res. 1983 Feb 25;11(4):1197-209. doi: 10.1093/nar/11.4.1197.
Of several phytotoxins isolated from culture filtrates of Phoma betae Frank PS-13, an incitant of leaf spot disease of sugar beet, three have been identified as aphidicolin, 3-deoxyaphidicolin and aphidicolin-17-monoacetate. Aphidicolin is a selective inhibitor of eukaryotic DNA polymerase alpha (Ikegami et al. (1978) Nature 275, 458-460). Consequently, we studied the action mechanism of 3-deoxyaphidicolin and aphidicolin-17-monoacetate. These aphidicolin analogues markedly inhibited the in vivo DNA synthesis of sea urchin embryos and HeLa cells but not RNA and protein syntheses. Only DNA polymerase alpha, not DNA polymerase beta and gamma, was inhibited by these drugs. The mode of action of these analogues on DNA polymerase alpha from the sea urchin was competitive inhibition with respect to dCTP with Ki values of 0.44 micrograms/ml for deoxyaphidicolin and 0.89 micrograms/ml for aphidicolin monoacetate, respectively. None of the other three dNTPs competed with these drugs. A similar inhibitory mode was observed using the enzyme from HeLa cells and toad oocytes. These drugs at a concentration of 2 micrograms/ml caused a delay in the cleavage of fertilized eggs of the sea urchin and decomposition before blastulation, indicating the possibility of achromosomal cleavage because of the absence of DNA synthesis. Based on the above, it is concluded that these analogues can be used as other inhibitors of eukaryotic DNA synthesis and DNA polymerase alpha.
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Bio Calculators
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
