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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/01/30 22:56:49」(JST)
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Aphidicolin
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| Names |
| IUPAC name
(3R,4R,4aR,6aS,8R,9R,11aS,11bS)-4,9-bis(hydroxymethyl)-4,11b-dimethyltetradecahydro-8,11a-methanocyclohepta[a]naphthalene-3,9-diol
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| Identifiers |
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CAS Number
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38966-21-1 Y |
| ChEMBL |
ChEMBL29711 Y |
| ChemSpider |
10280269 Y |
| Jmol interactive 3D |
Image |
| PubChem |
457964 |
InChI
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InChI=1S/C20H34O4/c1-17(11-21)15-4-3-13-9-14-10-19(13,7-8-20(14,24)12-22)18(15,2)6-5-16(17)23/h13-16,21-24H,3-12H2,1-2H3/t13-,14+,15-,16+,17-,18-,19-,20-/m0/s1 Y
Key: NOFOAYPPHIUXJR-APNQCZIXSA-N Y
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InChI=1/C20H34O4/c1-17(11-21)15-4-3-13-9-14-10-19(13,7-8-20(14,24)12-22)18(15,2)6-5-16(17)23/h13-16,21-24H,3-12H2,1-2H3/t13-,14+,15-,16+,17-,18-,19-,20-/m0/s1
Key: NOFOAYPPHIUXJR-APNQCZIXBU
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SMILES
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OC[C@@]4(O)CC[C@]31C[C@H]4C[C@@H]3CC[C@H]2[C@](C)(CO)[C@H](O)CC[C@]12C
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| Properties |
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Chemical formula
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C20H34O4 |
| Molar mass |
338.48 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Y verify (what is YN ?) |
| Infobox references |
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Aphidicolin is a tetracyclic diterpene antibiotic isolated from the fungus, Cephalosporum aphidicola with antiviral and antimitotic properties. Aphidicolin is a reversible inhibitor of eukaryotic nuclear DNA replication. It blocks the cell cycle at early S phase. It is a specific inhibitor of DNA polymerase A,D in eukaryotic cells and in some viruses (vaccinia[1][2] and herpesviruses) and an apoptosis inducer in HeLa cells. Natural aphidicolin is a secondary metabolite of the fungus Nigrospora oryzae.[3]
BibliographyEdit
- Dhillon VS, Husain SA, Ray GN (2003). "Expression of aphidicolin-induced fragile sites and their relationship between genetic susceptibility in breast cancer, ovarian cancer, and non-small-cell lung cancer patients". Teratog., Carcinog. Mutagen. Suppl 1: 35–45. doi:10.1002/tcm.10068. PMID 12616595.
- Mahy, Brian W J (2001). A dictionary of virology (3. ed.). San Diego, Calif. [u.a.]: Academic Press. p. 19. ISBN 978-0-12-465327-6.
ReferencesEdit
- ^ DeFilippes, FM (Nov 1984). "Effect of aphidicolin on vaccinia virus: isolation of an aphidicolin-resistant mutant.". Journal of Virology 52 (2): 474–82. PMC 254548. PMID 6436508.
- ^ Bucknall, R. A.; Moores, H.; Simms, R.; Hesp, B. (1 September 1973). "Antiviral Effects of Aphidicolin, a New Antibiotic Produced by Cephalosporium aphidicola". Antimicrobial Agents and Chemotherapy 4 (3): 294–298. doi:10.1128/AAC.4.3.294.
- ^ Aphidicolin product page from Fermentek
English Journal
- Further characterization of benzo[a]pyrene diol-epoxide (BPDE)-induced comet assay effects.
- Bausinger J, Schütz P, Piberger AL1, Speit G.
- Mutagenesis.Mutagenesis.2016 Mar;31(2):161-9. doi: 10.1093/mutage/gev067. Epub 2015 Sep 7.
- The present study aims to further characterize benzo[a]pyrene diol-epoxide (BPDE)-induced comet assay effects. Therefore, we measured DNA effects by the comet assay and adduct levels by high-performance liquid chromatography (HPLC) in human lymphocytes and A549 cells exposed to (±)-anti-benzo[a]pyr
- PMID 26346062
- Semisynthesis of new aphidicolin derivatives with high activity against Trypanosoma cruzi.
- Santos GB1, Krogh R2, Magalhaes LG2, Andricopulo AD2, Pupo MT1, Emery FS1.
- Bioorganic & medicinal chemistry letters.Bioorg Med Chem Lett.2016 Feb 15;26(4):1205-8. doi: 10.1016/j.bmcl.2016.01.033. Epub 2016 Jan 14.
- Chagas disease continues to be a difficult disease to eradicate, largely because of the widespread populations it affects as well as the highly toxic effects of current therapies. Thus, the exploration of innovative scaffolds, ideally with distinct mechanisms of action, is urgently needed. The natur
- PMID 26810263
- Mechanisms and consequences of ATMIN repression in hypoxic conditions: roles for p53 and HIF-1.
- Leszczynska KB1, Göttgens EL1, Biasoli D1, Olcina MM2, Ient J1, Anbalagan S1, Bernhardt S1, Giaccia AJ2, Hammond EM1.
- Scientific reports.Sci Rep.2016 Feb 15;6:21698. doi: 10.1038/srep21698.
- Hypoxia-induced replication stress is one of the most physiologically relevant signals known to activate ATM in tumors. Recently, the ATM interactor (ATMIN) was identified as critical for replication stress-induced activation of ATM in response to aphidicolin and hydroxyurea. This suggests an essent
- PMID 26875667
Japanese Journal
- 5-Hydroxymethylcytosine Marks Sites of DNA Damage and Promotes Genome Stability.
- Aphidicolin inhibits cell proliferation <i>via</i> the p53-GADD45β pathway in AtT-20 cells
- Aphidicolin inhibits cell proliferation via the p53-GADD45β pathway in AtT-20 cells
Related Links
- Aphidicolin from Nigrospora sphaerica Catalog Number A0781 Storage Temperature 2-8 C CAS RN 38966-21-1 Synonyms: ICI 69653, NSC-234714 Product Description Molecular formula: C 20H 34O 4 Molecular weight: 338.48 ...
- The influence of aphidicolin on cell multiplication and DNA synthesis was examined using synchronous mouse mastocytoma P-815 cells. Aphidicolin was cytotoxic specifically to the cells of the S phase of the cell cycle. This ...