(+)-Aphidicolin
| Code | Size | Price |
|---|
| BVT-0307-M001 | 1 mg | £80.00 |
Quantity:
| BVT-0307-M005 | 5 mg | £265.00 |
Quantity:
| BVT-0307-M025 | 25 mg | £910.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
20°C
Storage:
4°C
Documents
Further Information
Alternate Names/Synonyms:
NSC234714; BRN4689958; ICI69653
Appearance:
White to off-white solid.
CAS:
38966-21-1
EClass:
32160000
Form (Short):
liquid
GHS Symbol:
GHS07
Handling Advice:
Protect from light when in solution.
Hazards:
H302, H319
InChi:
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
InChiKey:
NOFOAYPPHIUXJR-APNQCZIXSA-N
Long Description:
Chemical. CAS: 38966-21-1. Formula: C20H34O4. MW: 338.5. Isolated from Phoma sp. BS 7210. Phytotoxin. Antibiotic. Antiviral and antineoplastic agent. Antileishmanial agent. Reversible inhibitor of eukaryotic nuclear DNA replication. Useful for cell synchronization. Blocks the cell cycle at G1/S phase. Prolongs the half life of DNA methyltransferase. DNA methylation/demethylation modulator. Specific DNA polymerase alpha and delta inhibitor in eukaryotic cells and in some viruses of animal origin. Acts synergistically with vincristine and doxorubicin. Apoptosis inhibitor/inducer.
MDL:
MFCD00083214
Molecular Formula:
C20H34O4
Molecular Weight:
338.5
Package Type:
Plastic Vial
Precautions:
P270, P280, P301, P312, P305, P351, P338
Product Description:
Phytotoxin. Antibiotic. Antiviral and antineoplastic agent. Antileishmanial agent. Reversible inhibitor of eukaryotic nuclear DNA replication. Useful for cell synchronization. Blocks the cell cycle at G1/S phase. Prolongs the half life of DNA methyltransferase. DNA methylation/demethylation modulator. Specific DNA polymerase alpha and delta inhibitor in eukaryotic cells and in some viruses of animal origin. Acts synergistically with vincristine and doxorubicin. Apoptosis inhibitor/inducer.
Purity:
>98% (HPLC)
Signal word:
Warning
SMILES:
[H][C@]12C[C@@H]3C[C@]1(CC[C@]3(O)CO)[C@@]1(C)CC[C@@H](O)[C@@](C)(CO)[C@]1([H])CC2
Solubility Chemicals:
Soluble in DMSO (50 mg/ml), methanol (10 mg/ml) or 100% ethanol; insoluble in water.
Source / Host:
Isolated from Phoma sp. BS 7210.
Transportation:
Non-hazardous
UNSPSC Category:
Natural Products/Extracts
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 1 year after receipt when stored at +4°C. After reconstitution protect from light at -20°C.
References
X-Ray crystallographic determination of the structure of the antibiotic aphidicolin: a tetracyclicditerpenoid containing a new ring system: K.M. Brundret, et al.; J. C. S. Chem. Commun. 1027 (1972) | Aphidicolin prevents mitotic cell division by interfering with the activity of DNA polymerase-alpha: S. Ikegami, et al.; Nature 275, 458 (1978) | New views of the biochemistry of eucaryotic DNA replication revealed by aphidicolin, an unusual inhibitor of DNA polymerase alpha: J.A. Huberman; Cell 23, 647 (1981) | Aphidicolin: a specific inhibitor of nuclear DNA replication in eukaryotes: S. Spadari, et al.; TIBS 7, 29 (1982) | Aphidicolin potentiates apoptosis induced by arabinosyl nucleosides in human myeloid leukemia cell lines: K. Kuwakado, et al.; Biochem. Pharmacol. 46, 1909 (1993) | Dissociation of nuclear and cytoplasmic cell cycle progression by drugs employed in cell synchronization: L. Urbani, et al.; Exp. Cell. Res. 219, 159 (1995) | Drug-induced apoptosis is not necessarily dependent on macromolecular synthesis or proliferation in the p53-negative human prostate cancer cell line PC-3: M.M. Borner, et al.; Cancer Res. 55, 2122 (1995) | TrkA neurogenic receptor regulates differentiation of neuroblastoma cells: W. Poluha, et al.;Oncogene10, 185 (1995) | Effect of aphidicolin on DNA methyltransferase in the nucleus: I. Suetake, et al.; Cell Struct. Funct. 23, 137 (1998) | Cytotoxicity of aphidicolin and its derivatives against neuroblastoma cells in vitro: synergism with doxorubicin and vincristine: M. Michaelis, et al.; Anticancer Drugs 11, 479 (2000) | Antileishmanial activities of aphidicolin and its semisynthetic derivatives: O. Kayser, et al.; Antimicrob. Agents Chemother. 45, 288 (2001) | Aphidicolin and bleomycin induced chromosome damage as biomarker of mutagen sensitivity: a twin study: B. Tedeschi, et al.; Mutat. Res. 546, 55 (2004) | Human papillomavirus episome stability is reduced by aphidicolin and controlled by DNA damage response pathways: T. G. Edwards, et al.; J. Virol. 87, 3979 (2013) | Aphidicolin-induced nuclear elongation in tobacco BY-2 cells: H. Yashura, et al.; Plant Cell Physiol. 55, 913 (2014) | Active and passive demethylation of male and female pronuclear DNA in the mammalian zygote: F. Guo, et al.; Cell Stem Cell 15, 447 (2014) | Structural basis for inhibition of DNA replication by aphidicolin: A.G. Baranovskiy, et al.; Nucl. Acids Res. 42, 14013 (2014) | Toward a cancer drug of fungal origin: A. Kornienko, et al.; Med. Res. Rev. 35, 937 (2015) | Aphidicolin: its chemistry and biosynthesis: J.R. Hanson; J. Chem. Res. 42, 395 (2018) | Stability of cytoplasmic nanoviscosity during cell cycle of HeLa cells synchronized with Aphidicolin: K. Szczepanski, et al.; Sci. Rep. 9, 1 (2019) | Mitotic DNA synthesis is differentially regulated between cancer and noncancerous cells: C.L. Graber-Feesl, et al.; Mol. Cancer Res. 17, 1687 (2019)