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Aphidicolin

SKU
A-1026
  • CAS:38966-21-1
  • Formula:C20H34O4
  • MW:338.5 Da
  • Appearance:White Powder
  • Purity:>99% (TLC)
Product Name Qty
Aphidicolin
1 mg
$102.00
Aphidicolin
5 mg
$402.90
Aphidicolin
25 mg
$1,524.90
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Description

Aphidicolin is a reversible inhibitor of nuclear DNA replication in eukaryotes and some animal viruses. It interferes with dCTP-specific binding sites on DNA polymerase-α. It also works on other DNA polymerases, however it does not work on DNA polymerase-β. 

Viruses inducing DNA polymerase-α, such as Herpes simplex, can be affected by aphidicolin because of its mechanism. It could be used for clinical study.

Isolated from Nigrospora oryzae.


Applications

• Control of cell proliferation

• DNA pol-β studies


References

• “Aphidicolin: a specific inhibitor of nuclear DNA replication in eukaryotes”

• “Effect of aphidicolin on viral and human DNA polymerases”

• "DNA Replication Dynamics of the GGGGCC Repeat of the C9orf72 Gene"

• "Structural basis for inhibition of DNA replication by aphidicolin"



More Information
Alternate Name/Synonyms
APC; ICI 69653; NSC 234714
SKU
A-1026
CAS #
38966-21-1
Chemical Name
(1S,2S,5R,6R,7R,10S,12R,13R)-6,13-bis(hydroxymethyl)-2,6-dimethyltetracyclo[10.3.1.01,10.02,7]hexadecane-5,13-diol
Chemical Formula
C20H34O4
Molecular Weight
338.5 Da
Appearance
White Powder
Purity
>99% (TLC)
Solubility
Methanol: Clear colorless solution at 10 mg/ml
Melting Point
230°C
Storage Temp
+4°C
THERAPEUTIC AREA
Not Available
USE
For research use only. Not intended for diagnostic or therapeutic use. Aphidicolin is a tetracyclic diterpene with antibiotic, antiviral and antimitotic properties by blocking the cell cycle at early S-phase. This property has been used to synchronise cell division and is useful as a tool in cell differentiation research. Aphidicolin induces apoptosis, prolongs the half-life of DNA methyltransferase, is active against Leishmania parasites and acts synergistically with the antitumor agents, vincristine and doxorubicin.
Merck Index
Merck Index: 13.734.2001
MDL NUMBER
MFCD00083214
CHEMACX
X1001937-7
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
SMILES
C[C@]12CC[C@H]([C@@]([C@@H]1CC[C@@H]3[C@@]24CC[C@@]([C@H](C3)C4)(CO)O)(C)CO)O
Peptide sequence
Not Applicable
RTECS
PB9185000
UN #'S
Not Applicable
PACKING GROUP
Not Applicable
HAZARD CLASS
Not Applicable
Handling
Warning.Toxic. Potential Carcinogenic. Do not use this compound if you are not fully trained or are unaware of the hazards involved. Wear gloves/mask when handling product. Avoid contact by all means of exposure. Avoid contact with skin, eyes or clothing. Do not breathe dust/fume/gas/mist/vapors/spray. Do not eat, drink or smoke when using this product. Use with local exhaust ventilation.
Citations
CELL BIOLOGY: Sororin cooperates with the acetyltransferase Eco2 to ensure DNA replication-dependent sister chromatid cohesion Andrea L. Lafont, Jianhua Song, and Susannah Rankin PNAS, Nov 2010; 107: 20364 - 20369.
Citations_Hyperlink
http://www.pnas.org/cgi/reprint/107/47/20364
Certificate of Analysis 1
A-1026, K1158H.pdf
Certificate of Analysis 2
A-1026, J1034E.pdf
Certificate of Analysis 3
A-1026, J1034D.pdf
GHS PICTOGRAMS
HandlingWarning.Toxic. Potential Carcinogenic. Do not use this compound if you are not fully trained or are unaware of the hazards involved. Wear gloves/mask when handling product. Avoid contact by all means of exposure. Avoid contact with skin, eyes or clothing. Do not breathe dust/fume/gas/mist/vapors/spray. Do not eat, drink or smoke when using this product. Use with local exhaust ventilation.
UN #'SNot Applicable
Packing GroupNot Applicable
CitationsAnálisis de la señalización por Ret: caracterización de la cascada molecular B-Raf/IKKS y regulación de Ret por Sprouty1
A balance between elongation and trimming regulates telomere stability in stem cells
Arabidopsis POT1 associates with the telomerase RNP and is required for telomere maintenance
Sororin cooperates with the acetyltransferase Eco2 to ensure DNA replication-dependent sister chromatid cohesion
Early and late steps in telomere overhang processing in normal human cells: the position of the final RNA primer drives telomere shortening
Endoplasmic reticulum stress-induced apoptosis requires bax for commitment and Apaf-1 for execution in primary neurons
Cytosine arabinoside rapidly activates Bax-dependent apoptosis and a delayed Bax-independent death pathway in sympathetic neurons
The limited role of NH2-terminal c-Jun phosphorylation in neuronal apoptosis: identification of the nuclear pore complex as a potential target of the JNK pathway
Secreted herpes simplex virus-2 glycoprotein G modifies NGF-TrkA signaling to attract free nerve endings to the site of infection
Inhibition of the c-Jun N-terminal kinase signaling pathway by the mixed lineage kinase inhibitor CEP-1347 (KT7515) preserves metabolism and growth of trophic factor-deprived neurons
Secreted herpes simplex virus-2 glycoprotein G alters thermal pain sensitivity by modifying NGF effects on TRPV1
Exposure to the polybrominated diphenyl ether mixture DE-71 damages the nigrostriatal dopamine system: role of dopamine handling in neurotoxicity
Cohesin acetylation promotes sister chromatid cohesion only in association with the replication machinery
RET modulates cell adhesion via its cleavage by caspase in sympathetic neurons
Human mismatch repair: reconstitution of a nick-directed bidirectional reaction
JNK-independent activation of c-Jun during neuronal apoptosis induced by multiple DNA-damaging agents
BH3-only Bcl-2 family members are coordinately regulated by the JNK pathway and require Bax to induce apoptosis in neurons
The activation loop phosphorylation of protein kinase D is an early marker of neuronal DNA damage
Identification of JNK-dependent and -independent components of cerebellar granule neuron apoptosis
Mixed-lineage kinase inhibitors require the activation of Trk receptors to maintain long-term neuronal trophism and survival
Formaldehyde-induced genome instability is suppressed by an XPF-dependent pathway
Alterations to the circuitry of the frontal cortex following exposure to the polybrominated diphenyl ether mixture, DE-71
Temporal differences in DNA replication during the S phase using single fiber analysis of normal human fibroblasts and glioblastoma T98G cells
DNA replication in early S phase pauses near newly activated origins
Developmental exposure to the organochlorine insecticide endosulfan damages the nigrostriatal dopamine system in male offspring
Early development and axis specification in the sea anemone Nematostella vectensis
Selective damage to dopaminergic transporters following exposure to the brominated flame retardant, HBCDD
Developmental exposure to the organochlorine insecticide endosulfan alters expression of proteins associated with neurotransmission in the frontal cortex
DNA damage checkpoint responses in the S phase of synchronized diploid human fibroblasts
Alteration to Dopaminergic Synapses Following Exposure to Perfluorooctane Sulfonate (PFOS), in Vitro and in Vivo
Herpes simplex virus glycoprotein G enhances chemotaxis through modi!cation of plasma membrane microdomains and receptor tra
TrkA COOH-terminal tail: its relevance on receptor stability and signaling for cell differentiation and survival
Defining Multiple Steps in Human Telomere End Processing
Telomere -associated proteins in Arabidopsis thaliana
Zellteilungsregulation meristematischer Wurzelzellen (Tabak BY-2) durch Phytohormone und Zucker
Genetic analysis of the Replication Protein A large subunit family in Arabidopsis reveals unique and overlapping roles in DNA repair, meiosis and DNA replication
Genetic and evolutionary analysis of plant replication protein A 1 (RPA1)
Fragile X Mental Retardation Protein regulates R-loop formation and prevents global chromosome fragility
Neuronal Hyperexcitability is a DLK-dependent Trigger of HSV-1 Reactivation that can be Induced by IL-1
Replication Stress Induces Global Chromosome Breakage in the Fragile X Genome
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