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Merck
CN

A4487

Aphidicolin

Ready Made Solution, from Nigrospora sphaerica

Synonym(s):

ICI 69653, NSC-234714

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About This Item

Empirical Formula (Hill Notation):
C20H34O4
CAS Number:
38966-21-1
Molecular Weight:
338.48
UNSPSC Code:
51102829
NACRES:
NA.85
EC Number:
200-664-3
MDL number:
MFCD00083214

Key Documents

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SMILES string

O[C@]1([C@H]2C[C@@]3([C@@]4([C@H]([C@@]([C@@H](CC4)O)(CO)C)CC[C@H]3C2)C)CC1)CO

InChI key

NOFOAYPPHIUXJR-APNQCZIXSA-N

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

biological source

Nigrospora sphaerica

vapor pressure

0.55 hPa ( 20 °C)

Quality Level

200

form

liquid, ready-to-use solution

color

clear colorless

solubility

H2O: miscible (completely)

antibiotic activity spectrum

neoplastics, viruses

mode of action

DNA synthesis | interferes, enzyme | inhibits

storage temp.

−20°C

Related Categories

Application

Aphidicolin, from Nigrospora sphaerica, was used for cell cycle synchronization of tobacco BY-2 cells. It is used to block the entry of cells into S-phase.

Biochem/physiol Actions

Aphidicolin specifically inhibits DNA polymerase α that is responsible for DNA replication. It also inhibits α-like DNA polymerases of plants and yeasts but does not inhibit synthesis of RNA and proteins. Aphidicolin competes for the dCTP-specific binding site on DNA polymerase α specifically. Aphidicolin has antiviral and antimitotic properties. It blocks the cell cycle at S phase. It has been shown to induce apoptosis in HeLa cells.

General description

Aphidicolin is a tetracyclic diterpene with antiviral and antimitotic properties used for cell cycle synchronization in various cell lines.

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Storage class (TRGS 510): Combustible liquids

Packaging

1 ml

Physical form

Aphidicolin Ready Made Solution supplied as a 1 mg/ml solution in DMSO.

Storage Class

10 - Combustible liquids

wgk

WGK 1

flash_point_f

188.6 °F - closed cup

flash_point_c

87 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
0000529942
0000529942
0000469102
0000469102
0000289532

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Hui Wang et al.
Cancer research, 77(8), 2148-2160 (2017-02-18)
Overexpression of the EVI1 oncogene is associated typically with aggressive myeloid leukemia, but is also detectable in breast carcinoma where its contributions are unexplored. Analyzing a tissue microarray of 608 breast carcinoma patient specimens, we documented EVI1 overexpression in both
G Pedrali-Noy et al.
Nucleic acids research, 8(2), 377-387 (1980-01-25)
Both the inhibitory effect of aphidicolin on the replicative alpha-polymerase and the reversibility of its action in vivo (Pedrali-Noy & Spadari, 1979, Biochem. Biophys. Res. Commun. 88, 1194-2002) allow the synchronization of cells in culture. Aphidicolin prevents G1 cells from
K Marheineke et al.
The Journal of biological chemistry, 276(20), 17092-17100 (2001-03-30)
DNA replication origins are located at random with respect to DNA sequence in Xenopus early embryos and on DNA replicated in Xenopus egg extracts. We have recently shown that origins fire throughout the S phase in Xenopus egg extracts. To
New views of the biochemistry of eucaryotic DNA replication revealed by aphidicolin, an unusual inhibitor of DNA polymerase alpha.
J A Huberman
Cell, 23(3), 647-648 (1981-03-01)
Varinderpal S Dhillon et al.
Teratogenesis, carcinogenesis, and mutagenesis, Suppl 1, 35-45 (2003-03-05)
Fragile sites are nonrandomly located gaps and/or breaks and their expres-sion can be induced by specific culture conditions. There are many reports in the literature that indicate that these sites can act as factors that predispose to specific chromosome aberrations
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