APHIDICOLIN
Background- Product Name
- APHIDICOLIN
- CAS No.
- 38966-21-1
- Chemical Name
- APHIDICOLIN
- Synonyms
- APC;ici69653;nsc-234714;APHIDICOLIN;(+)-APHIDICOLIN;,11a-beta,11b-beta))-;APHIDICOLIN USP/EP/BP;Aphidicolin, Ready Made Solution;(+)-APHIDICOLIN, NIGROSPORA ORYZAE;Aphidicolin, froM Nigrospora oryzae
- CBNumber
- CB6683304
- Molecular Formula
- C20H34O4
- Formula Weight
- 338.48
- MOL File
- 38966-21-1.mol
APHIDICOLIN Property
- Melting point:
- 218-220°C
- alpha
- D27 +12° (c = 1 in methanol)
- Boiling point:
- 394.61°C (rough estimate)
- Density
- 1.0057 (rough estimate)
- vapor pressure
- 0.55 hPa ( 20 °C)
- refractive index
- 1.4434 (estimate)
- Flash point:
- 87℃
- storage temp.
- 2-8°C
- solubility
- ethanol: soluble1mg/mL (stable at least a week at 4°C.)
- pka
- 14.24±0.70(Predicted)
- form
- White solid
- color
- colorless
- biological source
- Nigrospora sphaerica
- optical activity
- [α]27/D +12°, c = 1 in methanol(lit.)
- Water Solubility
- Soluble in DMSO or methanol. Insoluble in water. Store solutions at -20°
- Merck
- 13,734
- BRN
- 4689958
- Stability:
- Stable for 2 years from date of purchase from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 1 month.
- 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
- SMILES
- 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
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
N-Bromosuccinimide Price
- Product number
- 89458
- Product name
- Aphidicolin
- Purity
- analytical standard
- Packaging
- 5mg
- Price
- $1140
- Updated
- 2025/07/31
- Product number
- 5.04744
- Product name
- InSolution Aphidicolin - CAS 38966-21-1 - Calbiochem
- Packaging
- 1mg
- Price
- $172
- Updated
- 2025/07/31
- Product number
- 178273
- Product name
- Aphidicolin
- Packaging
- 1mg
- Price
- $148
- Updated
- 2025/07/31
- Product number
- 14007
- Product name
- (+)-Aphidicolin
- Purity
- ≥98%
- Packaging
- 1mg
- Price
- $86
- Updated
- 2024/03/01
- Product number
- 14007
- Product name
- (+)-Aphidicolin
- Purity
- ≥98%
- Packaging
- 5mg
- Price
- $274
- Updated
- 2024/03/01
APHIDICOLIN Chemical Properties,Usage,Production
Description
(+)-
Chemical Properties
White crystal
Uses
A DNA polymerase inhibitor. Blocks the cell cycle at the early S-phase
Uses
(+)-Aphidicolin is a naturally occurring tetracyclic diterpene with potential antiviral and antimitotical properties.
Uses
Aphidicolin is a tetracyclic diterpene antibiotic isolated from fungi, notably Cephalosporium, Nigrospora, Harziella and Phoma. Aphidicolin has antibiotic, antiviral and antimitotic properties, 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 is a reversible inhibitor of DNA replication by inhibiting selected DNA polymerases. Aphidicolin induces apoptosis, prolongs the half-life of DNA methyltransferase, is active against Leishmania parasites and acts synergistically with the antitumour agents, vincristine and doxorubicin.
Definition
ChEBI: A tetracyclic diterpenoid that has an tetradecahydro-8,11a-methanocyclohepta[a]naphthalene skeleton with two hydroxymethyl substituents at positions 4 and 9, two methyl substituents at positions 4 and 11b and two hydroxy substituents at positi ns 3 and 9. An antibiotic with antiviral and antimitotical properties. Aphidicolin is a reversible inhibitor of eukaryotic nuclear DNA replication.
General Description
A cell-permeable tetracyclic diterpene antibiotic. Cell synchronization agent. Blocks the cell cycle at the early S-phase. Specific inhibitor of DNA polymerase α and δ in eukaryotic cells and in some viruses of animal origin. Potentiates apoptosis induced by arabinosyl nucleosides in leukemia cell lines. Also induces apoptosis in HeLaS3 cells, but inhibits vincristine-induced apoptosis in the p53-negative human prostate cancer cell line PC-3.
Biochem/physiol Actions
Cell permeable: yes
storage
+4°C
Background
Aphidicolin is a tetracyclic diterpenoid first produced by the fungus Cephalosporium aphidicola. This antibiotic is a potent inhibitor of cellular deoxyribonucleic acid synthesis by targeting α, ε, and δ DNA polymerases in eukaryotic cells lines with little to no effect on β or γ DNA polymerases. Studies have shown that Aphidicolin specifically binds to α DNA polymerase, resulting in the formation of a pol α-DNA-aphidicolin ternary complex that blocks DNA replication. The uses for this compound include synchronized cells at the G1/S boundary and increased gene amplification.
References
[1] J SYVÄOJA. DNA polymerases alpha, delta, and epsilon: three distinct enzymes from HeLa cells.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1990, 87 17: 6664-6668. DOI:10.1073/pnas.87.17.6664
[2] LENORE URBANI Robert T S Steven W Sherwood. Dissociation of Nuclear and Cytoplasmic Cell Cycle Progression by Drugs Employed in Cell Synchronization[J]. Experimental cell research, 1995, 219 1: Pages 159-168. DOI:10.1006/excr.1995.1216
[3] KATSUJI KUWAKADO. Aphidicolin potentiates apoptosis induced by arabinosyl nucleotides in human myeloid leukemia cell lines[J]. Biochemical pharmacology, 1993, 46 11: Pages 1909-1916. DOI:10.1016/0006-2952(93)90631-6
[4] D X YIN R T S. Inhibition of apoptosis by overexpressing Bcl-2 enhances gene amplification by a mechanism independent of aphidicolin pretreatment.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1996, 93 8: 3394-3398. DOI:10.1073/pnas.93.8.3394
APHIDICOLIN Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from APHIDICOLIN manufacturers
- Product
- APHIDICOLIN 38966-21-1
- Price
- US $1.00/g
- Min. Order
- 1g
- Purity
- ≥98%
- Supply Ability
- g/kg/Ton
- Release date
- 2019-12-25