38966-21-1 Usage
Description
(+)-Aphidicolin is a natural tetracyclic diterpene first isolated from the fungus C. aphidicola and shown to have antiviral activity against herpes simplex. In eukaryotic cells, it is a cell-permeable, reversible inhibitor of DNA replication, specifically blocking the activity of DNA polymerases α, δ, and ε when used at low micromolar levels. Aphidicolin can be used, at 3 μM, to arrest cells in G1/S phase or to increase gene amplification frequency.
Chemical Properties
White crystal
Uses
Different sources of media describe the Uses of 38966-21-1 differently. You can refer to the following data:
1. (+)-Aphidicolin is a naturally occurring tetracyclic diterpene with potential antiviral and antimitotical properties.
2. 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.
3. A DNA polymerase inhibitor. Blocks the cell cycle at the early S-phase
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
References
1) Syvaoja et al. (1990), DNA polymerases alpha, delta, and epsilon: three distinct enzymes from HeLa cells; Proc. Natl. Acad. Sci. USA, 87 6664
2) Urbani et al. (1995), Dissociation of nuclear and cytoplasmic cell cycle progression by drugs employed in cell synchronization; Exp. Cell Res., 219 159
3) Kuwakado et al. (1993), Aphidicolin potentiates apoptosis induced by arabinosyl nucleosides in human myeloid leukemia cell lines; Biochem. Pharmacol., 46 1909
4) Yin and Schimke (1996), Inhibition of apoptosis by overexpressing Bcl-2 enhances gene amplification by a mechanism independent of aphidicolin pretreatment; Proc. Natl. Acad. Sci. USA, 93 3394
Check Digit Verification of cas no
The CAS Registry Mumber 38966-21-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,8,9,6 and 6 respectively; the second part has 2 digits, 2 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 38966-21:
(7*3)+(6*8)+(5*9)+(4*6)+(3*6)+(2*2)+(1*1)=161
161 % 10 = 1
So 38966-21-1 is a valid CAS Registry Number.
InChI: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
38966-21-1Relevant articles and documents
A New End Game for Aphidicolin
Rizzo, Carmelo J.,Smith, Amos B.
, p. 2793 - 2796 (1988)
A highly efficient, stereocontrolled synthesis of aphidicolin from its degradation product, 3α,18-isopropylidenedioxy-17-noraphidicolan-16-one, has been achieved.
The hydroxylation at C-17 in the biosynthesis of the diterpenoid aphidicolin
Hanson, James R.,Hitchcock, Peter B.,Jarvis, Andrew G.
, p. 1055 - 1059 (2007/10/03)
The hydroxylation at C-17 in aphidicolin biosynthesis is inhibited by a 17-thiol. A metabolite hydroxylated at C-17 and retaining the cyclopropane ring was obtained from 3α,18-dihydroxy-15β,16β-methanoaphidicolane whilst aphidicolin itself was obtained from 3α,18-dihydroxyaphidicolane when these substrates were incubated with the fungus, Cephalosporium aphidicola.
Rearrangements of the C/D Ring System of the Tetracyclic Diterpenoid, Aphidicolin
Hanson, James R.,Hitchcock, Peter B.,Jarvis, Andrew G.,Ratcliffe, Arnold H.
, p. 1773 - 1778 (2007/10/02)
The generation of a C-16 carbocation in the aphidicolane series by the hydrolysis of a 15β,16β- or a 16β,17-epoxide is shown to lead, inter alia, to skeletal rearrangement products arising from the migration of the C(12)-C(13) bond to C-16.
