(+)-Aphidicolin

Names

[ Name ]:
(+)-Aphidicolin

[Synonym ]:
(1S,2S,5R,6R,7R,10S,12R,13R)-6,13-Bis(hydroxymethyl)-2,6-dimethyltetracyclo[10.3.1.0.0]hexadecane-5,13-diol
9-dimethanol,tetradecahydro-3,9-11a-methano-11ah-cyclohepta(a)naphthalene-4
Aphidicholin
Apchidicolin
MFCD00083214
APC
(3R,4R,4aR,6aS,8R,9R,11aS,11bS)-4,9-bis(hydroxymethyl)-4,11b-dimethyltetradecahydro-8,11a-methanocyclohepta[a]naphthalene-3,9-diol
Aphidicolin from Nigrospora sphaerica
APHIDICOLIN
UNII:6B3F8QW8TU
aphidocolin
(3a,4a,5a,17a)-3,17-Dihydroxy-4-methyl-9,15-cyclo- C,18-dinor-14,15-secoandrostane-4,17-dimethanol
8,11a-Methano-11aH-cyclohepta[a]naphthalene-4,9-dimethanol, tetradecahydro-3,9-dihydroxy-4,11b-dimethyl-, (3R,4R,4aR,6aS,8R,9R,11aS,11bS)-

Biological Activity

[Description]:

Aphidicolin is an inhibitor of DNA polymerase α and δ, prevents mitotic cell division by interfering with the activity of DNA polymerase[1].Aphidicolin is an antibiotic produced by the mold Cephalosporium aphidicola. Aphidicolin is a potent inhibitor of cellular deoxyribonucleic acid synthesis and inhibits the growth of herpes simplex virus[2].Aphidicolin potentiates apoptosis induced by arabinosyl nucleosides in a human promyelocytic leukemia cell line[3].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Cell Cycle/DNA Damage >> DNA/RNA Synthesis

Research Areas >> Inflammation/Immunology

[References]

[1]. Dresler SL, et al. Involvement of DNA polymerase delta in DNA repair synthesis in human fibroblasts at late times after ultraviolet irradiation. Biochemistry. 1988 Aug 23;27(17):6379-83.

[2]. Bucknall RA, et al. Antiviral effects of aphidicolin, a new antibiotic produced by Cephalosporium aphidicola. Antimicrob Agents Chemother. 1973 Sep;4(3):294-8.

[3]. Kuwakado K, et al. Aphidicolin potentiates apoptosis induced by arabinosyl nucleosides in human myeloid leukemiacell lines. Biochem Pharmacol. 1993 Dec 3;46(11):1909-16.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
507.8±50.0 °C at 760 mmHg

[ Melting Point ]:
225-233ºC

[ Molecular Formula ]:
C₂₀H₃₄O₄

[ Molecular Weight ]:
338.482

[ Flash Point ]:
230.4±24.7 °C

[ Exact Mass ]:
338.245697

[ PSA ]:
80.92000

[ LogP ]:
1.69

[ Vapour Pressure ]:
0.0±3.0 mmHg at 25°C

[ Index of Refraction ]:
1.586

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: PB9185000

CHEMICAL NAME :: 8,11a-Methano-11aH-cyclohepta(a)naphthalene-4,9-dimet hanol, tetradecahydro-3,9-dihydroxy- 4,11b-dimethyl-, (3R-(3-alpha,4-alpha,4a-alpha,6a-beta,8-beta,9-beta,1 1a-beta,11b-beta))-

CAS REGISTRY NUMBER :: 38966-21-1

LAST UPDATED :: 199612

DATA ITEMS CITED :: 26

MOLECULAR FORMULA :: C20-H34-O4

MOLECULAR WEIGHT :: 338.54

WISWESSER LINE NOTATION :: L C6 B656 A 1B P BXTJ C1 FQ G1Q NQ N1Q

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :: Cytogenetic analysis

TEST SYSTEM :: Mammal - species unspecified Fibroblast

DOSE/DURATION :: 15 umol/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 160,103,1986

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Safety Phrases ]:
S22-S24

[ RIDADR ]:
NA 1993 / PGIII

[ WGK Germany ]:
3

[ RTECS ]:
PB9185000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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