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Nanafrocin

Names

[ CAS No. ]:
52934-83-5

[ Name ]:
Nanafrocin

[Synonym ]:
(1S-E)-3,4,5,10-Tetrahydro-9-hydroxy-1-methyl-5,10-dioxo-1H-naphtho[2,3-c]pyran-3-acetic Acid
4-deoxykalafunginic acid
1H-Naphtho[2,3-c]pyran-3-acetic acid, 3,4,5,10-tetrahydro-9-hydroxy-1-methyl-5,10-dioxo-, (1S,3R)-
dihydrokalafungin
2-[(1S,3R)-9-hydroxy-1-methyl-5,10-dioxo-3,4-dihydro-1H-benzo[g]isochromen-3-yl]acetic acid
Rosanomycin A
Nanafrocine
Nanafrocinum
nanaomycin A
nanafrocinum [INN_la]
(1S,3R)-3,4,5,10-Tetrahydro-9-hydroxy-1-methyl-5,10-dioxo-1H-naphtho[2,3-c]pyran-3-acetic Acid
OS 3966-A
[(1S,3R)-9-Hydroxy-1-methyl-5,10-dioxo-3,4,5,10-tetrahydro-1H-benzo[g]isochromen-3-yl]acetic acid
Nanafrocin

Biological Activity

[Description]:

Nanaomycin A is the first selective DNMT3B inhibitor with an IC50 of 500 nM. Nanaomycin A, a quinone antibiotics, reactivates silenced tumor suppressor genes in human cancer cells[1]. Nanaomycin A inhibits in vitro growth of the human malaria parasite Plasmodium falciparum with an IC80 value of 33.1 nM[2].

[Related Catalog]:

Research Areas >> Cancer
Research Areas >> Infection
Signaling Pathways >> Epigenetics >> DNA Methyltransferase

[Target]

DNMT3B:500 nM (IC50)


[In Vitro]

Nanaomycin A (10-10000 nM; 72 hours) has a distinct cytotoxic effect in all three cell lines[1]. Nanaomycin A (0.5, 5 μM; 72 hours) reveals induction of RASSF1A protein expression in A549 cells[1]. Nanaomycin A (5 μM; 72 hours) has an 18-fold relative induction[1]. Nanaomycin A not affects the enzymatic activity of DNMT1[1]. Cell Cytotoxicity Assay[1] Cell Line: HCT116 (colon), A549 (lung), and HL60 (bone marrow) human tumor cell lines Concentration: 10, 100, 1000, 10000 nM Incubation Time: 72 hours Result: Had a distinct cytotoxic effect in all three cell lines. Western Blot Analysis[1] Cell Line: A549 cells Concentration: 0.5, 5 μM Incubation Time: 72 hours Result: Revealed induction of RASSF1A protein expression. RT-PCR[1] Cell Line: A549 cells Concentration: 5 μM Incubation Time: 72 hours Result: Had an 18-fold relative induction.

[References]

[1]. Kuck D, et al.Nanaomycin A selectively inhibits DNMT3B and reactivates silenced tumor suppressor genes in human cancer cells.Mol Cancer Ther. 2010 Nov;9(11):3015-23.

[2]. Tanaka Y, et al.Heme-dependent radical generation: possible involvement in antimalarial action of non-peroxide microbial metabolites, nanaomycin A and radicicol.J Antibiot (Tokyo). 1999 Oct;52(10):880-8.

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
601.5±55.0 °C at 760 mmHg

[ Molecular Formula ]:
C16H14O6

[ Molecular Weight ]:
302.279

[ Flash Point ]:
229.0±25.0 °C

[ Exact Mass ]:
302.079041

[ PSA ]:
100.90000

[ LogP ]:
2.60

[ Vapour Pressure ]:
0.0±1.8 mmHg at 25°C

[ Index of Refraction ]:
1.649

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
QL6127000
CHEMICAL NAME :
1H-Naphtho(2,3-c)pyran-3-acetic acid, 3,4,5,10-tetrahydro-9-hydroxy-1-methyl-5,10-dioxo-, (1S-E)-
CAS REGISTRY NUMBER :
52934-83-5
LAST UPDATED :
199306
DATA ITEMS CITED :
7
MOLECULAR FORMULA :
C16-H14-O6
MOLECULAR WEIGHT :
302.30
WISWESSER LINE NOTATION :
T C666 BV EO IVT&&J D1 F1VQ NQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>200 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 33,728,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
52 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 33,728,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
290 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 28,860,1975
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
52 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 33,728,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
28200 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 28,860,1975
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
56 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 33,728,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
52 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 33,728,1980

Safety Information

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
22-24

[ RIDADR ]:
UN 2811 6.1/PG 3

Related Compounds