Nanaomycin A
Nanaomycin A is a selective inhibitor of DNA methyltransferase 3B (DNMT3B) with IC50 value of 500 nM [1].
In the biochemical in vitro methylation assay, Nanaomycin A showed selective inhibition of DNMT3B but not DNMT1 although it was docked to the catalytic domain of human DNMT1 in a multi-step docking approach. Nanaomycin A showed cell viability inhibition in HCT116, A549 and HL60 cells with IC50 values of 400 nM, 4100 nM and 800 nM, respectively. It decreased the genomic methylation level of these cells significantly. Besides that, Nanaomycin A treatment resulted in demethylation of the RASSF1A promoter in A549 cells. The demethylation caused by Nanaomycin A reactivated the transcription and expression of a silenced tumor suppressor gene [1].
References:
[1] Kuck D, Caulfield T, Lyko F, et al. Nanaomycin A selectively inhibits DNMT3B and reactivates silenced tumor suppressor genes in human cancer cells. Molecular cancer therapeutics, 2010, 9(11): 3015-3023.
- 1. Chao-Cheng Cho, Chun-Jung Lin, et al. "Mechanistic Insights into Harmine-Mediated Inhibition of Human DNA Methyltransferases and Prostate Cancer Cell Growth." ACS Chem Biol. 2023 Jun 16;18(6):1335-1350. PMID: 37188336
- 2. Daehwan Kim, Subin Kim, et al. "Autologous treatment for ALS with implication for broad neuroprotection." Transl Neurodegener. 2022 Mar 11;11(1):16. PMID: 35272709
- 3. Liu PY, Sokolowski N, et al. "The BET bromodomain inhibitor exerts the most potent synergistic anticancer effects with quinone-containing compounds and anti-microtubule drugs." Oncotarget. 2016 Nov 29;7(48):79217-79232. PMID: 27764794
- 4. Nicolson SC, Li C, et al. "Identification and validation of small molecules that enhance recombinant Adeno-associated virus transduction following high throughput screen." J Virol. 2016 May 4. pii: JVI.02953-15. PMID: 27147738
| Physical Appearance | A solid |
| Storage | Store at -20°C |
| M.Wt | 302.28 |
| Cas No. | 52934-83-5 |
| Formula | C16H14O6 |
| Synonyms | Nanafrocin, Nanafrocine, Nanafrocinum, Rosanomycin A |
| Solubility | insoluble in H2O; ≥15.1 mg/mL in DMSO; ≥31.07 mg/mL in EtOH with ultrasonic |
| Chemical Name | 2-[(1S,3S)-9-hydroxy-1-methyl-5,10-dioxo-3,4-dihydro-1H-benzo[g]isochromen-3-yl]acetic acid |
| SDF | Download SDF |
| Canonical SMILES | OC1=CC=CC(C(C2=C3[C@H](C)O[C@H](CC(O)=O)C2)=O)=C1C3=O |
| Shipping Condition | Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice. |
| General tips | We do not recommend long-term storage for the solution, please use it up soon. |
| Cell experiment[1]: | |
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Cell lines |
A549, HL60, HeLa and HCT116 cells |
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Preparation method |
The solubility of this compound in DMSO is >10 mM. General tips for obtaining a higher concentration: Please warm the tube at 37 °C for 10 minutes and/or shake it in the ultrasonic bath for a while.Stock solution can be stored below -20°C for several months. |
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Reaction Conditions |
Ranging from 10 nM to 10 μM for 72 h |
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Applications |
Nanaomycin A, initially identified by a virtual screening for inhibitors against DNMT1, as a compound inducing antiproliferative effects in three different tumor cell lines originating from different tissues. Nanaomycin A treatment reduced the global methylation levels in all three cell lines and reactivated transcription of the RASSF1A tumor suppressor gene. In biochemical assays, nanaomycin A revealed selectivity toward DNMT3B. |
| Animal experiment [2]: | |
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Animal models |
Guinea pigs |
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Applications |
The therapeutic effect of nanaomycin A and siccanin against experimental cutaneous Trichophyton mentagrophytes infection in guinea pigs was investigated. Topically applied formulation of nanaomycin A was very effective in improving the condition of lesions and in preventing fungal growth in the infected tissues. Nanaomycin A and siccanin were comparable in activity in experiments. |
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Other notes |
Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal. |
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References: 1. Kuck D1, Caulfield T, Lyko F 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. Kitaura K, Araki Y, Marumo H. The therapeutic effect of nanaomycin A against experimental Trichophyton mentagrophytes infection in guinea pigs. Kitaura K, Araki Y, Marumo H. |
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| Description | Nanaomycin A is a selective inhibitor of DNMT3B. | |||||
| Targets | DNMT3B | |||||
| IC50 | 500 nM | |||||
Quality Control & MSDS
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