52934-83-5

Basic information

• Product Name: NANAOMYCIN A
• Synonyms: (1s-e)-10-dioxo;1h-naphtho(2,3-c)pyran-3-aceticacid,3,4,5,10-tetrahydro-9-hydroxy-1-methyl-5,;os-3966-a;rosanomycina;Antibiotic OS 3966A, Nanafrocin, 1H-Naphtho[2,3-c]pyran-3-acetic acid,3,4,5,10-tetrahydro-9-hydroxy-1-methyl-5,10-dioxo-(1S,3R)-;(1S)-3,4,5,10-Tetrahydro-9-hydroxy-1-methyl-5,10-dioxo-1H-naphtho[2,3-c]pyran-3β-acetic acid;(1S,3R)-3,4,5,10-Tetrahydro-9-hydroxy-1-methyl-5,10-dioxo-1H-naphtho[2,3-c]pyran-3-acetic acid
• CAS NO: 52934-83-5
• Molecular Formula: C₁₆H₁₄O₆
• Molecular Weight: 302.281
• Mol File: 52934-83-5.mol

Chemical Properties

• Melting Point: 179°C
• Boiling Point: 363.32°C (rough estimate)
• Flash Point: 229°C
• Appearance: /
• Density: 1.2514 (rough estimate)
• Vapor Pressure: 2.56E-15mmHg at 25°C
• Refractive Index: 1.4600 (estimate)
• Storage Temp.: −20°C
• Solubility: insoluble in H2O; ≥15.1 mg/mL in DMSO; ≥31.07 mg/mL in EtOH with ultrasonic
• CAS DataBase Reference: NANAOMYCIN A(CAS DataBase Reference)
• NIST Chemistry Reference: NANAOMYCIN A(52934-83-5)
• EPA Substance Registry System: NANAOMYCIN A(52934-83-5)

Safety Data

• Hazard Codes: T
• Statements: 22-24
• Safety Statements: 36/37-45
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: QL6127000
• Hazardous Substances Data: 52934-83-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
NANAOMYCIN A is used as an antibiotic for treating bacterial infections. Its potent antimicrobial activity makes it a valuable compound in the development of new drugs to combat resistant bacteria.
Used in Research and Development:
NANAOMYCIN A serves as a crucial compound in the field of microbiology and pharmaceutical research. It is utilized for studying the mechanisms of antibiotic action, resistance, and the development of novel antimicrobial agents.
Used in Agricultural Industry:
In agriculture, NANAOMYCIN A can be employed as a biopesticide to control bacterial diseases in crops, thereby improving crop yield and reducing the reliance on chemical pesticides.

Biological Activity

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.

InChI:InChI=1/C16H14O6/c1-7-13-10(5-8(22-7)6-12(18)19)15(20)9-3-2-4-11(17)14(9)16(13)21/h2-4,7-8,17H,5-6H2,1H3,(H,18,19)/t7-,8+/m0/s1

Upstream product

• 29394-61-4 Kalafungin 
• 958730-34-2 6-deoxykalafungin 

Relevant articles and documents

Unveiling Two Consecutive Hydroxylations: Mechanisms of Aromatic Hydroxylations Catalyzed by Flavin-Dependent Monooxygenases for the Biosynthesis of Actinorhodin and Related Antibiotics

Flavin-dependent monooxygenases are ubiquitous in living systems and are classified into single- or two-component systems. Actinorhodin, produced by Streptomyces coelicolor, is a representative polycyclic polyketide that is hydroxylated through the action of the two-component ActVA-5/ActVB hydroxylase system. These homologous systems are widely distributed in bacteria, but their reaction mechanisms remain unclear. This in vitro investigation has provided chemical proof of two consecutive hydroxylations via hydroxynaphthalene intermediates involved in actinorhodin biosynthesis. The ActVA-5 oxygenase component catalyzed a stepwise dihydroxylation of the substrate, whereas the ActVB flavin reductase not only supplied a reduced cofactor, but also regulated the quinone–hydroquinone interconversion of an intermediate. Our study provides clues for understanding the general biosynthetic mechanisms of highly functionalized aromatic natural products with structural diversity.

Epoxyquinone formation catalyzed by a two-component flavin-dependent monooxygenase involved in biosynthesis of the antibiotic actinorhodin

The biosynthetic gene cluster of the aromatic polyketide antibiotic actinorhodin (ACT) in Streptomyces coelicolor A3(2) carries a pair of genes, actVA-ORF5 and actVB, that encode a two-component flavin-dependent monooxygenase (FMO). Our previous studies have demonstrated that the ActVA-ORF5/ActVB system functions as a quinone-forming C-6 oxygenase in ACT biosynthesis. Furthermore, we found that this enzyme system exhibits an additional oxygenation activity with dihydrokalafungin (DHK), a proposed intermediate in the ACT biosynthetic pathway, and generates two reaction products. These compounds were revealed to be monooxygenated derivatives of kalafungin, which is spontaneously formed through oxidative lactonization of DHK. Their absolute structures were elucidated from their NMR spectroscopic data and by computer modeling and X-ray crystallography as (5S,14R)-epoxykalafungin and (5R,14S)-epoxykalafungin, demonstrating an additional epoxyquinone-forming activity of the ActVA-ORF5/ActVB system in vitro.

Enantiodivergent total syntheses of nanaomycins and their enantiomers, kalafungins

The first, enantiospecific total syntheses of pyranonaphthoquinone antibiotics, nanaomycins D and A, and their enantiomers kalafungin and 4-deoxykalafunginic acid, are described by an 'enantiodivergent' strategy from a common optically active intermediate, (1S,3RS,4S)-3,4-dihydro-5,9,10-trimethoxy-1-methyl-1H-naphtho[2,3-c]pyr an-3,4-diol, which has been derived from L-rhamnose via condensation of 4-methoxy-3-(phenylsulfonyl)-1-(3H)-isobenzofuranone and methyl 3,4,6-trideoxy-α-L-glycero-hex-3-enopyranosid-2-ulose.