Naphthablin
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01985 |
| CAS | 167568-51-6 |
| Molecular Weight | 512.59 |
| Molecular Formula | C29H36O8 |
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Description
Naphthablin is an inhibitor produced by Str. aculeolatus.
Specification
| IUPAC Name | [8,10-dihydroxy-9-(1-hydroxy-2-methylbut-3-en-2-yl)-2,5,5-trimethyl-7,12-dioxo-1,2,3,4,4a,12b-hexahydronaphtho[2,3-c]isochromen-3-yl] 2-methylpropanoate |
| Canonical SMILES | CC1CC2C(CC1OC(=O)C(C)C)C(OC3=C2C(=O)C4=CC(=C(C(=C4C3=O)O)C(C)(CO)C=C)O)(C)C |
| InChI | InChI=1S/C29H36O8/c1-8-29(7,12-30)22-18(31)10-16-20(24(22)33)25(34)26-21(23(16)32)15-9-14(4)19(36-27(35)13(2)3)11-17(15)28(5,6)37-26/h8,10,13-15,17,19,30-31,33H,1,9,11-12H2,2-7H3 |
| InChI Key | NPKRLSYRZGLPCT-UHFFFAOYSA-N |
Properties
| Appearance | Orange Powder |
| Boiling Point | 673.8±55.0°C at 760 mmHg |
| Density | 1.3±0.1 g/cm3 |
Reference Reading
1. Naphthablins B and C, Meroterpenoids Identified from the Marine Sediment-Derived Streptomyces sp. CP26-58 Using HeLa Cell-Based Cytological Profiling
Hana Martucci, Scott E Campit, Stephanie R Gee, Walter M Bray, Trevor Gokey, A King Cada, Ten-Yang Yen, Katsuhiko Minoura, Anton B Guliaev, R Scott Lokey, Taro Amagata J Nat Prod. 2017 Mar 24;80(3):684-691. doi: 10.1021/acs.jnatprod.6b00996. Epub 2017 Jan 27.
HeLa cell-based cytological profiling (CP) was applied to an extract library of marine sediment-derived actinomycetes to discover new cytotoxic secondary metabolites. Among the hit strains, Streptomyces sp. CP26-58 was selected for further investigation to identify its cytotoxic metabolites. CP revealed that the known ionophore tetronasin (1) was responsible for the cytotoxic effect found in the extract. Furthermore, three naphthoquinone meroterpenoids, naphthablin A (2) and two new derivatives designated as naphthablins B (3) and C (4), were isolated from other cytotoxic fractions. The structures of the new compounds were elucidated based on analysis of their HRESIMS and comprehensive NMR data. The absolute configurations of the new compounds were deduced by simulating ECD spectra and calculating potential energies for the model compounds using density function theory (DFT) calculations. Compound 1 showed a significant cytotoxic effect against HeLa cells with an IC50 value of 0.23 μM, and CP successfully clustered 1 with calcium ionophores.
2. Isolation from Streptomyces of a novel naphthoquinone compound, naphthablin, that inhibits Abl oncogene functions
K Umezawa, S Masuoka, T Ohse, H Naganawa, S Kondo, Y Ikeda, N Kinoshita, M Hamada, T Sawa, T Takeuchi J Antibiot (Tokyo). 1995 Jul;48(7):604-7. doi: 10.7164/antibiotics.48.604.
In the course of our screening for inhibitors of abl oncogene function, a culture filtrate of Streptomyces aculeolatus, induced normal flat morphology in v-abl-expressing NIH3T3 cells. The active substance was isolated through ethyl acetate extraction, silica gel column chromatography, and reverse-phase HPLC. Mass and NMR spectroscopy including HMBC revealed that it had a novel naphthoquinone structure with a monoterpene, and we named it "naphthablin". Naphthablin inhibited Abl-induced morphological transformation in v-ablts-NIH3T3 cells at around 30 micrograms/ml, and specifically inhibited RNA synthesis.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
