Neoaureothin
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| Category | Antibiotics |
| Catalog number | BBF-02597 |
| CAS | 59795-94-7 |
| Molecular Weight | 477.55 |
| Molecular Formula | C28H31NO6 |
| Purity | ≥98% |
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Description
Neoaureothin is a metabolite produced by Streptomyces. It acts as an androgen receptor (AR) antagonist that inhibits binding of dihydrotestosterone (DHT) to ARs and inhibits DHT-induced expression of prostate-specific antigen in LNCaP cells (IC50 = 1.75 nM).
Specification
| Related CAS | 11042-60-7 (Deleted CAS) 28900-27-8 (Deleted CAS) |
| Synonyms | 4H-Pyran-4-one, 2-methoxy-3,5-dimethyl-6-[(2R,4Z)-tetrahydro-4-[(2E,4E,6E)-2,4,6-trimethyl-7-(4-nitrophenyl)-2,4,6-heptatrien-1-ylidene]-2-furanyl]-; 2-Methoxy-3,5-dimethyl-6-[(2R,4Z)-tetrahydro-4-[(2E,4E,6E)-2,4,6-trimethyl-7-(4-nitrophenyl)-2,4,6-heptatrien-1-ylidene]-2-furanyl]-4H-pyran-4-one; 4H-Pyran-4-one, 2-methoxy-3,5-dimethyl-6-[tetrahydro-4-[2,4,6-trimethyl-7-(4-nitrophenyl)-2,4,6-heptatrienylidene]-2-furanyl]-, (Z,E,E,E)-(+)-; (+)-Spectinabilin; NSC 260179; Spectinabilin; Spectinabiline |
| Storage | Store at -20°C |
| IUPAC Name | 2-methoxy-3,5-dimethyl-6-[(2R,4Z)-4-[(2E,4E,6E)-2,4,6-trimethyl-7-(4-nitrophenyl)hepta-2,4,6-trienylidene]oxolan-2-yl]pyran-4-one |
| Canonical SMILES | CC1=C(OC(=C(C1=O)C)OC)C2CC(=CC(=CC(=CC(=CC3=CC=C(C=C3)[N+](=O)[O-])C)C)C)CO2 |
| InChI | InChI=1S/C28H31NO6/c1-17(11-18(2)13-22-7-9-24(10-8-22)29(31)32)12-19(3)14-23-15-25(34-16-23)27-20(4)26(30)21(5)28(33-6)35-27/h7-14,25H,15-16H2,1-6H3/b17-11+,18-13+,19-12+,23-14-/t25-/m1/s1 |
| InChI Key | IZICQJAGBLBAMJ-QDYRYYKCSA-N |
Properties
| Appearance | Orange Yellow Acicular Crystal |
| Antibiotic Activity Spectrum | Fungi; Viruses |
| Boiling Point | 660.7°C at 760 mmHg |
| Melting Point | 105-106°C |
| Density | 1.2 g/cm3 |
| Solubility | Soluble in DMF, DMSO, Ethanol, Methanol, Water (Poorly) |
Reference Reading
1. The complete genomic sequence of Streptomyces spectabilis NRRL-2792 and identification of secondary metabolite biosynthetic gene clusters
Arkadeep Sinha, Silvia Phillips-Salemka, Tanu-Adhikari Niraula, Kevin A Short, Narayan P Niraula J Ind Microbiol Biotechnol. 2019 Aug;46(8):1217-1223. doi: 10.1007/s10295-019-02172-8. Epub 2019 Jun 13.
This is the first report of a fully annotated genomic sequence of Streptomyces spectabilis NRRL-2792, isolated and identified by The Upjohn Company in 1961. The genome was assembled into a single scaffold for annotation and analysis. The chromosome is linear, 9.5 Mb in size which is one of the largest Streptomyces genomes yet described, has a G+C content of 72%, and encodes for approximately 7943 genes. Antibiotic Secondary Metabolite Analysis Shell (antiSMASH) and Basic Local Alignment Search Tool (BLAST) bioinformatics analyses identified six complete secondary metabolite biosynthetic gene clusters for ectoine, melanin, albaflavenone, spectinomycin, 2-methylisoborneol and coelichelin. Additionally, biosynthetic clusters were identified that shared ≥ 90% gene content with complestatin, hopene, neoaureothin, or undecylprodigiosin. Thirty-one other likely secondary metabolite gene clusters were identified by antiSMASH. BLAST identified two subsets of undecylprodigiosin biosynthetic genes at polar opposites of the chromosome; their duplication was subsequently confirmed by primer walking.
2. Potent inhibition of HIV replication in primary human cells by novel synthetic polyketides inspired by Aureothin
Alexander Herrmann, Manfred Roesner, Thomas Werner, Stefanie M Hauck, Alisha Koch, Amelie Bauer, Martha Schneider, Ruth Brack-Werner Sci Rep. 2020 Jan 28;10(1):1326. doi: 10.1038/s41598-020-57843-9.
Overcoming the global health threat of HIV infection requires continuous pipelines of novel drug candidates. We identified the γ-pyrone polyketides Aureothin/Neoaureothin as potent hits by anti-HIV screening of an extensive natural compound collection. Total synthesis of a structurally diverse group of Aureothin-derivatives successfully identified a lead compound (#7) superior to Aureothin that combines strong anti-HIV activity (IC90<45 nM), photostability and improved cell safety. Compound #7 inhibited de novo virus production from integrated proviruses by blocking the accumulation of HIV RNAs that encode the structural components of virions and include viral genomic RNAs. Thus, the mode-of-action displayed by compound #7 is different from those of all current clinical drugs. Proteomic analysis indicated that compound #7 does not affect global protein expression in primary blood cells and may modulate cellular pathways linked to HIV infection. Compound #7 inhibited multiple HIV genotypes, including HIV-type 1 and 2 and synergistically inhibited HIV in combination with clinical reverse transcriptase and integrase inhibitors. We conclude that compound #7 represents a promising new class of HIV inhibitors that will facilitate the identification of new virus-host interactions exploitable for antiviral attack and holds promise for further drug development.
3. Emulating evolutionary processes to morph aureothin-type modular polyketide synthases and associated oxygenases
Huiyun Peng, Keishi Ishida, Yuki Sugimoto, Holger Jenke-Kodama, Christian Hertweck Nat Commun. 2019 Sep 2;10(1):3918. doi: 10.1038/s41467-019-11896-1.
Polyketides produced by modular type I polyketide synthases (PKSs) play eminent roles in the development of medicines. Yet, the production of structural analogs by genetic engineering poses a major challenge. We report an evolution-guided morphing of modular PKSs inspired by recombination processes that lead to structural diversity in nature. By deletion and insertion of PKS modules we interconvert the assembly lines for related antibiotic and antifungal agents, aureothin (aur) and neoaureothin (nor) (aka spectinabilin), in both directions. Mutational and functional analyses of the polyketide-tailoring cytochrome P450 monooxygenases, and PKS phylogenies give contradictory clues on potential evolutionary scenarios (generalist-to-specialist enzyme evolution vs. most parsimonious ancestor). The KS-AT linker proves to be well suited as fusion site for both excision and insertion of modules, which supports a model for alternative module boundaries in some PKS systems. This study teaches important lessons on the evolution of PKSs, which may guide future engineering approaches.
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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
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g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
