Setomimycin
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| Category | Antibiotics |
| Catalog number | BBF-03452 |
| CAS | 69431-87-4 |
| Molecular Weight | 580.58 |
| Molecular Formula | C34H28O9 |
| Purity | >95% by HPLC |
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Description
It is produced by the strain of Str. pseudovenezuelae AM-2947. It has anti-gram-positive bacteria and mycobacteria effects, and has the effect of inhibiting sarcoma-180.
Specification
| Synonyms | A-39183B; Antibiotic A-39183B |
| Storage | Store at-20°C |
| IUPAC Name | 4-acetyl-10-[(1R,2S)-1-acetyl-2,5,10-trihydroxy-2-methyl-4-oxo-1,3-dihydroanthracen-9-yl]-8,9-dihydroxy-3-methyl-4H-anthracen-1-one |
| Canonical SMILES | CC1=CC(=O)C2=C(C3=C(C=CC=C3O)C(=C2C1C(=O)C)C4=C5C(C(CC(=O)C5=C(C6=C4C=CC=C6O)O)(C)O)C(=O)C)O |
| InChI | InChI=1S/C34H28O9/c1-13-11-20(39)27-29(22(13)14(2)35)25(16-7-5-9-18(37)23(16)32(27)41)26-17-8-6-10-19(38)24(17)33(42)28-21(40)12-34(4,43)31(15(3)36)30(26)28/h5-11,22,31,37-38,41-43H,12H2,1-4H3/t22?,31-,34+/m1/s1 |
| InChI Key | BIEJOJJMQZEKED-DEFMRNBESA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | Red-orange Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Neoplastics (Tumor); Mycobacteria |
| Boiling Point | 841.9°C at 760 mmHg |
| Melting Point | 176-178°C |
| Density | 1.479 g/cm3 |
| Solubility | Soluble in Methanol, Chloroform |
Reference Reading
1. Isolation and anticancer activity evaluation of rare Bisaryl anthraquinone antibiotics from novel Streptomyces sp. strain of NW Himalayan region
Snigdha Sharma, Amit Kumar, Asha Chaubey, Amit Nargotra, Debaraj Mukherjee, Ravi Singh Manhas, Ajaz Ahmed, Syed Mudabir Ahmad, Khalid Bashir Mir, Utpal Nandi, Anindya Goswami, Harshita Tiwari, Diksha Manhas Chem Biol Interact . 2022 Sep 25;365:110093. doi: 10.1016/j.cbi.2022.110093.
Biosynthesis of bisaryl preanthraquinone antibiotics by various microorganisms differs in monomeric subunits as well as their dimerization positions leading to different configurations. The present study relates to the production of rare bisaryl anthraquinone antibiotics by a new Streptomyces strain isolated from Shivalik region of NW Himalayas. In vitro anticancer and anti-migratory effects of Setomimycin (9,9' bisanthraquinone antibiotic) was seen with a significant reduction in the expression of both MEK as well as ERK pathways in a dose dependent manner at 6.5 μM & 8 μM concentration in HCT-116 and 5.5 μM & 7 μM concentration in MCF-7 cells. In vivo studies in aggressive orthotopic mouse mammary carcinoma model (4T1) demonstrated about 76% reduction of primary tumor weight and 90.5% reduction in the tumor volume within two weeks. In vivo pharmacokinetics study of setomimycin revealed that it can be rapidly absorbed with an adequate plasma exposure and half-life which can be linked to its in vivo efficacy.
2. Setomimycin as a potential molecule for COVID‑19 target: in silico approach and in vitro validation
Sreedhar Madishetti, Asha Chaubey, Amit Nargotra, Debaraj Mukherjee, Mateen Noor, Raja B M Tripathi, Ajaz Ahmed, Ravishankar Ramachandran, Jyoti Vishwakarma, Ravi S Manhas, Harshita Tiwari Mol Divers . 2022 May 27;1-15. doi: 10.1007/s11030-022-10441-5.
COVID-19 pandemic caused by the SARS-CoV-2 virus has led to a worldwide crisis. In view of emerging variants time to time, there is a pressing need of effective COVID-19 therapeutics. Setomimycin, a rare tetrahydroanthracene antibiotic, remained unexplored for its therapeutic uses. Herein, we report our investigations on the potential of setomimycin as COVID-19 therapeutic. Pure setomimycin was isolated from Streptomyces sp. strain RA-WS2 from NW Himalayan region followed by establishing in silico as well as in vitro anti-SARS-CoV-2 property of the compound against SARS-CoV-2 main protease (Mpro). It was found that the compound targets Mproenzyme with an IC50value of 12.02 ± 0.046 μM. The molecular docking study revealed that the compound targets Glu166 residue of Mproenzyme, hence preventing dimerization of SARS-CoV-2 Mpromonomer. Additionally, the compound also exhibited anti-inflammatory and anti-oxidant property, suggesting that setomimycin may be a viable option for application against COVID-19 infections.
3. Genome Analysis of Streptomyces nojiriensis JCM 3382 and Distribution of Gene Clusters for Three Antibiotics and an Azasugar across the Genus Streptomyces
Seung-Young Kim, Chang-Gu Hyun, Hak Cheol Kwon, Jaeyoung Choi, Sung-Chul Hong, Jin-Soo Park, Da-Eun Kim Microorganisms . 2021 Aug 25;9(9):1802. doi: 10.3390/microorganisms9091802.
Streptomycesspp. have been major contributors of novel natural products that are used in many application areas. We found that the nojirimycin (NJ) producer JCM 3382 has antimicrobial activity againstStaphylococcus aureusvia cellular degradation. Genome analysis revealed 30 biosynthetic gene clusters, including those responsible for producing antibiotics, including an azasugar NJ. In-depth MS/MS analysis confirmed the production of 1-deoxynojirimycin (DNJ) along with NJ. In addition, the production of tambromycins, setomimycin, and linearmycins was verified by spectroscopic analyses, including LC-MS and NMR. The distribution of the clusters of genes coding for antibiotics in 2061Streptomycesgenomes suggested potential producers of tambromycin, setomimycin, and linearmycin. For a DNJ gene cluster, homologs ofgabT1andgutB1were commonly found; however,yktC1was identified in only 112 genomes. The presence of several types of clusters suggests that different strains may produce different types of azasugars. Chemical-profile-inspired comparative genome analysis may facilitate a more accurate assessment of the biosynthetic potential to produce secondary metabolites.
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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 ╳
