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MedKoo Cat#: 592748 | Name: Setomimycin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Setomimycin is an antibiotic. 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

Chemical Structure

Setomimycin
Setomimycin
CAS#69431-87-4

Theoretical Analysis

MedKoo Cat#: 592748

Name: Setomimycin

CAS#: 69431-87-4

Chemical Formula: C34H28O9

Exact Mass: 580.1733

Molecular Weight: 580.59

Elemental Analysis: C, 70.34; H, 4.86; O, 24.80

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Synonym
Setomimycin; Antibiotic A 39183B; AM-2947; AM 2947; AM2947
IUPAC/Chemical Name
(9,9'-Bianthracene)-4,4'(1H,1'H)-dione, 1,1'-diacetyl-2,3-dihydro-2,5,5',10,10'-pentahydroxy-2,2'-dimethyl-
InChi Key
BIEJOJJMQZEKED-UHFFFAOYSA-N
InChi Code
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
SMILES Code
C1[C@@]([C@@H](c2c(c3cccc(c3c(c2C1=O)O)O)c1c2cccc(c2c(c2C(C=C([C@@H](c12)C(=O)C)C)=O)O)O)C(=O)C)(C)O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Setomimycin is active against a variety of Gram-positive bacteria, including S. aureus, B. subtilis, B. cereus, and M. smegmatis (with MIC values of 1.56-3.13 µg/ml). Setomimycin also reduces tumor growth in a Sarcoma-180 mouse solid tumor model when administered at a dose of 200 mg/kg per day for seven days.
In vitro activity:
Setomimycin may be a viable option for application against COVID-19 infections. Setomimycin targeted the Mpro enzyme with an IC50 value of 12.02 ± 0.046 μM. Setomimycin targeted the Glu166 residue of Mpro enzyme, preventing dimerization of the SARS-CoV-2 Mpro monomer. Setomimycin also exhibited anti-inflammatory and anti-oxidant properties. Reference: Mol Divers. 2023 Apr;27(2):619-633. https://pubmed.ncbi.nlm.nih.gov/35622309/
In vivo activity:
To be determined

Preparing Stock Solutions

The following data is based on the product molecular weight 580.59 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Manhas RS, Ahmad SM, Mir KB, Ahmed A, Sharma S, Manhas D, Tiwari H, Kumar A, Nargotra A, Nandi U, Mukherjee D, Goswami A, Chaubey A. Isolation and anticancer activity evaluation of rare Bisaryl anthraquinone antibiotics from novel Streptomyces sp. strain of NW Himalayan region. Chem Biol Interact. 2022 Sep 25;365:110093. doi: 10.1016/j.cbi.2022.110093. Epub 2022 Aug 17. PMID: 35985519. 2. Manhas RS, Tiwari H, Noor M, Ahmed A, Vishwakarma J, Tripathi RBM, Ramachandran R, Madishetti S, Mukherjee D, Nargotra A, Chaubey A. Setomimycin as a potential molecule for COVID‑19 target: in silico approach and in vitro validation. Mol Divers. 2023 Apr;27(2):619-633. doi: 10.1007/s11030-022-10441-5. Epub 2022 May 27. Erratum in: Mol Divers. 2022 Aug 29;: PMID: 35622309; PMCID: PMC9136828.
In vitro protocol:
1. Manhas RS, Ahmad SM, Mir KB, Ahmed A, Sharma S, Manhas D, Tiwari H, Kumar A, Nargotra A, Nandi U, Mukherjee D, Goswami A, Chaubey A. Isolation and anticancer activity evaluation of rare Bisaryl anthraquinone antibiotics from novel Streptomyces sp. strain of NW Himalayan region. Chem Biol Interact. 2022 Sep 25;365:110093. doi: 10.1016/j.cbi.2022.110093. Epub 2022 Aug 17. PMID: 35985519. 2. Manhas RS, Tiwari H, Noor M, Ahmed A, Vishwakarma J, Tripathi RBM, Ramachandran R, Madishetti S, Mukherjee D, Nargotra A, Chaubey A. Setomimycin as a potential molecule for COVID‑19 target: in silico approach and in vitro validation. Mol Divers. 2023 Apr;27(2):619-633. doi: 10.1007/s11030-022-10441-5. Epub 2022 May 27. Erratum in: Mol Divers. 2022 Aug 29;: PMID: 35622309; PMCID: PMC9136828.
In vivo protocol:
To be determined
1: Hyun KA, Liang X, Xu Y, Kim SY, Boo KH, Park JS, Chi WJ, Hyun CG. Analysis of the Setomimycin Biosynthetic Gene Cluster from Streptomyces nojiriensis JCM3382 and Evaluation of Its α-Glucosidase Inhibitory Activity Using Molecular Docking and Molecular Dynamics Simulations. Int J Mol Sci. 2024 Oct 6;25(19):10758. doi: 10.3390/ijms251910758. PMID: 39409089; PMCID: PMC11476836. 2: Wang W, Liu JS, Zhou JW, Jia AQ. Synergistic effect of kanamycin and amikacin with setomimycin on biofilm formation inhibition of Listeria monocytogenes. Microb Pathog. 2023 Dec;185:106447. doi: 10.1016/j.micpath.2023.106447. Epub 2023 Nov 14. PMID: 37972742. 3: Manhas RS, Chander D, Chaubey A. Identification and taxonomy of Streptomyces justiciae strain RA-WS2: a novel setomimycin producing actinobacterium. 3 Biotech. 2023 Feb;13(2):47. doi: 10.1007/s13205-023-03459-5. Epub 2023 Jan 13. PMID: 36643399; PMCID: PMC9837335. 4: Manhas RS, Kumar A, Chaubey A. A biostatistical approach for augmenting rare bianthraquinone antibiotic production by Streptomyces sp. RA-WS2 using Taguchi design. AMB Express. 2022 Dec 14;12(1):155. doi: 10.1186/s13568-022-01497-5. PMID: 36515787; PMCID: PMC9751253. 5: Manhas RS, Tiwari H, Noor M, Ahmed A, Vishwakarma J, Tripathi RBM, Ramachandran R, Madishetti S, Mukherjee D, Nargotra A, Chaubey A. Correction to: Setomimycin as a potential molecule for COVID‑19 target: in silico approach and in vitro validation. Mol Divers. 2023 Jun;27(3):1527. doi: 10.1007/s11030-022-10488-4. Erratum for: Mol Divers. 2023 Apr;27(2):619-633. doi: 10.1007/s11030-022-10441-5. PMID: 36036846; PMCID: PMC9422929. 6: Manhas RS, Ahmad SM, Mir KB, Ahmed A, Sharma S, Manhas D, Tiwari H, Kumar A, Nargotra A, Nandi U, Mukherjee D, Goswami A, Chaubey A. Isolation and anticancer activity evaluation of rare Bisaryl anthraquinone antibiotics from novel Streptomyces sp. strain of NW Himalayan region. Chem Biol Interact. 2022 Sep 25;365:110093. doi: 10.1016/j.cbi.2022.110093. Epub 2022 Aug 17. PMID: 35985519. 7: Manhas RS, Tiwari H, Noor M, Ahmed A, Vishwakarma J, Tripathi RBM, Ramachandran R, Madishetti S, Mukherjee D, Nargotra A, Chaubey A. Setomimycin as a potential molecule for COVID‑19 target: in silico approach and in vitro validation. Mol Divers. 2023 Apr;27(2):619-633. doi: 10.1007/s11030-022-10441-5. Epub 2022 May 27. Erratum in: Mol Divers. 2023 Jun;27(3):1527. doi: 10.1007/s11030-022-10488-4. PMID: 35622309; PMCID: PMC9136828. 8: Park JS, Kim DE, Hong SC, Kim SY, Kwon HC, Hyun CG, Choi J. Genome Analysis of Streptomyces nojiriensis JCM 3382 and Distribution of Gene Clusters for Three Antibiotics and an Azasugar across the Genus Streptomyces. Microorganisms. 2021 Aug 25;9(9):1802. doi: 10.3390/microorganisms9091802. PMID: 34576698; PMCID: PMC8466323. 9: Mohamed OG, Khalil ZG, Salim AA, Cui H, Blumenthal A, Capon RJ. Lincolnenins A-D: Isomeric Bactericidal Bianthracenes from Streptomyces lincolnensis. J Org Chem. 2021 Aug 20;86(16):11011-11018. doi: 10.1021/acs.joc.0c02492. Epub 2020 Dec 15. PMID: 33320674. 10: Präg A, Grüning BA, Häckh M, Lüdeke S, Wilde M, Luzhetskyy A, Richter M, Luzhetska M, Günther S, Müller M. Regio- and stereoselective intermolecular oxidative phenol coupling in Streptomyces. J Am Chem Soc. 2014 Apr 30;136(17):6195-8. doi: 10.1021/ja501630w. Epub 2014 Apr 18. PMID: 24746278. 11: Omura S, Tanaka H, Iwai Y, Nishigaki K, Awaya J, Takahashi Y, Masuma R. A new antibiotic, setomimycin, produced by a strain of Streptomyces. J Antibiot (Tokyo). 1978 Nov;31(11):1091-8. doi: 10.7164/antibiotics.31.1091. PMID: 721705.