Eremomycin
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| Category | Antibiotics |
| Catalog number | BBF-00866 |
| CAS | 110865-90-2 |
| Molecular Weight | 1557.99 |
| Molecular Formula | C73H89ClN10O26 |
| Purity | >98% |
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Description
Eremomycin is a glycopeptide antibiotic produced by actinomycete INA-238. Activity against gram-positive bacteria.
Specification
| Related CAS | 121844-63-1 (sulfate) |
| Storage | Store at -20°C |
| IUPAC Name | (1S,2R,18R,19R,22S,25R,28R,40S)-2-[(2R,4S,5R,6S)-4-amino-5-hydroxy-4,6-dimethyloxan-2-yl]oxy-48-[(2S,3R,4S,5S,6R)-3-[(2R,4S,5R,6S)-4-amino-5-hydroxy-4,6-dimethyloxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-22-(2-amino-2-oxoethyl)-15-chloro-18,32,35,37-tetrahydroxy-19-[[(2R)-4-methyl-2-(methylamino)pentanoyl]amino]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentazaoctacyclo[26.14.2.23,6.214,17.18,12.129,33.010,25.034,39]pentaconta-3(50),4,6(49),8(48),9,11,14,16,29(45),30,32,34(39),35,37,46-pentadecaene-40-carboxylic acid |
| Canonical SMILES | CC1C(C(CC(O1)OC2C(C(C(OC2OC3=C4C=C5C=C3OC6=C(C=C(C=C6)C(C(C(=O)NC(C(=O)NC5C(=O)NC7C8=CC(=C(C=C8)O)C9=C(C=C(C=C9O)O)C(NC(=O)C(C(C1=CC=C(O4)C=C1)OC1CC(C(C(O1)C)O)(C)N)NC7=O)C(=O)O)CC(=O)N)NC(=O)C(CC(C)C)NC)O)Cl)CO)O)O)(C)N)O |
| InChI | InChI=1S/C73H89ClN10O26/c1-27(2)16-39(78-7)64(95)83-54-56(90)32-11-15-43(38(74)18-32)106-45-20-33-19-44(60(45)110-71-61(58(92)57(91)46(26-85)107-71)109-49-25-73(6,77)63(94)29(4)104-49)105-35-12-8-30(9-13-35)59(108-48-24-72(5,76)62(93)28(3)103-48)55-69(100)82-53(70(101)102)37-21-34(86)22-42(88)50(37)36-17-31(10-14-41(36)87)51(66(97)84-55)81-67(98)52(33)80-65(96)40(23-47(75)89)79-68(54)99/h8-15,17-22,27-29,39-40,46,48-49,51-59,61-63,71,78,85-88,90-94H,16,23-26,76-77H2,1-7H3,(H2,75,89)(H,79,99)(H,80,96)(H,81,98)(H,82,100)(H,83,95)(H,84,97)(H,101,102)/t28-,29-,39+,40-,46+,48-,49-,51+,52+,53-,54+,55-,56+,57+,58-,59+,61+,62-,63-,71-,72-,73-/m0/s1 |
| InChI Key | UECIPBUIMXSXEI-BNSVOVDNSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Solubility | Soluble in DMSO |
Reference Reading
1. Bacterial Cell Wall Analogue Peptides Control the Oligomeric States and Activity of the Glycopeptide Antibiotic Eremomycin: Solution NMR and Antimicrobial Studies
László Izsépi, Réka Erdei, Anna N Tevyashova, Natalia E Grammatikova, Andrey E Shchekotikhin, Pál Herczegh, Gyula Batta Pharmaceuticals (Basel). 2021 Jan 22;14(2):83. doi: 10.3390/ph14020083.
For some time, glycopeptide antibiotics have been considered the last line of defense against Methicillin-resistant Staphylococcus aureus (MRSA). However, vancomycin resistance of Gram-positive bacteria is an increasingly emerging worldwide health problem. The mode of action of glycopeptide antibiotics is essentially the binding of peptidoglycan cell-wall fragments terminating in the d-Ala-d-Ala sequence to the carboxylate anion binding pocket of the antibiotic. Dimerization of these antibiotics in aqueous solution was shown to persist and even to enhance the antibacterial effect in a co-operative manner. Some works based on solid state (ss) Nuclear Magnetic Resonance (NMR) studies questioned the presence of dimers under the conditions of ssNMR while in a few cases, higher-order oligomers associated with contiguous back-to-back and face-to-face dimers were observed in the crystal phase. However, it is not proved if such oligomers persist in aqueous solutions. With the aid of 15N-labelled eremomycin using 15N relaxation and diffusion NMR methods, we observed tetramers and octamers when the N-Ac-d-Ala-d-Ala dipeptide was added. To the contrary, the N-Ac-d-Ala or (N-Ac)2-l-Lys-d-Ala-d-Ala tripeptide did not induce higher-order oligomers. These observations are interesting examples of tailored supramolecular self-organization. New antimicrobial tests have also been carried out with these self-assemblies against MRSA and VRE (resistant) strains.
2. Hydrophilic interaction liquid chromatography method for eremomycin determination in pre-clinical study
Dmitry V Yaroshenko, Alexander V Grigoriev, Irina S Yaroshenko, Alla A Sidorova, Kirill L Kryshen, Mikhail G Chernobrovkin, Alexandra V Zatirakha, Alla V Chernobrovkina J Chromatogr A. 2021 Jan 25;1637:461750. doi: 10.1016/j.chroma.2020.461750. Epub 2020 Dec 10.
A complex of hydrophilic interaction liquid chromatography (HILIC) methods for simple and efficient determination of eremomycin (ERM) as an active pharmaceutical ingredient (API) of a novel drug is proposed for preclinical study, which includes the dissolution test and pharmacokinetic study on the animals. A home-made HILIC silica-based stationary phase (SP) containing diol functionalities and positively charged nitrogen atoms in its structure was synthesized for this research and applied for the first time for performing the first step of preclinical study (dissolution test) of the novel ERM-containing drug. HILIC method developed using novel home-made SP allowed us to avoid any interferences from polyethylene glycol (PEG) contained in the drug matrix thus providing a unique advantage of the proposed approach over RP HPLC. The home-made SP demonstrated better chromatographic performance as compared to the tested commercially available columns with various functionalities. Different retention behaviour and mechanisms with various electrostatic impact were demonstrated for two glycopeptide antibiotics, namely, ERM and its analogue vancomycin (VAN), on the home-made SP. For the second step of the preclinical study HILIC-MS/MS method for ERM determination in rabbit plasma was developed and validated in accordance with the EMA requirements and successfully applied to the preclinical study on rabbits after intravenous and intraperitoneal drug administration. The results of dissolution test and pharmacokinetic study revealed similar in vitro solubility of ERM and VAN and low ERM bioavailability, which proved the potential safety and efficiency of the novel drug.
3. Aminoalkylamides of Eremomycin Exhibit an Improved Antibacterial Activity
Elena I Moiseenko, Réka Erdei, Natalia E Grammatikova, Elena P Mirchink, Elena B Isakova, Eleonora R Pereverzeva, Gyula Batta, Andrey E Shchekotikhin Pharmaceuticals (Basel). 2021 Apr 19;14(4):379. doi: 10.3390/ph14040379.
After decades, the glycopeptide vancomycin is still the preferred antibiotic against resistant strains of Gram-positive bacteria. Although its clinical use is strictly regulated, the gradual spread of vancomycin-resistant bacteria, such as glycopeptide-resistant and glycopeptide-intermediate Staphylococcus aureus and vancomycin-resistant Enterococcus spp., is a serious health problem. Based on the literature data and previous studies, our main goal was to assess the antimicrobial potential and to study the structure-activity relationship of new eremomycin aminoalkylamides. We designed and synthesized a series of new eremomycin amides in which eremomycin is conjugated with a hydrophobic arylalkyl group via an alkylenediamine spacer, and tested their antibacterial activities on a panel of Gram-positive strains that were sensitive and resistant to a "gold-standard" vancomycin. Based on the data obtained, the structure-activity relationships were investigated, and a lead compound was selected for in-depth testing. Research carried out using an in vivo model of staphylococcus sepsis, acute toxicity studies, and the estimated therapeutic index also showed the advantage of the selected eremomycin amide derivative in particular, as well as the chosen direction in general.
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Bio Calculators
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
