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1. Investigation of the complex antibiotic INA-5812

Author

Roman S. Borisov, Igor A. Prokhorenko, V. V. Pogozheva, E. A. Rogozhin, Elena G. Gladkikh, L. G. Stoyanova, Andrey A. Formanovsky, Valeriya V. Kulyaeva, M. A. Sukonnikov, O. A. Lapchinskaya, Anton P. Tyurin, Vladimir A. Brylev, Ludmila A. Baratova, Marina V. Serebryakova, Vera A. Alferova, A. P. Topolyan, G. S. Katrukha, Alexander M. Korolev, P. V. Coodan, Maxim V. Shuvalov, Vadim N. Tashlitsky, Alexander L. Ksenofontov, A. V. Timofeeva, M. S. Slyundina, and Ilya A. Osterman

Subjects
0301 basic medicine, Tris, Chromatography, biology, medicine.drug_class, Organic Chemistry, Antibiotics, Fractionation, biology.organism_classification, Antimicrobial, Biochemistry, Streptomyces, High-performance liquid chromatography, Glycopeptide, 03 medical and health sciences, chemistry.chemical_compound, 030104 developmental biology, chemistry, medicine, Derivatization
Abstract

A concentrate with the antimicrobial activity has been isolated from the culture broth of Streptomyces roseoflavus INA-Ac-5812. Its further fractionation by reversed-phase HPLC has resulted in six fractions. It has been established by MALDI-TOF and ESI-MSn precision mass-spectrometry methods that the main components of the complex antibiotic are several closely related compounds, presumably of a glycopeptide nature. The fraction containing an individual component with a mass of 1845.788 Da has been characterized by UV/Vis absorbance and fluorescence spectra, amino acid analysis, and derivatization with tris(2,6-dimethoxyphenyl)methyl cation. The activity of fractions against pathogenic microbes has been studied. The results allow the supposition that the INA-5812 antibiotic complex is a glyco- or lipoglycopeptide antibiotic of a new type, which is very promising for further study.

Published
2016
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2. Derivatization of Aminoglycoside Antibiotics with Tris(2,6-dimethoxyphenyl)carbenium Ion

Author

A P, Topolyan, M A, Belyaeva, E E, Bykov, P V, Coodan, E A, Rogozhin, D A, Strizhevskaya, O M, Ivanova, A V, Ustinov, I V, Mikhura, I A, Prokhorenko, V A, Korshun, and A A, Formanovsky

Subjects
trityl cation, aminoglycoside antibiotics, mass-spectrometry, HPLC, Molecular Biology, Research Article
Abstract

Detection of aminoglycoside antibiotics by MS or HPLC is complicated, because a) carbohydrate molecules have low ionization ability in comparison with other organic molecules (particularly in MALDI-MS), and b) the lack of aromatics and/or amide bonds in the molecules makes common HPLC UV-detectors useless. Here, we report on the application of a previously developed method for amine derivatization with tris(2,6- dimethoxyphenyl)carbenium ion to selective modification of aminoglycoside antibiotics. Only amino groups bound to primary carbons get modified. The attached aromatic residue carries a permanent positive charge. This makes it easy to detect aminoglycoside antibiotics by MS-methods and HPLC, both as individual compounds and in mixtures.

Published
2016

3. Derivatization of aminoglycoside antibiotics with tris(2,6-dimethoxyphenyl)carbenium Ion

Author

Maria A. Belyaeva, A. V. Ustinov, P. V. Coodan, E E Bykov, Andrey A. Formanovsky, Vladimir A. Korshun, Igor A. Prokhorenko, A. P. Topolyan, I. V. Mikhura, E. A. Rogozhin, D. A. Strizhevskaya, and O. M. Ivanova

Subjects
Tris, 010405 organic chemistry, 010401 analytical chemistry, Aminoglycoside, AMINOGLYCOSIDE ANTIBIOTICS,MASS-SPECTROMETRY,TRITYL CATION,HPLC, Mass spectrometry, 01 natural sciences, Biochemistry, Combinatorial chemistry, 0104 chemical sciences, chemistry.chemical_compound, Residue (chemistry), Carbenium ion, chemistry, Molecular Medicine, Molecule, Amine gas treating, Derivatization, Molecular Biology, Biotechnology
Abstract

Detection of aminoglycoside antibiotics by MS or HPLC is complicated, because a) carbohydrate molecules have low ionization ability in comparison with other organic molecules (particularly in MALDI-MS), and b) the lack of aromatics and/or amide bonds in the molecules makes common HPLC UV-detectors useless. Here, we report on the application of a previously developed method for amine derivatization with tris(2,6-dimethoxyphenyl)carbenium ion to selective modification of aminoglycoside antibiotics. Only amino groups bound to primary carbons get modified. The attached aromatic residue carries a permanent positive charge. This makes it easy to detect aminoglycoside antibiotics by MS-methods and HPLC, both as individual compounds and in mixtures.

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