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Published in: Polymer Science, Series D 2/2023

01-06-2023

Microfluidic Synthesis of Oligohexamethylene Guanidine Hydrocitrate and Study of Its Antimicrobial Activity

Authors: D. O. Shatalov, I. S. Ivanov, A. V. Aydakova, D. A. Akhmetova, Yu. A. Koroleva, D. D. Kirilova, Yu. A. Azarova, P. I. Kurnosova, A. Yu. Dolgovskaya, O. A. Legon’kova, S. A. Kedik

Published in: Polymer Science, Series D | Issue 2/2023

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Abstract

Due to the growing problem of antibiotic resistance, the possibility of using alkylene guanidines as compounds exhibiting antimicrobial activity is discussed. Methods for the preparation of oligohexamethylene guanidine (OHMG) dihydrocarbonate using microfluidic technologies and the further synthesis of OHMG hydrocitrate are described. Structures of the compounds obtained were confirmed by 13С NMR spectroscopy, and the antimicrobial activity of OHMG hydrocitrate was evaluated.

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Literature
1.
go back to reference I. A. Burmistrova, A. G. Samoilova, T. E. Tyul’kova, E. V. Vaniev, G. S. Balasanyants, and I. A. Vasil’eva, “Drug resistance of M. tuberculosis (historical aspects, current state of knowledge),” Tuberkulyoz I Bolezni Legkikh 98, 54–61 (2020).CrossRef I. A. Burmistrova, A. G. Samoilova, T. E. Tyul’kova, E. V. Vaniev, G. S. Balasanyants, and I. A. Vasil’eva, “Drug resistance of M. tuberculosis (historical aspects, current state of knowledge),” Tuberkulyoz I Bolezni Legkikh 98, 54–61 (2020).CrossRef
2.
go back to reference S. Allcock, E. H. Young, M. Holmes, D. Gurdasani, G. Dougan, M. S. Sandhu, et al., “Antimicrobial resistance in human populations: challenges and opportunities,” Glob. Health Epidemiol. Genom No. 2, e4 (2017). S. Allcock, E. H. Young, M. Holmes, D. Gurdasani, G. Dougan, M. S. Sandhu, et al., “Antimicrobial resistance in human populations: challenges and opportunities,” Glob. Health Epidemiol. Genom No. 2, e4 (2017).
3.
go back to reference M. Bassetti, G. Poulakou, E. Ruppe, E. Bouza, S. J. Van Hal, and A. Brink, “Antimicrobial resistance in the next 30 years, humankind, bugs and drugs: a visionary approach,” Intensive Care Med. 43, 1464–1475 (2017).CrossRefPubMed M. Bassetti, G. Poulakou, E. Ruppe, E. Bouza, S. J. Van Hal, and A. Brink, “Antimicrobial resistance in the next 30 years, humankind, bugs and drugs: a visionary approach,” Intensive Care Med. 43, 1464–1475 (2017).CrossRefPubMed
4.
go back to reference M. Benincasa, S. Pacor, R. Gennaro, and M. Scocchi, “Rapid and reliable detection of antimicrobial peptide penetration into gram-negative bacteria based on fluorescence quenching,” Antimicrob. Agents Chemother. No. 53, 3501–3504 (2009).CrossRef M. Benincasa, S. Pacor, R. Gennaro, and M. Scocchi, “Rapid and reliable detection of antimicrobial peptide penetration into gram-negative bacteria based on fluorescence quenching,” Antimicrob. Agents Chemother. No. 53, 3501–3504 (2009).CrossRef
5.
go back to reference F. Brossier, A. Pham, C. Bernard, A. Aubry, V. Jarlier, N. Veziris, and W. Sougakoff, “Molecular investigation of resistance to second-line injectable drugs in multidrug-resistant clinical isolates of mycobacterium tuberculosis in France,” Antimicrob. Agents Chemother. 61, e01299–16 (2017).CrossRefPubMedPubMedCentral F. Brossier, A. Pham, C. Bernard, A. Aubry, V. Jarlier, N. Veziris, and W. Sougakoff, “Molecular investigation of resistance to second-line injectable drugs in multidrug-resistant clinical isolates of mycobacterium tuberculosis in France,” Antimicrob. Agents Chemother. 61, e01299–16 (2017).CrossRefPubMedPubMedCentral
6.
go back to reference V. V. Kanishchev and N. I. Eremeeva, “Some scientific and practical aspects of the effective use in medical organizations of disinfectants without the possibility of adaptation of pathogens to them,” Dezinfektsionnoe Delo, No. 4, 41–48 (2017). V. V. Kanishchev and N. I. Eremeeva, “Some scientific and practical aspects of the effective use in medical organizations of disinfectants without the possibility of adaptation of pathogens to them,” Dezinfektsionnoe Delo, No. 4, 41–48 (2017).
7.
go back to reference J. M. Blair, M. A. Webber, A. J. Baylay, D. O. Ogbolu, and L. J. Piddock, “Molecular mechanisms of antibiotic resistance,” Nat. Rev. Microbiol., No. 13, 42–51 (2015).CrossRef J. M. Blair, M. A. Webber, A. J. Baylay, D. O. Ogbolu, and L. J. Piddock, “Molecular mechanisms of antibiotic resistance,” Nat. Rev. Microbiol., No. 13, 42–51 (2015).CrossRef
8.
go back to reference J. K. Boparai and P. K. Sharma, “Mini review on antimicrobial peptides, sources, mechanism and recent applications,” Protein Pept. Lett., No. 27, 4–16 (2019).CrossRef J. K. Boparai and P. K. Sharma, “Mini review on antimicrobial peptides, sources, mechanism and recent applications,” Protein Pept. Lett., No. 27, 4–16 (2019).CrossRef
9.
go back to reference J. Borysowski and A. Gorski, “Is phage therapy acceptable in the immunocompromised host,” Int. J. Infect. Dis. 12, 466–471 (2008).CrossRefPubMed J. Borysowski and A. Gorski, “Is phage therapy acceptable in the immunocompromised host,” Int. J. Infect. Dis. 12, 466–471 (2008).CrossRefPubMed
10.
go back to reference Decree of the Government of the Russian Federation of September 25, 2017 No. 2045-r “Strategy for preventing the spread of antimicrobial resistance in the Russian Federation for the period up to 2030.” http://government.ru/docs/29477/. Decree of the Government of the Russian Federation of September 25, 2017 No. 2045-r “Strategy for preventing the spread of antimicrobial resistance in the Russian Federation for the period up to 2030.” http://​government.​ru/​docs/​29477/​.​
11.
go back to reference Z. X. Zhou, D. F. Wei, Y. Guan, A. N. Zheng, J. J. Zhong, and J. Appl, “Damage of Escherichia coli membrane by bactericidal agent polyhexamethylene guanidine hydrochloride: micrographic evidences,” Arch. Microbiol., No. 108, 898 (2010). Z. X. Zhou, D. F. Wei, Y. Guan, A. N. Zheng, J. J. Zhong, and J. Appl, “Damage of Escherichia coli membrane by bactericidal agent polyhexamethylene guanidine hydrochloride: micrographic evidences,” Arch. Microbiol., No. 108, 898 (2010).
12.
go back to reference D. O. Shatalov, S. A. Kedik, E. S. Zhavoronok, I. S. Ivanov, A. S. Evseeva, S. V. Belyakov, S. I. Biryulin, A. V. Kovalenko, and E. N. Mikhailenko, “Experience and prospects for the development of the use of synthetic antimicrobial substances,” Vse Mater. Entsiklopedicheskii Spravochnik, No. 8, 14 (2016). D. O. Shatalov, S. A. Kedik, E. S. Zhavoronok, I. S. Ivanov, A. S. Evseeva, S. V. Belyakov, S. I. Biryulin, A. V. Kovalenko, and E. N. Mikhailenko, “Experience and prospects for the development of the use of synthetic antimicrobial substances,” Vse Mater. Entsiklopedicheskii Spravochnik, No. 8, 14 (2016).
13.
go back to reference I. I. Vointseva and P. A. Gembitskii, Polyguanidines–Disinfectants and Polyfunctional Additives in Composite Materials (LKM-press, Moscow, 2009), pp. 303–304 [in Russian]. I. I. Vointseva and P. A. Gembitskii, Polyguanidines–Disinfectants and Polyfunctional Additives in Composite Materials (LKM-press, Moscow, 2009), pp. 303–304 [in Russian].
14.
go back to reference S. A. Kedik, I. P. Sedishev, A. V. Panov, E. S. Zhavoronok, and Kha Kam An’, RF Patent No. 2443684. S. A. Kedik, I. P. Sedishev, A. V. Panov, E. S. Zhavoronok, and Kha Kam An’, RF Patent No. 2443684.
15.
go back to reference A. Gerbst, “Microreactors and nanotechnologies,” Bio- i Nanotekhnol. No. 3, 78–88 (2012). A. Gerbst, “Microreactors and nanotechnologies,” Bio- i Nanotekhnol. No. 3, 78–88 (2012).
16.
go back to reference B. Matthew, M. B. Plutschack, B. Pieber, K. Gilmore, and H. Peter, “The hitchhiker’s guide to flow chemistry,” Chem. Rev. 117, 18 (2017). B. Matthew, M. B. Plutschack, B. Pieber, K. Gilmore, and H. Peter, “The hitchhiker’s guide to flow chemistry,” Chem. Rev. 117, 18 (2017).
17.
go back to reference D. A. Akhmedova, D. O. Shatalov, I. S. Ivanov, A. V. Aidakova, A. Gerbst, L. Grainer, A. P. Kaplun, A.S. Zhurbenko, and S. A. Kedik, “Application of microfluidic hardware in the synthesis of oligohexamethyleneguanidine derivatives,” Tonkie Khim. Tekhnol. 16, 307—317 (2021). D. A. Akhmedova, D. O. Shatalov, I. S. Ivanov, A. V. Aidakova, A. Gerbst, L. Grainer, A. P. Kaplun, A.S. Zhurbenko, and S. A. Kedik, “Application of microfluidic hardware in the synthesis of oligohexamethyleneguanidine derivatives,” Tonkie Khim. Tekhnol. 16, 307—317 (2021).
18.
go back to reference A. V. Kovalenko, D. O. Shatalov, S. A. Kedik, A. I. Gromakova, A. P. Kaplun, I. S. Ivanov, and I. V. Sterin, “The direction of development of drug therapy for infectious conjunctivitis (literature review),” Vopr. Biolog. Med. Farm. Khim. 22, 5–11 (2019). A. V. Kovalenko, D. O. Shatalov, S. A. Kedik, A. I. Gromakova, A. P. Kaplun, I. S. Ivanov, and I. V. Sterin, “The direction of development of drug therapy for infectious conjunctivitis (literature review),” Vopr. Biolog. Med. Farm. Khim. 22, 5–11 (2019).
19.
go back to reference S. V. Beliakov, D. O. Shatalov, S. A. Kedik, A. V. Aydakova, and N. A. Zasypkina, “Preliminary in vitro and in vivo evaluation of specific activity of branched oligohexamethyleneguanidine hydrochloride,” Drug Dev. Ind. Pharm 46, 1517–1523 (2020).CrossRefPubMed S. V. Beliakov, D. O. Shatalov, S. A. Kedik, A. V. Aydakova, and N. A. Zasypkina, “Preliminary in vitro and in vivo evaluation of specific activity of branched oligohexamethyleneguanidine hydrochloride,” Drug Dev. Ind. Pharm 46, 1517–1523 (2020).CrossRefPubMed
Metadata
Title
Microfluidic Synthesis of Oligohexamethylene Guanidine Hydrocitrate and Study of Its Antimicrobial Activity
Authors
D. O. Shatalov
I. S. Ivanov
A. V. Aydakova
D. A. Akhmetova
Yu. A. Koroleva
D. D. Kirilova
Yu. A. Azarova
P. I. Kurnosova
A. Yu. Dolgovskaya
O. A. Legon’kova
S. A. Kedik
Publication date
01-06-2023
Publisher
Pleiades Publishing
Published in
Polymer Science, Series D / Issue 2/2023
Print ISSN: 1995-4212
Electronic ISSN: 1995-4220
DOI
https://doi.org/10.1134/S1995421223020375

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