Generic placeholder image

Current Organic Synthesis

Editor-in-Chief

ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

Letter Article

Iso-octenidine: Promising Octenidine Analogue with Improved Solubility

Author(s): Igor K. Yakuschenko, Nataliya N. Pozdeeva, Viktoriya A. Mumyatova, Alexey A. Terentiev and Svyatoslav Ya. Gadomsky*

Volume 18, Issue 5, 2021

Published on: 31 December, 2020

Page: [443 - 445] Pages: 3

DOI: 10.2174/1570179417666201231104453

Price: $65

Abstract

Iso-octenidine, an isomer of octenidine dihydrochloride, was synthesized and studied for the first time. Iso-octenidine was demonstrated to be 3-fold more soluble in water in comparison to original octenidine, and both substances had remarkably similar antibacterial activity (tested on Escherichia Coli and Micrococcus luteus).

Keywords: Octenidine dihydrochloride, bispyridinium salts, alkylation reaction, organic synthesis, solubility, antibacterial activity.

Graphical Abstract

[1]
Kampf, G. Antiseptic stewardship biocide resistance and clinical implications;; Springer Nature, Switzerland, AG, 2018.
[http://dx.doi.org/10.1007/978-3-319-98785-9]
[2]
Klebes, M.; Ulrich, C.; Kluschke, F.; Patzelt, A.; Vandersee, S.; Richter, H.; Bob, A.; von Hutten, J.; Krediet, J.T.; Kramer, A.; Lademann, J.; Lange-Asschenfeld, B. Combined antibacterial effects of tissue-tolerable plasma and a modern conventional liquid antiseptic on chronic wound treatment. J. Biophotonics, 2015, 8(5), 382-391.
[http://dx.doi.org/10.1002/jbio.201400007] [PMID: 24659472]
[3]
Daeschlein, G. Antimicrobial and antiseptic strategies in wound management. Int. Wound J., 2013, 10(Suppl. 1), 9-14.
[http://dx.doi.org/10.1111/iwj.12175] [PMID: 24251838]
[4]
Hübner, N.O.; Siebert, J.; Kramer, A. Octenidine dihydrochloride, a modern antiseptic for skin, mucous membranes and wounds. Skin Pharmacol. Physiol., 2010, 23(5), 244-258.
[http://dx.doi.org/10.1159/000314699] [PMID: 20484966]
[5]
Ng, C.K.L.; Singhal, V.; Widmer, F.; Wright, L.C.; Sorrell, T.C.; Jolliffe, K.A. Synthesis, antifungal and haemolytic activity of a series of bis(pyridinium)alkanes. Bioorg. Med. Chem., 2007, 15(10), 3422-3429.
[http://dx.doi.org/10.1016/j.bmc.2007.03.018] [PMID: 17383187]
[6]
Ponnachan, P.; Vinod, V.; Pullanhi, U.; Varma, P.; Singh, S.; Biswas, R.; Kumar, A. Antifungal activity of octenidine dihydrochloride and ultraviolet-C light against multidrug-resistant Candida auris. J. Hosp. Infect., 2019, 102(1), 120-124.
[http://dx.doi.org/10.1016/j.jhin.2018.09.008] [PMID: 30261239]
[7]
Lo, L.C.; Ho, W.Y.; Chen, L.T. Compound having anti-viral activity. U.S. Patent 7,045,536, B2, 2006.
[8]
Küng, E.; Pietrzak, J.; Klaus, C.; Walochnik, J. In vitro effect of octenidine dihydrochloride against Trichomonas vaginalis. Int. J. Antimicrob. Agents, 2016, 47(3), 232-234.
[http://dx.doi.org/10.1016/j.ijantimicag.2015.12.010] [PMID: 26899578]
[9]
Küng, E.; Fürnkranz, U.; Walochnik, J. Chemotherapeutic options for the treatment of human trichomoniasis. Int. J. Antimicrob. Agents, 2019, 53(2), 116-127.
[http://dx.doi.org/10.1016/j.ijantimicag.2018.10.016] [PMID: 30612993]
[10]
Novakov Mikić, A.; Stojic, S. Study results on the use of different therapies for the treatment of vaginitis in hospitalised pregnant women. Arch. Gynecol. Obstet., 2015, 292(2), 371-376.
[http://dx.doi.org/10.1007/s00404-015-3638-9] [PMID: 25651828]
[11]
Briese, V.; Neumann, G.; Waldschläger, J.; May, T.W.; Siebert, J.; Gerber, B. Efficacy and tolerability of a local acting antiseptic agent in the treatment of vaginal dysbiosis during pregnancy. Arch. Gynecol. Obstet., 2011, 283(3), 585-590.
[http://dx.doi.org/10.1007/s00404-010-1414-4] [PMID: 20217109]
[12]
Friese, K.; Neumann, G.; Siebert, J. Topical antiseptics as an alternative in the treatment of acute vulvovaginal candidosis. Arch. Gynecol. Obstet., 2003, 268(3), 194-197.
[http://dx.doi.org/10.1007/s00404-002-0368-6] [PMID: 12942250]
[13]
Swidsinski, A.; Loening-Baucke, V.; Swidsinski, S.; Verstraelen, H. Polymicrobial Gardnerella biofilm resists repeated intravaginal antiseptic treatment in a subset of women with bacterial vaginosis: a preliminary report. Arch. Gynecol. Obstet., 2015, 291(3), 605-609.
[http://dx.doi.org/10.1007/s00404-014-3484-1] [PMID: 25245669]
[14]
Novakov Mikic, A.; Budakov, D. Comparison of local metronidazole and a local antiseptic in the treatment of bacterial vaginosis. Arch. Gynecol. Obstet., 2010, 282(1), 43-47.
[http://dx.doi.org/10.1007/s00404-009-1241-7] [PMID: 19809829]
[15]
Bailey, D.M. Antimicrobial bis-[4-(substituted-amino)-1-pyridinium]alkanes. U.S. Patent 4,206,215A, 1980.
[16]
Slee, A.M.; O’Connor, J.R.; Bailey, D.M. Relationship between structure and antiplaque and antimicrobial activities for a series of bispyridines. Antimicrob. Agents Chemother., 1983, 23(4), 531-535.
[http://dx.doi.org/10.1128/AAC.23.4.531] [PMID: 6859832]
[17]
Bailey, D.M.; DeGrazia, C.G.; Hoff, S.J.; Schulenberg, P.L.; O’Connor, J.R.; Paris, D.A.; Slee, A.M. Bispyridinamines: a new class of topical antimicrobial agents as inhibitors of dental plaque. J. Med. Chem., 1984, 27(11), 1457-1464.
[http://dx.doi.org/10.1021/jm00377a014] [PMID: 6492075]
[18]
Andrews, J.M. Determination of minimum inhibitory concentrations. J. Antimicrob. Chemother., 2001, 48(Suppl. 1), 5-16.
[http://dx.doi.org/10.1093/jac/48.suppl_1.5] [PMID: 11420333]
[19]
Vereshchagin, A.N.; Karpenko, K.A.; Egorov, M.P. Synthesis and antibacterial activity of new dimeric pyridinium chloridesbased on 2,2-bis(hydroxymethyl)propane-1,3-diyl spacer. Russ. Chem. Bull., 2020, 69, 620-623.
[http://dx.doi.org/10.1007/s11172-020-2808-5]
[20]
Paolini, J.P.; Lendvay, L.J.; Palopoli, F.P. N4, N4′-Decamethylenebis-4-aminopyridine and N9, N9′-decamethylenebis-9-aminoacridine. J. Med. Chem., 1969, 12(4), 701-702.
[http://dx.doi.org/10.1021/jm00304a037] [PMID: 4978366]
[21]
Han, Y.F.; Li, C.P-L.; Chow, E.; Wang, H.; Pang, Y-P.; Carlier, P.R. Dual-site binding of bivalent 4-aminopyridine- and 4-aminoquinoline-based AChE inhibitors: contribution of the hydrophobic alkylene tether to monomer and dimer affinities. Bioorg. Med. Chem., 1999, 7(11), 2569-2575.
[http://dx.doi.org/10.1016/S0968-0896(99)00178-9] [PMID: 10632067]
[22]
Zyizin, I.N.; Dorohov, V.G.; Yakuschenko, I.K.; Savchenko, V.I.; Perepelkin, P.Yu.; Aldoshin, S.M. Method of bis (4-alkykaminopyridine-1) alkanes production. RU Patent 2,332,402 C1, 2008.
[23]
Zyizin, I.N.; Dorohov, V.G.; Yakuschenko, I.K.; Savchenko, V.I.; Perepelkin, P.Yu.; Aldoshin, S.M. Method of obtaining 4-(alkylamino)pyridine. RU Patent 2,345,068 C2, 2009.

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy