Synthesis and Correlation of Aggregation and Antimicrobial Properties of Homochiral Quaternary Ammonium Bromides Derived from Camphoric Acid

[1] Balgavý P. Devínsky F. Cut-off effects in biological activities of surfactants. Adv Colloid Interface Sci. 1996;66:23–63. BalgavýP DevínskyF Cut-off effects in biological activities of surfactants Adv Colloid Interface Sci 1996 66 23 63 10.1016/0001-8686(96)00295-3 Search in Google Scholar

[2] Benkova M. Soukup O. Prchal L. et al. Synthesis, antimicrobial effect and lipophilicity-activity dependence of three series of dichained N-alkylammonium salts. Chemistry 2019;4:12076–12084. BenkovaM SoukupO PrchalL Synthesis, antimicrobial effect and lipophilicity-activity dependence of three series of dichained N-alkylammonium salts Chemistry 2019 4 12076 12084 10.1002/slct.201902357 Search in Google Scholar

[3] Birnie CR. Malamud D. Schnaare RL. Antimicrobial evaluation of N-alkyl betaines and N-alkyl-N,N-dimethylamine oxides with variations in chain length. Antimicrob Agents Chemother. 2000;44:2514–2517. BirnieCR MalamudD SchnaareRL Antimicrobial evaluation of N-alkyl betaines and N-alkyl-N,N-dimethylamine oxides with variations in chain length Antimicrob Agents Chemother 2000 44 2514 2517 10.1128/AAC.44.9.2514-2517.20009009410952604 Search in Google Scholar

[4] Brak K. Jacobsen EN. Asymmetric ion-pairing catalysis. Angew Chem Int Ed. 2013;52(2):534–561. BrakK JacobsenEN Asymmetric ion-pairing catalysis Angew Chem Int Ed 2013 52 2 534 561 10.1002/anie.201205449428495123192886 Search in Google Scholar

[5] Brigham KL. Mezrick B. Christman B. Magnuson M. King G. Berry LC. In vivo Transfection of Murine Lungs with a Functioning Prokaryotic Gene Using a Liposome Vehicle. Am J Med Sci. 1989; 298: 278–281. BrighamKL MezrickB ChristmanB MagnusonM KingG BerryLC In vivo Transfection of Murine Lungs with a Functioning Prokaryotic Gene Using a Liposome Vehicle Am J Med Sci 1989 298 278 281 10.1097/00000441-198910000-000132801762 Search in Google Scholar

[6] Bureš F. Quaternary Ammonium Compounds: Simple in Structure, Complex in Application. Top Curr Chem. 2019;377:14. BurešF Quaternary Ammonium Compounds: Simple in Structure, Complex in Application Top Curr Chem 2019 377 14 10.1007/s41061-019-0239-231062103 Search in Google Scholar

[7] Cortesi R. Bergamini P. Ravani L. et al. Long-chain cationic derivatives of PTA (1,3,5-triaza-7-phosphaadamantane) as new components of potential non-viral vectors. Int J Pharm. 2012; 431:176–182. CortesiR BergaminiP RavaniL Long-chain cationic derivatives of PTA (1,3,5-triaza-7-phosphaadamantane) as new components of potential non-viral vectors Int J Pharm 2012 431 176 182 10.1016/j.ijpharm.2012.04.01422513391 Search in Google Scholar

[8] Denyer SP Hugo WB. The mode of action of cetyltrimethylammonium bromide (CTAB) on Staphylococcus aureus. J Pharm Pharmacol. 1977;29:66P. DenyerSP HugoWB The mode of action of cetyltrimethylammonium bromide (CTAB) on Staphylococcus aureus J Pharm Pharmacol 1977 29 66P 10.1111/j.2042-7158.1977.tb11534.x22699 Search in Google Scholar

[9] Devínsky F. Lacko I. Mlynarčík D. Račanský V. Krasnec Ľ. Relationship between critical micelle concentrations and minimum inhibitory concentrations for some non-aromatic quaternary ammonium salts and amine oxides. Tenside Deterg. 1985;22:10–15. DevínskyF LackoI MlynarčíkD RačanskýV KrasnecĽ Relationship between critical micelle concentrations and minimum inhibitory concentrations for some non-aromatic quaternary ammonium salts and amine oxides Tenside Deterg 1985 22 10 15 10.1515/tsd-1985-220105 Search in Google Scholar

[10] Eagles JB. Hitchcock SR. Synthesis of D-camphor based γ-amino acid (1S,3R)-3-amino-2,2,3-trimethylcyclopentane carboxylic acid. Tetrahedron: Asymmetry. 2010;21(5):519–523. EaglesJB HitchcockSR Synthesis of D-camphor based γ-amino acid (1S,3R)-3-amino-2,2,3-trimethylcyclopentane carboxylic acid Tetrahedron: Asymmetry 2010 21 5 519 523 10.1016/j.tetasy.2010.03.022 Search in Google Scholar

[11] Feder-Kubis J. Tomczuk K. The effect of the cationic structures of chiral ionic liquids on their antimicrobial activities. Tetrahedron 2013;69(21):4190–4198. Feder-KubisJ TomczukK The effect of the cationic structures of chiral ionic liquids on their antimicrobial activities Tetrahedron 2013 69 21 4190 4198 10.1016/j.tet.2013.03.107 Search in Google Scholar

[12] Gilbert P. Moore LE. Cationic antiseptics: diversity of action under a common Epithet. J. Appl Microbiol 2005; 99: 703–715. GilbertP MooreLE Cationic antiseptics: diversity of action under a common Epithet J. Appl Microbiol 2005 99 703 715 10.1111/j.1365-2672.2005.02664.x16162221 Search in Google Scholar

[13] Jennings MC. Minbiole KPC. Wuest WM. Quaternary Ammonium Compounds: An Antimicrobial Mainstay and Platform for Innovation to Address Bacterial Resistance. ACS Infect Dis. 2015;1:288–303. JenningsMC MinbioleKPC WuestWM Quaternary Ammonium Compounds: An Antimicrobial Mainstay and Platform for Innovation to Address Bacterial Resistance ACS Infect Dis 2015 1 288 303 10.1021/acsinfecdis.5b0004727622819 Search in Google Scholar

[14] Joondan N. Jhaumeer-Laulloo S. Caumul P. A study of the antibacterial activity of L-Phenylalanine and L-Tyrosine esters in relation to their CMCs and their interactions with 1,2-dipalmitoylsn-glycero-3-phosphocholine, DPPC as model membrane. Microbiol Res. 2014;169:657–685. JoondanN Jhaumeer-LaullooS CaumulP A study of the antibacterial activity of L-Phenylalanine and L-Tyrosine esters in relation to their CMCs and their interactions with 1,2-dipalmitoylsn-glycero-3-phosphocholine, DPPC as model membrane Microbiol Res 2014 169 657 685 10.1016/j.micres.2014.02.01024667307 Search in Google Scholar

[15] Kaushik NK, Attri P, Kaushik N, Choi EH. Synthesis and Antiproliferative Activity of Ammonium and Imidazolium Ionic Liquids against T98G Brain Cancer Cells. Molecules 2012;17(12):13727–13739. KaushikNK AttriP KaushikN ChoiEH Synthesis and Antiproliferative Activity of Ammonium and Imidazolium Ionic Liquids against T98G Brain Cancer Cells Molecules 2012 17 12 13727 13739 10.3390/molecules171213727626855023174892 Search in Google Scholar

[16] Kim YH. Sun G. Functional Finishing of Acrylic and Cationic Dyeable Fabrics: Intermolecular Interactions. Text Res J. 2002; 72: 1052–1056. KimYH SunG Functional Finishing of Acrylic and Cationic Dyeable Fabrics: Intermolecular Interactions Text Res J 2002 72 1052 1056 10.1177/004051750207201203 Search in Google Scholar

[17] Klevens HB. Structure and aggregation in divte solutions of surface aktive agents. J Am Oil Chem Soc. 1953;30:74–80. KlevensHB Structure and aggregation in divte solutions of surface aktive agents J Am Oil Chem Soc 1953 30 74 80 10.1007/BF02635002 Search in Google Scholar

[18] Kopecká-Leitmanová A. Devinsky F. Mlynarčík D. Lacko I. Interaction of amine oxides and quaternary ammonium salts with membrane and membrane-associated processes in E. Coli cells: mode of action. Drug Metabol Drug Interact. 1989;7(1):29–51. Kopecká-LeitmanováA DevinskyF MlynarčíkD LackoI Interaction of amine oxides and quaternary ammonium salts with membrane and membrane-associated processes in E. Coli cells: mode of action Drug Metabol Drug Interact 1989 7 1 29 51 10.1515/DMDI.1989.7.1.292699283 Search in Google Scholar

[19] Lukáč M, Lacko I, Bukovský M et al. Synthesis and antimicrobial activity of a series of optically active quaternary ammonium salts derived from phenylalanine. Cent Eur J Chem. 2010;8:194–201. LukáčM LackoI BukovskýM Synthesis and antimicrobial activity of a series of optically active quaternary ammonium salts derived from phenylalanine Cent Eur J Chem 2010 8 194 201 10.2478/s11532-009-0126-8 Search in Google Scholar

[20] Malinak D. Dolezal R. Marek J. et al. 6-Hydroxyquinolinium salts differing in the length of alkyl side-chain: synthesis and antimicrobial activity. Bioorg Med Chem Lett. 2014;24:5238–5241. MalinakD DolezalR MarekJ 6-Hydroxyquinolinium salts differing in the length of alkyl side-chain: synthesis and antimicrobial activity Bioorg Med Chem Lett 2014 24 5238 5241 10.1016/j.bmcl.2014.09.06025442318 Search in Google Scholar

[21] Marek J. Joskova V. Dolezal R. et al. Synthesis, antimicrobial effect and surface properties of hydroxymethyl-substituted pyridinium salts. Lett Drug Des Discov. 2018;15:828–842. MarekJ JoskovaV DolezalR Synthesis, antimicrobial effect and surface properties of hydroxymethyl-substituted pyridinium salts Lett Drug Des Discov 2018 15 828 842 10.2174/1570180814666171110142233 Search in Google Scholar

[22] Menzel TM. Tischer M. Francois P. et al. Mode-of-Action studies of the Novel Bisquaternary Bisnaphthalimide MT02 against Staphylococcus aureus. Antimicrob Agents Chemother. 2011;55:311–320. MenzelTM TischerM FrancoisP Mode-of-Action studies of the Novel Bisquaternary Bisnaphthalimide MT02 against Staphylococcus aureus Antimicrob Agents Chemother 2011 55 311 320 10.1128/AAC.00586-10 Search in Google Scholar

[23] Merianos JJ. Quaternary ammonium antimicrobial compounds. In Disinfection, sterilization, and preservation, 4^th Edition, 1991, Lea & Febiger, Philadelphia. ISBN: 0-8121-1364-0. MerianosJJ Quaternary ammonium antimicrobial compounds In Disinfection, sterilization, and preservation 4th Edition 1991 Lea & Febiger Philadelphia ISBN: 0-8121-1364-0. Search in Google Scholar

[24] Miguel G. Cruz C. Faleiro ML. Simoes MTF. Figueiredo AC. Barroso JG. Pedro LG. Salvia officinalis L. essential oils: effect of hydrodistillation time on the chemical composition, antioxidant and antimicrobial activities. Nat Prod Res. 2011;25(5):526–541. MiguelG CruzC FaleiroML SimoesMTF FigueiredoAC BarrosoJG PedroLG Salvia officinalis L. essential oils: effect of hydrodistillation time on the chemical composition, antioxidant and antimicrobial activities Nat Prod Res 2011 25 5 526 541 10.1080/14786419.2010.499513 Search in Google Scholar

[25] Mikláš R, Miklášová N, Bukovský M, Devínsky F. Synthesis and antimicrobial properties of binaphthyl derived quaternary ammonium bromides. Acta Facult Pharm Univ Comenianae. 2012;59:39–47. MiklášR MiklášováN BukovskýM DevínskyF Synthesis and antimicrobial properties of binaphthyl derived quaternary ammonium bromides Acta Facult Pharm Univ Comenianae 2012 59 39 47 10.2478/v10219-012-0017-5 Search in Google Scholar

[26] Mikláš R, Miklášová N, Bukovský M, Horváth B, Kubincová J, Devínsky F. Synthesis, surface and antimicrobial properties of some quaternary ammonium homochiral camphor sulfonamides. Eur J Pharm Sci. 2014;65:29–37. MiklášR MiklášováN BukovskýM HorváthB KubincováJ DevínskyF Synthesis, surface and antimicrobial properties of some quaternary ammonium homochiral camphor sulfonamides Eur J Pharm Sci 2014 65 29 37 10.1016/j.ejps.2014.08.013 Search in Google Scholar

[27] Mlynarčík D. Denyer SP. Hugo WB. A study of the action of a bisquaternary ammonium salt, an amine oxide and an alkoxy phenylcarbamic acid ester on some metabolic functions in Staphylococcus aureus. Microbios 1981;30:27–35. MlynarčíkD DenyerSP HugoWB A study of the action of a bisquaternary ammonium salt, an amine oxide and an alkoxy phenylcarbamic acid ester on some metabolic functions in Staphylococcus aureus Microbios 1981 30 27 35 Search in Google Scholar

[28] Morel A. Silarska E. Trzeciak A M. Pernak J. Palladium-catalyzed asymmetric Heck arylation of 2,3-dihydrofuran – effect of prolinate salts. Dalton Trans. 2013; 42(4): 1215–1222. MorelA SilarskaE Trzeciak AM PernakJ Palladium-catalyzed asymmetric Heck arylation of 2,3-dihydrofuran – effect of prolinate salts Dalton Trans 2013 42 4 1215 1222 10.1039/C2DT31672B Search in Google Scholar

[29] Pérez L. Pinazo A. García MT et al. Cationic surfactants from lysine: Synthesis, micellization and biological evaluation. Eur J Med Chem. 2009;44:1884–1892. PérezL PinazoA GarcíaMT Cationic surfactants from lysine: Synthesis, micellization and biological evaluation Eur J Med Chem 2009 44 1884 1892 10.1016/j.ejmech.2008.11.003 Search in Google Scholar

[30] Pernak J. Skrzypczak A. 3-Alkylthiomethyl-1-ethylimidazolium chlorides. Correlation between critical micelle concentrations and minimum inhibitory concentrations. Eur J Med Chem. 1996;31:901–903. PernakJ SkrzypczakA 3-Alkylthiomethyl-1-ethylimidazolium chlorides. Correlation between critical micelle concentrations and minimum inhibitory concentrations Eur J Med Chem 1996 31 901 903 10.1016/S0223-5234(97)89853-4 Search in Google Scholar

[31] Pernak J. Kalewska J. Ksycińska H. Cybulski J. Synthesis and antimicrobial activities of some pyridinium salts with alkoxymethyl hydrophobic group. Eur J Med Chem. 2001;36:899–907. PernakJ KalewskaJ KsycińskaH CybulskiJ Synthesis and antimicrobial activities of some pyridinium salts with alkoxymethyl hydrophobic group Eur J Med Chem 2001 36 899 907 10.1016/S0223-5234(01)01280-6 Search in Google Scholar

[32] Piętka-Ottlik M., Frąckowiak R., Maliszewska I., Kołwzan B., Wilk KA. Ecotoxicity and biodegradability of antielectrostatic dicephalic cationic surfactants. Chemosphere 2012; 89: 1103–1111. Piętka-OttlikM , FrąckowiakR. MaliszewskaI. KołwzanB. WilkKA Ecotoxicity and biodegradability of antielectrostatic dicephalic cationic surfactants Chemosphere 2012 89 1103 1111 10.1016/j.chemosphere.2012.05.09022743183 Search in Google Scholar

[33] Rice LM. Grogan CH. Hypotensive agents VI. Substitued 3-Azabicyclo[3.2.1]octane derivates. J Org Chem. 1957;22:185–189. RiceLM GroganCH Hypotensive agents VI. Substitued 3-Azabicyclo[3.2.1]octane derivates J Org Chem 1957 22 185 189 10.1021/jo01353a025 Search in Google Scholar

[34] Rosen MJ. Surfactants and interfacial phenomena, 2^nd Edition, New York, John Wiley & Sons. ISBN: 0-471-83651-6; 1989. RosenMJ Surfactants and interfacial phenomena 2nd Edition New York John Wiley & Sons ISBN: 0-471-83651-6; 1989 Search in Google Scholar

[35] Ruiz-Navajas Y. Viuda-Martos M. Sendra M. Perez-Alvarez JA. Fernandez-Lopez J. Chemical characterization and antibacterial activity of Thymus moroderi and Thymus piperella essential oils, two Thymus endemic species from southeast of Spain. Food Control 2012;27(2):294–299. Ruiz-NavajasY Viuda-MartosM SendraM Perez-AlvarezJA Fernandez-LopezJ Chemical characterization and antibacterial activity of Thymus moroderi and Thymus piperella essential oils, two Thymus endemic species from southeast of Spain Food Control 2012 27 2 294 299 10.1016/j.foodcont.2012.04.005 Search in Google Scholar

[36] Sajomsang W. Gonil P. Ruktanonchai UR. Petchsangsai M. Opanasopit P. Puttipipatkhachorn S. Effects of molecular weight and pyridinium moiety on water-soluble chitosan derivatives for mediated gene delivery. Carbohydr Polym. 2013; 91(2): 508–517. SajomsangW GonilP RuktanonchaiUR PetchsangsaiM OpanasopitP PuttipipatkhachornS Effects of molecular weight and pyridinium moiety on water-soluble chitosan derivatives for mediated gene delivery Carbohydr Polym 2013 91 2 508 517 10.1016/j.carbpol.2012.08.053 Search in Google Scholar

[37] Schrank CL. Minbiole KPC. Wuest WM. Are Quaternary Ammonium Compounds, the Workhorse Disinfectants, effective against Severe Acute Respiratory Syndrome-Coronavirus-2? ACS Infect Dis. 2020;6(7):1553–1557. SchrankCL MinbioleKPC WuestWM Are Quaternary Ammonium Compounds, the Workhorse Disinfectants, effective against Severe Acute Respiratory Syndrome-Coronavirus-2? ACS Infect Dis 2020 6 7 1553 1557 10.1021/acsinfecdis.0c00265 Search in Google Scholar

[38] Semenov VE. Mikhailov AS. Voloshina AD. Et al. Antimicrobial activity of pyrimidinophanes with thiocytosine and uracil moieties. Eur J Med Chem 2011;46(9):4715–4724. SemenovVE MikhailovAS VoloshinaAD Antimicrobial activity of pyrimidinophanes with thiocytosine and uracil moieties Eur J Med Chem 2011 46 9 4715 4724 10.1016/j.ejmech.2011.05.034 Search in Google Scholar

[39] Shirakawa S. Liu K. Maruoka K. Catalytic Asymmetric Synthesis of Axially Chiral o-Iodoanilides by Phase-Transfer Catalyzed Alkylations. J Am Chem Soc. 2012; 134(2): 916–919. ShirakawaS LiuK MaruokaK Catalytic Asymmetric Synthesis of Axially Chiral o-Iodoanilides by Phase-Transfer Catalyzed Alkylations J Am Chem Soc 2012 134 2 916 919 10.1021/ja211069f Search in Google Scholar

[40] Soukup O. Benkova M. Dolezal R. et al. The wide-spectrum antimicrobial effect of novel N-alkyl monoquaternary amonium salts and their mixtures; the QSAR study against bakteria. Eur J Med Chem. 2020;206:112584. SoukupO BenkovaM DolezalR The wide-spectrum antimicrobial effect of novel N-alkyl monoquaternary amonium salts and their mixtures; the QSAR study against bakteria Eur J Med Chem 2020 206 112584 10.1016/j.ejmech.2020.112584 Search in Google Scholar

[41] Thebault P. de Givenchi ET. Levy R. Vandenberghe Y. Guittard F. Géribaldi S. Preparation and antimicrobial behaviour of quaternary ammonium thiol derivatives able to be grafted on metal surfaces. Eur J Med Chem. 2009;44:717–724. ThebaultP de GivenchiET LevyR VandenbergheY GuittardF GéribaldiS Preparation and antimicrobial behaviour of quaternary ammonium thiol derivatives able to be grafted on metal surfaces Eur J Med Chem 2009 44 717 724 10.1016/j.ejmech.2008.05.007 Search in Google Scholar

[42] Truong TKT. Olivier NVB. Aupoix A. Pegot B. Vo-Thanh G. Chiral Ionic Liquids Derived from (-)-Ephedrine and Carbohydrates: Synthesis, Properties and Applications to Asymmetric Synthesis and Catalysis. Curr Org Synth. 2012; 9(1): 53–64. TruongTKT OlivierNVB AupoixA PegotB Vo-ThanhG Chiral Ionic Liquids Derived from (-)-Ephedrine and Carbohydrates: Synthesis, Properties and Applications to Asymmetric Synthesis and Catalysis Curr Org Synth 2012 9 1 53 64 10.2174/157017912798889143 Search in Google Scholar

[43] Wong Y-L, Hubieki MP, Curfaman CL et al. A Structure–Activity Study of Spermicidal and Anti-HIV Properties of Hydroxylated Cationic Surfactants. Bioorg Med Chem. 2002;10:3599–3608. WongY-L HubiekiMP CurfamanCL A Structure–Activity Study of Spermicidal and Anti-HIV Properties of Hydroxylated Cationic Surfactants Bioorg Med Chem 2002 10 3599 3608 10.1016/S0968-0896(02)00245-6 Search in Google Scholar

[44] Zhang Y. Zhu W. Liu Y-L. et al. Chemo-Immunotherapeutic Antimalarials Targeting Isoprenoid Biosynthesis. ACS Med Chem Lett. 2013;4:423–427. ZhangY ZhuW LiuY-L Chemo-Immunotherapeutic Antimalarials Targeting Isoprenoid Biosynthesis ACS Med Chem Lett 2013 4 423 427 10.1021/ml4000436363051623610597 Search in Google Scholar

[45] Zhi DF. Zhang SB. Qureshi F. et al. Synthesis and biological activity of carbamate-linked cationic lipids for gene delivery in vitro. Bioorg Med Chem Lett. 2012; 22(11): 3837–3841. ZhiDF ZhangSB QureshiF Synthesis and biological activity of carbamate-linked cationic lipids for gene delivery in vitro Bioorg Med Chem Lett 2012 22 11 3837 3841 10.1016/j.bmcl.2012.01.09722542011 Search in Google Scholar