The thermal stability of the monosubstituted cationic cyclodextrin (CD) derivatives PEMEDA-β-CD and PEMPDA-β-CD, which differ in their substituent linker length (ethylene and propylene, respectively), was studied via (1)H NMR experiments. PEMPDA-β-CD exhibited higher resistance towards the Hofmann degradation and was chosen as a more suitable host molecule for further studies. Inclusion properties of PEMPDA-β-CD in solution with a series of simple aromatic guests (salicylic acid, p-methoxyphenol and p-nitroaniline) were determined by isothermal titration calorimetry (ITC) and compared to the native β-CD. Permanently charged cationic CD derivatives were successfully deposited on the anionic solid surface of polymeric Nafion(®) 117 membrane via electrostatic interactions. Deposition kinetics and coverage of the surface were determined by ELSD. Finally, the ability of the CD derivatives bound to the solid surface to encapsulate aromatic compounds from aqueous solution was measured by UV-vis spectroscopy. The obtained results are promising for future industrial applications of the monosubstituted β-CD derivatives, because the preparation of cationic CD derivatives is applicable in large scale, without the need of chromatographic purification. Their ionic deposition on a solid surface is simple, yet robust and a straightforward process as well.

Department of Chemical Physics and Optics Faculty of Mathematics and Physics Charles University Prague Ke Karlovu 3 121 16 Prague 2 Czech Republic

Department of Organic Chemistry Faculty of Science Charles University Prague Hlavova 8 128 40 Prague 2 Czech Republic

Institute of Macromolecular Chemistry AS CR v v i Heyrovskeho nam 22 16206 Prague 6 Czech Republic

Zobrazit více v PubMed

Villiers A. C R Hebd Seances Acad Sci. 1891;112:536–538.

Szejtli J. Chem Rev. 1998;98:1743–1754. doi: 10.1021/cr970022c. PubMed DOI

Szejtli J. J Inclusion Phenom Mol Recognit Chem. 1992;14:25–36. doi: 10.1007/BF01041363. DOI

Laza-Knoerr A L, Gref R, Couvreur P. J Drug Targeting. 2010;18:645–656. doi: 10.3109/10611861003622552. PubMed DOI

Popr M, Hybelbauerová S, Jindřich J. Beilstein J Org Chem. 2014;10:1390–1396. doi: 10.3762/bjoc.10.142. PubMed DOI PMC

Khan A R, Forgo P, Stine K J, D’Souza V T. Chem Rev. 1998;98:1977–1996. doi: 10.1021/cr970012b. PubMed DOI

Binkowski C, Hapiot F, Lequart V, Martin P, Monflier E. Org Biomol Chem. 2005;3:1129–1133. doi: 10.1039/b416018e. PubMed DOI

Cucinotta V, Contino A, Giuffrida A, Maccarrone G, Messina M. J Chromatogr, A. 2010;1217:953–967. doi: 10.1016/j.chroma.2009.11.094. PubMed DOI

Cai H, Nguyen T V, Vigh G. Anal Chem. 1998;70:580–589. doi: 10.1021/ac970822n. PubMed DOI

Mikuš P, Kaniansky D. Anal Lett. 2007;40:335–347. doi: 10.1080/00032710600867705. DOI

Tang W, Muderawan I W, Ong T-T, Ng S-C. Tetrahedron: Asymmetry. 2007;18:1548–1553. doi: 10.1016/j.tetasy.2007.06.017. DOI

Chankvetadze B, Endresz G, Blaschke G. Chem Soc Rev. 1996;25:141–153. doi: 10.1039/cs9962500141. DOI

Matsui Y, Ogawa K, Mikami S, Yoshimoto M, Mochida K. Bull Chem Soc Jpn. 1987;60:1219–1223. doi: 10.1246/bcsj.60.1219. DOI

Matsui Y, Okimoto A. Bull Chem Soc Jpn. 1978;51:3030–3034. doi: 10.1246/bcsj.51.3030. DOI

Sueur B, Leclercq L, Sauthier M, Castanet Y, Mortreux A, Bricout H, Tilloy S, Monflier E. Chem – Eur J. 2005;11:6228–6236. doi: 10.1002/chem.200500337. PubMed DOI

Nelles G, Weisser M, Back R, Wohlfart P, Wenz G, Mittler-Neher S. J Am Chem Soc. 1996;118:5039–5046. doi: 10.1021/ja9539812. DOI

Weisser M, Nelles G, Wohlfart P, Wenz G, Mittler-Neher S. J Phys Chem. 1996;100:17893–17900. doi: 10.1021/jp961547w. DOI

Henke C, Steinem C, Janshoff A, Steffan G, Luftmann H, Sieber M, Galla H-J. Anal Chem. 1996;68:3158–3165. doi: 10.1021/ac9512261. DOI

Fragoso A, Caballero J, Almirall E, Villalonga R, Cao R. Langmuir. 2002;18:5051–5054. doi: 10.1021/la0256679. DOI

Lee J-Y, Park S-M. J Phys Chem B. 1998;102:9940–9945. doi: 10.1021/jp9828235. DOI

Auletta T, Dordi B, Mulder A, Sartori A, Onclin S, Bruinink C M, Péter M, Nijhuis C A, Beijleveld H, Schönherr H, et al. Angew Chem. 2004;116:373–377. doi: 10.1002/ange.200352767. PubMed DOI

Yang X, Shi J, Johnson S, Swanson B. Sens Actuators, B. 1997;45:79–84. doi: 10.1016/S0925-4005(97)00273-6. DOI

Busse S, DePaoli M, Wenz G, Mittler S. Sens Actuators, B. 2001;80:116–124. doi: 10.1016/S0925-4005(01)00889-9. DOI

Grossi N, Espuche E, Escoubes M. Sep Purif Technol. 2001;22–23:255–267. doi: 10.1016/S1383-5866(00)00126-X. DOI

Kusumocahyo S P, Sumaru K, Kanamori T, Iwatsubo T, Shinbo T. J Membr Sci. 2004;230:171–174. doi: 10.1016/j.memsci.2003.11.017. DOI

Yang Y, Yang X, Liu Y-L, Liu Z-M, Yang H-F, Shen G-L, Yu R-Q. J Photochem Photobiol, A. 2005;171:137–144. doi: 10.1016/j.jphotochem.2004.10.006. DOI

Willerich I, Schindler T, Ritter H, Gröhn F. Soft Matter. 2011;7:5444–5450. doi: 10.1039/c1sm05405h. DOI

Faul C F J, Antonietti M. Adv Mater. 2003;15:673–683. doi: 10.1002/adma.200300379. DOI

Antonietti M, Conrad J, Thuenemann A. Macromolecules. 1994;27:6007–6011. doi: 10.1021/ma00099a011. DOI

Tieke B, El-Hashani A, Toutianoush A, Fendt A. Thin Solid Films. 2008;516:8814–8820. doi: 10.1016/j.tsf.2007.11.103. DOI

Cope A C, Mehta A S. J Am Chem Soc. 1963;85:1949–1952. doi: 10.1021/ja00896a012. DOI

Höfler T, Wenz G. J Inclusion Phenom Mol Recognit Chem. 1996;25:81–84. doi: 10.1007/BF01041541. DOI

Freyer M W, Lewis E A. Isothermal Titration Calorimetry: Experimental Design, Data Analysis, and Probing Macromolecule/Ligand Binding and Kinetic Interactions. In: Correia J J, Detrich H W III, editors. Biophysical Tools for Biologists, Volume One: In Vitro Techniques. Vol. 84. Academic Press; 2008. pp. 79–113. ((Methods in Cell Biology)). PubMed

Fielding L. Tetrahedron. 2000;56:6151–6170. doi: 10.1016/S0040-4020(00)00492-0. DOI

Hirose K. J Inclusion Phenom Macrocyclic Chem. 2001;39:193–209. doi: 10.1023/A:1011117412693. DOI

Junquera E, Peña L, Aicart E. J Pharm Sci. 1998;87:86–90. doi: 10.1021/js970117u. PubMed DOI

Junquera E, Ruiz D, Aicart E. J Colloid Interface Sci. 1999;216:154–160. doi: 10.1006/jcis.1999.6290. PubMed DOI

Sueishi Y, Miyakawa T. J Phys Org Chem. 1999;12:541–546. doi: 10.1002/(SICI)1099-1395(199907)12:7<541::AID-POC156>3.0.CO;2-8. DOI

Buvári A, Barcza L. J Chem Soc, Perkin Trans 2. 1988:543–545. doi: 10.1039/p29880000543. DOI

Kuroda Y, Yamada M, Tabushi I. J Chem Soc, Perkin Trans 2. 1989:1409–1415. doi: 10.1039/p29890001409. DOI

Effect of Counterions on the Soft Ionization Mass Spectra of Analytes with Multiple Permanent Charges

Mono-6-Substituted Cyclodextrins-Synthesis and Applications