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Solvation effect on the complexation of adamantyl glycoside with β-cyclodextrins


Leko, Katarina; Ribić, Rosana; Požar, Josip
Solvation effect on the complexation of adamantyl glycoside with β-cyclodextrins // Pharma NMR Conference, Application of NMR Spectroscopy in Pharmaceutical Industry, Programme & Book of Abstracts / Novak, Predrag ; Tomišić, Vladislav ; Bregović, Nikola (ur.).
Zagreb: IAPC, 2015. (poster, nije recenziran, sažetak, ostalo)


Naslov
Solvation effect on the complexation of adamantyl glycoside with β-cyclodextrins
(Solvation effect on the complexation of adamanthyl glycoside with beta- cyclodextrins)

Autori
Leko, Katarina ; Ribić, Rosana ; Požar, Josip

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, ostalo

Izvornik
Pharma NMR Conference, Application of NMR Spectroscopy in Pharmaceutical Industry, Programme & Book of Abstracts / Novak, Predrag ; Tomišić, Vladislav ; Bregović, Nikola - Zagreb : IAPC, 2015

Skup
Pharma NMR Conference, Application of NMR Spectroscopy in Pharmaceutical Industry

Mjesto i datum
Crveni otok, Rovinj, Hrvatska, 23.-25.09.2015

Vrsta sudjelovanja
Poster

Vrsta recenzije
Nije recenziran

Ključne riječi
adamantane ; β-cyclodextrin ; complexation ; solvation

Sažetak
(S)-N-(adamant-1-yl)-3-(β-D- mannopyranosyloxy)-2-methylpropanamide, was prepared by condensation of 1- adamantamine and mannose through short linker. The complexation thermodynamics of this compound with β-cyclodextrin and 6-O- monotosyl-β-cyclodextrin in water, methanol, ethylene glycol, formamide, and N-methylformamide was explored by means of microcalorimetry and NMR spectroscopy. The complex formation was observed in water, ethylene glycol and formamide. The temperature dependence (5 ≤ θ / ºC ≤ 65) of standard thermodynamic complexation parameters in these solvents was studied in detail. The structures of reaction products were investigated by means of NMR spectroscopy. The stabilities of the complexes were highest in water followed by formamide and ethylene glycol, whereby all reactions were enthalpically controlled at temperatures examined. The ΔrHº values for complexation reactions in formamide and ethylene glycol were rather similar in the studied temperature range, whereas the corresponding values in water decreased with the increase in temperature. The reaction entropies in all examined solvents were less favourable at higher than at lower temperatures. The stability constant of the synthetic macrocycle and adamantyl mannoside complex was lower than that with β-cyclodextrin. The main driving force for the formation of complexes can be attributed to solvophobic solvation of the host cavity and the adamantane subunit. The differences in the temperature dependence of the complex stabilities in water and both formamide and ethylene glycol can be explained by more pronounced changes of water structure with change in temperature.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
119-1191342-2960 - Elektroliti i koordinacijske reakcije u otopini (Vladislav Tomišić, )
119-1191344-3121 - Sinteze i enzimske transformacije biološki aktivnih spojeva (Srđanka Tomić-Pisarović, )

Ustanove
Prirodoslovno-matematički fakultet, Zagreb

Profili:

Avatar Url Rosana Ribić (autor)

Avatar Url Josip Požar (autor)

Avatar Url Katarina Leko (autor)

Citiraj ovu publikaciju

Leko, Katarina; Ribić, Rosana; Požar, Josip
Solvation effect on the complexation of adamantyl glycoside with β-cyclodextrins // Pharma NMR Conference, Application of NMR Spectroscopy in Pharmaceutical Industry, Programme & Book of Abstracts / Novak, Predrag ; Tomišić, Vladislav ; Bregović, Nikola (ur.).
Zagreb: IAPC, 2015. (poster, nije recenziran, sažetak, ostalo)
Leko, K., Ribić, R. & Požar, J. (2015) Solvation effect on the complexation of adamantyl glycoside with β-cyclodextrins. U: Novak, P., Tomišić, V. & Bregović, N. (ur.)Pharma NMR Conference, Application of NMR Spectroscopy in Pharmaceutical Industry, Programme & Book of Abstracts.
@article{article, year = {2015}, keywords = {adamantane, β-cyclodextrin, complexation, solvation}, title = {Solvation effect on the complexation of adamanthyl glycoside with beta- cyclodextrins}, keyword = {adamantane, β-cyclodextrin, complexation, solvation}, publisher = {IAPC}, publisherplace = {Crveni otok, Rovinj, Hrvatska} }