Extracavity effect in cyclodextrin/surfactant complexation

Carolyn Vargas, Jens Christian Sidney Schönbeck, Ina Heimann, Sandro Keller

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

Resumé

Cyclodextrin (CD) complexation is a convenient method to sequester surfactants in a controllable way, for example, during membrane-protein reconstitution. Interestingly, the equilibrium stability of CD/surfactant inclusion complexes increases with the length of the nonpolar surfactant chain even beyond the point where all hydrophobic contacts within the canonical CD cavity are saturated. To rationalize this observation, we have dissected the inclusion complexation equilibria of a structurally well-defined CD, that is, heptakis(2,6-di-O methyl)-CD (DIMEB), and a homologous series of surfactants, namely, n alkyl-N,N dimethyl-3 ammonio-1 propanesulfonates (SB3 x) with chain lengths ranging from x = 8 to 14. A combination of thermodynamic parameters obtained by isothermal titration calorimetry (ITC) and structural insights derived from nuclear magnetic resonance (NMR) spectroscopy and molecular dynamics (MD) simulations revealed that, upon inclusion, long-chain surfactants with x = 10 extend beyond the canonical CD cavity. This enables the formation of hydrophobic contacts between long surfactant chains and the extra-cavity parts of DIMEB, which make additional favorable contributions to the stability of the inclusion complex. These results explain the finding that the stability of CD/surfactant inclusion complexes monotonously increases with surfactant chain length even for long chains that completely fill the canonical CD cavity.
OriginalsprogEngelsk
TidsskriftLangmuir
Vol/bind34
Udgave nummer20
Sider (fra-til)5781–5787
Antal sider7
ISSN0743-7463
DOI
StatusUdgivet - 2018

Citer dette

Vargas, Carolyn ; Schönbeck, Jens Christian Sidney ; Heimann, Ina ; Keller, Sandro. / Extracavity effect in cyclodextrin/surfactant complexation. I: Langmuir. 2018 ; Bind 34, Nr. 20. s. 5781–5787.
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abstract = "Cyclodextrin (CD) complexation is a convenient method to sequester surfactants in a controllable way, for example, during membrane-protein reconstitution. Interestingly, the equilibrium stability of CD/surfactant inclusion complexes increases with the length of the nonpolar surfactant chain even beyond the point where all hydrophobic contacts within the canonical CD cavity are saturated. To rationalize this observation, we have dissected the inclusion complexation equilibria of a structurally well-defined CD, that is, heptakis(2,6-di-O methyl)-CD (DIMEB), and a homologous series of surfactants, namely, n alkyl-N,N dimethyl-3 ammonio-1 propanesulfonates (SB3 x) with chain lengths ranging from x = 8 to 14. A combination of thermodynamic parameters obtained by isothermal titration calorimetry (ITC) and structural insights derived from nuclear magnetic resonance (NMR) spectroscopy and molecular dynamics (MD) simulations revealed that, upon inclusion, long-chain surfactants with x = 10 extend beyond the canonical CD cavity. This enables the formation of hydrophobic contacts between long surfactant chains and the extra-cavity parts of DIMEB, which make additional favorable contributions to the stability of the inclusion complex. These results explain the finding that the stability of CD/surfactant inclusion complexes monotonously increases with surfactant chain length even for long chains that completely fill the canonical CD cavity.",
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Extracavity effect in cyclodextrin/surfactant complexation. / Vargas, Carolyn; Schönbeck, Jens Christian Sidney; Heimann, Ina; Keller, Sandro.

I: Langmuir, Bind 34, Nr. 20, 2018, s. 5781–5787.

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

TY - JOUR

T1 - Extracavity effect in cyclodextrin/surfactant complexation

AU - Vargas, Carolyn

AU - Schönbeck, Jens Christian Sidney

AU - Heimann, Ina

AU - Keller, Sandro

PY - 2018

Y1 - 2018

N2 - Cyclodextrin (CD) complexation is a convenient method to sequester surfactants in a controllable way, for example, during membrane-protein reconstitution. Interestingly, the equilibrium stability of CD/surfactant inclusion complexes increases with the length of the nonpolar surfactant chain even beyond the point where all hydrophobic contacts within the canonical CD cavity are saturated. To rationalize this observation, we have dissected the inclusion complexation equilibria of a structurally well-defined CD, that is, heptakis(2,6-di-O methyl)-CD (DIMEB), and a homologous series of surfactants, namely, n alkyl-N,N dimethyl-3 ammonio-1 propanesulfonates (SB3 x) with chain lengths ranging from x = 8 to 14. A combination of thermodynamic parameters obtained by isothermal titration calorimetry (ITC) and structural insights derived from nuclear magnetic resonance (NMR) spectroscopy and molecular dynamics (MD) simulations revealed that, upon inclusion, long-chain surfactants with x = 10 extend beyond the canonical CD cavity. This enables the formation of hydrophobic contacts between long surfactant chains and the extra-cavity parts of DIMEB, which make additional favorable contributions to the stability of the inclusion complex. These results explain the finding that the stability of CD/surfactant inclusion complexes monotonously increases with surfactant chain length even for long chains that completely fill the canonical CD cavity.

AB - Cyclodextrin (CD) complexation is a convenient method to sequester surfactants in a controllable way, for example, during membrane-protein reconstitution. Interestingly, the equilibrium stability of CD/surfactant inclusion complexes increases with the length of the nonpolar surfactant chain even beyond the point where all hydrophobic contacts within the canonical CD cavity are saturated. To rationalize this observation, we have dissected the inclusion complexation equilibria of a structurally well-defined CD, that is, heptakis(2,6-di-O methyl)-CD (DIMEB), and a homologous series of surfactants, namely, n alkyl-N,N dimethyl-3 ammonio-1 propanesulfonates (SB3 x) with chain lengths ranging from x = 8 to 14. A combination of thermodynamic parameters obtained by isothermal titration calorimetry (ITC) and structural insights derived from nuclear magnetic resonance (NMR) spectroscopy and molecular dynamics (MD) simulations revealed that, upon inclusion, long-chain surfactants with x = 10 extend beyond the canonical CD cavity. This enables the formation of hydrophobic contacts between long surfactant chains and the extra-cavity parts of DIMEB, which make additional favorable contributions to the stability of the inclusion complex. These results explain the finding that the stability of CD/surfactant inclusion complexes monotonously increases with surfactant chain length even for long chains that completely fill the canonical CD cavity.

U2 - 10.1021/acs.langmuir.8b00682

DO - 10.1021/acs.langmuir.8b00682

M3 - Journal article

VL - 34

SP - 5781

EP - 5787

JO - Langmuir

JF - Langmuir

SN - 0743-7463

IS - 20

ER -