Sterol Uptake by an Alkali-β-Cyclodextrin Metal–Organic Framework

Blight, Barry A.; Ahmad, Towseef I.; Shepherd, Helena J.; Jennings, Christopher S.; Ferland, Livia I.; Teat, Simon J.; Rossman, Jeremy S.

doi:10.1021/acs.cgd.9b01457

Title: Sterol Uptake by an Alkali-β-Cyclodextrin Metal–Organic Framework

Abstract

β-Cyclodextrin is well-known in cellular biology for its ability to moderate cholesterol levels in lipid bilayer membranes. Its use in extended network solids remains elusive due to the low symmetry of this macrocyclic system. Self-assembly of two different β-cyclodextrin metal–organic frameworks (MOFs) with extended nanotube structures is achieved by crystallization with excess potassium hydroxide, one in the presence of cholesterol. Here, we then further demonstrate the proclivity of one of these MOFs to absorb cholesterol and two other sterols from solution using NMR and confocal microscopy techniques. Finally, this work demonstrates that these network solids show great potential in both substrate delivery and/or extraction.

Authors:

^[1]; Ahmad, Towseef I. ^[2];

^[2]; Jennings, Christopher S. ^[3]; Ferland, Livia I. ^[3]; Teat, Simon J. ^[4];

^[5]

Univ. of New Brunswick, Fredericton NB (Canada); Univ. of Kent, Canterbury (United States)
Univ. of Kent, Canterbury (United States)
Univ. of New Brunswick, Fredericton NB (Canada)
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Advanced Light Source (ALS)
Univ. of Kent, Canterbury, KY (United States)

Publication Date:: 2019-11-15

Research Org.:: Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)

Sponsoring Org.:: USDOE Office of Science (SC), Basic Energy Sciences (BES); Univ. of Kent, Canterbury (United States)

OSTI Identifier:: 1580424

Grant/Contract Number:: AC02-05CH11231

Resource Type:: Accepted Manuscript

Journal Name:: Crystal Growth and Design

Additional Journal Information:: Journal Volume: 20; Journal Issue: 1; Journal ID: ISSN 1528-7483

Publisher:: American Chemical Society

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; coordination networks; metal-organic frameworks; cyclodextrin; cholesterol; organic molecule absorption

Citation Formats


                    Blight, Barry A., Ahmad, Towseef I., Shepherd, Helena J., Jennings, Christopher S., Ferland, Livia I., Teat, Simon J., and Rossman, Jeremy S. Sterol Uptake by an Alkali-β-Cyclodextrin Metal–Organic Framework.  United States: N. p., 2019. 
Web.  doi:10.1021/acs.cgd.9b01457.

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                    Blight, Barry A., Ahmad, Towseef I., Shepherd, Helena J., Jennings, Christopher S., Ferland, Livia I., Teat, Simon J., & Rossman, Jeremy S. Sterol Uptake by an Alkali-β-Cyclodextrin Metal–Organic Framework.  United States.  https://doi.org/10.1021/acs.cgd.9b01457

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                    Blight, Barry A., Ahmad, Towseef I., Shepherd, Helena J., Jennings, Christopher S., Ferland, Livia I., Teat, Simon J., and Rossman, Jeremy S. Fri .  
"Sterol Uptake by an Alkali-β-Cyclodextrin Metal–Organic Framework".  United States.  https://doi.org/10.1021/acs.cgd.9b01457.  https://www.osti.gov/servlets/purl/1580424.

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@article{osti_1580424,

  title        = {Sterol Uptake by an Alkali-β-Cyclodextrin Metal–Organic Framework},

  author       = {Blight, Barry A. and Ahmad, Towseef I. and Shepherd, Helena J. and Jennings, Christopher S. and Ferland, Livia I. and Teat, Simon J. and Rossman, Jeremy S.},

  abstractNote = {β-Cyclodextrin is well-known in cellular biology for its ability to moderate cholesterol levels in lipid bilayer membranes. Its use in extended network solids remains elusive due to the low symmetry of this macrocyclic system. Self-assembly of two different β-cyclodextrin metal–organic frameworks (MOFs) with extended nanotube structures is achieved by crystallization with excess potassium hydroxide, one in the presence of cholesterol. Here, we then further demonstrate the proclivity of one of these MOFs to absorb cholesterol and two other sterols from solution using NMR and confocal microscopy techniques. Finally, this work demonstrates that these network solids show great potential in both substrate delivery and/or extraction.},

  doi          = {10.1021/acs.cgd.9b01457},

  journal      = {Crystal Growth and Design},

  number       = 1,

  volume       = 20,

  place        = {United States},

  year         = {2019},

  month        = {11}

}

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Title: Sterol Uptake by an Alkali-β-Cyclodextrin Metal–Organic Framework

Abstract

Citation Formats

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Cyclodextrin based hydrogels: Inclusion complex formation and micellization of adamantane and cholesterol grafted polymers journal, September 2011

Dynamic Macromolecular Material Design-The Versatility of Cyclodextrin-Based Host-Guest Chemistry journal, June 2017

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Nontoxic and renewable metal–organic framework based on α-cyclodextrin with efficient drug delivery journal, January 2016

Differential effects of alpha-, beta- and gamma-cyclodextrins on human erythrocytes journal, December 1989

Influenza Virus M2 Protein Mediates ESCRT-Independent Membrane Scission journal, September 2010

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Alteration of the Myometrial Plasma Membrane Cholesterol Content with .beta.-Cyclodextrin Modulates the Binding Affinity of the Oxytocin Receptor journal, October 1995

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Use of cyclodextrins for manipulating cellular cholesterol content journal, November 1997

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Spectral displacement techniques for studying the binding of spectroscopically transparent ligands to cyclodextrins journal, May 1986

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BODIPY-Cholesterol: A New Tool to Visualize Sterol Trafficking in Living Cells and Organisms journal, November 2008

Supramolecular Cyclodextrin-Based Hydrogels for Controlled Gene Delivery
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Cation-Dependent Gold Recovery with α-Cyclodextrin Facilitated by Second-Sphere Coordination
journal, September 2016

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journal, May 2013

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journal, September 2019

Metal-Organic Frameworks for Chemiresistive Sensors
journal, August 2019

Photofunctional MOF-based hybrid materials for the chemical sensing of biomarkers
journal, January 2019

Metal-organic frameworks for multimodal bioimaging and synergistic cancer chemotherapy
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journal, August 2010

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journal, October 2012

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journal, December 2013

Minerals with metal-organic framework structures
journal, August 2016

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journal, August 2010

Controllable porosity conversion of metal-organic frameworks composed of natural ingredients for drug delivery
journal, January 2017

Nontoxic and renewable metal–organic framework based on α-cyclodextrin with efficient drug delivery
journal, January 2016

Differential effects of alpha-, beta- and gamma-cyclodextrins on human erythrocytes
journal, December 1989

Influenza Virus M2 Protein Mediates ESCRT-Independent Membrane Scission
journal, September 2010

Influenza Virus M2 Ion Channel Protein Is Necessary for Filamentous Virion Formation
journal, March 2010

Alteration of the Myometrial Plasma Membrane Cholesterol Content with .beta.-Cyclodextrin Modulates the Binding Affinity of the Oxytocin Receptor
journal, October 1995

Cell cholesterol efflux: integration of old and new observations provides new insights
journal, May 1999

Use of cyclodextrins for manipulating cellular cholesterol content
journal, November 1997

Cellular Cholesterol Efflux Mediated by Cyclodextrins
journal, July 1995

Spectral displacement techniques for studying the binding of spectroscopically transparent ligands to cyclodextrins
journal, May 1986

Crystal structure of the inclusion complex of cholesterol in β-cyclodextrin and molecular dynamics studies
journal, January 2018

Host−Guest Interaction Mediated Polymeric Assemblies: Multifunctional Nanoparticles for Drug and Gene Delivery
journal, January 2010

Preparation and guest-uptake protocol for a porous complex useful for 'crystal-free' crystallography
journal, January 2014

BODIPY-Cholesterol: A New Tool to Visualize Sterol Trafficking in Living Cells and Organisms
journal, November 2008