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:: Fri Nov 15 00:00:00 EST 2019

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.

Copy to clipboard


                    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

Copy to clipboard


                    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.

Copy to clipboard


                    
@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         = {Fri Nov 15 00:00:00 EST 2019},

  month        = {Fri Nov 15 00:00:00 EST 2019}

}

Copy to clipboard

Journal Article:

Free Publicly Available Full Text

Accepted Manuscript (DOE)

Publisher's Version of Record

https://doi.org/10.1021/acs.cgd.9b01457

Other availability

Search WorldCat to find libraries that may hold this journal

Citation Metrics:

Cited by: 12 works

Citation information provided by
Web of Science

Save / Share:

Export Metadata

Save to My Library

Works referenced in this record:

Supramolecular Cyclodextrin-Based Hydrogels for Controlled Gene Delivery
journal, March 2019

Rey-Rico, Ana; Cucchiarini, Magali
Polymers, Vol. 11, Issue 3
DOI: 10.3390/polym11030514

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

Osman, Shaaban K.; Brandl, Ferdinand P.; Zayed, Gamal M.
Polymer, Vol. 52, Issue 21
DOI: 10.1016/j.polymer.2011.07.059

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

Schmidt, Bernhard V. K. J.; Barner-Kowollik, Christopher
Angewandte Chemie International Edition, Vol. 56, Issue 29
DOI: 10.1002/anie.201612150

Cyclodextrin‐Based Multistimuli‐Responsive Supramolecular Assemblies and Their Biological Functions
journal, February 2019

Zhang, Ying‐Ming; Liu, Yao‐Hua; Liu, Yu
Advanced Materials, Vol. 32, Issue 3
DOI: 10.1002/adma.201806158

Cyclodextrin-metal–organic framework (CD-MOF): From synthesis to applications
journal, April 2019

Rajkumar, T.; Kukkar, Deepak; Kim, Ki-Hyun
Journal of Industrial and Engineering Chemistry, Vol. 72
DOI: 10.1016/j.jiec.2018.12.048

Nanoporous Carbohydrate Metal–Organic Frameworks
journal, December 2011

Forgan, Ross S.; Smaldone, Ronald A.; Gassensmith, Jeremiah J.
Journal of the American Chemical Society, Vol. 134, Issue 1
DOI: 10.1021/ja208224f

Strong and Reversible Binding of Carbon Dioxide in a Green Metal–Organic Framework
journal, October 2011

Gassensmith, Jeremiah J.; Furukawa, Hiroyasu; Smaldone, Ronald A.
Journal of the American Chemical Society, Vol. 133, Issue 39, p. 15312-15315
DOI: 10.1021/ja206525x

Cation-Dependent Gold Recovery with α-Cyclodextrin Facilitated by Second-Sphere Coordination
journal, September 2016

Liu, Zhichang; Samanta, Avik; Lei, Juying
Journal of the American Chemical Society, Vol. 138, Issue 36
DOI: 10.1021/jacs.6b04986

Selective isolation of gold facilitated by second-sphere coordination with α-cyclodextrin
journal, May 2013

Liu, Zhichang; Frasconi, Marco; Lei, Juying
Nature Communications, Vol. 4, Issue 1
DOI: 10.1038/ncomms2891

CD-MOF: A Versatile Separation Medium
journal, February 2016

Hartlieb, Karel J.; Holcroft, James M.; Moghadam, Peyman Z.
Journal of the American Chemical Society, Vol. 138, Issue 7
DOI: 10.1021/jacs.5b12860

γ-Cyclodextrin metal–organic framework for efficient separation of chiral aromatic alcohols
journal, January 2017

Yang, Cheng-Xiong; Zheng, Yu-Zhen; Yan, Xiu-Ping
RSC Advances, Vol. 7, Issue 58
DOI: 10.1039/C7RA06558B

Encapsulation of Ibuprofen in CD-MOF and Related Bioavailability Studies
journal, April 2017

Hartlieb, Karel J.; Ferris, Daniel P.; Holcroft, James M.
Molecular Pharmaceutics, Vol. 14, Issue 5
DOI: 10.1021/acs.molpharmaceut.7b00168

Unprecedented α-cyclodextrin metal-organic frameworks with chirality: Structure and drug adsorptions
journal, May 2017

Sha, Jingquan; Yang, Xiya; Sun, Longjiang
Polyhedron, Vol. 127
DOI: 10.1016/j.poly.2016.10.012

Engineering of the Filler/Polymer Interface in Metal–Organic Framework‐Based Mixed‐Matrix Membranes to Enhance Gas Separation
journal, July 2019

Ma, Liang; Svec, Frantisek; Lv, Yongqin
Chemistry – An Asian Journal, Vol. 14, Issue 20
DOI: 10.1002/asia.201900843

Rational design of tailored porous carbon-based materials for CO ₂ capture
journal, January 2019

Zhang, Zhen; Cano, Zachary Paul; Luo, Dan
Journal of Materials Chemistry A, Vol. 7, Issue 37
DOI: 10.1039/C9TA07297G

Rapid Cycling and Exceptional Yield in a Metal-Organic Framework Water Harvester
journal, August 2019

Hanikel, Nikita; Prévot, Mathieu S.; Fathieh, Farhad
ACS Central Science, Vol. 5, Issue 10
DOI: 10.1021/acscentsci.9b00745

Metal–organic frameworks: A tunable platform to access single-site heterogeneous catalysts
journal, September 2019

Wasson, Megan C.; Buru, Cassandra T.; Chen, Zhijie
Applied Catalysis A: General, Vol. 586
DOI: 10.1016/j.apcata.2019.117214

Metal-Organic Frameworks for Chemiresistive Sensors
journal, August 2019

Koo, Won-Tae; Jang, Ji-Soo; Kim, Il-Doo
Chem, Vol. 5, Issue 8
DOI: 10.1016/j.chempr.2019.04.013

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

Yan, Bing
Journal of Materials Chemistry C, Vol. 7, Issue 27
DOI: 10.1039/C9TC01477B

Metal-organic frameworks for multimodal bioimaging and synergistic cancer chemotherapy
journal, November 2019

Zhang, Zhan; Sang, Wei; Xie, Lisi
Coordination Chemistry Reviews, Vol. 399
DOI: 10.1016/j.ccr.2019.213022

Application of zirconium MOFs in drug delivery and biomedicine
journal, February 2019

Abánades Lázaro, Isabel; Forgan, Ross S.
Coordination Chemistry Reviews, Vol. 380
DOI: 10.1016/j.ccr.2018.09.009

An Adaptable Peptide-Based Porous Material
journal, August 2010

Rabone, J.; Yue, Y. - F.; Chong, S. Y.
Science, Vol. 329, Issue 5995
DOI: 10.1126/science.1190672

Enhanced Stability in Rigid Peptide-Based Porous Materials
journal, October 2012

Martí-Gastaldo, Carlos; Warren, John E.; Stylianou, Kyriakos C.
Angewandte Chemie International Edition, Vol. 51, Issue 44
DOI: 10.1002/anie.201203929

Guest-Adaptable and Water-Stable Peptide-Based Porous Materials by Imidazolate Side Chain Control
journal, December 2013

Katsoulidis, Alexandros P.; Park, Kyo Sung; Antypov, Dmytro
Angewandte Chemie International Edition, Vol. 53, Issue 1
DOI: 10.1002/anie.201307074

Minerals with metal-organic framework structures
journal, August 2016

Huskić, Igor; Pekov, Igor V.; Krivovichev, Sergey V.
Science Advances, Vol. 2, Issue 8
DOI: 10.1126/sciadv.1600621

Metal-Organic Frameworks from Edible Natural Products
journal, August 2010

Smaldone, Ronald A.; Forgan, Ross S.; Furukawa, Hiroyasu
Angewandte Chemie International Edition, Vol. 49, Issue 46, p. 8630-8634
DOI: 10.1002/anie.201002343

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

Liu, Jiang; Bao, Tian-Yi; Yang, Xi-Ya
Chemical Communications, Vol. 53, Issue 55
DOI: 10.1039/C7CC03673F

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

Sha, Jing-Quan; Zhong, Xiao-Hua; Wu, Lian-He
RSC Advances, Vol. 6, Issue 86
DOI: 10.1039/C6RA16549D

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

Ohtani, Yoshiro; Irie, Tetsumi; Uekama, Kaneto
European Journal of Biochemistry, Vol. 186, Issue 1-2
DOI: 10.1111/j.1432-1033.1989.tb15171.x

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

Rossman, Jeremy S.; Jing, Xianghong; Leser, George P.
Cell, Vol. 142, Issue 6
DOI: 10.1016/j.cell.2010.08.029

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

Rossman, J. S.; Jing, X.; Leser, G. P.
Journal of Virology, Vol. 84, Issue 10
DOI: 10.1128/JVI.00119-10

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

Klein, Uwe; Gimpl, Gerald; Fahrenholz, Falk
Biochemistry, Vol. 34, Issue 42
DOI: 10.1021/bi00042a009

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

Rothblat, George H.; de la Llera-Moya, Margarita; Atger, Veronique
Journal of Lipid Research, Vol. 40, Issue 5
DOI: 10.1016/S0022-2275(20)32113-1

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

Christian, A. E.; Haynes, M. P.; Phillips, M. C.
Journal of Lipid Research, Vol. 38, Issue 11
DOI: 10.1016/S0022-2275(20)34940-3

Cellular Cholesterol Efflux Mediated by Cyclodextrins
journal, July 1995

Kilsdonk, Elisabeth P. C.; Yancey, Patricia G.; Stoudt, Genevieve W.
Journal of Biological Chemistry, Vol. 270, Issue 29
DOI: 10.1074/jbc.270.29.17250

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

Selvidge, LeRoy A.; Eftink, Maurice R.
Analytical Biochemistry, Vol. 154, Issue 2
DOI: 10.1016/0003-2697(86)90005-9

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

Christoforides, Elias; Papaioannou, Andreas; Bethanis, Kostas
Beilstein Journal of Organic Chemistry, Vol. 14
DOI: 10.3762/bjoc.14.69

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

Zhang, Jianxiang; Sun, Hongli; Ma, Peter X.
ACS Nano, Vol. 4, Issue 2
DOI: 10.1021/nn901213a

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

Inokuma, Yasuhide; Yoshioka, Shota; Ariyoshi, Junko
Nature Protocols, Vol. 9, Issue 2
DOI: 10.1038/nprot.2014.007

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

Hölttä-Vuori, Maarit; Uronen, Riikka-Liisa; Repakova, Jarmila
Traffic, Vol. 9, Issue 11
DOI: 10.1111/j.1600-0854.2008.00801.x

Similar Records in DOE PAGES and OSTI.GOV collections:

ESR technique for noninvasive way to quantify cyclodextrins effect on cell membranes

Journal Article Grammenos, A., E-mail: A.Grammenos@ulg.ac.be ; Mouithys-Mickalad, A. ; Guelluy, P. H. ; ... - Biochemical and Biophysical Research Communications

Research highlights: {yields} ESR: a new tool for cyclodextrins study on living cells. {yields} Cholesterol and phospholipid extraction by Rameb in a dose- and time-dependent way. {yields} Extracted phospholipids and cholesterol form stable aggregates. {yields} ESR spectra show that lipid rafts are damaged by Rameb. {yields} Quantification of the cholesterol extraction on cell membranes in a noninvasive way. -- Abstract: A new way to study the action of cyclodextrin was developed to quantify the damage caused on cell membrane and lipid bilayer. The Electron Spin Resonance (ESR) spectroscopy was used to study the action of Randomly methylated-beta-cyclodextrin (Rameb) on livingmore »« less
https://doi.org/10.1016/J.BBRC.2010.06.050
Rates of spontaneous exchange of synthetic radiolabeled sterols between lipid vesicles

Journal Article Kan, Chucheng ; Yan, Jiasheng ; Bittman, R - Biochemistry; (United States)

{sup 14}C-labeled sterols with structural variation in the polar function (3{alpha}-OH, 3-O(CH{sub 2}){sub 2}O-(CH{sub 2}){sub 2}O(CH{sub 2}){sub 2}OH, 3 {alpha}-NH{sub 2}, 3{beta}-NH{sub 2}, and 3-OC(O)CHN{double bond}N) and at the 7 position (7-oxo, 7{alpha}-OH, and 7{beta}-OH) were synthesized and incorporated into unilamellar vesicles for studies of the rates of transfer to an excess of acceptor vesicles. Cholesterol, cholestanol, and epicholesterol underwent full exchange in a single kinetic pool, and 90% of the 3{alpha}-triethoxycholesterol was exchangeable in one pool. Biphasic kinetics with full exchangeability were observed for cholesterylamines, which bear a positive charge at the 3 position; the slow phase reflects themore »« less
https://doi.org/10.1021/bi00121a040
Quantification of Randomly-methylated-{beta}-cyclodextrin effect on liposome: An ESR study

Journal Article Grammenos, A., E-mail: A.Grammenos@ulg.ac.be ; Bahri, M. A. ; Guelluy, P. H. ; ... - Biochemical and Biophysical Research Communications

In the present work, the effect of Randomly-methylated-{beta}-cyclodextrin (Rameb) on the microviscosity of dimyristoyl-L-{alpha} phosphatidylcholine (DMPC) bilayer was investigated using the electron spin resonance (ESR) technique. The ability of Rameb to extract membrane cholesterol was demonstrated. For the first time, the percentage of cholesterol extracted by Rameb from cholesterol doped DMPC bilayer was monitored and quantified throughout a wide Rameb concentration range. The effect of cholesterol on the inner part of the membrane was also investigated using 16-doxyl stearic acid spin label (16-DSA). 16-DSA seems to explore two different membrane domains and report their respective microviscosities. ESR experiments also establishmore »« less
https://doi.org/10.1016/J.BBRC.2009.08.172
Ombuin-3-O-β-D-glucopyranoside from Gynostemma pentaphyllum is a dual agonistic ligand of peroxisome proliferator-activated receptors α and δ/β

Journal Article Malek, Mastura Abd ; Hoang, Minh-Hien ; Jia, Yaoyao ; ... - Biochemical and Biophysical Research Communications

Highlights: ► Ombuin-3-O-β-D-glucopyranoside is a dual ligand for PPARα and δ/β. ► Ombuin-3-O-β-D-glucopyranoside reduces cellular lipid levels in multiple cell types. ► Cells stimulated with ombuine up-regulated target genes in cholesterol efflux. ► Cells stimulated with ombuine regulated target fatty acid β-oxidation and synthesis. ► Ombuin-3-O-β-D-glucopyranoside could ameliorate hyperlipidemia and hepatic steatosis. -- Abstract: We demonstrated that ombuin-3-O-β-D-glucopyranoside (ombuine), a flavonoid from Gynostemma pentaphyllum, is a dual agonist for peroxisome proliferator-activated receptors (PPARs) α and δ/β. Using surface plasmon resonance (SPR), time-resolved fluorescence resonance energy transfer (FRET) analyses, and reporter gene assays, we showed that ombuine bound directly to PPARαmore »« less
https://doi.org/10.1016/J.BBRC.2012.12.020
Selective Photodimerization in a Cyclodextrin Metal–Organic Framework

Journal Article Chen, Xiao-Yang ; Chen, Haoyuan ; Đorđević, Luka ; ... - Journal of the American Chemical Society

For the most part, enzymes contain one active site wherein they catalyze in a serial manner chemical reactions between substrates both efficiently and rapidly. Imagine if a situation could be created within a chiral porous crystal containing trillions of active sites where substrates can reside in vast numbers before being converted in parallel into products. Here, we report how it is possible to incorporate 1-anthracenecarboxylate (1-AC^–) as a substrate into a γ-cyclodextrin-containing metal–organic framework (CD-MOF-1), where the metals are K⁺ cations, prior to carrying out [4+4] photodimerizations between pairs of substrate molecules, affording selectively one of four possible regioisomers. Onemore »« less
https://doi.org/10.1021/jacs.1c03277

Full Text Available

Similar Records
Related Works
dataset (2)

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

Abstract

Citation Formats

Supramolecular Cyclodextrin-Based Hydrogels for Controlled Gene Delivery journal, March 2019

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

Cyclodextrin‐Based Multistimuli‐Responsive Supramolecular Assemblies and Their Biological Functions journal, February 2019

Cyclodextrin-metal–organic framework (CD-MOF): From synthesis to applications journal, April 2019

Nanoporous Carbohydrate Metal–Organic Frameworks journal, December 2011

Strong and Reversible Binding of Carbon Dioxide in a Green Metal–Organic Framework journal, October 2011

Cation-Dependent Gold Recovery with α-Cyclodextrin Facilitated by Second-Sphere Coordination journal, September 2016

Selective isolation of gold facilitated by second-sphere coordination with α-cyclodextrin journal, May 2013

CD-MOF: A Versatile Separation Medium journal, February 2016

γ-Cyclodextrin metal–organic framework for efficient separation of chiral aromatic alcohols journal, January 2017

Encapsulation of Ibuprofen in CD-MOF and Related Bioavailability Studies journal, April 2017

Unprecedented α-cyclodextrin metal-organic frameworks with chirality: Structure and drug adsorptions journal, May 2017

Engineering of the Filler/Polymer Interface in Metal–Organic Framework‐Based Mixed‐Matrix Membranes to Enhance Gas Separation journal, July 2019

Rational design of tailored porous carbon-based materials for CO 2 capture journal, January 2019

Rapid Cycling and Exceptional Yield in a Metal-Organic Framework Water Harvester journal, August 2019

Metal–organic frameworks: A tunable platform to access single-site heterogeneous catalysts 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 journal, November 2019

Application of zirconium MOFs in drug delivery and biomedicine journal, February 2019

An Adaptable Peptide-Based Porous Material journal, August 2010

Enhanced Stability in Rigid Peptide-Based Porous Materials journal, October 2012

Guest-Adaptable and Water-Stable Peptide-Based Porous Materials by Imidazolate Side Chain Control journal, December 2013

Minerals with metal-organic framework structures journal, August 2016

Metal-Organic Frameworks from Edible Natural Products 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

Supramolecular Cyclodextrin-Based Hydrogels for Controlled Gene Delivery
journal, March 2019

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

Cyclodextrin‐Based Multistimuli‐Responsive Supramolecular Assemblies and Their Biological Functions
journal, February 2019

Cyclodextrin-metal–organic framework (CD-MOF): From synthesis to applications
journal, April 2019

Nanoporous Carbohydrate Metal–Organic Frameworks
journal, December 2011

Strong and Reversible Binding of Carbon Dioxide in a Green Metal–Organic Framework
journal, October 2011

Cation-Dependent Gold Recovery with α-Cyclodextrin Facilitated by Second-Sphere Coordination
journal, September 2016

Selective isolation of gold facilitated by second-sphere coordination with α-cyclodextrin
journal, May 2013

CD-MOF: A Versatile Separation Medium
journal, February 2016

γ-Cyclodextrin metal–organic framework for efficient separation of chiral aromatic alcohols
journal, January 2017

Encapsulation of Ibuprofen in CD-MOF and Related Bioavailability Studies
journal, April 2017

Unprecedented α-cyclodextrin metal-organic frameworks with chirality: Structure and drug adsorptions
journal, May 2017

Engineering of the Filler/Polymer Interface in Metal–Organic Framework‐Based Mixed‐Matrix Membranes to Enhance Gas Separation
journal, July 2019

Rational design of tailored porous carbon-based materials for CO ₂ capture
journal, January 2019

Rapid Cycling and Exceptional Yield in a Metal-Organic Framework Water Harvester
journal, August 2019

Metal–organic frameworks: A tunable platform to access single-site heterogeneous catalysts
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
journal, November 2019

Application of zirconium MOFs in drug delivery and biomedicine
journal, February 2019

An Adaptable Peptide-Based Porous Material
journal, August 2010

Enhanced Stability in Rigid Peptide-Based Porous Materials
journal, October 2012

Guest-Adaptable and Water-Stable Peptide-Based Porous Materials by Imidazolate Side Chain Control
journal, December 2013

Minerals with metal-organic framework structures
journal, August 2016

Metal-Organic Frameworks from Edible Natural Products
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