Online citations, reference lists, and bibliographies.
Please confirm you are human
(Sign Up for free to never see this)
← Back to Search

Properties And Stability Of A Liquid Crystal Form Of Cyclosporine-the First Reported Naturally Occurring Peptide That Exists As A Thermotropic Liquid Crystal.

D. Lechuga-Ballesteros, Ahmad M. Abdul-Fattah, C. Stevenson, D. Bennett
Published 2003 · Chemistry, Medicine

Save to my Library
Download PDF
Analyze on Scholarcy
Share
A new solid-state form of cyclosporine produced by spray-drying exhibited characteristics consistent with a liquid crystal. No sharp diffraction peaks were observed by powder X-ray diffraction; however, analysis by both small-angle X-ray diffraction (SAXR) and microscopic under polarized light (PLM) confirmed the existence of two-dimensional ordered liquid crystal. Hot stage microscopy revealed a solid-to-liquid transition, in the range of 118 to 125 degrees C. Moreover, the solid-to-liquid transition showed frequency dependence by dielectric analysis (DEA), and was coincidental with a stepwise heat capacity change measured by differential scanning Calorimetry (DSC). The two-dimensional order was maintained above the solid-to-liquid transition temperature indicated by low-angle diffraction by SAXR and birefringence by PLM. However, birefringence was lost at temperatures above 170 degrees C, indicating the conversion of the liquid crystal into an isotropic liquid. In situ annealing experiments, by DSC, revealed the presence of an endotherm, unexplained by either a phase transition or solvent loss, and it is believed to be the result of a structural rearrangement that has no impact on the macroscopic properties of the material. Spray-dried cyclosporine at room temperature is therefore a frozen thermotropic liquid crystal due to the presence of two-dimensional order and the lack of substantial residual solvent. This is, to our knowledge, the first report of the existence of a thermotropic liquid crystal of a naturally occurring peptide.
This paper references
10.1021/CEN-V061N005.P024
Liquid Crystals: A colorful state of matter
G. Brown (1983)
10.1023/A:1015841824760
Kinetics and Mechanism of Isomerization of Cyclosporin A
R. Oliyai (2004)
10.1016/S0022-5223(97)70331-3
Treatment of refractory acute allograft rejection with aerosolized cyclosporine in lung transplant recipients.
R. Keenan (1997)
10.1002/HLCA.19850680319
Peptide conformations. Part 31. The conformation of cyclosporin a in the crystal and in solution
H. Loosli (1985)
10.1117/12.429685
Elastin-mimetic protein polymers: biologically derived smart materials
R. Andrew McMillan (2001)
10.1107/S0108270189011480
Neutron structure of the immunosuppressant cyclosporin A
R. Knott (1990)
10.1002/JPS.2600840621
Dielectric analysis in the characterization of amorphous pharmaceutical solids. 1. Molecular mobility in poly(vinylpyrrolidone)-water systems in the glassy state.
S. Duddu (1995)
10.1111/J.1399-3011.1992.TB00314.X
Conformation of cyclosporin A in polar solvents.
S. Ko (1992)
10.1063/1.443693
Dielectric relaxations in a supercooled liquid and glassy smectic phase
G. P. Johari (1982)
10.1080/026782997208749
Poly(L-lysine) containing azobenzene units in the side chains: influence of the degree of substitution on liquid crystalline structure and thermotropic behaviour
B. Gallot (1997)
10.1143/JJAP.41.L720
Smectic Liquid Crystal Observed in Thermotropic System of Rigid-Rod Poly(γ-octadecyl L-glutamate) : Structure and Mechanical and Thermal Properties of Condensed Matter
K. Okoshi (2002)
Melting behaviour and thermotropic mesomorphism of fenoprofen salts
T. Rades (1994)
10.1023/A:1018817801444
Differences in Crystallization Behavior Between Quenched and Ground Amorphous Ursodeoxycholic Acid
E. Yonemochi (2004)



This paper is referenced by
Liquid-Crystal and Nano-Crystal Technology for Solubilization of Poorly Water Soluble Drugs
S. Maiti (2012)
10.1016/j.trac.2020.116144
Small-angle scattering for characterization of pharmaceutical materials
S. Thakral (2021)
10.1002/JPS.20589
Structure and physical stability of hydrates and thermotropic mesophase of calcium benzoate.
Akira Terakita (2006)
Fast gelation of self-assembling peptide nanofibres triggered by electromagnetic radiation heating
M. Mazza (2011)
Hygroscopicity of pharmaceutical crystals.
D. Chen (2009)
10.1016/j.ijpharm.2011.08.010
Enhanced dissolution of inhalable cyclosporine nano-matrix particles with mannitol as matrix former.
K. Yamasaki (2011)
10.1016/J.JAEROSCI.2008.02.002
A novel production method for inhalable cyclosporine A powders by confined liquid impinging jet precipitation
H. Chiou (2008)
SPHERICAL CRYSTALLIZATION: A TOOL OF PARTICLE ENGINEERING FOR MAKING DRUG POWDER SUITABLE FOR DIRECT COMPRESSION
Man Mohan Gupta (2010)
10.1211/0022357056208
Thermotropic liquid crystalline drugs
H. Bunjes (2005)
10.1016/j.ejps.2013.05.014
Physicochemical and biopharmaceutical characterization of amorphous solid dispersion of nobiletin, a citrus polymethoxylated flavone, with improved hepatoprotective effects.
S. Onoue (2013)
10.1016/j.jconrel.2009.04.014
In vitro and in vivo characterization on amorphous solid dispersion of cyclosporine A for inhalation therapy.
S. Onoue (2009)
10.2478/s11658-008-0041-6
Oral cyclosporine A - the current picture of its liposomal and other delivery systems
A. Czogalla (2008)
18 Recrystallization of Drugs : Significance on Pharmaceutical Processing
Y. Javadzadeh (2017)
10.1021/acs.molpharmaceut.7b00499
Insights into Water-Induced Phase Separation in Itraconazole-Hydroxypropylmethyl Cellulose Spin Coated and Spray Dried Dispersions.
Naila A. Mugheirbi (2017)
10.1016/J.SUPFLU.2005.10.004
Micronization of cyclosporine using dense gas techniques
Andrian Tandya (2006)
10.1016/j.ijpharm.2010.08.007
Improved dissolution and pharmacokinetic behavior of cyclosporine A using high-energy amorphous solid dispersion approach.
S. Onoue (2010)
10.1039/B923942A
Liquid crystal phase formation by biopolymers
I. W. Hamley (2010)
10.1016/j.ijpharm.2019.118630
Cyclosporine A-loaded UniORV®: Pharmacokinetic and safety characterization.
Yosuke Iyama (2019)
10.1016/j.ijpharm.2015.12.019
Amorphous cyclosporin A nanoparticles for enhanced dermal bioavailability.
Gregori B. Romero (2016)
10.1007/s11095-013-1279-x
Spatial Characterization of Hot Melt Extruded Dispersion Systems Using Thermal Atomic Force Microscopy Methods: The Effects of Processing Parameters on Phase Separation
J. Moffat (2013)
10.1007/s11947-014-1326-6
Protein Modification During Ingredient Preparation and Food Processing: Approaches to Improve Food Processability and Nutrition
D. Sun-Waterhouse (2014)
10.1088/0957-4484/21/2/025101
Incorporation of liquid lipid in lipid nanoparticles for ocular drug delivery enhancement.
Jie Shen (2010)
10.1002/9783527652693.CH11
Application of Broadband Dielectric Spectroscopy to Study Molecular Mobility in Pharmaceutical Systems
K. Grzybowska (2016)
10.1007/s11095-006-9015-4
General Trends in the Desolvation Behavior of Calcium Salts
F. Atassi (2006)
LIQUID CRYSTALS AS NOVEL VESICULAR DELIVERY SYSTEM : A REVIEW
Dr. L. K. Omray (2013)
10.15171/apb.2019.028
Formulation and Physicochemical Characterization of Cyclosporine Microfiber by Electrospinning
Shahla Mirzaeei (2019)
10.1016/j.ijpharm.2009.12.040
Understanding the quality of protein loaded PLGA nanoparticles variability by Plackett-Burman design.
Z. Rahman (2010)
10.1080/03639040601155665
Cyclosporine A: A Review of Current Oral and Intravenous Delivery Systems
Pascal R Beauchesne (2007)
10.1590/S1516-14392008000200016
Development and characterization of an intraocular biodegradable polymer system containing cyclosporine-A for the treatment of posterior uveitis
J. B. Saliba (2008)
10.1016/j.molliq.2020.112959
The impact of various azole antifungals on the liquid crystalline ordering in itraconazole
D. Heczko (2020)
10.4018/978-1-5225-0751-2.CH009
Liquid Crystal Systems in Drug Delivery
K. K. Chaudhary (2017)
10.1002/JPS.20435
Pharmaceutical liquid crystals: the relevance of partially ordered systems.
C. Stevenson (2005)
See more
Semantic Scholar Logo Some data provided by SemanticScholar