Photochemical Applications to the Study of Complexity Phospholipid Bilayer Environments
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1 Virginia Commonwealth University VCU Scholars Compass Theses and Dissertations Graduate School 2006 Photochemical Applications to the Study of Complexity Phospholipid Bilayer Environments Christopher John Wohl Jr. Virginia Commonwealth University Follow this and additional works at: Part of the Chemistry Commons The Author Downloaded from This Dissertation is brought to you for free and open access by the Graduate School at VCU Scholars Compass. It has been accepted for inclusion in Theses and Dissertations by an authorized administrator of VCU Scholars Compass. For more information, please contact
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5 Table of Contents Page... Acknowledgements List of Tables... vlll List of Schemes... List of Figures... ix x Chapter 1 Introduction Phospholipid Bilayer Membrane Architecture and Properties SpiropyranIMerocyanine Properties and Photophysics This Work Excited State Dynamics of Spiropyran-Derived Merocyanine Isomers Overview Merocyanine Isomers Background Pump-Probe Spectroscopy Resolution of MC Isomers Analysis of Selective MC Isomer Excitation Data Summary Isomerization Dynamics of Photochromic Spiropyran Molecular Switches in Phospholipid Bilayers Overview Introduction... 71
6 3.3 Transient Absorption Spectroscopy SP2 Ring-opening / Isomerization Sensitivity to Bilayer Viscosity Modified Krarners Thoery Applied to SP2 Isomerization Rate Constants Summary Phospholipid Bilayer Free Volume Analysis Employing the Thermal Ring- Closing Reaction of Merocyanine Molecular Switches Overview Bilayer Free Volume Effects and Selective Merocyanine Localization SP31MC3 Synthesis Merocyanine Thermal Ring-Closing Kinetics Measurements Merocyanine Solvatochromism and Arrhenius Analysis Development of the Phospholipid Bilayer Free Volume Profile Summary Nonlinear Optical Spectroscopic Studies of Thermalization Dynamics of Phospholipid Bilayer Liposomes Embedded with Porphyrin Sensitizers Overview Energy Transfer and Porphyrin Molecules Transient Grating Spectroscopy Experimental Porphyrin Bilayer Embedding and Photoacoustic Data vi
7 5.6 Modeling the Thermalization Behavior of Membrane-embedded... Porphyrin Molecules Summary References Appendices 176 vii A B Determination of the Intrinsic Barrier for the Spiropyran Isomerization... Reaction 176 Merocyanine Absorption Spectra in Gel and Liquid Phase Saturated... Phosphatidylcholine Bilayers 178 C Linear Dichroism Experimental Details and Analysis D Liposome Preparation and Experimental Details 186
8 List of Tables Page Table 1 : MC1 excited state lifetimes and isomer spectral assignments Table 2: Lipid phase transition temperatures, MC2 absorption maxima and experimental SP2 isomerization rate constants in gel and liquid phase bilayers Table 3 : Merocyanine MC1 - MC3 photophysical properties in toluene solution and in phosphatidylcholine bilayers Table 4: Analysis of the free volume properties of liquid phase phosphatidylcholine... bilayers. 120
9 List of Schemes Page Scheme 1 : A) Architecture of a phospholipid vesicle. B) Structure of DMPC... 4 Scheme 2: Spiropyran exists in equilibrium with the ring-opened merocyanine form Scheme 3: MC and SP molecular sensitizers Scheme 4: Spiropyran-derived merocyanine isomers Scheme 5: Optical scheme of the ultrafast pump-probe spectrometer Scheme 6: Reaction pathways upon selective merocyanine isomer excitation Scheme 7: SP2 photochemical reaction pathways in phospholipid bilayers Scheme 8: Merocyanine localization and orientation in different regions of a phosphatidylcholine bilayer and the structures of DPPC and DMPC Scheme 9: Porphyrin structures and energy transfer model in a phospholipid bilayer Scheme 10: Transient grating diagram and photoacoustic peak-shift schematic
10 List of Figures - Page Figure 1 : A) Four region model of a phospholipid bilayer. B) Molecular density distribution of various bilayer components... 6 Figure 2: Phospholipid bilayer free volume voids determined by molecular dynamics simulations Figure 3 : The thermotropic structures of phospholipid membranes Figure 4: Schematic representation of transient phospholipid domains Figure 5: Hypothetic phase diagram for a two-component phospholipid bilayer Figure 6: A) The potential energy surface for the merocyanine thermal decoloration reaction. B) Merocyanine resonance forms Figure 7: The conical intersection between ground and excited states in the spiropyran ring-opening reaction Figure 8: The photochemical reaction mechanism determined for direct merocyanine excitation Figure 9: A model for the diffusion of ring-opened spirooxazine in phospholipid bilayers Figure 10: A) SPl/MCl absorption spectra. B) Fluroescence emission and (C) excitation spectra of MC1 in toluene. D) Shift in the maximum of the fluorescence excitation spectrum with variation of the emission detection wavelength Figure 1 1 : Transient absorption difference spectra measured 1 ps after excitation in toluene
11 Figure 12: Time-resolved transient absorption spectra of MC1 with excitation at 630 nm (A) and 490 nm (B) in toluene Figure 13: 2 ns transient absorption difference spectra of MC1 in toluene Figure 14: Transient absorption kinetics of MC1 isomers measured at 480 (A), 568 (B) and 650 (C) nm in toluene Figure 15: Comparison of 480 and 650 nm kinetics of MC1 in toluene measured with 630 nm excitation Figure 16: A) SP2lDMPC time-resolved transient absorption spectra. B) Transient absorption kinetics of SP2 measured at 568 nm in toluene and DMPC bilayers Figure 17: Temperature dependence of SP2 isomerization rate constants Figure 18: DMPC bilayer viscosity temperature dependence determined from SP2 isomerization data Figure 19: Reduced rate (F(q)) temperature dependence in liquid phase DMPC bilayers Figure 20: A) MC2 and MC3 absorption spectra in organic solvents. B) Solvatochromic shifts for MC2 in organic solvents Figure 2 1 : Merocyanine absorption spectra in DPPC bilayers Figure 22: MC1 (A) and MC3 (B) ring-closing kinetics in toluene solution and in DPPC bilayers Figure 23: A) MC2 ring-closing kinetics at several temperatures. B) Temperature dependence of MC1 ring-closing rate constants in DPPC, DMPC, and toluene solution xi
12 Figure 24: MC2 (A) and MC3 (B) ring-closing rate constant temperature dependence in DPPC, DMPC, and toluene solution Figure 25: A) Electronic absorption spectra of porphyrins in acetone and in phospholipid bilayers. B) Fluorescence emission intensity temperature dependence of porphyrin/dmpc liposomes Figure 26: Modified Stern-Volmer plot of porphyrin 1 / DMPC fluorescence emission quenching with iodide , Figure 27: Transient grating kinetics of porphyrin 3 aqueous solution Figure 28: Transient grating kinetics of porphyrin 2 / DMPC liposomes Figure 29: Amplitude (A), period (B), and acoustic peak delay (C) temperature dependence for porphyrin 2 1 DMPC and porphyrin 3 aqueous solutions. D) Experimentally determined first acoustic peak maxima Figure 30: Porphyrin 2 / DMPC liposome transient grating data measured at 10 (A) and 24 (B) "C Figure 3 1 : Temperature dependence of thermal relaxation rate constants determined for porphyrin 2 / DMPC liposomes Figure 32: Isomerization rate constants of SP2 in n-alcohol solutions Figure 33: Merocyanine MC 1 - MC3 absorption spectra measured in phospholipid bilayers at different temperatures , ,..,, Figure 34: Orientational distribution functions for MC1 - MC3 in DPPC (A) and DMPC (B) xii
13 Abstract PHOTOCHEMICAL APPLICATIONS TO THE STUDY OF COMPLEXITY PHOSPHOLIPID BILAYER ENVIRONMENTS By Christopher John Wohl Jr, Ph.D. A Dissertation submitted in partial fulfillment of the requirements for the degree of Doctor of Philosophy in Chemistry at Virginia Commonwealth University. Virginia Commonwealth University, 2006 Major Director: Dr. Darius Kuciauskas Assistant Professor, Department of Chemistry The physical and biophysical properties of a biological membrane model, phosphatidylcholine bilayers, were investigated using novel spiropyranlmerocyanine molecular probes. The feintosecond to second dynamics of this system's photochenlistry enabled bilayer viscosity and free volume to be studied over a broad time scale. Spiropyrans/n~erocyanines with different polarity were synthesized by changing the substitution of the indole moiety enabling determination of.the trans-membrane properties
14 of the bilayer. xiv In addition, transient grating spectroscopy was used to study thermal energy transfer in phospholipid bilayers on a picosecond time scale. Femtosecond transient absorption spectroscopy was used to study the photo-induced spiropyran ring-opening and isomerization reactions that produce the highly polar merocyanine species. The hindered rotation of the merocyanine bridge results in several metastable merocyanine isomers. The merocyanine ground state was determined to be populated predominantly by two isomers (TTC and TTT). Selective photoexcitation of these isomers results in excited state isomerization producing a third isomer (z = 60 ps). Merocyanine thermal ring-closing was observed on a seconds time scale. Reaction kinetics, and solvatochromic and photochromic properties of merocyanines and spiropyrans were used to determine the bilayer physical properties. Bilayer viscosity was determined from merocyanine isomerization kinetics. Phospholipid bilayer free volume (the unoccupied volume enclosed in the bilayer) was determined from a modified Kramers' analysis. The greatest fiee volume was found in the extreme interior of the bilayer, while the head-group region exhibited the least fiee volume in qualitative agreement with molecular dynamics simulations of these bilayer systems. Free volumes determined via ps experiments were lower than those determined on a seconds time scale due to reduced acyl chain dynamics on the ps time scale. Femtosecond transient grating spectroscopy was used to study the rate of thermal energy transfer from photo-excited porphyrin molecules to the surrounding solvent. Thermal energy transfer was observed as photo-acoustic waves propelled through the
15 system upon relaxation of photo-excited porphyrin molecules in aqueous solution and xv embedded in bilayers. For liposome solutions, a bimodal energy transfer model was developed. The determined rate constants suggest that energy transfer occurs predominantly via thermal diffusion and vibrational energy transfer, while lipid dynamics (isomerizations) are not involved. This document was created in Microsoft Word 2002 SP3.
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