The BV Droplets Down Under: From Model Emulsions to Drug Delivery
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1 The BV Droplets Down Under: From Model Emulsions to Drug Delivery Clive Prestidge Ian Wark Research Institute, The ARC Special Research Centre for Particle and Material Interfaces, University of South Australia, TM
2 Windsurfing in the Bristol Channel
3 Definitely not the Bristol Channel!
4 Memories of those good old days at Bristol in the late 80 s with Brian as your supervisor Civilised with a high level of decorum
5 The BV Birthday Always a Special Day.. Kick a few students into a Mini Bus
6 Treat him like a King and make him the centre of attention
7 Feed him a nice big cake
8 Respect from your Supervisor???? But some students just got a bit too friendly!!
9
10
11 BV s BV s PDMS Balls Droplets CH 3 NH 3 NH 3 EtO Si OEt OEt CH 3 EtO Si OEt Non-Cross linked Droplets: Viscous & deformable (η < 5 mnm -2 s) CH 3 Cross linked droplets Deformability control: viscous to viscoelastic - Highly monodispersed (~1μm in diameter) - Emulsifier free, negatively charged with IEP ph 2.5 T. M. Obey & B. Vincent, J. Colloid Interface Sci., 163 (1994) 454. M. I. Goller et al., Colloids Surf. A:, (1997) 183.
12 The BV Droplets an excellent model colloid with controllable deformability Interaction forces of the BV droplets Rheological studies on concentrated emulsions of the BV droplets Block copolymers at the BV droplet - water interface Nanoparticles at the BV droplet - water interface Molecular transport across the BV droplet - water interface.
13 Deformable BV droplets are more colloidally stable Do the BV Balls Squash? Liquid droplets ccc (mm) Cross-linked droplets ph
14 Interaction forces on the BV droplets determined using colloid probe atomic force microscopy (AFM) Photodiode Laser Potential from PD Deflection of cantilever Probe Cantilever Target Interdroplet forces Hooke s Law F = k c x k c : spring constant of cantilever x : deflection of cantilever
15 (Deflection) Force 0 Deformable Nondeformable D C B Drive distance A A B C D A B C D
16 Approach Rate Dependence Force Low rate Drive distance Force High rate Drive distance
17 Interaction Forces between BV Droplets and AFM colloid probe -6 50% ( ), 45% ( ), 40% ( ), 35% ( ), 30% ( ). ln (Force/2πR) Arbitrary Separation (nm) Gillies and Prestidge, Langmuir, 21, , 2005
18 Deformation & Hysteresis- influence of cross-linking: 3 50% ( ), 45% ( ), 40% ( ), 35% ( ), 30% ( ). Force/2πR (mn/m) Nominal Separation (nm) Gillies and Prestidge, Langmuir, 21, , 2005
19 Liquid-like BV Droplets: Influence of Surfactant (SDS) ( ) No SDS ( )10-4 M ( )10-3 M ( )10-2 M Force/2πR (mn/m) R PDMS = 10 μm Nominal Separation (nm) GS Gillies, CA Prestidge, Adv. Colloid Interface Sci, , , 2004.
20 Spring constant controlled by interfacial tension Spring Constant (mn/m) R PDMS = 10 μm 10-2 M SDS 10-3 M SDS Interfacial Tension (mn/m) No SDS 10-4 M SDS GS Gillies, CA Prestidge, Adv. Colloid Interface Sci, , , 2004.
21 Liquid-like BV Droplets: Influence of size Spring Constant (mn/m) /Radius (μm -1 ) Laplace pressure controls spring constant GS Gillies, CA Prestidge, Adv. Colloid Interface Sci, , , 2004.
22 Cross-linked BV Droplets: Approach Rate Dependence 3.5 Fast (4 μm/s) Force/2πR (mn/m) Slow (0.25 μm/s) Nominal Separation (nm) Gillies and Prestidge, Langmuir, 21, , 2005
23 Force/2πR (mn/m) Cross-linked BV Droplets: Load Dependence Approach rate = 1 μm/s Nominal Separation (nm)
24 Nano-Rheology of a BV Droplet Viscoelasticity of a Sphere (Attard, Phys. Rev. E, 2001) 3.5 Force/2πR (mn/m) E t /τ () t = E + E E 0 1 μm/s (low load) E e E Nominal Separation (nm) E 0 = 1.2 MPa, E = 0.8 MPa and τ = 0.12 s 1 μm/s 0.25 μm/s Gillies and Prestidge, Langmuir, 21, , 2005
25 Rheological studies on concentrated emulsions of the BV droplets Shear Viscosity Layers Clusters Order- Disorder Transition Suspensions 3D Network Compression Emulsions Shear Rate
26 Viscosity versus volume fraction Relative Viscosity Silica BV droplets (cross linked) BV droplets (liquid) Krieger-Dougherty Hard spheres Volume Fraction / % Saiki, Prestidge and Horn, Colloids and Surfaces A, 299, 65-72, 2006.
27 PEO-PPO-PEO Copolymers at the BV droplet - water interface PEO PPO
28 Adsorbed Amount of F108 Adsorbed Amt (mg m -2 ) C eq (ppm) Liquid droplets Cross-linked droplets Polystyrene latex Silica Prestidge, Barnes and Simovic, Adv. Colloid Interface Sci, , , 2004.
29 Adsorbed Layer Thickness of F Thickness (nm) Concentration (ppm) Liquid droplets Cross-linked droplets Polystyrene latex Silica Prestidge, Barnes and Simovic, Adv. Colloid Interface Sci, , , 2004.
30 PEO-PPO-PEO Copolymers δ Silica Polystyrene latex Cross-linked PDMS droplet Liquid PDMS droplet
31 Nanoparticles at the BV droplet - water interface Hydrophilic ccc (mm) Hydrophobic Surface Coverage Simovic and Prestidge, Langmuir, 20, , 2004.
32 Adsorption of hydrophilic silica nanoparticles to Droplets 10-3 M NaCl; 10-2 M NaCl; 10-1 M NaCl Adsorbed amount (mgm -2 ) Equilibrium concentration (wt%) h = a (1/θ 1/2 1) h- lateral separation a-particle diameter θ-plateau fraction coverage Simovic & Prestidge, Langmuir 19 (2003)
33 Adsorption of hydrophobic silica nanoparticles (10-4 M NaCl) ph: 9; 7; 5; Adsorbed amount (mgm -2 ) Equilibrium concentration (wt%) Simovic & Prestidge, Langmuir 19 (2003)
34 Adsorption of hydrophobic silica nanoparticles (10-4 M NaCl) ph: 9; 7; 5; 4 Adsorbed amount (mgm -2 ) Liquid BV Droplets Equilibrium concentration (wt%) Adsorbed amount (mgm -2 ) Cross-linked BV Droplets Equilibrium concentration (wt%) Multilayer adsorption Strong ph dependency Adsorption affinity is greater for liquid droplets Simovic & Prestidge, Langmuir 19 (2003)
35 Molecular transport across the BV droplet-water interface Dibutyl phthlate (DBP) USP rotating paddle method + ultracentrifugation + HPLC analysis
36 DBL release from BV Droplets: low loading levels 0.28mg/100ml DBP released (mg/100ml) bare PDMS droplets hydrophobic nanoparticle coatings Activation Energy ~580 kjmol -1 Pluronic F-68 Activation energy for release = 52.8 kjmol -1 Washington et al. J. Controlled Release 33 (1995) Time (min.) Prestidge & Simovic: Int. J. Pharmaceutics, 324, , European J. of Pharmaceutics and Biopharmaceutics, 66,
37 DBL release from BV Droplets: high loading levels 2.8mg/100ml Amount released (mg/100ml) Nanoparticle coatings: hydrophobic hydrophilic bare BV Droplets Time (h) Prestidge & Simovic: Int. J. Pharmaceutics, 324, , European J. of Pharmaceutics and Biopharmaceutics, 66,
38 Lipophilic drug Vehicle (oil droplet) Towards Drug Delivery 1. Drug incorporation into lipid vehicle 2. Vehicle encapsulation by nanoparticles 3. Vehicle drying Hydrophilic silica nanoparticles (~ 50 nm) Wet coated droplet Dermal Delivery 4. Vehicle redispersion Oral Delivery Dry coated droplets (for storage)
39 Improved Photo-stability of Vitamin A in Nanoparticle Coated Emulsions Isomerisation All-trans Vitamin A UV light 9-cis Vitamin A (Biopotency: 100%) (Biopotency: 24% ) Formulation k, min -1 ( 10 4 ) t 1/2 (day) Control Emulsion Nanoparticle coating A Nanoparticle coating B N. Ghouchi Eskandar, S. Simovic and C. A. Prestidge, Phys ChemChem Phys, 9 (48), , 2007.
40 Schematic of a Static Franz Diffusion Cell Delivery to the skin
41 Nanoparticle coated droplets improve the skin penetration of Vitamin A
42 Dry capsules for oral delivery: Spray drying Freeze-drying Phase coacervation Drying method + formulation composition controls: Structure Stability Delivery characteristics
43 Internal structure of capsules is controllable and facilitates capsule performance
44 In vivo studies: 14 improved oral delivery of poorly soluble drugs, e.g.indomethicin 12 Me O CH 2 COOH 10 Me Con.C(ug/ml) 8 6 Lipoceramic capsule O N Cl Drug suspension Time(h) Increased bioavailability Faster action
45 In vivo Bioavailability of Celecoxib Capsule 1 Capsule 2 Capsule 3 Emulsion 2 Emulsion 1 Celebrex Miglyol Oil Aq susp.
46 In-vitro / In-vivo Correlation Bioavailability (%) Lipoceramic Capsules Celebrex Celecoxib % of dissolved drug after 15 min.
47 Concluding Remarks BV s monodispersed silicone emulsions are an excellent model colloid Investigations of the BV droplets have improved understanding of emulsion interfaces The BV droplets have inspired the development of new drug delivery systems based on emulsions and nanoparticles
48 Acknowledgements Dr Graeme Gillies (AFM studies) Dr Yasushi Saiki (rheology studies) Dr Tim Barnes (polymer interaction) Dr Spomenka Simovic (nanoparticle interaction) Angel Tan (oral delivery) Nasrin Eskandar (dermal delivery)
49 Nano-structured Drug Delivery Systems at the Wark Dendrimers Mesoporous Particles Liposomes Emulsions + Micro/Nano Capsules Nanoparticles Drug encapsulation Formulation stability Controlled release Improving bioavailability Controlled circulation Targeted delivery DNA-lipids Functional Nanoparticle Research at the Wark TM : Towards a new generation of diagnostic and therapeutic nanomaterials.
50
51 Hydrophobic nanoparticles: restricted (limited) coalescence Initial interfacial coverage in the range 0.7 and 0.9: chain structures 45 min. 2h
52 Initial interfacial coverage of hydrophobic nanoparticles of ~0.6: dendritic structures Simovic & Prestidge: Langmuir 20, 8357, 2004
53 Data Analysis: Nano-Rheology Viscoelasticity of a Sphere (Attard, Phys. Rev. E, 2001) E(t) Long time-scale Modulus E E t /τ () t = E + E E 0 E E τ e Short time-scale Modulus E 0 log (time)
54 Absolute F (%) Pure celecoxib susp. Oil disp. Bare liquid systems (n 3; One-way ANOVA: p < 0.1 ) Bioavailability L-bare droplets L-Maltodex. CELEBREX Celecoxib formulations L-S(aq,oil) L-S(aq) Redispersed dry capsules
55 C max (μg/ml) CELEBREX L-Si(aq) L-Si(aq+oil) T max (min) 420 Oil disp. 360 L-bare droplets Pure celecoxib susp. L-bare droplets L-Maltodex Pure celecoxib susp. L-Maltodex. L-Si(aq) CELEBREX L-Si(aq+oil) Oil disp p<0.01 p< Celecoxib formulations Celecoxib formulations
56 Model Drug: Celecoxib (BCS Class II drug) Indications: Anti-inflammatory drug primarily for rheumatoid arthritis & osteoarthritis Celecoxib properties Hydrophobic (log P 3.5) Low solubility (7 µg/ml) High T max (3 h) Cohesiveness; Low bulk density & compressibility; Poor flow properties Pharmaceutical limitations Incomplete & variable absorption; Excessive dose-dumping; No liquid formulation exists Slow onset of action (pain relieving) Difficult processing into solid dosage forms (tablets)
57 Celecoxib Pharmacokinetics: Bioavailability in Orally Dosed Rats Subject: fasted male Sprague-Dawley rats Capsule B Capsule C Capsule A
58 Ex-vivo delivery of Vitamin A to abdominal pig skin: Nanoparticle coatings facilitate better skin delivery from emulsions
59 Crosslinked BV Droplets and a Silica Sphere Ln (Force/2πR) Δh P(h)=P 0 e -κh hard sphere behaviour Arbitrary Separation (nm) h Δh
60 Nanoparticle coated emulsions facilitate better skin retention and less penetration of vitamin A in comparison with commercial products. Topical delivery of vitamin A to upper layers of skin with minimum transport across the skin and minimal systemic exposure. Skin layers
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