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Commercialization Development of Consumer Products Guerbet Glycosides Rauzah Hashim April 2015 Project Background MOSTI Strategic Research Top-Down Glycolipids as Functional Material 2002-2006 High Impact Research- MOHE April 2015 Fundamental Science in Self-Assembly Understanding Guerbet glycosides self-assembly structures and dynamics for functional nanobiotechnology 2011-2016 Mimicking Natural Products Phospholipids Phosphotidyl- Sphingomyline choline Glycolipids MGDG Glucosylcerebroside Branched Chain Glycosides Synthetic Glycolipids Alkylpolyglucoside OH OH HO OH OH HO O O O HO nO n Ease of Preparation Guerbet Glycosides at Geneva ITEX 2005 Nature-Like Synthetic Alkyl Branched-Chain Glycolipids: A Review on Chemical Structure and Self-Assembly Properties. Liq. Cryst. 2012, 39, 1–17. Success in Geneva Gold Medal, I.TEX Geneva, 2005 Special Award, The Mayor of Taipei and Taiwan ProvincialGovernment, 2005 Gold Medal One of best manuscripts Liquid Crystals 2012 4/29/2017 2005 4 Glycolipids Self-Assembly Structural Determination Gurbert Glycoside Patented product Fundamental Studies Formulation of products Product testing Scale-up Branched Chain Guerbet Glycosides Summary Liquid crystal at RT for branched glycosides of Guerbet Guerbet chains give better hydrophobicity Chain branching support non-lamellar curved phases Chain asymmetry leads to denser packing hydration OH’s stabilize the lamellar arrangement Possible different bilayer structures Sugar stereochemistry plays subtle role in self-assembly Liquid Crystals,39 (1), 1-17, 2012 Guerbet Materials Guerbet glycoside literatures prepared using a glycosidation described elsewhere. Rauzah Hashim*, et al. Invited Article Liquid Crystals, 2012, 39 (1), 1-17 Rauzah Hashim*, et al. Thin Solid Films, 2006, 509, 27-35 Guerbet alcohol, was first synthesized by Marcel Guerbet (1899). Guerbet alcohol contains two asymmetric chains differ by two methylene units, and the two chains branch at the ß-carbon position, which is also chiral. Guerbet glycoside series is a Guerbet sugar, Other Guerbet materials alcohol, ester, and acid, all of which have been used in many industrial applications. O’Lenick, A. J., Jr. Guerbet Chemistry. J. Surfactants Deterg. 2001, 4, 311-315 Our Competitors Commercialization Roadmap Upstream → Resources Present Product Downstream → Applications Cosmetic Creams HO HO OH OH O CnH2n+1 O HO O HO O CmH2m+1 OH Liposome Palm Oil Derived Branched Alcohols April 2015 The Product Specialty Chemical Low Market Volume (no Bulk-Material) Target Market Industry Cosmetic and Pharmaceutical Industry (Patent evaluated) Example DDS, Diagnostic Bio- & Med-Tech Companies Material for Product-Development April 2015 Economic Analysis MY Cosmetic Market Volume: Annual Growth: Skin Care: (Data: 2003) ~ RM 2.8 billion ~ 3-5 % ~ ¼ of total Volume Glycoside based delivery system Market Novelty: target liquid crystal delivery system April 2015 Hexasome Liposome Cubosome Commercialization Status Quo Established Product Preparation Basic Product Characterization Patent April 2015 MY PI 20051074 Compound Class Application of Compound Properties List of patent approved Singapore Patent No. 200706665/7, Oct. 31, 2008 South Africa Patent No. 2007/8477, Jul. 30, 2008 Malaysia Patent No. MY-138164-A, Apr. 30, 2009 U.S. Patent No. US8,304,525, Nov. 6, 2012 China Patent No. CN 200680008448, Jun. 12, 2013 Japan Patent No. 5392467, Oct. 25, 2013 Application Development Cycle Compatibility Lyotropic Systems (Water) Synthesis Optimization Prod.-Property April 2015 Physical Characterization Protein Crystals Formulation Liposome Guerbet Glycoside Toxicity (Creams) Product Biological Tests Cosmetics Chemical Analysis Application Development Lyotropic Systems (Water) Formulation Cosmetics (Creams) Liposome Protein Crystallization Physical Characterization (OPM, SWAX, Densiometry …) • • • • CMC Surface Tension Phase Analysis Water Swelling … April 2015 • Rheology • ThermoStability • Encapsultn. Efficiency • Vesicle Stability • Phase Stability • Filtering Efficiency Commercialization Ways HIR 2 Other Government Grant (EPU) Industrial Partners Missing Industrial Input Limited Resources Product Licensing Industrial Grant (?) April 2015 Update 2015: Publication 2014, Influence of nonionic branched-chain alkyl glycosides on a model nano-emulsion for drug delivery systems, Colloids and Surfaces B: Biointerfaces,115: 267 274 2014, Lyotropic Phase Behaviour and Structural Parameters of Monosaccharide and Disaccharide Guerbet Branched-chain β-D-glycosides. Advanced Materials Research Vol. 895, 111-115 2014. Amphiphilic designer nano- carriers for controlled release, from drug delivery to diagnostics, Med. Chem. Commun., 5 (11): 1602 – 1618 2013, Effect of vesicles membrane packing behaviour on skin penetration of model lipophilic drug, Journal of Microencapsulation, 30(3):265-273 2012, Physico- Chemical Characterization of Natural-Like Branched- Chain Glycosides towards Formation of Hexosomes and Vesicles, Langmuir, 2012, 28(5), 2395-2403 April 2015 Update 2015 Testing for Field effect study Dielectric measurements Pyroelectricity 2006, Liquid Crystals, 33(3): 361-366. 2006, Phys. Rev. E 73: 011916 2014. Phase sensitive molecular dynamics of self-assembly glycolipid thin films: A dielectric spectroscopy investigation.J. Chem. Phys. 141, 085101 Thin Solid Films (2010), 518 4412 4416 Simulation studies April 2015 2014. Conformational Dynamics of Dry Lamellar Crystals of Sugar Based Lipids: An Atomistic Simulation Study, PLOS One : June 30, 2014DOI: 10.1371/journal.pone.0101110 Physical Chemistry Chemical Physics, 2014, 16, 324-334 2012, Journal of Physical Chemistry B, 116(38), 11626-11634 Thank You. April 2015