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25 YEARS OF SOL-GEL RESEARCH: From basic science to an exporting company David Avnir Institute of Chemistry The Hebrew University of Jerusalem INAB visit, January 10, 2011, HUJI Nanocenter 1. Let us start with the summary * Specialty pharmaceuticals company developing innovative topical drug products for the dermatology market * Israeli HUJI know-how * Established: 1997 * No. Employees: 40 Millions of people worldwide are already using Sol-Gel’s sunscreen product UV-PearlsTM Sol-Gel’s investors * US VCs: Argonaut Ventures, Stata Ventures * Israeli VCs: Medica, Jerusalem Venture Partners, Evergreen, the Challenge Fund, Millennium, the Jesselson Family Fund, others * Industries: DSM (Holland), Merck KGaA (Germany) Dr. Alon Seri-Levy, CEO 2. What is “sol-gel”? Glasses and ceramics are made traditionally at very high temperatures The sol-gel process * Glasses and ceramics are made at room temperature * A polymerization process - similar to the preparation of plastics * Silicon-oxide building blocks are converted to glass * Nano-features of these materials: # Nanoporosity (0.5 – 50nm) # Nanosized (~1nm) elementary building blocks # Nanoholes (few nm) Silica X 50,000 10 The Sol-Gel Process Sol Stage Gel Stage Xerogel Stage Nano-sized features: – Thin Films – Fibers – Powders, patricles – Hollow Spheres – Aerogels – Membranes – Porous Monoliths – Dense Ceramic Publications in the sol-gel materials field 3500 Papers Patents (cumulative) 3000 2500 2000 1500 1000 500 0 1980 1985 1990 1995 Year 2000 2005 2010 The main contribution of Israeli science to the sol-gel field: Merging organic chemistry and biochemistry with the field of glasses and ceramics Organic functionalization by physical entrapment of molecules within sol-gel matrices Sol Gel Xerogel monomer * Small molecules oligomer * Polymers sol-particle * Proteins entrapped molecule * Nanoparticles Optics applications Chemical industry applications: Catalysis M. Pagliaro – Sicily, Silicycle – Canada, jointly with Yissum SiliaCat TEMPO: Oxidizing agent for alcohols • Stoichiometric • Catalytic Other oxidizing agents CrO2 MnO2 TPAP (ruthenium) Swern oxidation Dess-Martin periodinane 2 U.S. Patent 6,797,773 B1, 2004 Org. Process Res. Dev. 2007, 11, 766 2 TEMPO O O Si O O N H n SiliaCat® TEMPO Toxicity - Hazard N O 3. Sol-Gel Technologies How does a sunscreen molecule work? Octyl methoxycinnamate (OMC) 1. The sunscreen molecule absorbs the UV light. 2. The excited state of that molecule converts the excess energy into heat (IR) and remains the same. 3. Some of the excited molecules are involved in unwanted reactions. The choice of silica glass • Inert • Transparent • Photostable • Defined as Generally Recognized As Safe (GRAS) Core-shell capsules for carrying functional contents The concept: The sun-rays The sunscreen capsules The skin X 200,000 24 It works! Protecting the skin from penetration of sunscreens * First prototype (1999) * Merck enters, invests $1M (2001) * First export (2002) * Market is reached (2003) * Sold to Merck (2008) Sunglasses for the Skin About 379,000 results for UV-pearls Maccabi health-care provider Patent wars New Products: The Delivery NanoPearls Delivery Pearls for controlled release – drugs, vitamins, food additives, antibiotics Control the rate of release of BPO for acne treatment 70% Fraction of Released Benzoyl Peroxide 60% 50% 40% 30% Brevoxyl 8% 20% NeoBenz Micro 5.5% SGT - 5 10% SGT - 10 SGT - 15 SGT - 20 0% 0 20 40 60 80 Time (Minutes) 100 120 140 160 180 Cool Pearls™ anti-acne treatment Efficacy after 4 Weeks Gold-standard tretment BEFORE Cool Pearls™ BEFORE AFTER AFTER Cool Pearls™ treatment has significantly less side effects Overall Skin Irritation after 2 Weeks 120 Moderate to Severe 100 % 80 None to Slight 60 40 20 0 Cool Pearls Ex tra Proactiv Ex tra Cool Pearls Regular Proactiv Regular As a result: * $9M raised in the middle of the major 2009 crisis (right after Lehman’s collapse) Inherent difficulties of entrepreneurship in Israel * “War zone” * Far from the market * Limited networking * Limited reservoir of specific experts * Limited cash-flow resources (“the 8 months horizon”) * Government regulations and assistance, still in need of improvement. In other words… But…