Presentation on theme: "March 5, 2004.Southern Bio-products Conference Water-soluble Polysaccharides “ From Nuts to Soup ” Recent Advances Robert Y. Lochhead School of Polymers."— Presentation transcript:
March 5, 2004.Southern Bio-products Conference Water-soluble Polysaccharides “ From Nuts to Soup ” Recent Advances Robert Y. Lochhead School of Polymers & High Performance Materials The University of Southern Mississippi
March 5, 2004.Southern Bio-products Conference Outline Review Recent Advances In Polysaccharides –Focus on Applications –Focus on specialty high profit Medical Food Cosmetics
March 5, 2004.Southern Bio-products Conference Removing Unpleasant Taste from Medicine Mask taste by quick disintegration: –Tablet with medication contains mannitol (to improve taste) Sodiumcarboxymethylcellulose (disintegrant) Sodium glutamate (Corrigent) Koike, Masahiko; United States Patent Application20040033258, February 19, 2004 Assigned to TAKEDA PHARMACEUTICALS NORTH AMERICA, INC
March 5, 2004.Southern Bio-products Conference Gum Karaya Gum Karaya, (Sterculia gum), –dried exudation of the Sterculia Urens tree and other species of Sterculia. –The tree is native to India. Complex polysaccharide –molecular weight as high as 9.500.000 –yields galactose, rhamnose and galacturonic acid on hydrolysis. –occurs as a partially acetylated derivative. –acid number varies from 13.4 to 22.7. Imparts stability –through binding and emulsifying properties
March 5, 2004.Southern Bio-products Conference Bioadhesives. Mucous membranes –For example mucosa of the buccal cavity –have a rich blood supply –desirable site for topical administration of active agents for systemic delivery. Transmucosal delivery of active agents –avoids first-pass metabolism by the liver –avoids poor uptake or inactivation in the gastro- intestinal tract.
March 5, 2004.Southern Bio-products Conference Bioadhesives. Actives that can be delivered via bioadhesives: –steroids estrogens, progestins and related compounds androgens and anabolic steroids; –non-steroidal anti-inflammatory agents ketoprofen; diclofenac; propranolol; thyroid hormones; –pH sensitive peptides and small proteins such as insulin and ACTH; –physostigmine; scopolamine; verapamil; and gallopamil. –Local treatments to alleviate pain in the buccal cavity.
March 5, 2004.Southern Bio-products Conference Bioadhesives. Requirements for a successful bioadhesive device – for topical administration of active agents – prolonged periods of time The release liner should be easily peelable from the bioadhesive portion the bioadhesive portion must maintain intimate contact with the site of application –For 1 to 24 hours – sufficiently adhesive and cohesive –controlled delivery of the active ingredients in wet and moist environments –non-toxic, non irritating –easily removable.
March 5, 2004.Southern Bio-products Conference Bioadhesives. Gum Karaya and Polyvinylpyrrolidone –Improved bioadhesive –Excellent controlled release. Houze, David; Mantelle, Juan; Kanios, David; United States Patent Application20040018241, January 29, 2004, Assigned to NOVEN PHARMACEUTICALS, INC
March 5, 2004.Southern Bio-products Conference Sulfated Polysaccharides
March 5, 2004.Southern Bio-products Conference Carrageenan –obtained by extraction with water or alkaline water of certain Rhodophyceae (red seaweed). It is a hydrocolloid – consisting mainly of the potassium, sodium, magnesium, and calcium sulfate esters of galactose and 3.6-anhydro-galactose copolymers. 3 types: Kappa, lambda, iota
March 5, 2004.Southern Bio-products Conference Carrageenan 3 categories of meat: –pale, soft, and exudative (PSE) Due to postmortem generation of lactic acid –dark, firm, and dry or non-exudative (DFD) –"normal" meat acceptable subjectively between PSE meat and DFD meat. Carrageenan + soy protein –Prevents occurrence of PSE meat Keller, Heinz ; United States Patent Application20040037930, February 26, 2004 Assignee: Rhodia Inc.
March 5, 2004.Southern Bio-products Conference … However Carrageenan may cause stomach lesions, cancer Wednesday, October 17, 2001By Environmental News Network Strawberry cheesecake like this may be stabilized and thickened with carrageenan. Containers of pudding, ice cream, yogurt, or cottage cheese may include the ingredient carrageenan, a thickener derived from red seaweed. For decades, it has been presumed to be safe to eat, but new research from a medical doctor on the faculty of the University of Iowa shows that presumption may be wrong. Carrageenan is a water-soluble polymer, also known as a gum, that is used as a fat substitute in processed meats and can be found in condensed milk and some soy milk products. "Evidence from animal models has demonstrated
March 5, 2004.Southern Bio-products Conference Heparin Heparin is a sulfated polysaccharide –mean molecular weight of 12000-15000 daltons – isolated from the intestinal mucous membranes of cattle, sheep and pigs –Treats motoneuron diseases amyotrophic lateral sclerosis progressive spinal muscular atrophy infantile muscular atrophy primary lateral sclerosis Stutzmann, Jean-Marie; Uzan, Andre; United States Patent Application20040038938 Assignee: AVENTIS PHARMACEUTICALS INC.
March 5, 2004.Southern Bio-products Conference Sulfated Polysaccharides Heparin acts as an anticoagulant by accelerating the inhibition of thrombin and factor Xa by antithrombin Dermatan sulfate (DS), a sulfated glycosaminoglycan that has antithrombotic activity in laboratory animals The two are synergistic. Hirsh, Jack;Johansen, Kristian; Weitz, Jeffrey I.; United States Patent Application20040038932
March 5, 2004.Southern Bio-products Conference Curdlan Sulfate Sulfated polysaccharide –Sulfated polysaccharides are known to have anti-retroviral activity (JPA S62-215529) antimalarial activity (WO95/08334).
March 5, 2004.Southern Bio-products Conference Hyaluronic acid Used extensively in eye surgery
March 5, 2004.Southern Bio-products Conference Mucosal Membranes Mucosal membranes are lined by epithelial or endothelial cells having "tight junctions" –physiologically connect the enterocytes apically. Examples of membranes –located in or on the skin, ear, eye, nose, gastrointestinal tract (e.g., mouth, throat, esophagus, stomach, large intestine, small intestine, etc.), reproductive tract (e.g., vagina, uterus, etc.) Mucosa have limited permeability to therapeutic agents – especially if molecular weight > 500 daltons includes most peptides and proteins.
March 5, 2004.Southern Bio-products Conference Sulfated chitin and chitosan to deliver actives across mucosal membranes Sulphated chitinous polymer – a primary carrier delivers therapeutic agent across a membrane Kydonieus, Agis; Elson, Clive; Thanou, Maya; United States Patent Application20040038870, February 26, 2004
March 5, 2004.Southern Bio-products Conference Aloe Vera Polysaccharide Aloe (Liliaceae) is a shrubby tropical/subtropical plant which has succulent and elongate leaves. Aloe barbadensis Miller (Aloe vera Linne) is the most widely used for its therapeutic properties. Aloe vera plants contain two major juice materials: –yellow exudate Contains a high concentration of anthraquinone compounds that has been used throughout the centuries as a cathartic and for medicinal purges; – a clear mucilaginous gel used since ancient times to treat burns and other wounds increases the rate of healing and reduces the risk of infection. –Grindlay, D.; Reynolds, T., J. Ethnopharmcol. 1986, 16(2-3), 117-151; –Joshi, S. P., J. Med. Aromat. Plant Sci. 1998, 20(3), 768-773.
March 5, 2004.Southern Bio-products Conference Aloe Vera Polysaccharide Aloe gel comprises a mucilage of polysaccharide substances. – Most are glucomannans, mannans or pectins –polysaccharide fraction ("NP18298") having an apparent molecular weight above 2 million daltons is a powerful immunostimulant 0.015% of the original dry weight the most potent polysaccharide fraction characterized to this point potent for macrophage activation Elsobly, Mahmoud; (Oxford, MS) ; Ross, Samir; (Oxford, MS) ; Pasco, David Stanley; (Oxford, MS) ; Pugh, Nirmal Derek; (Oxford, MS)., United States Patent Application20040038931, February 26, 2004,
March 5, 2004.Southern Bio-products Conference Galactomannans
March 5, 2004.Southern Bio-products Conference Guar Gum Guar is a native plant of India –principally for its green fodder –pods are used for food and feed. –It has soil-enriching properties since it is a legume. – the primary importance of guar is the commercial value of its seed gum (galactomannan gum). Guar was introduced into the United States from India in 1903
March 5, 2004.Southern Bio-products Conference Locust Bean Gum Locust bean gum –obtained from the endosperm of the Carob or locust seed (Ceratonia siliqua). –carob paste was used by Egyptians to treat bindings for wrapping mummies, –by Greeks as laxative, –by Arabs as a weight standard. –Locust bean gum is currently being produced in parts of Spain/Portugal, Italy, Greece, Cyprus, Algeria, Morocco, Israel and Turkey
March 5, 2004.Southern Bio-products Conference Locust Bean Gum retards ice crystal growth shows viscosity synergy with xanthan.
March 5, 2004.Southern Bio-products Conference Galactomannans in Chemotherapy Galactomannan is isolated from Gleditsia triacanthos or Medicago falcata – Molecular mass of 40,000-200,000 D. –used to reduce toxicity of a therapeutic agent mixed with the agent prior to administration chemotherapeutic agents are adriamycin or 5-Fluorouracil treats cancer chronic leukemia, breast cancer, sarcoma, ovarian carcinoma, rectal cancer, throat cancer, melanoma, colon cancer, bladder cancer, lung cancer, mammary adenocarcinoma, gastrointestinal cancer, stomach cancer, prostate cancer, pancreatic cancer, or Kaposi's sarcoma. Klyosov, Anatole; Platt, David; United States Patent Application20040038935, Assigned to Pro-Pharmaceuticals, Inc
March 5, 2004.Southern Bio-products Conference Glucomannans to Treat Obesity Konjac (Amorphophallus konjac) is a plant –the tuber is the source of the konjac flour highly viscous sol of glucomannan and soluble starches when reconstituted in water. The principal soluble constituent is glucomannan –a polysaccharide comprised of D-glucose and D-mannose Also useful in industrial applications –films, oil drilling fluids and paints
March 5, 2004.Southern Bio-products Conference Glucomannans to Treat Obesity Pharmaceutical compositions for treating obesity –a lipase inhibitor, (orlistat) –Glucomannan Prevents oily leakage Bailly, Jacques; Martin, Rainer Eugen; Raab, Susanne; United States Patent Application20040033983 Assignee : HOFFMANN-LA ROCHE INC
March 5, 2004.Southern Bio-products Conference Dextran Colloidal Metals for Medical Diagnosis For immunological assays –colloidal metal particles for labeling biomolecules –must stabilize the biomolecule-coated metal particles –add stabilizing and blocking substance non-saturated, "sticky" sites on the particles are blocked. aggregation of the particles is minimized re-diffusion of the relevant biomolecule is reduced. inert proteins are used –But they are not versatile Core-shell crosslinked, water-soluble polymers Core-shell particles stabilized with amino-dextrans –No cross-linking needed –Facile processing, cheap, versatile Sluka, Peter; Heimerl, Sebastian; Kuerzinger, Konrad; Fischer, Thomas; United States Patent Application 20040038431, February 26, 2004,
March 5, 2004.Southern Bio-products Conference Alginate
March 5, 2004.Southern Bio-products Conference Alginate Origin: –Seaweeds in Northern Waters Red Weeds –Phaeophycase Giant kelp – Macrocystis pyrifera
March 5, 2004.Southern Bio-products Conference Alginate http://22.214.171.124/Biomed.nsf/0/b2f1464fb38d059bc12566d7004d73e9?OpenDocument
March 5, 2004.Southern Bio-products Conference Alginate ‘Egg Box’ Model http://126.96.36.199/Biomed.nsf/0/b2f1464fb38d059bc12566d7004d73e9?OpenDoc ument Grant, G.T., Morris, E.R., Rees, D.A., Smith, P.J.C. and Thom, D., FEBS letters, 32(1) (1973), pp195-198
March 5, 2004.Southern Bio-products Conference Alginates for Improving Bread & Doughnuts Consumers prefer bread with a soft and glutinous mouth feel –Contains large amounts of gelatinized starch Cannot return its shape after cutting & slicing –Addition of hydroxypropyl alginate Confers shape retention and good mouth feel. Takahashi, Toshihiro; Sugitani, Hiromi; United States Patent Application 20040033300, February 19, 2004, Assigned to KIBUN FOOD CHEMIFA CO., LTD.
March 5, 2004.Southern Bio-products Conference Alginate Coacervates Gelled Alginate + Guar –Coating for fresh meat No crosslinking required –Better than collagen Need smoked cross-linking Goorhuis, Johannes Gerardus Maria; United States Patent Application20040037922, February 26, 2004
March 5, 2004.Southern Bio-products Conference Hydrogels and Superporous Hydrogels Interpenetrating networks of poly(acrylic acid) and a polysaccharide-: –alginic acid (sodium salt) – chitosan –sodium salt of carboxymethylcellulose –Pectin, starch – xanthan, Gellan – carrageenan, gum arabic, guar gum, ghatti gum, tragacanth gum, pontianac gum, karaya gum, agar-agar – methyl cellulose, and hydroxypropyl methylcellulose … for enhanced elasticity
March 5, 2004.Southern Bio-products Conference Hydrophobically-modified Polysaccharides polysaccharides partially modified by cholesterol. – stabilize liposomes for chemotherapy and immunotherapy. –liposomes coated by polysaccharide derivatives improved drug carrier.
March 5, 2004.Southern Bio-products Conference Hydrophobically-Modified Hydrophilic Polymers Outline –Hydrophilic polymers modified by hydrophobic moieties –Combination of surfactant and polymer properties in one molecule –Self-associate in aqueous solution to form complex micellar structures
March 5, 2004.Southern Bio-products Conference HYDROPHOBICALLY MODIFIED HYDROXYETHYL CELLULOSE Mol wt. = 300,000 One cetyl group per 143 anhydroglucose residues Rigid backbone Huggins k = 2.63 indicates association eve in dilute solution –Nishikawa, Yekta, Pham Winnik, & Sau; Langmuir, (Dec, 1998), 14, 7119,