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Complexation2555

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犖犖.犖犖.犖犖ム険犖犖犖犖 犢犖ム鹸犖犖犖犖巌犖犖犖犖 犖.犖犖. 犖犖犖朽犖 犢犖￥犖犖о鹸犖о険犖犖犖犖伍献 1 DefinitionofComplex DefinitionofComplex Complexation (犖犖迦牽犢犖犖巌犖犖迦牽犢犖犖巌犖犖犖) 犖) 犖犖劇賢犖犖迦牽犢犖犖巌犖犖園犖犖萎見犖犖劇賢犖犖園犖犖犖犖巌牽犖巌権犖迦牽犖萎見犖э犖迦犖犖迦牽 2 犖犖犖巌犖犖謹犖犢犖 犖犖謹犖犢犖￥犖犢犖迦犖犖迦鍵 犖э犖迦犖園犖犖萎犖園犖犖犖犖犢犖犖犖犖園犖犖萎犖犖о顕犢犖ム犖犖犖犖劇賢犖犖園犖犖萎犖犖犖犖犖巌 Complex 犖犖犖劇賢 Coordinate compound:犖犖劇賢 犖犖迦牽 compound:犖犖 犢犖犖巌犖犖犖 犖犖朽犢犖犖巌犖犖迦 犖犖ム犖犖犖迦牽犢犖犢犖ム鍵犖犖園犖犖刻犖犖巌犖ム犖犖犖犖犖 犖犖犖劇賢 犖犖蹩巌犖巌牽犖巌権犖迦牽犖萎見犖э犖迦犖犖犖犢犖ム鍵犢犖犖 犖犖迦検犖犖む県犖蹩朽犖犖 Lewis Coordinationnumber 犖犖劇賢犖犢犖迦犖о犖犖園犖犖萎犖園犖犖犖÷犖犖朽犖∇原犖犢犖犖犖朽犖∇硯 犖犖萎見犖э犖迦 Ligand 犢犖ム鍵 Acceptor 犢犖犖犖迦牽犢犖犖巌犖犖犖犖犖園犖犢 2 DefinitionofComplex DefinitionofComplex Donor, Ligand,Complexing agent Donor, Ligand,Complexing 犖犖劇賢犖犖迦牽犖犖朽犢犖犖犖犖ム顕犖犖犖犖劇賢犖÷元犖犖犖萎犖 犖犖謹犖犖犖迦検犖迦牽犖犢犖犖犖刻犖犖巌犖ム犖犖犖犖犖犢犖 Acceptor, Substrate Acceptor, 犖犖劇賢犖犖迦牽犖犖謹犖犖犖迦検犖迦牽犖犖犖園犖犖刻犖犖巌犖ム犖犖犖犖犖犖犖迦 Ligand 犢犖 3 1
犖犖迦牽犢犖犖巌犖犖犖犖÷元犖犖伍犖犖÷犖園犖巌賢犖萎犖犖犖朽犢犖犖ム元犢犖∇犢犖犖犖迦 犖犖迦牽犖犖園犖犖犖 Solubility (犖犖迦犖迦牽犖ム鍵犖ム顕犖) Absorbency (犖犖迦牽犖犖項犖犖ム厳犖犢犖犖) C d ti it (犖犖迦牽犖犢犢犖迦犖犖犖) Conductivity Partition coefficient (犖犖園検犖犖犖萎肩犖巌犖犖巌犖犖迦牽犢犖犖犖犖迦) Chemical reactivity (犖犖о顕犖÷犖о犖犖犖蹩巌犖巌牽犖∇顕犢犖犖÷元) 犖 Stability (犖犖о顕犖÷犖犖犖園硯) Pharmacokinetic (犢犖犖犖園犖犖ム犖犖迦肩犖犖ｏ) 4 Classification of complexes 1. Metal ion complexes Acceptor = 犢犖犖犖犖犖犖犖犢犖ム見犖 犖犖迦牽犢犖犖巌犖犖犖犖犖犖巌犖犖朽犖÷険犖犖÷元犖犖 2. Organic molecular complexes Acceptor = 犢犖÷犖ム犖伍献犖犖犖犖犖迦牽犖犖巌犖犖犖朽権 Ligand 犢犖ム鍵 acceptor犖犖園犖犖園犖犖о権犖犖園犖犖萎賢犖劇犖犢犖犖朽犢犖￥犢犖犖犖園犖犖萎犖犖о顕犢犖ム犖 犢犖犖 hydrophobicinteraction,vanDer Waals, ionicinteraction,hydrogenbond 3. Inclusion/Occlusion compound Inclusion/ Acceptor犢犖ム鍵 donor犖犖園犖犖園犢犖犖犖項 molecular network 5 1. Metalioncomplexes 犖犢犖迦犖犖犢犖犖犖犖犖萎犖犖 犖犖園犖犖朽 1.1 Inorganic complexes (Coordination complexes) Ligand 犢犖犖 H2O:,H3N:,NC-:, Cl-: 犖犢犖迦見犖犖迦犖朽犢犖犖犖刻犖犖巌犖ム犖犖犖犖犖 犢犖ム鍵犢犖犖巌犖犖迦牽犢犖犖巌犖犖犖犖犖園犢犖犖犖犖犖犖犖犢犖ム見犖萎犖о権犖犖園犖犖 coordinate covalent Example E l Cyanocobalamin (VitaminB12):犢犖犖犖犖迦牽犢犖犖巌犖犖犖 犖犖萎見犖э犖迦 carbon犖犖園 cobalt犖犖謹犖犢犖犖巌犢犖犖犖犖犖÷犖迦犖 Cisplatin 犢犖犖犖∇顕犢犖犖÷元犖犢犖迦犖園 犢犖犢犖犖 antineoplastic drug 犖犢犖迦見犖犖園犖犖園犖犖迦検犖萎犖犢犖犖犖犖巌犖犖迦犢 犢犖犖∇犖ム犖犖犖迦牽犖犖犖犖む犖犖巌犖犖劇賢犖犖迦検犖迦牽犖犖犖園犖犖園 DNA犢犖ム鍵犢犖犖犖犖朽犖犖犖犢犖犖ム献犖÷鍵犢犖犢犖犢犖 犖÷元 ligand 犖犖劇賢 H3N:犢犖ム鍵 Cl-: Cl- NH3 犖÷元 acceptor犖犖劇賢 Pt2+ Pt2+ - Cl NH3 6 2
1. Metal ion complexes 1.2 Chelates 犖犖犖萎犖犖犖犖о権 donor犖犖犖犖犖ム幻犖÷犖謹犖犢犖 犖犖園犖犖園犢犖犖犖犖犖犖犖犢犖ム見犖萎犖о権 犖犖園犖犖 Ionic 犖犖犖劇賢犖犖園犖犖 Covalent Ligand 犖犖迦犖犖∇弦犢犖犖犖項 mono-, di- ,tri-, quadri-, Li d di t i di penta-, hexadentate 犖犖園硯犖犖犖迦犖犖犖 Chelates 犢犖犖ｏ犖迦犖犖迦権 Hemoglobin :acceptor犖犖劇賢犖犖迦犖伍犖犖ム犖 7 1. Metal ion complexes Ligand犖犖朽犖犢犖迦犖犢犖犖巌 chelatecomplex犖犖朽犢犖￥犖ム鍵犖ム顕犖∇犢犢犖 犢犖犖朽権犖 chelatingagent ExampleOxine,dimethylglyoxime 犖犖犖萎犖∇犖 犢犖犖犢犖迦犖園犢犖ム見犖萎犖朽犢犖￥犖犖犖犖犖迦牽犖犖犖犖犖迦犖犖迦牽犖ム鍵犖ム顕犖 犢犖犖∇犢犖迦犖 犢犖ム見犖萎犖犖犖萎犖犖 Ligand犖犖朽犖犢犖迦犖犢犖犖巌 chelatecomplex犖犖朽犖ム鍵犖ム顕犖∇犢犢犖 犢犖犖朽権犖 sequesteringagent 8 1. Metal ion complexes Exampleof Sequesteringagent EthyleneDiamineTetra Acetic acid (EDTA) 犖犖犖萎犖∇犖 犖犖迦見犖犖迦犢犖犖 犖犖犖萎犖∇犖 犖犢犖迦見犖犖迦犖朽犢犖犖 Sequestering agent 犢犖 犖犢犖迦牽犖園犖∇顕犖犖朽犖÷元犖犢犢犖 犖犖о権犖犖園犢犖ム見犖萎見犖犖園犖犖朽 犖犖迦犖犖犖÷顕犢犖犖犢犢犖迦犖朽犢犖犢犖犖犖朽権犖÷権犖 犖犖謹犖ム 犢犖犖犖迦肩犖犖迦牽犢犖犖巌 oxidation 犖犖犖 EDTA 犖犖о犖犖犖萎犖犖犢犖犖∇顕犢犖犖犖朽権犖 犖犖о権犖∇厳犖犖犖迦権犖 犖犖迦牽犢犖犢犖犖犖園犖犖迦権犖迦犖犖犖朽権犖 9 3
2. Organic molecular complexes 2.1 Quinhydrone complexes Benzoquinone + Hydroquinone = Green crystal 犖犖犖萎犖∇犖 :犢犖犢犖犖 pH electrode 10 2. Organic molecular complexes 2.2 Picric acid complexes Picric acid + weak base Example 犖犖園硯犖∇顕 Butesin picrate O O C4H9 NO2 C 犖む犖犖巌犖犖迦犢犖犖犖園犖о鹸犖犖∇顕 :anesthetic + HO NO2 antiseptic NO2 NH2 犖犖項犢犖犖犖∇顕犢犖犖犖朽権犖 : 1% ointment 2 for burn and skin abrasion 11 2. Organic molecular complexes 2.3 Caffeine and other drug complexes **Caffeine犢犖犖犖犖迦牽犖犖о権犖犖朽犖犖迦検犖迦牽犖犢犖犖巌犖÷犖迦犖迦牽犖ム鍵犖ム顕犖∇犖ム鍵犖犖о顕犖 犖犖犖犖園硯犖犖犖犖犖園硯犖∇顕犖犖ム顕犖∇犖犖巌** Caffeine + paracetamol /aspirin p p 犢犖犖巌犖÷犖迦犖迦牽犖ム鍵犖ム顕犖∇犖犖犖∇顕犖犖園犖犖犖犖犖犖犖巌 Caffeine+ Benzocaine 犖ム犖犖迦牽犢犖犖巌犢犖犢犖犖犢犖ム犖巌肩犖犖犖 Benzocaine Improve absorption and bioavailability 犖犖犖 Benzocaine 12 4
2. Organic molecular complexes 2.4 Polymer complexes Povidone + ajmaline : 犢犖犖巌犖÷賢犖園犖犖迦犖迦牽犖ム鍵犖ム顕犖∇犖犖犖∇顕 Polyolefin container + Paraben :犖犖迦牽犖犖園犢犖犖朽権 犖犖ム幻犖 paraben 犖犖項犖犖園険犖犢犖犖∇犖迦犖犖萎犖犖犖犖伍権犖迦犖朽犖犢犖迦犖о権犢犖犖ム鹸犢犖÷賢犖ｏ b 犢 犖 犢 犖犖犖巌犖犖朽 犖犖謹犢犖犖ム厳犖 paraben 犢犖犖犢犖迦牽犖園犖∇顕犖犖犖∇献犖 犖犖犖萎肩犖巌犖犖巌犖迦 犖犖犖 paraben 犢犖犖犖迦牽犖∇険犖犖∇険犢犖犖犖迦牽犢犖犖犖巌犖犖犖犢犖犖劇犖犖犖伍献犖巌犖犖犖朽権犖犖謹 犖ム犖ム犖犖о権 13 2. Organic molecular complexes Ion Ionexchangeresin 犖犖劇賢 insoluble matrix (or support structure) 犖犖謹犖犢犖犖∇犖園犖о犖犖犖萎賢犖∇弦犢犖犖犖項犖犖犖犢犖÷犖犖犖朽犖犖犖犖迦犢犖ム犖 (犢犖犖犖犖迦犖犖項犖犖犖ム顕犖 12 犖犖犖萎検犖迦 1-2 mm) 犢犖犖∇犖園犖о犖犖÷元犖犖朽犖迦硯犖犖犖劇賢犢犖犖ム厳犖犖 犖犢犖迦犖迦 organic polymer substrate 犖÷元犖犖項犢犖迦犖о犖÷顕犖犖犖犖犖劇犖犖犖巌硯 犖犢犖迦犖犖犖迦検犖迦牽犖犖犖園犢犖ム鍵犖犖ワ犖犖∇犖犖犖犖犖犖犖巌 犖犖迦犢 犢犖犖犖迦権 犖犖謹犖犖犖迦牽犖犖園犢犖犖犖犖犢犖犖迦検犖迦犖犢犖犖犖巌 犖犖萎犖犖巌犖犖謹犖犢犖犢犖о献犖 犢 犢犖犖朽権犖о犖園犖犖朽犖÷犖迦牽犖犖ワ犖犖∇犖犖犖犖犖犖犖犖犖迦犢犖犖犖巌犖 犖 14 2. Organic molecular complexes ApplicationofIonexchangeresininPharmaceuticals Ionexchangeresin 1. 犢犖犢犖犖犖犖園硯犖∇顕犖犢犖迦犖園 犖犖園硯犖犖犖迦犖∇顕犖犖朽賢犖∇弦犢犖犖犖項犢犖犖犖巌犢犖ム犢犖犖ム元犖∇犢犖犖犖犖 犢 犢 犢 p y y Sodiumpolystyrenesulfonate :treat Hyperkalemia 犢犖犖∇犖犖巌犖犖迦牽犢犖ム犢犖犖ム元犢犖∇犖犖萎見犖э犖迦 Na+犖犖犖犖犖園硯犖∇顕 犖犖園 K+ 犢犖犢犖ム厳犖犖 Colestipol:treathypercholesterolemia Cholestyramine :treathypercholesterolemia Colestipol andCholestyramine =Bileacid sequestrant 15 5
2. Organic molecular complexes Ion Ionexchangeresin 2.犢犖犢犖犖犖犖迦牽犖犖о権犢犖犖犢犖迦牽犖園犖∇顕 犢犖犖 犢犖犖犢犖迦牽犖園犖∇顕犢犖÷犖 犖∇顕犢犖犖犖犖項献 犖∇顕犖犢犢犖 犢犖犖о犖犖萎犖犖. 犖犖ム犖犖犖犖迦犖犖朽犢犖￥犖犖朽犖犖犖犖園硯犖∇顕 犖犖о権犖犖о犖犖伍検犖犖迦牽犖犖ム犖犖ワ犖犖∇犖園硯犖∇顕犖犖迦犖犢犖迦牽犖園 犢犖犖犖∇弦犢犖犖犖項犖∇顕犖犖犖 犖む犖犖巌犖犖迦 犢犖犖犖犖迦牽犖犖о権犢犖犖犖犖園硯犢犖犖∇顕犢犖÷犖 犢犖犖巌犖÷犖о顕犖÷犖犖犖園硯犖犖迦犢犖犖÷元犖犖犖犖犖園硯犖∇顕犖犢犖迦犖園 16 3. Inclusion/Occlusion compound Inclusion/ (Host (Hostguestcomplexes) Oneofconstituentofcomplex(Guest) is specifiedtrapped inlatticeorcagelike crystaloftheother(Host) Architectureofmolecule>Chemical affinity 17 3. Inclusion/Occlusion compound Inclusion/ 3.1 Channel type Example:Urea + Straight-chain hydrocarbon or fatty acid Use extract Monostearin from Dienestrol cream 18 6
3. Inclusion/Occlusion compound Inclusion/ 3.2 Layer type Example Montmorillonite ( bentonite) can (in ) trap hydrocarbon, alcohol and glycol between the layer of their lattices. Graphite 19 3. Inclusion/Occlusion compound Inclusion/ 3.3 Clathrates Acage-like lattice which the coordinate compound is entrapped. entrapped No chemical bond Example Wafarin sodium USP trappingwater and isopropyl alcohol in a cage. 20 3. Inclusion/Occlusion compound Inclusion/ 3.4 Monomolecular type The entrapment of asingle guest molecule in the cavity of one host molecule. Example Cyclodextrin Homogeneouscyclic oligosacharides build up from glucopyranose unit 犢犖犢犖犖犖犖犖ｏ犖迦犖犖犖萎犖犖犖犖о権犖犖÷弦 ethyleneglycol犖犢犖迦犖о犖÷顕犖 犖÷元犖犖項犖ｏ犖迦犖犖ワ犖迦権犖÷犖犖伍 21 7
3. Inclusion/Occlusion compound Inclusion/ 22 3. Inclusion/Occlusion compound Inclusion/ 23 3. Inclusion/Occlusion compound Inclusion/ Characteristic 留 - CD 硫 - CD 粒 - CD Number of 6 7 8 glucopyranose unit Molecular weight 972.85 1134.99 1297.14 (Dalton) Solubility in water 14.5 18.5 23.2 (g/ml) Cavity volume in 1 g 0.10 0.14 0.20 (ml) 24 8
3. Inclusion/Occlusion compound Inclusion/ Pharmaceutical application ofCyclodextrin 犢犖犖巌犖÷犖迦犖迦牽犖ム鍵犖ム顕犖 犢犖ム鍵犖犖園犖犖迦犖迦牽犖ム鍵犖ム顕犖∇犖犖犖∇顕 hydrophobic drug 犢犖犖÷犖о顕犖÷犖犖犖о犖犖犖犖о権犖迦肩犖迦犖 犢犖犖巌犖÷犖о顕犖÷犖犖犖園硯犖犖犖犖犖園硯犖∇顕犖犢犖迦犖園 犢犖犖ム元犢犖∇犖∇顕犢犖犖犖項犖犖犖犢犖犖ム硯犢犖犖犖∇弦犢犖犖犖項犖犖ム原犖犢犖 犢犖犖 Nitroglycerine 犖ム犖犖犖犖÷犖ム鍵犖犖迦犖犖犖犖犖園硯犖∇顕犖犖迦犖犖犖巌 犖犖о権犖ム犖犖園犖犖迦犖迦牽犖犖萎犖犖∇犖犖犖犖迦牽犖犖犖÷犖ム鍵犖犢犢犖迦検犖園犖犖犖÷牽犖萎犖犖∇犖迦犖犢犖迦牽犖園 25 3. Inclusion/Occlusion compound Inclusion/ 3.5 Molecular sieves The atom are arranged in three dimensions to produce cages and channels. channels Example: Zeolite, Dextrin, Silica gel Use: separate molecule of different dimension 26 Protein binding:犖犖園硯犖犖犖迦犖犖犖犖犖迦牽犢犖犖巌犖犖迦牽 binding:犖犖 犢犖犖巌犖犖犖犢犖犖ｏ犖迦犖犖迦権 Plasma protein facilitated the distribution of drugs inactivate the drug by reduce concentration of free drug retard the excretion of adrug The interaction of drug and plasmaprotein may plasmaprotein cause: cause: displacement of hormone or coadministered drug aconfiguration change in the protein drug-protein complex is biological active 27 9
Proteinbinding Plasma protein Albumin : most important plasma protein High Hi h concentration i bind both acidic and basic drug 留 - acid glycoprotein 1 bind basic drug > acidic drug 28 References 1.犖犖伍犖迦肩犖巌犖 犖犖園犖犖萎肩犖迦牽犖犖犖. Metalcomplexformation[犖犖犖犢犖ム]2547[犖犖迦 犢犖÷厳犢犖 25 犖犖巌犖犖迦犖 2552].犖犖迦 http://pharmacy.kku.ac.th/analyse1/index.php?p=5&page= 1. 2.Complexation[online]2012[citedon22July2012]. Availablefrom http://pharmacy.davidyim.name/mediawiki/index.php?titl e=Complexation_%28PHM224Y%29&printable=yes 3.GennaroAR.Remington:thescienceandpracticeof pharmacy.19thed.Pennsylvania:Mackpublishing Company;1995. 4. Ionexchangeresin [online]2009[citedon25August 2009].Availablefromhttp://en.wikipedia.org/wiki/Ion- exchange_resin. 29 10

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Complexation2555

  • 1. 犖犖.犖犖.犖犖ム険犖犖犖犖 犢犖ム鹸犖犖犖犖巌犖犖犖犖 犖.犖犖. 犖犖犖朽犖 犢犖￥犖犖о鹸犖о険犖犖犖犖伍献 1 DefinitionofComplex DefinitionofComplex Complexation (犖犖迦牽犢犖犖巌犖犖迦牽犢犖犖巌犖犖犖) 犖) 犖犖劇賢犖犖迦牽犢犖犖巌犖犖園犖犖萎見犖犖劇賢犖犖園犖犖犖犖巌牽犖巌権犖迦牽犖萎見犖э犖迦犖犖迦牽 2 犖犖犖巌犖犖謹犖犢犖 犖犖謹犖犢犖￥犖犢犖迦犖犖迦鍵 犖э犖迦犖園犖犖萎犖園犖犖犖犖犢犖犖犖犖園犖犖萎犖犖о顕犢犖ム犖犖犖犖劇賢犖犖園犖犖萎犖犖犖犖犖巌 Complex 犖犖犖劇賢 Coordinate compound:犖犖劇賢 犖犖迦牽 compound:犖犖 犢犖犖巌犖犖犖 犖犖朽犢犖犖巌犖犖迦 犖犖ム犖犖犖迦牽犢犖犢犖ム鍵犖犖園犖犖刻犖犖巌犖ム犖犖犖犖犖 犖犖犖劇賢 犖犖蹩巌犖巌牽犖巌権犖迦牽犖萎見犖э犖迦犖犖犖犢犖ム鍵犢犖犖 犖犖迦検犖犖む県犖蹩朽犖犖 Lewis Coordinationnumber 犖犖劇賢犖犢犖迦犖о犖犖園犖犖萎犖園犖犖犖÷犖犖朽犖∇原犖犢犖犖犖朽犖∇硯 犖犖萎見犖э犖迦 Ligand 犢犖ム鍵 Acceptor 犢犖犖犖迦牽犢犖犖巌犖犖犖犖犖園犖犢 2 DefinitionofComplex DefinitionofComplex Donor, Ligand,Complexing agent Donor, Ligand,Complexing 犖犖劇賢犖犖迦牽犖犖朽犢犖犖犖犖ム顕犖犖犖犖劇賢犖÷元犖犖犖萎犖 犖犖謹犖犖犖迦検犖迦牽犖犢犖犖犖刻犖犖巌犖ム犖犖犖犖犖犢犖 Acceptor, Substrate Acceptor, 犖犖劇賢犖犖迦牽犖犖謹犖犖犖迦検犖迦牽犖犖犖園犖犖刻犖犖巌犖ム犖犖犖犖犖犖犖迦 Ligand 犢犖 3 1
  • 2. 犖犖迦牽犢犖犖巌犖犖犖犖÷元犖犖伍犖犖÷犖園犖巌賢犖萎犖犖犖朽犢犖犖ム元犢犖∇犢犖犖犖迦 犖犖迦牽犖犖園犖犖犖 Solubility (犖犖迦犖迦牽犖ム鍵犖ム顕犖) Absorbency (犖犖迦牽犖犖項犖犖ム厳犖犢犖犖) C d ti it (犖犖迦牽犖犢犢犖迦犖犖犖) Conductivity Partition coefficient (犖犖園検犖犖犖萎肩犖巌犖犖巌犖犖迦牽犢犖犖犖犖迦) Chemical reactivity (犖犖о顕犖÷犖о犖犖犖蹩巌犖巌牽犖∇顕犢犖犖÷元) 犖 Stability (犖犖о顕犖÷犖犖犖園硯) Pharmacokinetic (犢犖犖犖園犖犖ム犖犖迦肩犖犖ｏ) 4 Classification of complexes 1. Metal ion complexes Acceptor = 犢犖犖犖犖犖犖犖犢犖ム見犖 犖犖迦牽犢犖犖巌犖犖犖犖犖犖巌犖犖朽犖÷険犖犖÷元犖犖 2. Organic molecular complexes Acceptor = 犢犖÷犖ム犖伍献犖犖犖犖犖迦牽犖犖巌犖犖犖朽権 Ligand 犢犖ム鍵 acceptor犖犖園犖犖園犖犖о権犖犖園犖犖萎賢犖劇犖犢犖犖朽犢犖￥犢犖犖犖園犖犖萎犖犖о顕犢犖ム犖 犢犖犖 hydrophobicinteraction,vanDer Waals, ionicinteraction,hydrogenbond 3. Inclusion/Occlusion compound Inclusion/ Acceptor犢犖ム鍵 donor犖犖園犖犖園犢犖犖犖項 molecular network 5 1. Metalioncomplexes 犖犢犖迦犖犖犢犖犖犖犖犖萎犖犖 犖犖園犖犖朽 1.1 Inorganic complexes (Coordination complexes) Ligand 犢犖犖 H2O:,H3N:,NC-:, Cl-: 犖犢犖迦見犖犖迦犖朽犢犖犖犖刻犖犖巌犖ム犖犖犖犖犖 犢犖ム鍵犢犖犖巌犖犖迦牽犢犖犖巌犖犖犖犖犖園犢犖犖犖犖犖犖犖犢犖ム見犖萎犖о権犖犖園犖犖 coordinate covalent Example E l Cyanocobalamin (VitaminB12):犢犖犖犖犖迦牽犢犖犖巌犖犖犖 犖犖萎見犖э犖迦 carbon犖犖園 cobalt犖犖謹犖犢犖犖巌犢犖犖犖犖犖÷犖迦犖 Cisplatin 犢犖犖犖∇顕犢犖犖÷元犖犢犖迦犖園 犢犖犢犖犖 antineoplastic drug 犖犢犖迦見犖犖園犖犖園犖犖迦検犖萎犖犢犖犖犖犖巌犖犖迦犢 犢犖犖∇犖ム犖犖犖迦牽犖犖犖犖む犖犖巌犖犖劇賢犖犖迦検犖迦牽犖犖犖園犖犖園 DNA犢犖ム鍵犢犖犖犖犖朽犖犖犖犢犖犖ム献犖÷鍵犢犖犢犖犢犖 犖÷元 ligand 犖犖劇賢 H3N:犢犖ム鍵 Cl-: Cl- NH3 犖÷元 acceptor犖犖劇賢 Pt2+ Pt2+ - Cl NH3 6 2
  • 3. 1. Metal ion complexes 1.2 Chelates 犖犖犖萎犖犖犖犖о権 donor犖犖犖犖犖ム幻犖÷犖謹犖犢犖 犖犖園犖犖園犢犖犖犖犖犖犖犖犢犖ム見犖萎犖о権 犖犖園犖犖 Ionic 犖犖犖劇賢犖犖園犖犖 Covalent Ligand 犖犖迦犖犖∇弦犢犖犖犖項 mono-, di- ,tri-, quadri-, Li d di t i di penta-, hexadentate 犖犖園硯犖犖犖迦犖犖犖 Chelates 犢犖犖ｏ犖迦犖犖迦権 Hemoglobin :acceptor犖犖劇賢犖犖迦犖伍犖犖ム犖 7 1. Metal ion complexes Ligand犖犖朽犖犢犖迦犖犢犖犖巌 chelatecomplex犖犖朽犢犖￥犖ム鍵犖ム顕犖∇犢犢犖 犢犖犖朽権犖 chelatingagent ExampleOxine,dimethylglyoxime 犖犖犖萎犖∇犖 犢犖犖犢犖迦犖園犢犖ム見犖萎犖朽犢犖￥犖犖犖犖犖迦牽犖犖犖犖犖迦犖犖迦牽犖ム鍵犖ム顕犖 犢犖犖∇犢犖迦犖 犢犖ム見犖萎犖犖犖萎犖犖 Ligand犖犖朽犖犢犖迦犖犢犖犖巌 chelatecomplex犖犖朽犖ム鍵犖ム顕犖∇犢犢犖 犢犖犖朽権犖 sequesteringagent 8 1. Metal ion complexes Exampleof Sequesteringagent EthyleneDiamineTetra Acetic acid (EDTA) 犖犖犖萎犖∇犖 犖犖迦見犖犖迦犢犖犖 犖犖犖萎犖∇犖 犖犢犖迦見犖犖迦犖朽犢犖犖 Sequestering agent 犢犖 犖犢犖迦牽犖園犖∇顕犖犖朽犖÷元犖犢犢犖 犖犖о権犖犖園犢犖ム見犖萎見犖犖園犖犖朽 犖犖迦犖犖犖÷顕犢犖犖犢犢犖迦犖朽犢犖犢犖犖犖朽権犖÷権犖 犖犖謹犖ム 犢犖犖犖迦肩犖犖迦牽犢犖犖巌 oxidation 犖犖犖 EDTA 犖犖о犖犖犖萎犖犖犢犖犖∇顕犢犖犖犖朽権犖 犖犖о権犖∇厳犖犖犖迦権犖 犖犖迦牽犢犖犢犖犖犖園犖犖迦権犖迦犖犖犖朽権犖 9 3
  • 4. 2. Organic molecular complexes 2.1 Quinhydrone complexes Benzoquinone + Hydroquinone = Green crystal 犖犖犖萎犖∇犖 :犢犖犢犖犖 pH electrode 10 2. Organic molecular complexes 2.2 Picric acid complexes Picric acid + weak base Example 犖犖園硯犖∇顕 Butesin picrate O O C4H9 NO2 C 犖む犖犖巌犖犖迦犢犖犖犖園犖о鹸犖犖∇顕 :anesthetic + HO NO2 antiseptic NO2 NH2 犖犖項犢犖犖犖∇顕犢犖犖犖朽権犖 : 1% ointment 2 for burn and skin abrasion 11 2. Organic molecular complexes 2.3 Caffeine and other drug complexes **Caffeine犢犖犖犖犖迦牽犖犖о権犖犖朽犖犖迦検犖迦牽犖犢犖犖巌犖÷犖迦犖迦牽犖ム鍵犖ム顕犖∇犖ム鍵犖犖о顕犖 犖犖犖犖園硯犖犖犖犖犖園硯犖∇顕犖犖ム顕犖∇犖犖巌** Caffeine + paracetamol /aspirin p p 犢犖犖巌犖÷犖迦犖迦牽犖ム鍵犖ム顕犖∇犖犖犖∇顕犖犖園犖犖犖犖犖犖犖巌 Caffeine+ Benzocaine 犖ム犖犖迦牽犢犖犖巌犢犖犢犖犖犢犖ム犖巌肩犖犖犖 Benzocaine Improve absorption and bioavailability 犖犖犖 Benzocaine 12 4
  • 5. 2. Organic molecular complexes 2.4 Polymer complexes Povidone + ajmaline : 犢犖犖巌犖÷賢犖園犖犖迦犖迦牽犖ム鍵犖ム顕犖∇犖犖犖∇顕 Polyolefin container + Paraben :犖犖迦牽犖犖園犢犖犖朽権 犖犖ム幻犖 paraben 犖犖項犖犖園険犖犢犖犖∇犖迦犖犖萎犖犖犖犖伍権犖迦犖朽犖犢犖迦犖о権犢犖犖ム鹸犢犖÷賢犖ｏ b 犢 犖 犢 犖犖犖巌犖犖朽 犖犖謹犢犖犖ム厳犖 paraben 犢犖犖犢犖迦牽犖園犖∇顕犖犖犖∇献犖 犖犖犖萎肩犖巌犖犖巌犖迦 犖犖犖 paraben 犢犖犖犖迦牽犖∇険犖犖∇険犢犖犖犖迦牽犢犖犖犖巌犖犖犖犢犖犖劇犖犖犖伍献犖巌犖犖犖朽権犖犖謹 犖ム犖ム犖犖о権 13 2. Organic molecular complexes Ion Ionexchangeresin 犖犖劇賢 insoluble matrix (or support structure) 犖犖謹犖犢犖犖∇犖園犖о犖犖犖萎賢犖∇弦犢犖犖犖項犖犖犖犢犖÷犖犖犖朽犖犖犖犖迦犢犖ム犖 (犢犖犖犖犖迦犖犖項犖犖犖ム顕犖 12 犖犖犖萎検犖迦 1-2 mm) 犢犖犖∇犖園犖о犖犖÷元犖犖朽犖迦硯犖犖犖劇賢犢犖犖ム厳犖犖 犖犢犖迦犖迦 organic polymer substrate 犖÷元犖犖項犢犖迦犖о犖÷顕犖犖犖犖犖劇犖犖犖巌硯 犖犢犖迦犖犖犖迦検犖迦牽犖犖犖園犢犖ム鍵犖犖ワ犖犖∇犖犖犖犖犖犖犖巌 犖犖迦犢 犢犖犖犖迦権 犖犖謹犖犖犖迦牽犖犖園犢犖犖犖犖犢犖犖迦検犖迦犖犢犖犖犖巌 犖犖萎犖犖巌犖犖謹犖犢犖犢犖о献犖 犢 犢犖犖朽権犖о犖園犖犖朽犖÷犖迦牽犖犖ワ犖犖∇犖犖犖犖犖犖犖犖犖迦犢犖犖犖巌犖 犖 14 2. Organic molecular complexes ApplicationofIonexchangeresininPharmaceuticals Ionexchangeresin 1. 犢犖犢犖犖犖犖園硯犖∇顕犖犢犖迦犖園 犖犖園硯犖犖犖迦犖∇顕犖犖朽賢犖∇弦犢犖犖犖項犢犖犖犖巌犢犖ム犢犖犖ム元犖∇犢犖犖犖犖 犢 犢 犢 p y y Sodiumpolystyrenesulfonate :treat Hyperkalemia 犢犖犖∇犖犖巌犖犖迦牽犢犖ム犢犖犖ム元犢犖∇犖犖萎見犖э犖迦 Na+犖犖犖犖犖園硯犖∇顕 犖犖園 K+ 犢犖犢犖ム厳犖犖 Colestipol:treathypercholesterolemia Cholestyramine :treathypercholesterolemia Colestipol andCholestyramine =Bileacid sequestrant 15 5
  • 6. 2. Organic molecular complexes Ion Ionexchangeresin 2.犢犖犢犖犖犖犖迦牽犖犖о権犢犖犖犢犖迦牽犖園犖∇顕 犢犖犖 犢犖犖犢犖迦牽犖園犖∇顕犢犖÷犖 犖∇顕犢犖犖犖犖項献 犖∇顕犖犢犢犖 犢犖犖о犖犖萎犖犖. 犖犖ム犖犖犖犖迦犖犖朽犢犖￥犖犖朽犖犖犖犖園硯犖∇顕 犖犖о権犖犖о犖犖伍検犖犖迦牽犖犖ム犖犖ワ犖犖∇犖園硯犖∇顕犖犖迦犖犢犖迦牽犖園 犢犖犖犖∇弦犢犖犖犖項犖∇顕犖犖犖 犖む犖犖巌犖犖迦 犢犖犖犖犖迦牽犖犖о権犢犖犖犖犖園硯犢犖犖∇顕犢犖÷犖 犢犖犖巌犖÷犖о顕犖÷犖犖犖園硯犖犖迦犢犖犖÷元犖犖犖犖犖園硯犖∇顕犖犢犖迦犖園 16 3. Inclusion/Occlusion compound Inclusion/ (Host (Hostguestcomplexes) Oneofconstituentofcomplex(Guest) is specifiedtrapped inlatticeorcagelike crystaloftheother(Host) Architectureofmolecule>Chemical affinity 17 3. Inclusion/Occlusion compound Inclusion/ 3.1 Channel type Example:Urea + Straight-chain hydrocarbon or fatty acid Use extract Monostearin from Dienestrol cream 18 6
  • 7. 3. Inclusion/Occlusion compound Inclusion/ 3.2 Layer type Example Montmorillonite ( bentonite) can (in ) trap hydrocarbon, alcohol and glycol between the layer of their lattices. Graphite 19 3. Inclusion/Occlusion compound Inclusion/ 3.3 Clathrates Acage-like lattice which the coordinate compound is entrapped. entrapped No chemical bond Example Wafarin sodium USP trappingwater and isopropyl alcohol in a cage. 20 3. Inclusion/Occlusion compound Inclusion/ 3.4 Monomolecular type The entrapment of asingle guest molecule in the cavity of one host molecule. Example Cyclodextrin Homogeneouscyclic oligosacharides build up from glucopyranose unit 犢犖犢犖犖犖犖犖ｏ犖迦犖犖犖萎犖犖犖犖о権犖犖÷弦 ethyleneglycol犖犢犖迦犖о犖÷顕犖 犖÷元犖犖項犖ｏ犖迦犖犖ワ犖迦権犖÷犖犖伍 21 7
  • 8. 3. Inclusion/Occlusion compound Inclusion/ 22 3. Inclusion/Occlusion compound Inclusion/ 23 3. Inclusion/Occlusion compound Inclusion/ Characteristic 留 - CD 硫 - CD 粒 - CD Number of 6 7 8 glucopyranose unit Molecular weight 972.85 1134.99 1297.14 (Dalton) Solubility in water 14.5 18.5 23.2 (g/ml) Cavity volume in 1 g 0.10 0.14 0.20 (ml) 24 8
  • 9. 3. Inclusion/Occlusion compound Inclusion/ Pharmaceutical application ofCyclodextrin 犢犖犖巌犖÷犖迦犖迦牽犖ム鍵犖ム顕犖 犢犖ム鍵犖犖園犖犖迦犖迦牽犖ム鍵犖ム顕犖∇犖犖犖∇顕 hydrophobic drug 犢犖犖÷犖о顕犖÷犖犖犖о犖犖犖犖о権犖迦肩犖迦犖 犢犖犖巌犖÷犖о顕犖÷犖犖犖園硯犖犖犖犖犖園硯犖∇顕犖犢犖迦犖園 犢犖犖ム元犢犖∇犖∇顕犢犖犖犖項犖犖犖犢犖犖ム硯犢犖犖犖∇弦犢犖犖犖項犖犖ム原犖犢犖 犢犖犖 Nitroglycerine 犖ム犖犖犖犖÷犖ム鍵犖犖迦犖犖犖犖犖園硯犖∇顕犖犖迦犖犖犖巌 犖犖о権犖ム犖犖園犖犖迦犖迦牽犖犖萎犖犖∇犖犖犖犖迦牽犖犖犖÷犖ム鍵犖犢犢犖迦検犖園犖犖犖÷牽犖萎犖犖∇犖迦犖犢犖迦牽犖園 25 3. Inclusion/Occlusion compound Inclusion/ 3.5 Molecular sieves The atom are arranged in three dimensions to produce cages and channels. channels Example: Zeolite, Dextrin, Silica gel Use: separate molecule of different dimension 26 Protein binding:犖犖園硯犖犖犖迦犖犖犖犖犖迦牽犢犖犖巌犖犖迦牽 binding:犖犖 犢犖犖巌犖犖犖犢犖犖ｏ犖迦犖犖迦権 Plasma protein facilitated the distribution of drugs inactivate the drug by reduce concentration of free drug retard the excretion of adrug The interaction of drug and plasmaprotein may plasmaprotein cause: cause: displacement of hormone or coadministered drug aconfiguration change in the protein drug-protein complex is biological active 27 9
  • 10. Proteinbinding Plasma protein Albumin : most important plasma protein High Hi h concentration i bind both acidic and basic drug 留 - acid glycoprotein 1 bind basic drug > acidic drug 28 References 1.犖犖伍犖迦肩犖巌犖 犖犖園犖犖萎肩犖迦牽犖犖犖. Metalcomplexformation[犖犖犖犢犖ム]2547[犖犖迦 犢犖÷厳犢犖 25 犖犖巌犖犖迦犖 2552].犖犖迦 http://pharmacy.kku.ac.th/analyse1/index.php?p=5&page= 1. 2.Complexation[online]2012[citedon22July2012]. Availablefrom http://pharmacy.davidyim.name/mediawiki/index.php?titl e=Complexation_%28PHM224Y%29&printable=yes 3.GennaroAR.Remington:thescienceandpracticeof pharmacy.19thed.Pennsylvania:Mackpublishing Company;1995. 4. Ionexchangeresin [online]2009[citedon25August 2009].Availablefromhttp://en.wikipedia.org/wiki/Ion- exchange_resin. 29 10