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by: Ezequiel Orn


Marketplace > University of Texas at Austin > Biology > BIO 329W > COOPERATV BIOLOGICAL SCIENCES
Ezequiel Orn
GPA 3.89


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Class Notes
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This 10 page Class Notes was uploaded by Ezequiel Orn on Sunday September 6, 2015. The Class Notes belongs to BIO 329W at University of Texas at Austin taught by Staff in Fall. Since its upload, it has received 53 views. For similar materials see /class/181740/bio-329w-university-of-texas-at-austin in Biology at University of Texas at Austin.




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Date Created: 09/06/15
nr 7 100 gt 1 Develonmanl and cllnlcal spccnum ol 11 various amifungals Year Guneric Tvpcls of infection or which grug is principally used developed drug suner ciql dermalophylosis candidosls locally invasive viscera and system 1903 Potassium iodide vmphangem sparolrichosis l907 Whilliald39s oimmem 1 1940 Undecylenic acid Gnu wet 194950 N min 7 39 vs 66 w w wd k V 1550 Hydroxystilbamidine Nonh American blasmmvcoses 195455 Svadroxyquinuline derivaxives 1957 AmphoxericinB lBSB Grisealulvin 195360 Pimaricin Myco c keralilis 1961 Acrisnrcln 1953 Haloprcgin t 5368 Talnaita e 7371541 195368 Flucyzosine Cladiosparium Sp cwpxb caccosis H 4 196970 Miconazola m4 39 I ier514 196970 Lu Clolnrnazole Zg 4 197475 1 Eco azole 0 F Q WI V quotquot 7ng J 1 general effectiveness limixed elfec vaness 9f gm 5 2 Includes Dilyriasis Versicolorand linea nigra palmaris 9 4 f W 5 a 97 M qv US A 6 6156 MM f2MoIa sz s cmavga e 174306 Viva 247 we ar Ww 4 7gtJ A44M 545 4901 F0 W 41 5 MM V 439 a 14 442 Ybln IV saunme Topical lmmvemus ml in walor doso nuns dosn arms am arms Some Acrmcm Hyazoxvsumxamimnc Poxassium mun Kola uvwbae Limimd Clommardu Flunvlnsnu when Griszofuwin k 14 Prucrcany Pimnn Maconnwl my 4 39nsolubla stlnun Amplnmicin a J Micommh Econnqle uncin R Hydraxyquina na wmnem39 0 mm wdmvucn dd Tuku llx K lemon i Table l Fungal infections Sim olinfuclion Disease Fungus Therapy mg Aspergillosis Aspzrgillmfumigalm 39 Blastfzxycosis Blasmmyce dermmidi L c WWW brasiiensis la 2 Ampholencm B and ccrlaln lmldazolc dmgs C occidiuidom ycosis Caccidiaidcs immitis I Hisloplasmusis H islaplaxmn Capraalum H dubossi Wuundh C hrcmomycoscs Cladaspon39um currianii Phialoplmrn spp 39 V I Amphotcricin B and certain imidazolc drugs Mycelumus 16 spp Idcnll cd Spormriulmsis Sparolllrix clzcnkii S in and mucous membranes Candidmis 439 939 I39W 39 quot Dermumphymsis Epidermaphymu spp I Tricwhhymn s39p39p Opportu nigtlic pul hugcns Val H No a June was CH CH OCH CH K We H35 N on 10 cm CH3 mac 0 CH CHJ DCH n 039 AW mummy am CH1 CH CH CH3 0 HO 0 H H0 0 N OH OH OH OH OH OH OH OH mac 3 OH Hjc J OH O 0 COOH COOH O OH OH OH OH O OH O OH OH OH OH OH symmm M NM N W KNNH S 53 Val H Nn5 June 2003 Fungal cell wau a eHor schmucandms nikkamyclns Mammrv Q 1 Prmmn cell wall u 16 glucan a v 1 am An Chum Mamhmns phosphu pid birayer wim mammal enzyme pmzerns and argosmw mmecmas mrger or palyenes uplasuc Sleml synmesvs a the ana um r rgel rm MUIHS yammam relic phenybmorpnulolmas DNA and RNA synmasis AcewmoA avgsls or Q i no Ergnsmrm IIucywsm g HMGrCaA T Mevalonate ms em39 1 Mlcmmbuie assemmy 8193 m gnssmulvm 00 53073 4A Ulmenmyl V Anna evgoslrauienol l x m Emmw39 Pmmln symhesos mgsx iur sordalins TRENDS m MaoMTDW mm mu m ml h gAmphotericin B PonE r r x l l Phospholipid N u a we Q 9 J water Lipid 339 on Ho i 3 3 OH N x H 41 f 7 39 C CH r I No WhamW I 39 QVnm quot0 3 ul 5 H HO Lipid aQelo Q PALM 3 llij quot0 l quot g my Figure 13 1 A hypothetical model of a pore formed by amphoteriein B in a lipd bilayer membranr Considerable evidence supports the hypothesis that amphoteticin B and nystatin can form pores in ani cial lipid bilayer membranes When the antibiotic is added to both sides of the membrane the pores J quire anion selective Since sucrose radius 52 A is not permi ted to pass through the radius of 1M pore is thought to be less than 45A The pore is formed by severaolyene molecules packed side by Sid In a cylinder formation The principal interactions between the antibiotic and the membrane involve hquot drophobic bonds between the lipophilic heptaene segment of the antibioric and the sterols The dashed lines represent possible hydrogen bonds The solid circles oriented at the membrane surfa ces represent thf polar head groups of the phospholipids and the wavy lines denote the hydrophobic fatty acid chains lquot this con guration amphotericin B is 2024 A long and extends into but does extend across the distant39 of the bilayer The ion conductance of arti cial bilayct membranes is markedly porentiared when the antibiotic is added to both sides presumably because continuous pores passing from one membrane surfI to the other can be readily formedquot Adapted from Andrcoli Figure 11 7 s 02quot Table 2 Therapy of Choice for selected systemic mycoses Alter 2x Preferred Allemalivc Disease agenl agents Aspergillosis Amplmlericin B Ilraconazole flucylosine or rifampicin Blaslomycosis Ampholericin E or llraconazole39 keloconazolc Fluconazole Candi sis Ampholcricin 13 2 Keloconazole invasive lucylosine Fluconazoe or disseminated Chromornycosis Flucytusine t Ketoconazole amphotericin B Coccidioido Ampholericin B or Fluconazole mycosis keloconazole Miconazo e Ilraconazole Cryptococcosis Ampholericin B Fluconazole and ucytosine llraconazole39 Hisloplasmosis Ampholcricin B or IIraconazole 39eloconazo c Fluconazole Mucormycosis Ampholericin B None I A 4 u r r mycosis ampholericin B Miconazole Ilraconazole39 Pseudoallescher Miconazole Kelocanazole iasis Sporotrichosis Amphulcricin B llraconazule39 extracumneous ZFluconazole 39lnvestigalional drug in certain countries Hydrophllic slrelch 39 Hydrophobic stretch quot NH Mycosamine ring Figure 1 Slructural features of ampholericin B After 29 Ale nemmpemc Conhnue anliblmins Day 1 Day 743 Becomes ehtile Oonlinue anubiohas Nebrlle bul Melanie and and neulmpenlc and add neulmpenlc neulraphils recovered aner day 7 amphmericln B i 7 7 7 o 1 other away 4 and mo or Figure 3 Algorithm for lhe initiaI managemem of febrile neunupcnii palienlsv Adapted from 15L 3 RATIONAL DEVELOPMENT OF ABELCET i Lipidbased engineering he usefulness of lipidbased engineering such as liposomes as targeted carriers of pharmacological agents stems from their waterrlipid structure and par ticulate nature Liposomes are primarily composed of biodegradable reusable phospholiplds which are structurally characterised by a hydrophilic head attached to a hydrophobic tailt When placed in water they arrange themselves spontaneously into bilayer structures so that the hydrophobic tails are shielded from the water by hydrophilic heads As it is thermoe dynamically unfavourable to have hydrophobic edges adjacent to water the bilayer sheets form a closed sys tem with water both inside and outside the bilayer Figure 4 56 Waterrsoluble substances such as certain drugs enzymes or genes can be entrapped within the aque ous spaces of the bilayer whereas fatsolublc entities Watersoluble agent Fatsoluble agent Figure 4 Schematic atan of f nnrl wdlt r sllul1le agents encapsulated in a llposotne After ism such as polyene antibiotics and other lipid soluble drugs can be incorporated into the lipid layers 561 Preparation techniques allowing control over size lamellarity trapped aqueous volume and solute dis tribution in the final emulsions have led to a rapid expansion in this field 57 Lipidrbased engineering also offers an adaptable means of redesigning the properties of pharmaceuti cals Pharmaceutical agents designed in this way have unique pharmacokinellc and pharmacodynamic char acteristics The way lipidrbased drugs are distributh throughout the body differs from that of conventional drugs Studies have shown that lipidrhased drugs appear to be retained selectively in the organs of the reticuloendothelial system RES such as the liver spleen lungs lymph nodes and to a lesserextent bone marrow One explanation for this is the phagocytic nature of the system 7 lipid rich particles can be ingested by phagocytic cells such as monocytes pror virling a mechanism for targeting to sites of infection and a means of intracellular drug delivery The tenr dency of lipid based drugs to accumulate at sites of infection inflammation and neoplasms is probably due to ingestion and delivery by phagocytic cells In addition it may be due to the disease process enlarge ing the spaces between the endotheltal cells lining local capillaries at those sites permitting the extra vasalion of liposomal or lipidbased rltugs 56 lipidelased engineering of pharmacokinetlcsphar macodynamics has been described tor a variety of biologically active compounds including polyene antifungals anthracyclines aminoglycoside anti biotics and prostaglandins 56 Although redesigning pharmaceuticals in this way can attenuate toxicities of associated drugs efficacy of the treatment should not c mpromised and should be thoroughly investi gated example a stud y Pahls and Schaffner which compared theantifungal activity of a unilamellar liposomal prepatation of amphotertcin B with conventional amphotericin I in vitro and in models of systemic and localised candidiasts in immunosu p essed mice reported that the liposomal amphotericin 8 preparation had 4A times less anllfungal activity than conventional amphotericin B 58 Ln 2 Maw RNA 5FUTP UMP 5 FUDP pyrophosphorylase SFluorouracil w 5 FUMP M 31 t 39 cytosine 4 z deaminase MAMquot 5FdUMP 5Flucvtosine MAquot we uptake into the thymidvlam lungaJ cell 4r M synthetase W a to l dUMP W 3 Man I M DAM Mw Figure13 4 Action of ucytosine in fungi SFlu ytosine is transported into the fungal cell whw it is deaminated to 5 uorouracil SFU The 5FU is then convened to S uorouracihribose mmqu Phosphate SFUMP which can either be con verted to39SFUTP and incorporated into RNAor be converted by ribonucleotide rcducrase w 39539 FdUMP which is a potent inhibitor of thymidr39L SYnthctasc he arrows w39 b rks n n sc39nt those ac 39 av W 390 absent in various ucytosine39resistanr fun i Km 9 duCaJarr 5 Biochemical basis for the activity and selectivity of oral antifungal drugs H VANDEN BOSSCHE P MARICHAL J GORRENS MC COENE Department ofComparzttive Biochemistry Janssen Research Foundation Beerse Belgium Summary The ergosterol biosynthesisinhibiting EBI anti fungals constitute the most important group ofcorn pounds developed for the control of fungal diseases in man Currently representatives of two classes of EBI antifungals are available the squalene epoxi dase inhibitors and those that interfere with cyto chrome P450 dependenl ergosterol synthesis The allylamines cg terbinafine inhibit squalene epoxidase in sensitive fungi Trichophy ton menlagmphyte being the most sensitive species 39 menr Ketoco The most important developments have come from the introduction of the Nsubsrituted imida zoles and triazoles the socalled azole antifungals Most of the currently available imidazoles eg mi conazole clottimazole econazole and the triazole derivative terconazole are mainly for topical treat nazole was the rst azole derivative orally active against yeasts den39natophytes and di morphic fungi The new triazole inaconazole ap pears to be among the most promising orally active systemic agents All the azole antifungals inhibit the cytochrome P450dependent Ida demethy Fig 1 The fungal ergosterol biasyn I thctic a w Showing the steps In hibited by the main i antiI ungal agean r r 39 Fayn ul l Squalene HO Ho Q Allylamines thiocarbamares CD Azoles Momholines Squalenezaoxide Incryoalluanlslrmvolmlrtu u rm In mun ltgalm mm mt H0 Lanosrerol HO Etgostetol wmamtiuul mam lungizrttortrrwmm mu unnatural mo in lughat drum to w on pnwtlllilmlkm


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