Faculty of Pharmacy, Lj. (FFALJ)
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Sinteza in vrednotenje difosfatnih ligandov za fosfotransferazo, udeleženo v biosintezi celične stene Clostridium difficile = Synthesis and evaluation of diphosphate ligands for phosphotransferase involved in Clostridium difficile cell wall biosynthesis : magistrski študijski program Laboratorijska biomedicinaGerhold, PetraBakterije so majhni enocelični organizmi, ki se razlikujejo po obliki in velikosti. Njihova celična struktura vključuje citoplazmo z organeli, citoplazemsko membrano, bakterijsko steno ter v ... nekaterih primerih tudi bakterijsko kapsulo. Obstajata dve glavni skupini bakterij: gramnegativne in grampozitivne, ki se razlikujejo po debelini in strukturi celične stene. Encim MurA je bistven pri sintezi peptidoglikana v celični steni, kar predstavlja privlačno tarčo za sintezo protibakterijskih učinkovin. Zaradi prekomerne in nepremišljene uporabe protimikrobnih učinkovin je prišlo do pojava rezistence bakterij, ki predstavlja eno največjih groženj javnemu zdravstvu v 21. stoletju. Zato sta pospešeno iskanje in razvoj novih protibakterijskih učinkovin nujna. Ena od bakterij, ki predstavlja velik problem bolnišničnih okužb, je Clostridium difficile. Pri sintezi polisaharidov so v celični steni C. difficile odkrili nov encim manozil-1-fosfotransferazo (ManPT), ki predstavlja potencialno tarčo za razvoj novih potibakterijskih zdravilnih učinkovin. Namen te magistrske naloge je bila sinteza derivatov glukozamina in galaktozamina s fosfatnimi skupinami, ki bi oponašali substrat za encim ManPT. Izhodni spojini pri sintezah sta bili D-glukozamin hidroklorid in D-galaktozamin hidroklorid. Sledila je šeststopenjska sinteza, v kateri smo sladkor acetilirali, selektivno odščitili anomerno -OH skupino in nato nanj uvedli zaščiten fosfat. Po odstranitvi zaščite smo spojino združili z 11-fenoksiundecil fosfatom, tako da je nastal difosfat in nato izvedli globalno odščito. Pri sintezi α-D-glukozamin-1-fosfata smo v prvi stopnji zaščitili amino skupino. Ostali koraki so ostali enaki kot pri sladkorjih brez amina. Končnim spojinam smo določili zaviralno aktivnost na encimu MurA ter minimalno inhibitorno koncentracijo (MIK) na bakterijah E. coli in S. aureus. Zaviralno delovanje na encimu MurA sta izkazovali spojini 8 (IC50 = 16 μM) in 26 (IC50 = 100 μM). Hillova koeficienta pri obeh spojinah znašata 2 ali več, kar kaže na nespecifično zaviranje encima MurA. Spojina 26 je izkazovala tudi protibakterijsko delovanje na sevu S. aureus z MIK 0,625 mg/mL. Uspešno sintetizirane spojine bodo v prihodnje uprabili na Inštitutu Jožefa Stefana, kjer želijo pripraviti kokristale z encimom ManPT.Type of material - master's thesis ; adult, seriousPublication and manufacture - Ljubljana : [P. Gerhold], 2023Language - slovenianCOBISS.SI-ID - 174488835
Author
Gerhold, Petra
Other authors
Mravljak, Janez, farmacevt |
Hrast, Martina
Topics
Bakterije |
Kemija |
Glukozamin |
Clostridium difficile |
encim MurA |
encim ManPT |
zaviralci |
derivati glukozamina |
derivati galaktozamina
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Knjižnica mlab 0000000579 GERHOLD PETRA Sinteza 0000000353 IN: 0017920 Knjižnica mlab 579 GERHOLD PETRA Sinteza 353 IN: 0017920 |
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Database name | Field | Year |
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Links to authors' personal bibliographies | Links to information on researchers in the SICRIS system |
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Gerhold, Petra | ![]() |
Mravljak, Janez, farmacevt | 23419 |
Hrast, Martina | 32036 |
Source: Personal bibliographies
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