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master's thesis
Istraživanje odnosa između strukture i djelovanja beta-laktama
diplomski rad
2016. urn:nbn:hr:167:844636
Mikulić, Anita
University of Split
Faculty of Chemistry and Technology
Division of Chemistry
University of Split
School of Medicine
Pharmacy

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Mikulić, A. (2016). Istraživanje odnosa između strukture i djelovanja beta-laktama : diplomski rad (Master's thesis). Split: University of Split, Faculty of Chemistry and Technology; Split: University of Split, School of Medicine. Retrieved from https://urn.nsk.hr/urn:nbn:hr:167:844636

Mikulić, Anita. "Istraživanje odnosa između strukture i djelovanja beta-laktama : diplomski rad." Master's thesis, University of Split, Faculty of Chemistry and Technology; University of Split, School of Medicine, 2016. https://urn.nsk.hr/urn:nbn:hr:167:844636

Mikulić, Anita. "Istraživanje odnosa između strukture i djelovanja beta-laktama : diplomski rad." Master's thesis, University of Split, Faculty of Chemistry and Technology; University of Split, School of Medicine, 2016. https://urn.nsk.hr/urn:nbn:hr:167:844636

Mikulić, A. (2016). 'Istraživanje odnosa između strukture i djelovanja beta-laktama : diplomski rad', Master's thesis, University of Split, Faculty of Chemistry and Technology; University of Split, School of Medicine, accessed 07 December 2024, https://urn.nsk.hr/urn:nbn:hr:167:844636

Mikulić A. Istraživanje odnosa između strukture i djelovanja beta-laktama : diplomski rad [Master's thesis]. Split: University of Split, Faculty of Chemistry and Technology; Split: University of Split, School of Medicine; 2016 [cited 2024 December 07] Available at: https://urn.nsk.hr/urn:nbn:hr:167:844636

A. Mikulić, "Istraživanje odnosa između strukture i djelovanja beta-laktama : diplomski rad", Master's thesis, University of Split, Faculty of Chemistry and Technology, Split; University of Split, School of Medicine, Split, 2016. Available at: https://urn.nsk.hr/urn:nbn:hr:167:844636

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Metadata
TitleIstraživanje odnosa između strukture i djelovanja beta-laktama : diplomski rad
Title (english)Exploring the ratio between structure and beta-lactams activity : master's thesis
AuthorAnita Mikulić
MentorMarica Medić-Šarić (mentor)
Committee memberDavorka Sutlović (predsjednik povjerenstva)
Committee memberIvana Mudnić (član povjerenstva)
Committee memberMarica Medić-Šarić (član povjerenstva)
GranterUniversity of Split
Faculty of Chemistry and Technology
(Division of Chemistry)
Split
GranterUniversity of Split
School of Medicine
(Pharmacy)
Split
Defense date and country2016-10-17, Croatia
Scientific / art field,
discipline and subdiscipline		BIOMEDICINE AND HEALTHCARE
Pharmacy
Abstract
Cilj ovog diplomskog rada je prikazati utjecaj strukture beta-laktamskih antibiotika prvenstveno penicilina i cefalosporina na njihovo djelovanje. Osnovu strukture penicilina i cefalosporina čine 6-APK i 7- ACK. Penicilini i cefalosporini se međusobno razlikuju u pobočnim lancima. Prikazane su reakcije biotransformacije prolijekova u tijelu, promjene na strukturi penicilina u kiselom i lužnatom mediju te reakcije biotransformacije cefalosporina. Enzim penicilinaza katalizira cijepanje β-laktamskog prstena, meticilin je prvi polusintetički penicilin otporan na S. aureus β-laktamazu. Njegov „sterički štit“ čine dvije metoksi- skupine u orto položaju na aromatskom prstenu pobočnog lanca. Problem nestabilnosti penicilina u kiselini je riješen uvođenjem elektron privlačne funkcionalne skupine na α-poziciji u pobočnom lancu. Hidrolizom cefalosporina nastaju manje aktivni alkoholi. Treća generacija cefalosporina ima povećanu djelotvornost protiv Gram- negativnih bakterija posebice onih rezistentih na druge antibiotike. Penicilini i cefalosporini pokazuju djelomičnu i nepotpunu križnu reaktivnost do 7%. Prolijekovi pivampicilin i cefuroksim aksetil se u tijelu enzimski hidroliziraju u „matične spojeve“ ampicilin i cefuroksim. Povezivanjem lijeka s dihidropiridinskim nosačem omogućuje prolazak kroz krvo-moždanu barijeru. Strukturna jezgra penicilina i cefalosporina je esencijalna za antimikrobnu aktivnost. Varijacijama na pobočnim lancima mijenjaju se fizikalna, kemijska i biološka svojstva. Križne alergijske reakcije mogu se očekivati između penicilina i cefalosporina sa sličnim pobočnim lancima. Prolijek koncept omogućuje povećanje lipofilnosti i farmakoloških svojstava β-laktamskih antibiotika.
Abstract (english)
The objective of this study was to show structure influence on the beta-lactams activity, particularly on the penicillins and cephalosporins activity. 6-APA and 7-ACA form the base of penicillins and cephaosporins structure, penicillins and cephalosporins differ in the side chains. Biotransformations of prodrugs and of cephalosporins and also changes in penicillins structure in acid or alkaline media were observed in this study. Penicillinase enzyme catalyzes the cleavage of β-lactam ring, methicillin is the first semisynthetic penicillin resistant to S. aureus β-lactamase. Its "steric shield" is consisted of the two methoxy groups in the ortho position on the aromatic ring of the side chain. Penicillin acid sensitivity is solved by introducing electron-withdrawing groups on the α-position of the side chain. Cephalosporins acetyloxy group is readily hydrolysed by esterase enzymes to give the less active alcohol. Third-generation cephalosporins show better activity against Gram- negative bacteria, many of which are resistant to other β-lactams. Penicillins and cephalosporins show partial and incomplete cross-reactivity up to 7%. Prodrugs pivampicillin and cefuroxime axetil are enzyme hydrolyzed into "parent compounds" ampicillin and cefuroksim in the body. Linking the drug with dihydropyridine carrier makes the passing through blood-brain barrier possible. Nucleus of penicillins and cephalosporins is essential for antimicrobial activity. Modifications in the side chain change physical, chemical and biological properties. Cross allergic reactions can be expected between penicillin and cephalosporin with similar side chains. Prodrug concept allows increasing lipophilicity and pharmacological properties of β-lactam antibiotics.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:167:844636
Study programmeTitle: Pharmacy
Study programme type: university
Study level: integrated undergraduate and graduate
Academic / professional title: magistar/magistra farmacije (magistar/magistra farmacije)
Type of resourceText
File originBorn digital
Access conditionsOpen access
Terms of useLicence In copyright icon
Created on2016-11-24 10:48:53