Karakterizacija inkluzijskih kompleksa nabumetona i β-ciklodekstrina spektroskopijom NMR

master's thesis

• Title (english): Characterization of nabumetone and β-cyclodextrin inclusion complexes using NMR spectroscopy
• Author: Melita Kelrajter
• Mentor: Ana Čikoš (mentor)
• Committee member: Nives Galić (predsjednik povjerenstva)
• Committee member: Ivana Biljan (član povjerenstva)
• Committee member: Branimir Bertoša (član povjerenstva)
• Committee member: Predrag Novak (član povjerenstva)
• Granter: University of Zagreb; Faculty of Science; (Department of Chemistry); Zagreb
• Defense date and country: 2022-02-24, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

Nabumeton je protuupalni lijek II. skupine biofarmaceutskog sustava klasifikacije djelatnih
tvari budući da ga karakterizira izuzetno niska topljivost u vodi koja uzrokuje njegovu
ograničenu bioraspoloživost. Topljivost u vodi može se povećati kompleksiranjem s
ciklodekstrinima. Molekule ciklodekstrina imaju jedinstvenu strukturu sličnu krnjem stošcu, s
hidrofobnom šupljinom s unutrašnje strane i hidrofilnom površinom s vanjske strane,
zahvaljujući kojoj mogu tvoriti inkluzijske komplekse s različitim molekulama gostiju.
Inkluzijski kompleksi nastaju pomoću hidrofobnih interakcija između molekula gostiju i
ciklodekstrinske hidrofobne šupljine. U ovom radu istražen je mehanizam ulaska nabumetona
u šupljinu β-ciklodekstrina i stvaranje inkluzijskog kompleksa. Za karakterizaciju korištene
su tehnike spektroskopije nuklearne magnetske rezonancije (NMR) za istraživanje strukture
(1H, 13C, COSY, HSQCe, HMBC), kao i one kojima se ispituju interakcije između različitih
molekula u otopini (NOESY, ROESY, DOSY). U diplomskom radu dokazano je stvaranje
inkluzijskog kompleksa i posljedično povećanje topljivosti nabumetona u vodi.

Abstract (english)

Nabumetone is an anti-inflammatory drug belonging to 2nd group of the biopharmaceutical
active substances classification system due to extremly low solubility in water, which is the
cause of its limited bioavailability. The solubility in water can be increased by creating
complexes with cyclodextrins. These molecules have a unique frusto-conical structure with a
hydrophobic cavity and a hydrophilic surface, enabling them to form inclusion complexes
with different guest molecules. The formation of inclusion complexes occurs through
hydrophobic interactions between guest molecules and the cyclodextrin hydrophobic cavity.
In this study, the mehanism of nabumetone inclusion into β-cyclodextrin was researched. To
characterize the nabumetone/β-cyclodextrin inclusion complex, nuclear magnetic resonance
spectroscopy (NMR) techniques for structural research (1H, 13C, COSY, HSQCe, HMBC), as
well as those that examine interactions between different molecules (NOESY, ROESY,
DOSY) were used. In this study, the formation of inclusion complex between β-cyclodextrin
and nabumetone was established, resulting in increased water solubility of the drug.

• Keywords: β-ciklodekstrin; inkluzijski kompleksi; nabumeton; NMR; topljivost
• Keywords (english): β-cyclodextrin; inclusion complex; nabumetone; NMR; solubility
• Language: croatian
• URN:NBN: urn:nbn:hr:217:732659
• Study programme: Title: Graduate university studies in chemistry; specializations in: Research programme; Course: Research programme; Study programme type: university; Study level: graduate; Academic / professional title: magistar/magistra kemije (magistar/magistra kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access; Embargo expiration date: 2024-02-24
• Created on: 2022-03-04 11:28:21