Studij interakcija kationskih kaliksarena s nukleotidima, DNA i RNA

master's thesis

• Title (english): Study of cationic calixarenes interactions with nucleotides, DNA and RNA
• Author: Ena Otković
• Mentor: Ivo Piantanida (mentor)
• Committee member: Snežana Miljanić (predsjednik povjerenstva)
• Committee member: Željka Soldin (član povjerenstva)
• Committee member: Marko Močibob (član povjerenstva)
• Committee member: Adriana Kenđel (član povjerenstva)
• Granter: University of Zagreb; Faculty of Science; (Department of Chemistry); Zagreb
• Defense date and country: 2021-09-22, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES

Abstract

Ranije sintetizirani spojevi kaliks[4]arena i kaliks[6]arena su okarakterizirani u biološki
relevantnom vodenom mediju. Spojevi pokazuju fluorescenciju iskorištenu za studij
nekovalentnih interakcija s nukleozid-monofosfatima, no preslabih promjena za studij vezanja
na dvolančane DNA/RNA. Metodom kompeticije vezanja na DNA/RNA s poznatom bojom,
etidijevim bromidom, samo kationski analozi su pokazali afinitet prema DNA i RNA, što uz
selektivnu stabilizaciju AT-DNA ukazuje na vezanje u mali utor DNA. Na dvolančanu RNA
kationski spojevi se vežu u veliki utor. Nenabijeni analozi ne pokazuju biološki relevantne
interakcije s DNA/RNA, ukazujući na važnost pozitivnog naboja. Kaliksareni s nukleozidmonofosfatima tvore interkalandni tip kompleksa u kojemu je nukleobaza smještena između
aromatskih jedinica na jednom od rubova kaliksarena. Neutralni analozi vežu nukleozidmonofosfate s nešto većim afinitetom nego kationski analozi, koji pokazuju selektivnost
fluorescentnog odogovora prema pirimidinskim nukleobazama, naspram purinskih.

Abstract (english)

Previously synthesized calix[4]arene and calix[6]arene compounds were characterized
spectrophotometrically in a biologically relevant aqueous medium. The compounds show weak
but applicable fluorescence allowing study of the noncovalent interactions with nucleosidemonophosphates, while interactions with double-stranded DNA/RNA were studied by
competition with ethidium bromide and thremal denaturation experiment. Only cationic analogs
showed biorelevant interactions within DNA minor groove or RNA major goove binding site.
Neutral analogues do not interact with DNA/RNA, stressing importance of positive charge. The
tested calixarenes bind nucleoside-monophosphates to form an intercaland type of calixarenenucleobase complex, nucleobase inserted between the aryl-substituents at the calixarene rim.
Neutral analogs bind nucleoside-monophosphates with higher affinity than cationic analogs but
cationic analogs show fluorimetric selectivity towards pyrimidine nucleobases.

• Keywords: cirkularni dikroizam; fluorescencija; kaliksaren; nukleinske kiseline; nukleotidi
• Keywords (english): calixarene; circular dichroism; fluorescence; nucleic acids; nucleotides
• Language: croatian
• URN:NBN: urn:nbn:hr:217:945458
• Project: Number: IP-2020-02-3786; Title: Biomimetički “funnel” i “bowl” supramolekularni sustavi za selektivno prepoznavanje DNA/RNA; Title: Biomimetic “funnel” and “bowl” supramolecular systems for the selective recognition of DNA/RNA; Acronym: CALIXDNA / CALIXDNA; Leader: Aleksandar Višnjevac; Jurisdiction: Croatia; Funder: HRZZ; Funding stream: IP
• 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: 2021-12-23
• Created on: 2021-10-19 15:34:43