Razvoj sintetskog puta za pripravu konjugata D-glukoze i dietilentriaminpentaoctene kiseline (DTPA)

master's thesis

• Title (english): Synthetic route development for the preparation of the conjugate of D-glucose and diethylenetriaminepentaacetic acid (DTPA)
• Author: Aleksandar Mandić
• Mentor: Đani Škalamera (mentor)
• Mentor: Marina Šekutor (mentor)
• Committee member: Đani Škalamera (predsjednik povjerenstva)
• Committee member: Biserka Prugovečki (član povjerenstva)
• Committee member: Aleksandra Maršavelski (član povjerenstva)
• Committee member: Vesna Petrović Peroković (član povjerenstva)
• Granter: University of Zagreb; Faculty of Science; (Department of Chemistry); Zagreb
• Defense date and country: 2023-09-21, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U sklopu ovog diplomskog rada pripravljen je „late-stage” međuprodukt koji se sastoji od benzilirane D-glukoze i trietilen-glikol-ditosilata (10) u svrhu priprave konjugata D-glukoze i dietilentriaminpentaoctene kiseline (DTPA) (1). Konjugat 1 teranostički je agens koji se može koristiti u ciljanoj dostavi radiofarmaceutika u stanice raka, a sve u svrhu radioterapije i/ili dijagnostike. Ukupna struktura konjugata 1 sastavljena je od tri jedinice: D-glukoze, trietilenglikola i DTPA. U ovom radu ispitana je uspješnost nekoliko različitih sintetskih pristupa u pripravi spoja 1. Rad uključuje sintezu, pročišćavanje, izolaciju i karakterizaciju dobivenih
međuprodukata. Sam cilj ovog rada je pronalazak efikasne sintetske rute do spoja 1 sa što manje koraka, a sa što većim prinosom, polazeći iz komercijalno dostupnih spojeva. Dobiveni spojevi okarakterizirani su spektroskopskim metodama (IR, 1H i 13C NMR).

Abstract (english)

In this diploma thesis „late-stage” intermediate for the preparation of the conjugate of D-glucose and diethylenetriaminepentaacetic acid (DTPA) (1) was synthesized, consisting of benzylated D-glucose and triethylene glycol ditosylate (10). Conjugate 1 is a theranostic agent, whose structure can be used for the selective delivery of radiopharmaceutics into cancer cells with the aim of a radiotherapy treatment and/or diagnostics. The full structure of 1 is comprised of: D-glucose, triethylene glycol and DTPA. In this work, the effectiveness of several different synthetic approaches in the preparation of compound 1 was examined. The thesis includes the synthesis, purification, isolation and characterization of prepared intermediates in the synthetic route. The aim of this work is to find an efficient synthetic route towards compound 1 with as few steps as possible, and with as high a yield as possible, starting from commercially available compounds. Obtained compounds were characterized with spectroscopic methods (IR, 1H and 13C NMR).

• Keywords: bifunkcionalni kelirajući agens (BFCA); D-glukoza; dietilentriaminpentaoctena kiselina (DTPA); dijagnostičko oslikavanje; rak; radiofarmaceutici; trietilen-glikol
• Keywords (english): bifunctional chelating agent (BFCA); cancer; D-glucose; diagnostic imaging; diethylenetriaminepentaacetic acid (DTPA); radiopharmaceuticals; triethylene glycol
• Language: croatian
• URN:NBN: urn:nbn:hr:217:907229
• 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: Embargoed access; Embargo expiration date: 2025-09-21
• Created on: 2023-10-13 13:03:28