Synthesis of Purine-1,4,7,10-Tetraazacyclododecane Conjugate and Its Complexation Modes with Copper(II)

Molecules 2025
Aleksejs Burcevs, Gediminas Jonusauskas, Irina Novosjolova, Māris Turks

Purine-1,4,7,10-tetraazacyclododecane (cyclen) conjugate was designed to study its Cu2+ ions complexation capability. Several synthetic approaches were tested to achieve the target compound. The optimal approach involved stepwise modifications of purine N9, C8, and C6 positions that, in nine consecutive steps, provided purine–cyclen conjugate. The synthetic sequence involved Mitsunobu-type alkylation at N9 and iodination at C8, followed by Stille, SNAr, CuAAC, and alkylation reactions. The designed purine–cyclen conjugate is able to complex Cu2+ ions in both the cyclen part and between the purine N7 and triazole N2 positions. The complexation pattern and equilibrium were studied using the NMR titration technique in MeCN-d3 and absorption spectra.

Keywords
purines, fluorescence, metal ion complexation, synthesis, cyclen
DOI
10.3390/molecules30071612
Hyperlink
https://www.mdpi.com/1420-3049/30/7/1612

Burcevs, A., Jonusauskas, G., Novosjolova, I., Turks, M. Synthesis of Purine-1,4,7,10-Tetraazacyclododecane Conjugate and Its Complexation Modes with Copper(II). Molecules, 2025, Vol. 30, No. 7, pp.1-21. e-ISSN 1420-3049. Available from: doi:10.3390/molecules30071612

Publication language
English (en)