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Pregled bibliografske jedinice broj: 753706

Pre-Organized Dinucleosides with Pendant Porphyrins for the Formation of Sandwich Type Complexes with DABCO with High Association Constants


Merkaš, Sonja; Bouatra, Souhaila; Rein, Régis; Piantanida, Ivo; Žinić, Mladen; Solladié, Nathalie
Pre-Organized Dinucleosides with Pendant Porphyrins for the Formation of Sandwich Type Complexes with DABCO with High Association Constants // Journal of porphyrins and phthalocyanines, 19 (2015), 1/3; 535-546 doi:10.1142/S1088424615500431 (međunarodna recenzija, članak, znanstveni)


Naslov
Pre-Organized Dinucleosides with Pendant Porphyrins for the Formation of Sandwich Type Complexes with DABCO with High Association Constants

Autori
Merkaš, Sonja ; Bouatra, Souhaila ; Rein, Régis ; Piantanida, Ivo ; Žinić, Mladen ; Solladié, Nathalie

Izvornik
Journal of porphyrins and phthalocyanines (1088-4246) 19 (2015), 1/3; 535-546

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Porphyrines; Nucleosides; Binding Studies; Supramolecular Complexes

Sažetak
We report herein the synthesis of a dinucleotide bearing pendant porphyrins dedicated to adopt a pre-organized coformation with face-to-face porphyrins, and capable to self-organize in a stable sandwich type complexe with bidentate base such as DABCO. Earlier studies demonstrated that a peptidic linker doesn’t provide sufficient pre-organization to enhance significantly the association constant with bidentate bases such as DABCO on the contrary of some other flexible linkers such as uridine or 2’-deoxyuridine. We document herein that the gain in stability for the formation of sandwich type host-guest complex with DABCO can be even greater when a dinucleotide linker is used. Such pre-organization increases the association constants by one to two orders of magnitude when compared to the association constants of the same bidentate ligands with a reference Zn(II) porphyrin. Comparison of these results with those obtained for rigid tweezers shows a better efficiency of the flexible nucleosidic dimers. We thus document the fact that the choice of rigid spacers is not the only way to pre-organize bis-porphyrins, and that some well-chosen nucleosidic linkers offer an interesting option for the synthesis of such devices. Furthermore, the chirality and enantio-purity of the nucleosidic linkers paves the way toward the selective complexation of enantio-pure bidentate guests and the resolution of racemates.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
098-0982904-2912 - Samo-udruživanje u gelovima i sinteza funkcionalnih hibridnih materijala (Leo Frkanec, )
098-0982914-2918 - Dizajn, sinteza i ispitivanje interakcija malih molekula s DNA, RNA i proteinima (Ivo Piantanida, )

Ustanove
Institut "Ruđer Bošković", Zagreb

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus


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