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The conjugates of ferrocene-1, 1′-diamine and amino acids. A novel synthetic approach and conformational analysis


Kovačević, Monika; Kodrin, Ivan; Cetina, Mario; Kmetič, Ivana; Murati, Teuta; Čakić Semenčić, Mojca; Roca, Sunčica; Barišić, Lidija
The conjugates of ferrocene-1, 1′-diamine and amino acids. A novel synthetic approach and conformational analysis // Dalton transactions, 44 (2015), 16405-16420 doi:10.1039/c5dt01610j (međunarodna recenzija, članak, znanstveni)


Naslov
The conjugates of ferrocene-1, 1′-diamine and amino acids. A novel synthetic approach and conformational analysis

Autori
Kovačević, Monika ; Kodrin, Ivan ; Cetina, Mario ; Kmetič, Ivana ; Murati, Teuta ; Čakić Semenčić, Mojca ; Roca, Sunčica ; Barišić, Lidija

Izvornik
Dalton transactions (1477-9226) 44 (2015); 16405-16420

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

Ključne riječi
Bioorganometalics ; conformational analysis ; DFT calculations ; ferrocene ; peptidomimetics

Sažetak
A novel synthetic approach toward a poorly explored bioorganometallic consisting of ferrocene-1, 1′-diamine bearing structurally and chirally diverse amino acid sequences is reported. Until now, ferrocene-1, 1′-diamine was suitable for accommodating only identical amino acid sequences at its N-termini, leading to the symmetrically disubstituted homochiral products stabilized through a 14-membered intramolecular hydrogen-bonded ring as is seen in antiparallel β-sheet peptides. The key step of the novel synthetic pathway is the transformation of Ac–Ala–NH–Fn–COOH (5) (Fn = 1, 1′-ferrocenylene) to orthogonally protected Ac–Ala–NH–Fn–NHBoc (7). The spectroscopic analysis (IR, NMR, CD) of the novel compounds, corroborated with DFT studies, suggests the interesting feature of the ferrocene-1, 1′-diamine scaffold. The same hydrogen-bonding pattern, i.e. a 14-membered hydrogen-bonded ring, was determined both in solution and in the solid state, thus making them promising, yet simple scaffolds capable of mimicking β-sheet peptides. In vitro screening of potential anticancer activity in Hep G2 human liver carcinoma cells and Hs 578 T human breast cancer cells revealed a cytotoxic pattern for novel compounds (150–500 μM) with significantly decreased cell proliferation.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
058-1191344-3122 - Metalocenski biokonjugati, heterocikli i makromolekule (Veronika Kovač, )
119-1193079-3069 - Novi organski i koordinacijski spojevi - sinteza i suodnos struktura-svojstvo (Branko Kaitner, )
HRZZ-IP-2013-11-7444 - Organske molekule u kondenziranoj fazi: međudjelovanja i modeliranje (Hrvoj Vančik, )

Ustanove
Prehrambeno-biotehnološki fakultet, Zagreb,
Institut "Ruđer Bošković", Zagreb,
Tekstilno-tehnološki fakultet, Zagreb,
Prirodoslovno-matematički fakultet, Zagreb

Citiraj ovu publikaciju

Kovačević, Monika; Kodrin, Ivan; Cetina, Mario; Kmetič, Ivana; Murati, Teuta; Čakić Semenčić, Mojca; Roca, Sunčica; Barišić, Lidija
The conjugates of ferrocene-1, 1′-diamine and amino acids. A novel synthetic approach and conformational analysis // Dalton transactions, 44 (2015), 16405-16420 doi:10.1039/c5dt01610j (međunarodna recenzija, članak, znanstveni)
Kovačević, M., Kodrin, I., Cetina, M., Kmetič, I., Murati, T., Čakić Semenčić, M., Roca, S. & Barišić, L. (2015) The conjugates of ferrocene-1, 1′-diamine and amino acids. A novel synthetic approach and conformational analysis. Dalton transactions, 44, 16405-16420 doi:10.1039/c5dt01610j.
@article{article, year = {2015}, pages = {16405-16420}, DOI = {10.1039/c5dt01610j}, keywords = {bioorganometalics, conformational analysis, DFT calculations, ferrocene, peptidomimetics}, journal = {Dalton transactions}, doi = {10.1039/c5dt01610j}, volume = {44}, issn = {1477-9226}, title = {The conjugates of ferrocene-1, 1′-diamine and amino acids. A novel synthetic approach and conformational analysis}, keyword = {bioorganometalics, conformational analysis, DFT calculations, ferrocene, peptidomimetics} }

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
  • MEDLINE


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