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Guanidino-aryl derivatives: protonation and structure tuning for spectrophotometric recognition of ds-DNA and ds-RNA


Đud, Mateja; Glasovac, Zoran; Margetić, Davor; Piantanida, Ivo
Guanidino-aryl derivatives: protonation and structure tuning for spectrophotometric recognition of ds-DNA and ds-RNA // New journal of chemistry, 44 (2020), 11537-11545 doi:10.1039/D0NJ01879A (međunarodna recenzija, članak, znanstveni)


Naslov
Guanidino-aryl derivatives: protonation and structure tuning for spectrophotometric recognition of ds-DNA and ds-RNA

Autori
Đud, Mateja ; Glasovac, Zoran ; Margetić, Davor ; Piantanida, Ivo

Izvornik
New journal of chemistry (1144-0546) 44 (2020); 11537-11545

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

Ključne riječi
Aryl-guanidine ; DNA/RNA recognition ; Fluorescence ; Circular dichroism ; Dye aggregation

Sažetak
A series of aryl-substituted guanidines revealed pKa about 10 in aqueous medium, thus positioning themselves between more basic aliphatic guanidines (pKa >13) and acidic guanidinocarbonyl-pyrrole (pKa 6). The study revealed that for the biorelevant (micromolar) affinity toward ds-DNA and ds-RNA the minimal size of aryl-unit is anthracene. Further aryl-increase (pyrene, porphyrin) did not result in stronger affinity toward ds-DNA/RNA, nor gave significant thermal stabilisation of DNA/RNA double helix, thus suggesting that aromatic stacking interactions between compounds and DNA/RNA are not dominant binding interaction. Generally, results suggested that aryl- guanidines binding to DNA/RNA grooves by combination of hydrophobic, electrostatic, H-bonding and Van der Waals interactions, whereby fluorescence of the two largest aromatics (pyrene, porphyrin) was highly sensitive in fine probing of DNA/RNA groove properties. In addition, pyrene and porphyrin analogues at excess to polynucleotide binding sites aggregated within polynucleotide groove, yielding fine recognition between various ds- DNA and ds-RNA by induced circular dichroism signals.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
HRZZ-IP-2013-11-9310 - Nekovalentne interakcije u dizajnu novih fotoosjetljivih molekula (Davor Margetić, )
HRZZ-IP-2018-01-3298 - Cikloadicijske strategije prema policikličkim gvanidinima (Davor Margetić, )
HRZZ-IP-2018-01-5475 - Višekromoforne probe za prepoznavanje pojedinih struktura DNA, RNA i proteina (Ivo Piantanida, )

Ustanove
Institut "Ruđer Bošković", Zagreb

Profili:

Avatar Url Davor Margetić (autor)

Avatar Url Zoran Glasovac (autor)

Avatar Url Ivo Piantanida (autor)

Avatar Url Mateja Đud (autor)

Citiraj ovu publikaciju

Đud, Mateja; Glasovac, Zoran; Margetić, Davor; Piantanida, Ivo
Guanidino-aryl derivatives: protonation and structure tuning for spectrophotometric recognition of ds-DNA and ds-RNA // New journal of chemistry, 44 (2020), 11537-11545 doi:10.1039/D0NJ01879A (međunarodna recenzija, članak, znanstveni)
Đud, M., Glasovac, Z., Margetić, D. & Piantanida, I. (2020) Guanidino-aryl derivatives: protonation and structure tuning for spectrophotometric recognition of ds-DNA and ds-RNA. New journal of chemistry, 44, 11537-11545 doi:10.1039/D0NJ01879A.
@article{article, year = {2020}, pages = {11537-11545}, DOI = {10.1039/D0NJ01879A}, keywords = {Aryl-guanidine, DNA/RNA recognition, Fluorescence, Circular dichroism, Dye aggregation}, journal = {New journal of chemistry}, doi = {10.1039/D0NJ01879A}, volume = {44}, issn = {1144-0546}, title = {Guanidino-aryl derivatives: protonation and structure tuning for spectrophotometric recognition of ds-DNA and ds-RNA}, keyword = {Aryl-guanidine, DNA/RNA recognition, Fluorescence, Circular dichroism, Dye aggregation} }

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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