Selenium-Substituted Monomethine Cyanine Dyes as Selective G-Quadruplex Spectroscopic Probes with Theranostic Potential
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Selenium-Substituted Monomethine Cyanine Dyes as Selective G-Quadruplex Spectroscopic Probes with Theranostic Potential. / Fabijanic, Ivana; Kurutos, Atanas; Paic, Ana Tomasic; Tadic, Vanja; Kamounah, Fadhil S.; Horvat, Lucija; Brozovic, Anamaria; Crnolatac, Ivo; Radic Stojkovic, Marijana.
In: Biomolecules, Vol. 13, No. 1, 128, 2023.Research output: Contribution to journal › Journal article › Research › peer-review
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TY - JOUR
T1 - Selenium-Substituted Monomethine Cyanine Dyes as Selective G-Quadruplex Spectroscopic Probes with Theranostic Potential
AU - Fabijanic, Ivana
AU - Kurutos, Atanas
AU - Paic, Ana Tomasic
AU - Tadic, Vanja
AU - Kamounah, Fadhil S.
AU - Horvat, Lucija
AU - Brozovic, Anamaria
AU - Crnolatac, Ivo
AU - Radic Stojkovic, Marijana
PY - 2023
Y1 - 2023
N2 - The binding interactions of six ligands, neutral and monocationic asymmetric monomethine cyanine dyes comprising benzoselenazolyl moiety with duplex DNA and RNA and G-quadruplex structures were evaluated using fluorescence, UV/Vis (thermal melting) and circular dichroism (CD) spectroscopy. The main objective was to assess the impact of different substituents (methyl vs. sulfopropyl vs. thiopropyl/thioethyl) on the nitrogen atom of the benzothiazolyl chromophore on various nucleic acid structures. The monomethine cyanine dyes with methyl substituents showed a 100-fold selectivity for G-quadruplex versus duplex DNA. Study results indicate that cyanines bind with G-quadruplex via end pi-pi stacking interactions and possible additional interactions with nucleobases/phosphate backbone of grooves or loop bases. Cyanine with thioethyl substituent distinguishes duplex DNA and RNA and G-quadruplex structures by distinctly varying ICD signals. Furthermore, cell viability assay reveals the submicromolar activity of cyanines with methyl substituents against all tested human cancer cell lines. Confocal microscopy analysis shows preferential accumulation of cyanines with sulfopropyl and thioethyl substituents in mitochondria and indicates localization of cyanines with methyl in nucleus, particularly nucleolus. This confirms the potential of examined cyanines as theranostic agents, possessing both fluorescent properties and cell viability inhibitory effect.
AB - The binding interactions of six ligands, neutral and monocationic asymmetric monomethine cyanine dyes comprising benzoselenazolyl moiety with duplex DNA and RNA and G-quadruplex structures were evaluated using fluorescence, UV/Vis (thermal melting) and circular dichroism (CD) spectroscopy. The main objective was to assess the impact of different substituents (methyl vs. sulfopropyl vs. thiopropyl/thioethyl) on the nitrogen atom of the benzothiazolyl chromophore on various nucleic acid structures. The monomethine cyanine dyes with methyl substituents showed a 100-fold selectivity for G-quadruplex versus duplex DNA. Study results indicate that cyanines bind with G-quadruplex via end pi-pi stacking interactions and possible additional interactions with nucleobases/phosphate backbone of grooves or loop bases. Cyanine with thioethyl substituent distinguishes duplex DNA and RNA and G-quadruplex structures by distinctly varying ICD signals. Furthermore, cell viability assay reveals the submicromolar activity of cyanines with methyl substituents against all tested human cancer cell lines. Confocal microscopy analysis shows preferential accumulation of cyanines with sulfopropyl and thioethyl substituents in mitochondria and indicates localization of cyanines with methyl in nucleus, particularly nucleolus. This confirms the potential of examined cyanines as theranostic agents, possessing both fluorescent properties and cell viability inhibitory effect.
KW - selenium-substituted cyanine dyes
KW - DNA
KW - RNA interaction
KW - G-quadruplex selective recognition
KW - Induced Circular Dichroism
KW - mitochondrial accumulation
KW - cell viability inhibitory effect
KW - HUMAN TELOMERE
KW - NUCLEIC-ACIDS
KW - CIRCULAR-DICHROISM
KW - SYNTHETIC APPROACH
KW - EQUILIBRIUM
KW - BINDING
KW - INTERCALATION
KW - CONSTANTS
KW - RNA
U2 - 10.3390/biom13010128
DO - 10.3390/biom13010128
M3 - Journal article
C2 - 36671513
VL - 13
JO - Biomolecules
JF - Biomolecules
SN - 2218-273X
IS - 1
M1 - 128
ER -
ID: 337733802