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Article

Spectroscopic Properties of Two 5′-(4-Dimethylamino)Azobenzene Conjugated G-Quadruplex Forming Oligonucleotides

1
Department of Pharmacy, School of Medicine, University of Naples “Federico II”, Via D. Montesano 49, 80131 Naples, Italy
2
Institute of Food Sciences, National Research Council of Italy, via Roma 64, 83100 Avellino, Italy
3
Department of Physics “Ettore Pancini”, University of Naples Federico II, Via Cinthia, 21—Building 6, 80126 Naples, Italy
*
Author to whom correspondence should be addressed.
Int. J. Mol. Sci. 2020, 21(19), 7103; https://doi.org/10.3390/ijms21197103
Received: 31 July 2020 / Revised: 10 September 2020 / Accepted: 24 September 2020 / Published: 26 September 2020
The synthesis of two 5′-end (4-dimethylamino)azobenzene conjugated G-quadruplex forming aptamers, the thrombin binding aptamer (TBA) and the HIV-1 integrase aptamer (T30695), was performed. Their structural behavior was investigated by means of UV, CD, fluorescence spectroscopy, and gel electrophoresis techniques in K+-containing buffers and water-ethanol blends. Particularly, we observed that the presence of the 5′-(4-dimethylamino)azobenzene moiety leads TBA to form multimers instead of the typical monomolecular chair-like G-quadruplex and almost hampers T30695 G-quadruplex monomers to dimerize. Fluorescence studies evidenced that both the conjugated G-quadruplexes possess unique fluorescence features when excited at wavelengths corresponding to the UV absorption of the conjugated moiety. Furthermore, a preliminary investigation of the trans-cis conversion of the dye incorporated at the 5′-end of TBA and T30695 showed that, unlike the free dye, in K+-containing water-ethanol-triethylamine blend the trans-to-cis conversion was almost undetectable by means of a standard UV spectrophotometer. View Full-Text
Keywords: G-quadruplexes; conjugated aptamers; CD G-quadruplexes; fluorescence G-quadruplexes; azobenzenes; trans-cis conversion; 5′-(4-dimethylamino)azobenzene phosphoramidite derivative G-quadruplexes; conjugated aptamers; CD G-quadruplexes; fluorescence G-quadruplexes; azobenzenes; trans-cis conversion; 5′-(4-dimethylamino)azobenzene phosphoramidite derivative
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MDPI and ACS Style

Imperatore, C.; Varriale, A.; Rivieccio, E.; Pennacchio, A.; Staiano, M.; D’Auria, S.; Casertano, M.; Altucci, C.; Valadan, M.; Singh, M.; Menna, M.; Varra, M. Spectroscopic Properties of Two 5′-(4-Dimethylamino)Azobenzene Conjugated G-Quadruplex Forming Oligonucleotides. Int. J. Mol. Sci. 2020, 21, 7103. https://doi.org/10.3390/ijms21197103

AMA Style

Imperatore C, Varriale A, Rivieccio E, Pennacchio A, Staiano M, D’Auria S, Casertano M, Altucci C, Valadan M, Singh M, Menna M, Varra M. Spectroscopic Properties of Two 5′-(4-Dimethylamino)Azobenzene Conjugated G-Quadruplex Forming Oligonucleotides. International Journal of Molecular Sciences. 2020; 21(19):7103. https://doi.org/10.3390/ijms21197103

Chicago/Turabian Style

Imperatore, Concetta; Varriale, Antonio; Rivieccio, Elisa; Pennacchio, Angela; Staiano, Maria; D’Auria, Sabato; Casertano, Marcello; Altucci, Carlo; Valadan, Mohammadhassan; Singh, Manjot; Menna, Marialuisa; Varra, Michela. 2020. "Spectroscopic Properties of Two 5′-(4-Dimethylamino)Azobenzene Conjugated G-Quadruplex Forming Oligonucleotides" Int. J. Mol. Sci. 21, no. 19: 7103. https://doi.org/10.3390/ijms21197103

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