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Open AccessArticle

Exploring the Photodynamic Properties of Two Antiproliferative Benzodiazopyrrole Derivatives

1
Department of Pharmacy, University of Naples Federico II, 80131 Naples, Italy
2
Department of Physics “Ettore Pancini”, University of Naples Federico II, 80126 Naples, Italy
3
CoNISMa–Italian Interuniversity Consortium on Marine Sciences, Piazzale Flaminio 9, 00196 Rome, Italy
4
Department of Pharmacy/DIFARMA, University of Salerno, 84084 Fisciano, Salerno, Italy
*
Authors to whom correspondence should be addressed.
These authors contributed equally to this work.
Int. J. Mol. Sci. 2020, 21(4), 1246; https://doi.org/10.3390/ijms21041246
Received: 13 December 2019 / Revised: 7 February 2020 / Accepted: 11 February 2020 / Published: 13 February 2020
(This article belongs to the Special Issue Solution Chemical Kinetics 2019)
The identification of molecules whose biological activity can be properly modulated by light is a promising therapeutic approach aimed to improve drug selectivity and efficacy on the molecular target and to limit the side effects compared to traditional drugs. Recently, two photo-switchable diastereomeric benzodiazopyrrole derivatives 1RR and 1RS have been reported as microtubules targeting agents (MTAs) on human colorectal carcinoma p53 null cell line (HCT 116 p53-/-). Their IC50 was enhanced upon Light Emitting Diode (LED) irradiation at 435 nm and was related to their cis form. Here we have investigated the photo-responsive behavior of the acid derivatives of 1RR and 1RS, namely, d1RR and d1RS, in phosphate buffer solutions at different pH. The comparison of the UV spectra, acquired before and after LED irradiation, indicated that the transcis conversion of d1RR and d1RS is affected by the degree of ionization. The apparent rate constants were calculated from the kinetic data by means of fast UV spectroscopy and the conformers of the putative ionic species present in solution (pH range: 5.7–8.0) were modelled. Taken together, our experimental and theoretical results suggest that the photo-conversions of trans d1RR/d1RS into the corresponding cis forms and the thermal decay of cis d1RR/d1RS are dependent on the presence of diazonium form of d1RR/d1RS. Finally, a photo-reaction was detected only for d1RR after prolonged LED irradiation in acidic medium, and the resulting product was characterized by means of Liquid Chromatography coupled to High resolution Mass Spectrometry (LC-HRMS) and Nuclear Magnetic Resonance (NMR) spectroscopy. View Full-Text
Keywords: photoswitchable azoheteroarene; diazo derivative; cis-trans conversion; fast UV spectroscopy; LC-HRMS; conformational analysis; DFT optimization photoswitchable azoheteroarene; diazo derivative; cis-trans conversion; fast UV spectroscopy; LC-HRMS; conformational analysis; DFT optimization
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Imperatore, C.; Valadan, M.; Tartaglione, L.; Persico, M.; Ramunno, A.; Menna, M.; Casertano, M.; Dell’Aversano, C.; Singh, M.; d’Aulisio Garigliota, M.L.; Bajardi, F.; Morelli, E.; Fattorusso, C.; Altucci, C.; Varra, M. Exploring the Photodynamic Properties of Two Antiproliferative Benzodiazopyrrole Derivatives. Int. J. Mol. Sci. 2020, 21, 1246.

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