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dc.contributor.author | Soldevila Serrano, Sonia | es_ES |
dc.contributor.author | Bosca Mayans, Francisco | es_ES |
dc.date.accessioned | 2021-03-25T04:31:53Z | |
dc.date.available | 2021-03-25T04:31:53Z | |
dc.date.issued | 2020-02-15 | es_ES |
dc.identifier.issn | 1386-1425 | es_ES |
dc.identifier.uri | http://hdl.handle.net/10251/164224 | |
dc.description.abstract | [EN] The self-association of fluoroquinolones (FQ) in water would play a relevant role in their translocations across lipid membranes. Triplet excited states of these drugs have been shown as reporters of FQ self-association using laser flash photolysis technique. A study using low-temperature phosphorescence technique was performed with quinolone derivatives such as enoxacin (ENX), norfloxacin (NFX), pefloxacin (PFX), ciprofloxacin (CPX, ofloxacin (OFX), nalidixic acid (NLA), pipemidic acid (PPA) and piromidic acid (PRA) to explore emission changes associated with self-associations and to shed some light on the triplet excited state energy (E-T) discrepancies described in the literature for most of these drugs. The emissions obtained at 77 K in buffered aqueous medium revealed that the amphoteric nature of the quinolones CPX, NFX, PFX, ENX, OFX and PPA must generate their self-associations because a redshift of their phosphorescence maxima is produced by FQ concentrations increases. Hence, this effect was not observed for NLA and PRA or when all quinolones were analysed using ethanol or ethylene glycol aqueous mixtures as glassed solvents. Interestingly, the presence of these organic mixtures produced a blue-shift in the phosphorescence emission maximum of each FQ. Additionally, laser flash photolysis experiments with PRA and the amphoteric quinolone PPA, compounds with the same skeleton but different peripheral substituent, confirm the expected correlations between the amphoteric nature of compounds and their self-associations in aqueous media because the excimer generation was only detected for PPA. Now, the discrepancies described in the literature for the ET of FQs can be understood considering that changes of medium polarity or proticity as well as the temperature can considerably modify their ET values. Thereby, low-temperature phosphorescence technique, is an effective way to detect molecular self-associations and surrounding changes in quinolones that opens the possibility to evaluate these effects in other drug families. (C) 2019 Elsevier B.V. All rights reserved. | es_ES |
dc.description.sponsorship | Financial support from Spanish government (grant CTQ2014-54729-C2-2-P) and the Generalitat Valenciana (PROMETEO program, 2017-075). | es_ES |
dc.language | Inglés | es_ES |
dc.publisher | Elsevier | es_ES |
dc.relation.ispartof | Spectrochimica Acta Part A Molecular and Biomolecular Spectroscopy | es_ES |
dc.rights | Reconocimiento - No comercial - Sin obra derivada (by-nc-nd) | es_ES |
dc.subject | Fluoroquinolones | es_ES |
dc.subject | Laser flash photolysis | es_ES |
dc.subject | Excimers | es_ES |
dc.subject | Triplet energy | es_ES |
dc.subject | Phosphorescence | es_ES |
dc.subject | Self-associations | es_ES |
dc.title | Assessing physical properties of amphoteric fluoroquinolones using phosphorescence spectroscopy | es_ES |
dc.type | Artículo | es_ES |
dc.identifier.doi | 10.1016/j.saa.2019.117569 | es_ES |
dc.relation.projectID | info:eu-repo/grantAgreement/MINECO//CTQ2014-54729-C2-2-P/ES/DISEÑO DE NUEVAS PRODROGAS ANTICANCERIGENAS FOTOACTIVABLES/ | es_ES |
dc.relation.projectID | info:eu-repo/grantAgreement/GVA//PROMETEO%2F2017%2F075/ES/Reacciones fotoquímicas de biomoléculas/ | es_ES |
dc.rights.accessRights | Abierto | es_ES |
dc.contributor.affiliation | Universitat Politècnica de València. Instituto Universitario Mixto de Tecnología Química - Institut Universitari Mixt de Tecnologia Química | es_ES |
dc.description.bibliographicCitation | Soldevila Serrano, S.; Bosca Mayans, F. (2020). Assessing physical properties of amphoteric fluoroquinolones using phosphorescence spectroscopy. Spectrochimica Acta Part A Molecular and Biomolecular Spectroscopy. 227:1-7. https://doi.org/10.1016/j.saa.2019.117569 | es_ES |
dc.description.accrualMethod | S | es_ES |
dc.relation.publisherversion | https://doi.org/10.1016/j.saa.2019.117569 | es_ES |
dc.description.upvformatpinicio | 1 | es_ES |
dc.description.upvformatpfin | 7 | es_ES |
dc.type.version | info:eu-repo/semantics/publishedVersion | es_ES |
dc.description.volume | 227 | es_ES |
dc.identifier.pmid | 31670049 | es_ES |
dc.relation.pasarela | S\430609 | es_ES |
dc.contributor.funder | Generalitat Valenciana | es_ES |
dc.contributor.funder | Ministerio de Economía y Competitividad | es_ES |
dc.description.references | Domagala, J. M., Hanna, L. D., Heifetz, C. L., Hutt, M. P., Mich, T. F., Sanchez, J. P., & Solomon, M. (1986). New structure-activity relationships of the quinolone antibacterials using the target enzyme. The development and application of a DNA gyrase assay. Journal of Medicinal Chemistry, 29(3), 394-404. doi:10.1021/jm00153a015 | es_ES |
dc.description.references | Cramariuc, O., Rog, T., Javanainen, M., Monticelli, L., Polishchuk, A. V., & Vattulainen, I. (2012). Mechanism for translocation of fluoroquinolones across lipid membranes. Biochimica et Biophysica Acta (BBA) - Biomembranes, 1818(11), 2563-2571. doi:10.1016/j.bbamem.2012.05.027 | es_ES |
dc.description.references | Sun, J., Sakai, S., Tauchi, Y., Deguchi, Y., Chen, J., Zhang, R., & Morimoto, K. (2002). Determination of lipophilicity of two quinolone antibacterials, ciprofloxacin and grepafloxacin, in the protonation equilibrium. European Journal of Pharmaceutics and Biopharmaceutics, 54(1), 51-58. doi:10.1016/s0939-6411(02)00018-8 | es_ES |
dc.description.references | Sun, J., Sakai, S., Tauchi, Y., Deguchi, Y., Cheng, G., Chen, J., & Morimoto, K. (2003). Protonation equilibrium and lipophilicity of olamufloxacin (HSR-903), a newly synthesized fluoroquinolone antibacterial. European Journal of Pharmaceutics and Biopharmaceutics, 56(2), 223-229. doi:10.1016/s0939-6411(03)00099-7 | es_ES |
dc.description.references | Furet, Y. X., Deshusses, J., & Pechère, J. C. (1992). Transport of pefloxacin across the bacterial cytoplasmic membrane in quinolone-susceptible Staphylococcus aureus. Antimicrobial Agents and Chemotherapy, 36(11), 2506-2511. doi:10.1128/aac.36.11.2506 | es_ES |
dc.description.references | Maurer, N., Wong, K. F., Hope, M. J., & Cullis, P. R. (1998). Anomalous solubility behavior of the antibiotic ciprofloxacin encapsulated in liposomes: a 1H-NMR study. Biochimica et Biophysica Acta (BBA) - Biomembranes, 1374(1-2), 9-20. doi:10.1016/s0005-2736(98)00125-4 | es_ES |
dc.description.references | Cuquerella, M. C., Andreu, I., Soldevila, S., & Bosca, F. (2012). Triplet Excimers of Fluoroquinolones in Aqueous Media. The Journal of Physical Chemistry A, 116(21), 5030-5038. doi:10.1021/jp301800q | es_ES |
dc.description.references | Lhiaubet-Vallet, V., Sarabia, Z., Boscá, F., & Miranda, M. A. (2004). Human Serum Albumin-Mediated Stereodifferentiation in the Triplet State Behavior of (S)- and (R)-Carprofen. Journal of the American Chemical Society, 126(31), 9538-9539. doi:10.1021/ja048518g | es_ES |
dc.description.references | Bosca, F. (2012). Seeking to Shed Some Light on the Binding of Fluoroquinolones to Albumins. The Journal of Physical Chemistry B, 116(11), 3504-3511. doi:10.1021/jp208930q | es_ES |
dc.description.references | Cuquerella, M. C., Lhiaubet-Vallet, V., Miranda, M. A., & Bosca, F. (2017). Drug–DNA complexation as the key factor in photosensitized thymine dimerization. Physical Chemistry Chemical Physics, 19(7), 4951-4955. doi:10.1039/c6cp08485k | es_ES |
dc.description.references | Alfredson, T. V., Maki, A. H., & Waring, M. J. (1991). Optically detected triplet-state magnetic resonance studies of the DNA complexes of the bisquinoline analog of echinomycin. Biochemistry, 30(40), 9665-9675. doi:10.1021/bi00104a014 | es_ES |
dc.description.references | Alfredson, T. V., & Maki, A. H. (1990). Phosphorescence and optically detected magnetic resonance studies of echinomycin-DNA complexes. Biochemistry, 29(38), 9052-9064. doi:10.1021/bi00490a024 | es_ES |
dc.description.references | Li, J., Li, J., Shuang, S., & Dong, C. (2005). Study of the luminescence behavior of seven quinolones on a paper substrate. Analytica Chimica Acta, 548(1-2), 134-142. doi:10.1016/j.aca.2005.04.053 | es_ES |
dc.description.references | Sun, C., Ping, H., Zhang, M., Li, H., & Guan, F. (2011). Spectroscopic studies on the lanthanide sensitized luminescence and chemiluminescence properties of fluoroquinolone with different structure. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 82(1), 375-382. doi:10.1016/j.saa.2011.07.065 | es_ES |
dc.description.references | Rieutord, A., Vazquez, L., Soursac, M., Prognon, P., Blais, J., Bourget, P., & Mahuzier, G. (1994). Fluoroquinolones as sensitizers of lanthanide fluorescence: application to the liquid chromatographic determination of ciprofloxacin using terbium. Analytica Chimica Acta, 290(1-2), 215-225. doi:10.1016/0003-2670(94)80058-8 | es_ES |
dc.description.references | Sortino, S., De Guidi, G., Giuffrida, S., Monti, S., & Velardita, A. (1998). pH Effects on the Spectroscopic and Photochemical Behavior of Enoxacin: A Steady-State and Time-Resolved Study. Photochemistry and Photobiology, 67(2), 167. doi:10.1562/0031-8655(1998)067<0167:peotsa>2.3.co;2 | es_ES |
dc.description.references | Martínez, L., Bilski, P., & Chignell, C. F. (1996). Effect of Magnesium and Calcium Complexation on the Photochemical Properties of Norfloxacin. Photochemistry and Photobiology, 64(6), 911-917. doi:10.1111/j.1751-1097.1996.tb01855.x | es_ES |
dc.description.references | Bilski, P., Martinez, L. J., Koker, E. B., & Chignell, C. F. (1996). Photosensitization by Norfloxacin is a Function of pH. Photochemistry and Photobiology, 64(3), 496-500. doi:10.1111/j.1751-1097.1996.tb03096.x | es_ES |
dc.description.references | Bosca, F., Lhiaubet-Vallet, V., Cuquerella, M. C., Castell, J. V., & Miranda, M. A. (2006). The Triplet Energy of Thymine in DNA. Journal of the American Chemical Society, 128(19), 6318-6319. doi:10.1021/ja060651g | es_ES |
dc.description.references | Lhiaubet-Vallet, V., Cuquerella, M. C., Castell, J. V., Bosca, F., & Miranda, M. A. (2007). Triplet Excited Fluoroquinolones as Mediators for Thymine Cyclobutane Dimer Formation in DNA. The Journal of Physical Chemistry B, 111(25), 7409-7414. doi:10.1021/jp070167f | es_ES |
dc.description.references | Cuquerella, M. C., Lhiaubet-Vallet, V., Bosca, F., & Miranda, M. A. (2011). Photosensitised pyrimidine dimerisation in DNA. Chemical Science, 2(7), 1219. doi:10.1039/c1sc00088h | es_ES |
dc.description.references | Lhiaubet-Vallet, V., Bosca, F., & Miranda, M. A. (2009). Photosensitized DNA Damage: The Case of Fluoroquinolones. Photochemistry and Photobiology, 85(4), 861-868. doi:10.1111/j.1751-1097.2009.00548.x | es_ES |
dc.description.references | Albini, A., & Monti, S. (2003). Photophysics and photochemistry of fluoroquinolones. Chemical Society Reviews, 32(4), 238. doi:10.1039/b209220b | es_ES |
dc.description.references | Cuquerella, M. C., Miranda, M. A., & Bosca, F. (2006). Role of Excited State Intramolecular Charge Transfer in the Photophysical Properties of Norfloxacin and Its Derivatives. The Journal of Physical Chemistry A, 110(8), 2607-2612. doi:10.1021/jp0559837 | es_ES |
dc.description.references | Lorenzo, F., Navaratnam, S., & Allen, N. S. (2008). Formation of Secondary Triplet Species after Excitation of Fluoroquinolones in the Presence of Relatively Strong Bases. Journal of the American Chemical Society, 130(37), 12238-12239. doi:10.1021/ja8044713 | es_ES |