Photosensitization Reactions of Fluoroquinolones and Their Biological Consequences

Abstract

This review focuses on damage photosensitized by the fluoroquinolone (FQ) antibacterial drugs. Different models are employed to study biosubstrate photodamage mediated by FQs (organisms, cells, isolated biomolecules and super molecules). Being that the effect of environment (polarity of the medium, ions, pH, binding with bio-molecules, etc.) is crucial in FQ photochemistry, photobiological reactions can be consequently dramatically influenced. Thus, the photosensitization processes induced by FQs are here discussed taking into account that such extensive and cross-targeted pathological implications request an excursus covering photosensitization in systems of increasing molecular complexity. In vivo and in vitro evidences for photoallergy, phototoxicity, photomutagenesis and photocarcinogenesis mediated by FQs are discussed.

Photoinduced Damage to Cellular DNA: Direct and Photosensitized Reactions†

“…It is well documented that the reaction of 1 O 2 (Type II ROS) leads to the specific formation of 8-oxoGua whereas Type I gives rise, among other degradation products, 8-oxoGua and 2,6-diamino-4-hydroxy-5-formamidopyrimidine (FapyGua), to the transient formation of the guanine radical cation (Gua •+ ) in DNA. In that respect, several detailed mechanistic studies have provided relevant information on the contribution of the oxidation mechanisms to the degradation of nucleosides and isolated DNA (174)(175)(176). Among fluoroquinolones (for recent reviews, see Lhiaubet-Vallet et al [175] and de Guidi et al [176]), lomefloxacin and, to a lesser extent, enoxacin act as predominant Type I photosensitizers whereas ofloxacin and norfloxacin react with DNA mainly through 1 O 2 oxidation (93).…”

“…In that respect, several detailed mechanistic studies have provided relevant information on the contribution of the oxidation mechanisms to the degradation of nucleosides and isolated DNA (174)(175)(176). Among fluoroquinolones (for recent reviews, see Lhiaubet-Vallet et al [175] and de Guidi et al [176]), lomefloxacin and, to a lesser extent, enoxacin act as predominant Type I photosensitizers whereas ofloxacin and norfloxacin react with DNA mainly through 1 O 2 oxidation (93). It was subsequently confirmed that ofloxacin oxidized predominantly DNA mostly through the Type II mechanism (177) as also shown for norfloxacin (178).…”

Spectroscopic characterization, photoinduced processes and cytotoxic properties of substitutedN-ethyl selenadiazoloquinolones

“…[11,[14][15][16][17][18][19] In addition to the optimization of the biological properties of novel quinolone derivatives, the photoactivity of these compounds can be utilized in target phototherapeutic applications, such as photodynamic therapy. [20][21][22][23][24] Introducing the selenadiazole ring to a 4-oxoquinoline moiety was expected to enhance the biological activity and to affect the desired photoactivity, via shifting the absorption bands to the visible region. Based on these presumptions, a group of selenadiazoloquinolones were synthesized and studied in our laboratories previously.…”

Exposure to moxifloxacin and cytomegalovirus replication is associated with skin squamous cell carcinoma development in lung transplant recipients

“…Such an association of moxifloxacin with SCC development has not been recognized previously in LTR. The photosensitizing potential of fluoroquinolones in vitro and in vivo is well known and may thus play a role in SCC formation in this context. It is noteworthy that moxifloxacin is reported to have mild photosensitization effects compared with other quinolones such as, for example, ciprofloxacin .…”

“…The photosensitizing potential of fluoroquinolones in vitro and in vivo is well known and may thus play a role in SCC formation in this context. It is noteworthy that moxifloxacin is reported to have mild photosensitization effects compared with other quinolones such as, for example, ciprofloxacin . Interestingly, exposure to other fluoroquinolones including ciprofloxacin and levofloxacin did not significantly associate with SCC in our study.…”