Visible light-mediated photodegradation of imidazoline drugs in the presence of Riboflavin: Possible undesired effects on imidazoline-based eye drops

Challier, Cecilia; Mártire, Daniel O.; Garcı́a, Norman A.; Criado, Susana

doi:10.1016/j.jphotochem.2016.09.009

Cited by 8 publications

(4 citation statements)

References 48 publications

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“…In addition, upon irradiation of Rf solutions under aerobic conditions, singlet molecular oxygen, O 2 ( 1 Δ g ), is also formed by energy transfer from 3 Rf* to ground state oxygen (Type II photosensitization). Consequently, the Type I and Type II photooxidation of several substrates sensitized by Rf was the topic of several publications .…”

Section: Introductionmentioning

confidence: 99%

“…The photoinduced generation of reactive oxygen species (ROS) motivated the testing of the photosensitizing ability of Rf for a number of applications. For instance, light irradiation of Rf in aqueous medium was demonstrated to be effective as antibacterial agent , as crosslinker for corneal stiffening , for blood product sterilization and for the treatment of skin lesions .…”

Section: Introductionmentioning

confidence: 99%

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Photodynamic Therapy in HeLa Cells Incubated with Riboflavin and Pectin‐coated Silver Nanoparticles

Aiello

Castrogiovanni

Parisi

et al. 2018

Photochem & Photobiology

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Riboflavin (Rf) is an endogenous photosensitizer, which can participate in Type I and Type II processes. We have recently shown that the yield of the triplet excited states of Rf is enhanced in the presence of pectin-coated silver nanoparticles (Pec@AgNP) due to formation of a complex between Rf and Pec@AgNP (Rf-Pec@AgNP). Consequently, under aerobic conditions, the amounts of singlet molecular oxygen and superoxide radical anion generated are also larger in the presence of the nanoparticles. This result made us suspect that the nanoparticles could have a beneficial effect in Rf-based PDT. To prove this hypothesis, we here compared the photodamage in HeLa cells incubated with Rf in the presence and in the absence of Pec@AgNP applying several optical assays. We used fluorescence imaging of irradiated HeLa cells incubated with Annexin V and propidium iodide to evaluate the occurrence of apoptosis/necrosis, the reduction of the tetrazolium dye MTT to formazan and neutral red uptake to prove cell viability, as well as synchrotron infrared microscopy of single cells to evaluate possible structural changes of DNA and nuclear proteins. The enhanced photodamage observed in the presence of Pec@AgNP seems to indicate that Rf enters into the cells complexed with the nanoparticles.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Photodynamic Therapy in HeLa Cells Incubated with Riboflavin and Pectin‐coated Silver Nanoparticles

Aiello

Castrogiovanni

Parisi

et al. 2018

Photochem & Photobiology

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“…Ataluren concentration did not decrease upon direct light exposure, pointing out that the drug may resist to the light in the proposed formulation. Further, when riboflavin, a natural photosensitizing agent constituent of the eye, was added, no degradation was observed, which indicates that ataluren may not degrade through the photosensitized process naturally occurring in the eye [ 22 ]. Still, precaution should be taken as ataluren concentration decreased upon exposure when nanoparticles of titanium dioxide P25, a powerful photocatalyst, were added [ 23 ].…”

Section: Discussionmentioning

confidence: 99%

Formulation and Stability of Ataluren Eye Drop Oily Solution for Aniridia

et al. 2020

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Congenital aniridia is a rare and severe panocular disease characterized by a complete or partial iris defect clinically detectable at birth. The most common form of aniridia occurring in around 90% of cases is caused by PAX6 haploinsufficiency. The phenotype includes ptosis, nystagmus, corneal limbal insufficiency, glaucoma, cataract, optic nerve, and foveal hypoplasia. Ataluren eye drops aim to restore ocular surface PAX6 haploinsufficiency in aniridia-related keratopathy (ARK). However, there are currently no available forms of the ophthalmic solution. The objective of this study was to assess the physicochemical and microbiological stability of ataluren 1% eye drop in preservative-free low-density polyethylene (LDPE) bottle with an innovative insert that maintains sterility after opening. Because ataluren is a strongly lipophilic compound, the formulation is complex and involves a strategy based on co-solvents in an aqueous phase or an oily formulation capable of totally dissolving the active ingredient. The visual aspect, ataluren quantification by a stability-indicating chromatographic method, and microbiological sterility were analyzed. The oily formulation in castor oil and DMSO (10%) better protects ataluren hydrolysis and oxidative degradation and permits its complete solubilization. Throughout the 60 days period, the oily solution in the LDPE bottle remained clear without any precipitation or color modification, and no drug loss and no microbial development were detected. The demonstrated physical and microbiological stability of ataluren 1% eye drop formulation at 22–25 °C might facilitate clinical research in aniridia.

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“…3 Rf* is a very strong oxidant ( E ° ( 3 Rf*/Rf· – ) = 1.62 V), which mediates the direct oxidation of most biomolecules: lipids, amino acids, and proteins. 3 Rf* can also transfer its excitation energy to molecular oxygen, giving rise to the formation of singlet oxygen ( 1 O 2 ), which is able to oxidize several substrates. − As a result of the reactions of biomolecules with 3 Rf* and/or 1 O 2 , Rf in combination with UV–visible light can be employed as a photosensitizer (PS) in photodynamic therapy (PDT) and as an inhibitor of the growth of several types of bacteria, viruses, and fungi by photodynamic inactivation (PDI). − …”

Section: Introductionmentioning

confidence: 99%

Riboflavin-Mediated Photooxidation of Gold Nanoparticles and Its Effect on the Inactivation of Bacteria

et al. 2020

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Photodynamic inactivation (PDI) of microorganisms, based on the ability of photosensitizers to produce reactive oxygen species (ROS) under adequate irradiation, emerges as a promising technique to face the increasing bacterial resistance to conventional antimicrobials. In this work, we analyze the combined action of Riboflavin (Rf) and pectin-coated gold nanoparticles (PecAuNP) on Staphylococcus aureus (S. aureus) and Pseudomonas aeruginosa (P. aeruginosa) as suitable PDI strategy. We demonstrate that gold ions can be generated upon Rf-photosensitized oxidation of PecAuNP. Transient absorption spectroscopy shows that the Rf cationic radical can accept an electron from the nanoparticles to yield Au(I) ions, which in aqueous medium is disproportionate to yield Au0 and Au(III). Microbiological assays showed that the presence of PecAuNP enhanced the antibacterial activity of photoirradiated Rf toward S. aureus and P. aeruginosa, in line with the well-known antibacterial activity of gold ions. Moreover, the irradiation of Rf solutions containing about 100 μM PecAuNP enabled the solutions to be bactericidal against both bacteria.

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Visible light-mediated photodegradation of imidazoline drugs in the presence of Riboflavin: Possible undesired effects on imidazoline-based eye drops

Cited by 8 publications

References 48 publications

Photodynamic Therapy in HeLa Cells Incubated with Riboflavin and Pectin‐coated Silver Nanoparticles

Photodynamic Therapy in HeLa Cells Incubated with Riboflavin and Pectin‐coated Silver Nanoparticles

Formulation and Stability of Ataluren Eye Drop Oily Solution for Aniridia

Riboflavin-Mediated Photooxidation of Gold Nanoparticles and Its Effect on the Inactivation of Bacteria

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