Photostability of Terbinafine Under UVA Irradiation: The Effect of UV Absorbers.

Abstract:

:The photostability of drugs administered topically on unprotected skin is a complex phenomenon that could be connected with the loss of activity or, rather rarely, the occurrence of toxic degradation products. In this study, an in-depth investigation of the photostability of terbinafine, in both solutions and formulations, was conducted, taking into account the presence of UV absorbers such as TiO2 , ZnO, avobenzone, 3-(4-methylbenzylidene)camphor, octocrylene, benzophenone-1 and benzophenone-2. The clear photocatalytic degradation of terbinafine in ethanol solution was observed in the presence of TiO2 and/or ZnO. In other cases, terbinafine was stable, with the exception of, in the presence of octocrylene. The presumed degradation products of terbinafine were identified for the first time using LC/MS/MS, and transformation pathways were proposed. In the case of a cream formulation, the percentage of initial terbinafine content was almost unchanged in the presence of the UV absorbers benzophenone-1, benzophenone-2 and 3-(4-methylbenzylidene)camphor. In vitro cytotoxicity risk assessment of terbinafine based on photostability under UVA irradiation was evaluated using the human skin fibroblast BJ (ATCC® CRL-2522™), and this showed no statistically significant difference in cell viability for all samples analyzed.

journal_name

Photochem Photobiol

authors

Kryczyk-Poprawa A,Żmudzki P,Koczurkiewicz P,Pękala E,Hubicka U

doi

10.1111/php.13075

subject

Has Abstract

pub_date

2019-07-01 00:00:00

pages

911-923

issue

4

eissn

0031-8655

issn

1751-1097

journal_volume

95

pub_type

杂志文章
  • Spectroscopic studies of cutaneous photosensitizing agents--XIV. The spin trapping of free radicals formed during the photolysis of halogenated salicylanilide antibacterial agents.

    abstract::Several antibacterial halogenated salicylanilides, including 3,3',4',5-tetrachlorosalicylanilide (TCSA) and 3,4',5-tribromosalicylanilide (TBSA) are known to cause photoallergy. We have carried out photochemical and spin trapping studies to determine whether free radicals may be involved in the photoallergic response....

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/j.1751-1097.1989.tb04162.x

    authors: Chignell CF,Sik RH

    更新日期:1989-09-01 00:00:00

  • Role of nuclear factor-kappa B in colon cancer cell apoptosis mediated by aminopyropheophorbide photosensitization.

    abstract::Aminopyropheophorbide (APP) is a second generation of photosensitizer for photodynamic therapy (PDT). We demonstrated that APP strongly absorbed red light and, after being taken up by colon cancer cells (HCT-116 cells), was localized in cytoplasmic and internal membranes but not in mitochondria. The APP-mediated photo...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:

    authors: Matroule JY,Hellin AC,Morlière P,Fabiano AS,Santus R,Merville MP,Piette J

    更新日期:1999-10-01 00:00:00

  • Metformin, an antidiabetic agent reduces growth of cutaneous squamous cell carcinoma by targeting mTOR signaling pathway.

    abstract::The biguanide metformin is widely used for the treatment of Type-II diabetes. Its antiproliferative and pro-apoptotic effects in various tumor cells suggest its potential candidacy for cancer chemoprevention. Herein, we report that metformin significantly inhibited human epidermoid A431 tumor xenograft growth in nu/nu...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/j.1751-1097.2012.01165.x

    authors: Chaudhary SC,Kurundkar D,Elmets CA,Kopelovich L,Athar M

    更新日期:2012-09-01 00:00:00

  • Urokinase activity in corneal fibroblasts may be modulated by DNA damage and secreted proteins.

    abstract::Proteases like urokinase-type plasminogen activator (uPA) play an important role in tumor invasion. Cells derived from ultraviolet radiation (UVR)-induced corneal sarcomas of Monodelphis domestica produce relatively high levels of uPA compared to the untransformed keratocytes suggesting a mechanism for their invasiven...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1562/0031-8655(2001)073<0318:uaicfm>2.0.co;2

    authors: Green WB,McGuire PG,Miska KB,Kusewitt DF

    更新日期:2001-03-01 00:00:00

  • Synthesis and spectroscopic characterization of photo-affinity peptide ligands to study rhodopsin-G protein interaction.

    abstract::G protein-coupled receptors (GPCRs) are involved in the control of virtually all aspects of our behavior and physiology. Activated receptors catalyze nucleotide exchange in heterotrimeric G proteins (composed of alpha.GDP, beta and gamma subunits) on the inner surface of the cell membrane. The GPCR rhodopsin and the G...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/j.1751-1097.2008.00304.x

    authors: Chen Y,Herrmann R,Fishkin N,Henklein P,Nakanishi K,Ernst OP

    更新日期:2008-07-01 00:00:00

  • Design and Synthesis of Coumarin-Imidazole Hybrid Chromophores: Solvatochromism, Acidochromism and Nonlinear Optical Properties.

    abstract::A set of linear and asymmetric coumarin-imidazole hybrid compounds having a N,N-diethylamine at 7-position and imidazole at 3-position on the coumarin were synthesized. Insertion of thiophene π-spacer between coumarin and imidazole moieties (5b, 5d) leads to redshifted absorption and emission compared to 5a and 5c. Al...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/php.13024

    authors: Bhagwat AA,Avhad KC,Patil DS,Sekar N

    更新日期:2019-05-01 00:00:00

  • Distribution of 5-aminolevulinic acid-induced porphyrins in noduloulcerative basal cell carcinoma.

    abstract::Microscopic fluorescence photometry incorporating a light-sensitive thermo-electrically cooled charge-coupled device (CCD) camera was employed to investigate the fluorescence distribution of 5-aminolevulinic acid (ALA)-induced porphyrins in 22 patients with a total number of 52 noduloulcerative basal cell carcinomas (...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/j.1751-1097.1995.tb09154.x

    authors: Peng Q,Warloe T,Moan J,Heyerdahl H,Steen HB,Nesland JM,Giercksky KE

    更新日期:1995-11-01 00:00:00

  • Surface Functionalization of Green-synthesized Reduced Graphene Oxide with PPIX Enhances Photosensitization of Cancer Cells.

    abstract::Photosensitizer-functionalized reduced graphene oxide (rGO) nanoparticles are promising materials for photodynamic therapy in cancer management. In this study, rGO is synthesized by a green route employing glucose as the reducing agent and functionalized with photosensitizer, protoporphyrin IX (PPIX) in a convenient, ...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/php.13316

    authors: Shuvra Smita S,Das A,Barui A

    更新日期:2020-11-01 00:00:00

  • Solar UVB dosimetry by amplification of short and long segments in phage lambda DNA.

    abstract::DNA UVB dosimeters, consisting of minidots of dried bacteriophage DNA placed on a UV-transparent polymer film, were analyzed by polymerase chain reactions (PCR). Ultraviolet-B dosimetry obtained with amplification of phage lambda DNA of segments of 1.08 kilobase pairs (kbp) and 2.24 kbp was compared with that obtained...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/j.1751-1097.1997.tb03205.x

    authors: Yoshida H,Regan JD

    更新日期:1997-11-01 00:00:00

  • Ecotoxicological effects of combined UVB and organic contaminants in coastal waters: A review.

    abstract::Organisms living in coastal waters are exposed to anthropogenic contaminants from terrestrial drainage, ice melting and maritime traffic and to enhanced UVB radiation (UVBR; 280-320 nm) caused by decreased concentrations of ozone in the stratosphere. This article reviews available information about the combined effect...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章,评审

    doi:10.1562/2005-09-18-ra-688.1

    authors: Pelletier E,Sargian P,Payet J,Demers S

    更新日期:2006-07-01 00:00:00

  • Diastereoselectivity and site dependency in the photochemistry of ketoprofen in the bovine serum albumin matrix.

    abstract::The photodegradation of the S(+)- and R(-)-ketoprofen (KP) enantiomers in the bovine serum albumin matrix was studied by steady-state photolysis with the use of lambda(irr) > 320 nm and transient absorption spectroscopy with lambda(exc) = 355 nm, at 1/1 and 2/1 KP/BSA molar ratios. R(-)-KP was found to be more labile ...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1562/2005-07-11-RA-608

    authors: Monti S,Manet I,Manoli F,Morrone R,Nicolosi G,Sortino S

    更新日期:2006-01-01 00:00:00

  • A comparative pilot study of symptom improvement before and after phototherapy in Korean patients with perennial allergic rhinitis.

    abstract::Although allergic rhinitis is not life threatening, it significantly influences the quality of a patient's life. This study is intended to evaluate the safety and efficacy of phototherapy with low-level energy of a 650 nm laser irradiation system in perennial allergic rhinitis patients. This clinical trial was an open...

    journal_title:Photochemistry and photobiology

    pub_type: 临床试验,杂志文章

    doi:10.1111/php.12032

    authors: Lee HM,Park MS,Park IH,Lee SH,Lee SK,Kim KS,Choi H

    更新日期:2013-05-01 00:00:00

  • Photochemical and Photodynamical Properties of Sulfur-Substituted Nucleic Acid Bases.

    abstract::Sulfur-substituted nucleobases (a.k.a., thiobases) are among the world's leading prescriptions for chemotherapy and immunosuppression. Long-term treatment with azathioprine, 6-mercaptopurine and 6-thioguanine has been correlated with the photoinduced formation of carcinomas. Establishing an in-depth understanding of t...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章,评审

    doi:10.1111/php.12975

    authors: Ashwood B,Pollum M,Crespo-Hernández CE

    更新日期:2019-01-01 00:00:00

  • Application of CFD simulation to predicting upper-room UVGI effectiveness.

    abstract::This study outlines the potential for Computational Fluid Dynamics (CFD) simulation to be used to predict upper-room ultraviolet germicidal irradiation (UVGI) effectiveness to aid system design and the development of future guidance. A numerical study of two wall-mounted UVGI lamps in a mechanically ventilated test ch...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/php.12013

    authors: Gilkeson CA,Noakes C

    更新日期:2013-07-01 00:00:00

  • Furocoumarin-induced epidermal melanogenesis does not protect against skin photocarcinogenesis in hairless mice.

    abstract::Topical 6,4,4'-trimethylangelicin (TMA) plus UVA was used to induce intense epidermal pigmentation in inbred HRA.HRII-c/+/Skh hairless pigmented mice over a 13 day period. Subsequent UVB/UVA exposure was used to assess the photoprotective properties of this tan using skin tumors as an endpoint. Comparisons were always...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:

    authors: Kipp C,Lewis EJ,Young AR

    更新日期:1998-01-01 00:00:00

  • Ex vivo fluorescence imaging of normal and malignant urothelial cells to enhance early diagnosis.

    abstract::Urinary cytology is a noninvasive and unconstraining technique for urothelial cancer diagnosis but lacks sensitivity for detecting low-grade lesions. In this study, the fluorescence properties of classical Papanicolaou-stained urothelial cytological slides from patients or from cell lines were monitored to investigate...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/j.1751-1097.2007.00079.x

    authors: Steenkeste K,Lécart S,Deniset A,Pernot P,Eschwège P,Ferlicot S,Lévêque-Fort S,Briandet R,Fontaine-Aupart MP

    更新日期:2007-09-01 00:00:00

  • Empirical evaluation of a simple analytical formula for the ultraviolet index.

    abstract::This paper focuses on the estimation of the UV Index (UVI) for all sky conditions using a simple analytical parameterization involving three independent variables: the solar zenith angle, the total ozone column and the clearness index. Measurements of the UVI made at Badajoz and Cáceres (Southwestern Spain) from Janua...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/j.1751-1097.2010.00860.x

    authors: Antón M,Serrano A,Cancillo ML,García JA,Madronich S

    更新日期:2011-03-01 00:00:00

  • Photophysical properties of 2-nitro-5,10,15,20-tetra-p-tolylporphyrins.

    abstract::Tetraarylporphyrins substituted with nitro groups at beta-pyrrolic positions are potential candidates for electron-accepting pigments in model systems for photosynthesis. The photophysics of 2-nitro-5,10,15,20-tetra-p-tolylporphyrin and its zinc analog have been studied in order to evaluate this potential. The ground ...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/j.1751-1097.1990.tb01733.x

    authors: Gust D,Moore TA,Luttrull DK,Seely GR,Bittersmann E,Bensasson RV,Rougée M,Land EJ,De Schryver FC,Van der Auweraer M

    更新日期:1990-04-01 00:00:00

  • Genetic variability in the response of normal murine hematopoietic progenitor cells to extracorporeal photochemotherapy.

    abstract::Normal hematopoietic progenitor cells from 129S6/SvEv mice are substantially less sensitive to Merocyanine 540 (MC540)-mediated photodynamic therapy (PDT) than hematopoietic progenitors from sex- and age-matched C57BL/6 mice. When exposed to a combination of MC540 and light commonly used for the extracorporeal purging...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1562/0031-8655(2000)072<0810:gvitro>2.0.co;2

    authors: Tsujino I,Sieber F

    更新日期:2000-12-01 00:00:00

  • DNA Ligases I and III Support Nucleotide Excision Repair in DT40 Cells with Similar Efficiency.

    abstract::In eukaryotic cells helix-distorting DNA lesions like cyclobutane pyrimidine dimers (CPDs) and 6-4 pyrimidine-pyrimidone photoproducts (6-4 PPs) are efficiently removed by nucleotide excision repair (NER). NER is a multistep process where in the end, subsequent to replication over the gap, the remaining nick is sealed...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/php.12487

    authors: Paul-Konietzko K,Thomale J,Arakawa H,Iliakis G

    更新日期:2015-09-01 00:00:00

  • Photoreaction of new psoralen analogs with DNA: sequence and mutation specificity in the Escherichia coli lacZ gene.

    abstract::New thio- and seleno-analogs of psoralen were synthesized and analyzed for their photoreactivity toward DNA. Using oligonucleotides of defined sequence, we first showed that these derivatives predominantly generated interstrand crosslinks at 5'-TpA sites. We also observed a surprisingly high reactivity of 7H-thiopyran...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/j.1751-1097.1997.tb08646.x

    authors: Collet M,Sage E,Piette J

    更新日期:1997-08-01 00:00:00

  • Ring opening photoreactions of 5-bromouracil and 5-bromo-2'-deoxyuridine with selected alkylamines.

    abstract::Several studies in the literature indicate that histones (lysine rich proteins found associated with DNA in eukaryotic chromatin), as well as poly-L-lysine, can be photocross-linked by ultraviolet (UV) light to DNA in which 5-bromo-2'-deoxyuridine has been substituted for thymidine. To gain some insight into the possi...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/j.1751-1097.1991.tb08486.x

    authors: Shetlar MD,Rose RB,Hom K,Shaw AA

    更新日期:1991-05-01 00:00:00

  • Light emission accompanies oxygen uptake during the peroxidative metabolism of tetracyclines.

    abstract::Tetracycline molecules offer several sites for peroxidative metabolism of the type known to lead to oxygen consumption and electronic excitation. Accordingly, when tetracycline and chlortetracycline were exposed to horseradish peroxidase in the presence of hydrogen peroxide, oxygen was taken up and light emission was ...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/j.1751-1097.1993.tb09588.x

    authors: Gilio VE,Cilento G

    更新日期:1993-09-01 00:00:00

  • Fluence Rate Determines PDT Efficiency in Breast Cancer Cells Displaying Different GSH Levels.

    abstract::Photodynamic therapy (PDT) appears as a promising alternative in the treatment of breast cancer since it can be highly effective in curing cancer while preserving normal tissue. However, predicting outcomes in PDT still constitutes a great challenge. One of the parameters that are usually empirically determined is the...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/php.13182

    authors: Dos Santos AF,de Almeida DRQ,Terra LF,Wailemann RAM,Gomes VM,Arini GS,Ravagnani FG,Baptista MS,Labriola L

    更新日期:2020-05-01 00:00:00

  • Theoretical study of the reaction formalhydrazone with singlet oxygen. Fragmentation of the C=N bond, ene reaction and other processes.

    abstract::Photobiologic and synthetic versatility of hydrazones has not yet been established with (1)O2 as a route to commonly encountered nitrosamines. Thus, to determine whether the "parent" reaction of formalhydrazone and (1)O2 leads to facile C=N bond cleavage and resulting nitrosamine formation, we have carried out CCSD(T)...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/php.12199

    authors: Rudshteyn B,Castillo A,Ghogare AA,Liebman JF,Greer A

    更新日期:2014-03-01 00:00:00

  • Photochemical Immobilization of Polymers on a Surface: Controlling Film Thickness and Wettability.

    abstract::In this manuscript, we demonstrate the control of film thickness and surface wettability in the photochemical immobilization of poly (vinyl alcohol) (PVA) to a self-assembled monolayer (SAM) containing a phthalimide chromophore. Surface attachment is characterized by ellipsometry and contact angle measurements. The we...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/php.12751

    authors: Carroll GT,Turro NJ,Mammana A,Koberstein JT

    更新日期:2017-10-01 00:00:00

  • The measurement and analysis of normal incidence solar UVB radiation and its application to the photoclimatherapy protocol for psoriasis at the Dead Sea, Israel.

    abstract::The broad-band normal incidence UVB beam radiation has been measured at Neve Zohar, Dead Sea basin, using a prototype tracking instrument composed of a Model 501A UV-Biometer mounted on an Eppley Solar Tracker Model St-1. The diffuse and beam fraction of the solar global UVB radiation have been determined using the co...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/j.1751-1097.2010.00842.x

    authors: Kudish AI,Harari M,Evseev EG

    更新日期:2011-01-01 00:00:00

  • Circadian gating of photoinduction of commitment to cell-cycle transitions in relation to photoperiodic control of cell reproduction in Euglena.

    abstract::A novel type of circadian and photoperiodic control of the cell division cycle was found in photoautotrophic Euglena gracilis. When algae entrained to 24 h light-dark (LD) cycles (14 h L) were transferred to continuous darkness (DD) at the eighth hour of the final LD photoperiod, cell-cycle transition was arrested in ...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1562/0031-8655(2002)076<0105:cgopoc>2.0.co;2

    authors: Hagiwara SY,Bolige A,Zhang Y,Takahashi M,Yamagishi A,Goto K

    更新日期:2002-07-01 00:00:00

  • Transient and stationary spectroscopy of cytochrome c: ultrafast internal conversion controls photoreduction.

    abstract::Photoreduction of cytochrome c (Cyt c) has been reinvestigated using femtosecond-to-nanosecond transient absorption and stationary spectroscopy. Femtosecond spectra of oxidized Cyt c, recorded in the probe range 270-1000 nm, demonstrate similar evolution upon 266 or 403 nm excitation: an ultrafast 0.3 ps internal conv...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/j.1751-1097.2007.00219.x

    authors: Löwenich D,Kleinermanns K,Karunakaran V,Kovalenko SA

    更新日期:2008-01-01 00:00:00

  • Germ Cell Testicular Cancer Incidence, Latitude and Sunlight Associations in the United States and Australia.

    abstract::International patterns suggest germ cell testicular cancer (GCTC) incidence may be lower in lower latitudes. To investigate this possibility, we examined GCTC incidence by latitude (population centroid in 2000) for men ≥15 years within two reasonably homogeneous countries, the United States and Australia. In the Unite...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/php.12617

    authors: Biggar RJ,Baade PD,Sun J,Brandon LE,Kimlin M

    更新日期:2016-09-01 00:00:00