Photoreactions of psoralens with lecithins

Zarebska, Z; Waszkowska, E.; Caffieri, Sergio; Dall’Acqua, Francesco

doi:10.1016/s1011-1344(98)00170-5

Cited by 10 publications

(8 citation statements)

References 15 publications

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“…These photo-adducts are considered to be less toxic for keratinocytes, thus exhibiting a miniscule phototoxic reactions in the skin [34]. In other words, photoradiation accompanied by isomerization of double bonds in fatty acid molecules, photo-oxidation of phospholipids and psoralen and splitting of fatty acid adducts, all together helps in maintaining the cellular homeostasis in the stratum corneum and deeper layers of dermis [4]. The studies ratified significant importance of developing the phospholipid-based carriers of 8-MOP, which proved to be highly effective in attaining enhanced permeability and biocompatibility properties along with reduced phototoxic adverse affects of drug for long-term therapy.…”

Section: Skin Photosensitization and Histopathologymentioning

confidence: 99%

“…It is popularly recommended for PUVA therapy, which remains as the ''gold standard'' for vitiligo treatment [3]. When drug is activated by UVA light, 8-MOP undergoes cyclo-addiction reaction with pyrimidine bases of nucleic acids to form stable cyclo-adducts [4]. Although this mechanism is very effective in treating dermatological disorders, yet some noted side effects have been observed after being exposed to PUVA therapy owing to the formation of psoralen-photo adducts, leading eventually to cause skin cancer and photo-toxicity [3].…”

Section: Introductionmentioning

confidence: 99%

“…J Drug Target, Early Online:[1][2][3][4][5][6][7][8][9][10][11][12][13][14] Journal of Drug Targeting Downloaded from informahealthcare.com by Kungliga Tekniska Hogskolan on 08/12/15For personal use only.…”

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confidence: 99%

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Nanosized ethosomes-based hydrogel formulations of methoxsalen for enhanced topical delivery against vitiligo: formulation optimization, in vitro evaluation and preclinical assessment

Garg

Beg

et al. 2015

Journal of Drug Targeting

101

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The present investigation aimed for the development and characterization of ethosomes-based hydrogel formulations of methoxsalen for enhanced topical delivery and effective treatment against vitiligo. The ethosomes were prepared by central composite design (CCD) and characterized for various quality attributes like vesicle shape, size, zeta potential, lamellarity, drug entrapment and drug leaching. The optimized ethosomes were subsequently incorporated int Carbopol® 934 gel and characterized for drug content, rheological behavior, texture profile, in vitro release, ex vivo skin permeation and retention, skin photosensitization and histopathological examination. Ethosomes were found to be spherical and multilamellar in structures having nanometric size range with narrow size distribution, and high encapsulation efficiency. Ethosomal formulations showed significant skin permeation and accumulation in the epidermal and dermal layers. The fluorescence microscopy study using 123 Rhodamine exhibited enhanced permeation of the drug-loaded ethosomes in the deeper layers of skin. Also, the developed formulation showed insignificant phototoxicity and erythema vis-à-vis the conventional cream. The results were cross-validated using histopathological examination of skin segments. In a nutshell, the ethosomes-based hydrogel formulation was found to be a promising drug delivery system demonstrating enhanced percutaneous penetration of methoxsalen with reduced phototoxicity and erythema, thus leading to improved patient compliance for the treatment against vitiligo.

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Section: Skin Photosensitization and Histopathologymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Nanosized ethosomes-based hydrogel formulations of methoxsalen for enhanced topical delivery against vitiligo: formulation optimization, in vitro evaluation and preclinical assessment

Garg

Beg

et al. 2015

Journal of Drug Targeting

101

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“…Preparation of photoadduct. The photoadduct of arachidonic acid was obtained according to the procedures used to produce photoadducts of psoralen to lecithin (Zarębska et al, 1998). Briefly, a mixture of AA and PSO at a molar ratio 8 : 1 was irradiated in ethanol with 30 J/cm 2 of UVA in a pyrex tube for 90 min with two HQV125 Osram lamps.…”

Section: Isolation and Culture Of Primary Human Lymphocytesmentioning

confidence: 99%

Apoptosis induced by membrane damage in human lymphocytes; effects of arachidonic acid and its photoproducts.

Zarebska¹,

Zielińska²,

Zhukov³

et al. 2005

Acta Biochim Pol

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The effect of arachidonic acid (AA) combined with UVA irradiation was studied in a model system mimicking phototherapy PUVA (psoralen+UVA) ex vivo in vitro. The contribution of damage to the plasma membrane by PUVA was tested on human lymphocytes derived from healthy donors. The effect of arachidonic acid (AA) combined with UVA irradiation was compared with that of a psoralen photoadduct to AA added to the culture. The adduct, obtained photochemically and purified, was characterized by NMR and MS spectrometry as a cycloadduct of psoralen to the vinylene bond of the acid (AA<>PSO).The reactions of cultured cells, manifested 20 h after treatment by changes in apoptosis and mitochondrial depolarization, were monitored by flow cytometry by tagging lymphocytes with appropriate fluorescent probes. Treatment of lymphocyte suspension within AA doses from 40 to 100 mM gradually induced a shift from Anx-V + (single positive cells) to late apoptotic, Anx-V + PI + (double positive cells) in a dose dependent manner. The adduct, AA<>PSO, induced apoptotic changes at a concentration 2-3 times higher than free AA. Combination of psoralen (1 mM ) or arachidonic acid (20-120 mM) with UVA irradiation (2-6 J/cm 2 ) accelerated theVol. 52 No. Abbreviations: AA, arachidonic acid; AA<>PSO, arachidonic-acid-psoralen-photoadduct; Anx-V, annexin V tagged with fluorescein isothiocyanate (FITC); JC-1, 5,5¢,6,6¢-tetrachloro-1,1¢,3,3¢-tetraethylbenzimidazolylcarbocyanine iodide; MMP, mitochondrial membrane potential; PI, propidium iodide; PLA2, phospholipase 2; PSO, psoralen; PUVA (psoralen+UVA); UVA, waveband of irradiation, (320-400 nm).

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“…By UVA irradiation furocoumarins induce various lesions in a living cell: damage to unsatured fatty acids and lecithins of membranes [8,9] and to ribosomes [10,11]. However the main damage is provoked in DNA [12].…”

Section: Introductionmentioning

confidence: 99%

Photochemical and photobiological properties of furocoumarins and homologues drugs

Bordin

1999

International Journal of Photoenergy

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Abstract. Furocoumarins are natural photosensitizing drugs used in PUVA photochemotherapy and in photopheresis. Their therapeutic effectiveness is connected to the lesions they induce to various cell components, membranes, ribosomes, mitochondria, and in particular to DNA, damaged by formation of monofunctional adducts and of inter-strand cross-links (ISC). ISC represent a severe damage, mainly correlated to the main side effects observed in photochemotherapy, skin phototoxicity and genotoxicity. Searching for new monofunctional derivatives, two tetramethylfuroquinolinones, 1,4,6,8-tetramethyl-2H-furo[2,3-h]quinolin-2-one (FQ) and 4,6,8,9-tetramethyl-2H-furo[2,3-h]-quinolin-2-one (HFQ) were studied. Both compounds are very active; however while FQ produced many chromosomal aberrations and strong skin erythemas, HFQ practically did not induce such side effects. FQ and HFQ formed high levels of monoadducts but no ISC in DNA, but both provoked many DNA-protein cross-links (DPC). FQ induced these lesions by a biphotonic reaction: at first a furan-side monoadduct is formed, which is then converted into a DPC; thus the FQ molecule seemed to form the bridge between DNA and proteins. HFQ formed DPC by a single step (DPC at zero length, like UVC). For these features, HFQ appears to be the first molecule belonging to a new class of active but not phototoxic drugs for photomedicine.

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Photoreactions of psoralens with lecithins

Cited by 10 publications

References 15 publications

Nanosized ethosomes-based hydrogel formulations of methoxsalen for enhanced topical delivery against vitiligo: formulation optimization, in vitro evaluation and preclinical assessment

Nanosized ethosomes-based hydrogel formulations of methoxsalen for enhanced topical delivery against vitiligo: formulation optimization, in vitro evaluation and preclinical assessment

Apoptosis induced by membrane damage in human lymphocytes; effects of arachidonic acid and its photoproducts.

Photochemical and photobiological properties of furocoumarins and homologues drugs

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