Triplet Excited States and Singlet Oxygen Production by Analogs of Red Wine Pyranoanthocyanins.

Abstract:

:During the maturation of red wines, the anthocyanins of grapes are transformed into pyranoanthocyanins, which possess a pyranoflavylium cation as their basic chromophore. Photophysical properties of the singlet and triplet excited states of a series of synthetic pyranoflavylium cations were determined at room temperature in acetonitrile solution acidified with 0.10 mol dm-3 trifluoroacetic acid (TFA, to inhibit competitive excited state proton transfer) and at 77 K in a rigid TFA-acidified isopropanol glass. In solution, the triplet states of these pyranoflavylium cations are efficiently quenched by molecular oxygen, resulting in sensitized formation of singlet oxygen, as confirmed by direct detection of the triplet-state decay by laser flash photolysis and of singlet oxygen monomol emission in the near infrared. The strong visible light absorption, the relatively small singlet-triplet energy differences, the excited state redox potentials and the reasonably long lifetimes of pyranoflavylium triplet states in the absence of molecular oxygen suggest that they might be useful as triplet sensitizers and/or as cationic redox initiators in polar aprotic solvents like acetonitrile.

journal_name

Photochem Photobiol

authors

Silva GTM,Thomas SS,Silva CP,Schlothauer JC,Baptista MS,Freitas AA,Bohne C,Quina FH

doi

10.1111/php.12973

subject

Has Abstract

pub_date

2019-01-01 00:00:00

pages

176-182

issue

1

eissn

0031-8655

issn

1751-1097

journal_volume

95

pub_type

杂志文章
  • Ex vivo application of delta-aminolevulinic acid induces high and specific porphyrin levels in human skin tumors: possible basis for selective photodynamic therapy.

    abstract::In photodynamic therapy with topically applied delta-aminolevulinic acid porphyrins are acting as photosensitizers. The profile of porphyrin metabolites in normal or in neoplastic skin after administration of delta-aminolevulinic acid has not been determined in detail yet. Thus, to study porphyrin biosynthesis in huma...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/j.1751-1097.1997.tb03146.x

    authors: Fritsch C,Batz J,Bolsen K,Schulte KW,Zumdick M,Ruzicka T,Goerz G

    更新日期:1997-07-01 00:00:00

  • In vitro investigations on the effect of dermal fibroblasts on keratinocyte responses to ultraviolet B radiation.

    abstract::Exposure to ultraviolet radiation is closely linked to the development of skin cancers in humans. The ultraviolet B (UVB) radiation wavelength (280-320 nm), in particular, causes DNA damage in epidermal keratinocytes, which are linked to the generation of signature premalignant mutations. Interactions between dermal f...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/php.12317

    authors: Fernandez TL,Van Lonkhuyzen DR,Dawson RA,Kimlin MG,Upton Z

    更新日期:2014-11-01 00:00:00

  • The photochemistry of the retinoids as studied by steady-state and pulsed methods.

    abstract::The retina and retinal pigment epithelium contain a number of retinoids in a metabolic pathway that eventually forms the visual pigments. This study investigates the photochemistry of those retinoids that may contribute to light-induced damage to the retina. These include retinal (RAL), retinol (ROL), retinylpalmitate...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/j.1751-1097.1996.tb05673.x

    authors: Dillon J,Gaillard ER,Bilski P,Chignell CF,Reszka KJ

    更新日期:1996-05-01 00:00:00

  • Photobiological information obtained from XPA gene-deficient mice.

    abstract::The XPA gene-deficient mouse, an animal model of xeroderma pigmentosum (XP), develops enhanced photobiologic reactions including acute inflammation, immunosuppression and skin carcinogenesis, because of the defect in the excision repair of ultraviolet-induced DNA lesions. The results strongly suggest that nuclear DNA ...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章,评审

    doi:10.1562/2006-03-02-IR-829

    authors: Horio T,Miyauchi-Hashimoto H,Kuwamoto K,Yamazaki F,Okamoto H

    更新日期:2007-01-01 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

  • A comparison of fluorescence methods used in the pharmacokinetic studies of Zn(II)phthalocyanine in mice.

    abstract::The pharmacokinetics of Zn phthalocyanine (ZnPc) encapsulated in dipalmitoyl-phosphatidylcholine (DPPC) liposomes, injected intravenously in Skh:HR-1 nude mice, was monitored by two in vitro techniques and one in vivo technique, all based on fluorescence spectroscopy. The in vitro methods involve either fluorescence m...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/j.1751-1097.1991.tb08475.x

    authors: Biolo R,Jori G,Kennedy JC,Nadeau P,Pottier R,Reddi E,Weagle G

    更新日期:1991-01-01 00:00:00

  • m-THPC-mediated photodynamic therapy (PDT) does not induce resistance to chemotherapy, radiotherapy or PDT on human breast cancer cells in vitro.

    abstract::Photodynamic therapy (PDT) uses laser light to activate a photosensitizer that has been absorbed preferentially by cancer cells after systemic administration. A phototoxic reaction ensues resulting in cell death and tissue necrosis. Some cells, however, may survive PDT. This study was performed to determine if survivi...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:

    authors: Hornung R,Walt H,Crompton NE,Keefe KA,Jentsch B,Perewusnyk G,Haller U,Köchli OR

    更新日期:1998-10-01 00:00:00

  • On the Formation of Thymine Photodimers in Thymine Single Strands and Calf Thymus DNA.

    abstract::Solar light leads to thymine dimers that are mutagenic and primary cause of skin cancer. Here, we report absorption and synchrotron radiation circular dichroism (CD) spectra of Tn single strands with different number n of bases (n = 2-7, 10, 11) recorded after various 254 nm irradiation times. From a principal compone...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/php.12183

    authors: Baggesen LM,Hoffmann SV,Nielsen SB

    更新日期:2014-01-01 00:00:00

  • Flavin-based Blue-Light photosensors: a photobiophysics update.

    abstract::This review deals with the biophysical aspects of flavin-based photosensors, comprising cryptochromes, LOV (Light, Oxygen and Voltage) and BLUF (Blue Light sensing Using FAD) proteins. Special emphasis is given to structural issues, photocycle quantum yields and energetics, mechanism of the light-triggered reactions, ...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章,评审

    doi:10.1111/j.1751-1097.2007.00196.x

    authors: Losi A

    更新日期:2007-11-01 00:00:00

  • Analysis of two kinds of tree as physical barriers against erythemal UVB radiation received.

    abstract::Differences between global radiation UVER (erythemal ultraviolet solar radiation) received under full sun and diffuse radiation received under the shadow of two types of tree are analyzed to check the importance of these components on human exposure to UV radiation. Blue Line spores dosimeters of VioSpor were used for...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/php.12020

    authors: Ysasi GG,Ribera LJ

    更新日期:2013-05-01 00:00:00

  • Is phototherapy safe for HIV-infected individuals?

    abstract::Patients infected with human immunodeficiency virus (HIV) have a high prevalence of UV radiation-responsive skin diseases including psoriasis, pruritus, eosinophilic folliculitis and eczemas. On the other hand, UV has been shown to suppress T cell-mediated immune responses and to induce activation and replication of H...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章,评审

    doi:10.1111/j.1751-1097.1996.tb02450.x

    authors: Adams ML,Houpt KR,Cruz PD Jr

    更新日期:1996-08-01 00:00:00

  • Investigation of photocatalytic effect of SnO2 nanoparticles synthesized by hydrothermal method on the decolorization of two organic dyes.

    abstract::Tin oxide nanoparticles about 4 nm in size were successfully synthesized using hydrothermal method. The photocatalytic activity of the particles was determined by the decolorization of malachite green (MG) and titanium yellow (TY) under UV light. 12 ppm of MG and TY were used for the solution with an initial volume of...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/j.1751-1097.2010.00863.x

    authors: Esen B,Yumak T,Sınağ A,Yıldız T

    更新日期:2011-03-01 00:00:00

  • Chronology of the apoptotic events induced in the K562 cell line by photodynamic treatment with hematoporphyrin and monoglucosylporphyrin.

    abstract::Photodynamic treatment of promyelocytic K562 cells in the presence of a monoglucosylporphyrin or hematoporphyrin leads to a sequence of events recognized as hallmarks of apoptosis: a drop in mitochondrial potential, concurrent with a drop in ATP level and a decrease in cell respiration, translocation of phosphatidylse...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:

    authors: Carré V,Jayat C,Granet R,Krausz P,Guilloton M

    更新日期:1999-01-01 00:00:00

  • The Mechanism of CIRP in Regulation of STAT3 Phosphorylation and Bag-1/S Expression Upon UVB Radiation.

    abstract::Cold-inducible RNA binding protein (CIRP) is a stress-inducible protein, which could be activated by various cellular stresses, such as hypothermia, hypoxia and UV irradiation. Our previous study indicated that UVB radiation (3 mJ cm-2 ) induces CIRP expression, which promotes keratinocytes growth, survival and eventu...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/php.12981

    authors: Sun W,Liao Y,Yi Q,Wu S,Tang L,Tong L

    更新日期:2018-11-01 00:00:00

  • Facile Fabrication of Porous ZnS and ZnO Films by Coaxial Electrospinning for Highly Efficient Photodegradation of Organic Dyes.

    abstract::Porous ZnS and ZnO nano-crystal films were fabricated via a three-step procedure. First, Zn(CH3 COO)2 /Silk Fibroin nanofiber mats were prepared by coaxial electrospinning. Second, Zn(CH3 COO)2 /Silk Fibroin mats were immersed in NaS solution to react with S2- to obtain ZnS/Silk Fibroin nanofiber mats. Finally, ZnO po...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/php.12836

    authors: Wang H,Liang L,Cheng X,Luo Y,Sun S

    更新日期:2018-01-01 00:00:00

  • Antimicrobial photodynamic therapy and photodynamic inactivation, or killing bugs with dyes and light--a symposium-in-print.

    abstract::In antimicrobial photodynamic therapy, the photosensitizer (PS) in its ground singlet state absorbs light to give the excited singlet state that can transition to the long-lived triplet state. This PS triplet may undergo energy transfer (Type 2) or electron transfer (Type 1) to oxygen to form reactive oxygen species (...

    journal_title:Photochemistry and photobiology

    pub_type: 社论

    doi:10.1111/j.1751-1097.2012.01139.x

    authors: Hamblin MR

    更新日期:2012-05-01 00:00:00

  • Chlorophyll fluorescence imaging for the noninvasive assessment of anthocyanins in whole grape (Vitis vinifera L.) bunches.

    abstract::The distribution of anthocyanins in grape (Vitis vinifera L.) bunches from the Sangiovese cultivar was measured nondestructively by chlorophyll fluorescence imaging using two excitation light bands at 550 and 650 nm in sequence. The pixel intensity in the derived logarithm of the fluorescence excitation ratio image wa...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/j.1751-1097.2008.00424.x

    authors: Agati G,Traversi ML,Cerovic ZG

    更新日期:2008-11-01 00:00:00

  • Targeting of phototoxic drugs to antigen-specific T lymphocytes in vitro using antigen-presenting cell membranes.

    abstract::We have used the complex of antigen with class II major histocompatibility proteins (Ia) in membrane-bound form to target a phototoxic compound to antigen-specific T cell hybridomas in vitro. The iodoacetamidyl ester of phototoxic pyrene was bound covalently to antigen-presenting cells (APC), and protein antigens were...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/j.1751-1097.1995.tb02352.x

    authors: Chang NH,Rayner DC,Boggs JM

    更新日期:1995-05-01 00:00:00

  • Attitudes, Beliefs, and Measures Taken by Parents to Protect Their Children from the Sun in Guangzhou City, China.

    abstract::Excessive sun exposure can cause sunburn, suntan, skin photoaging, and even skin cancer. Skin photoaging conflicts with the human pursuit of a young and beautiful appearance. Some research data indicate that the incidence of skin cancer in the Chinese has been increasing, although it remains lower than in whites. To e...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/php.12623

    authors: Wan M,Hu R,Li Y,Wang Y,Xie X,Yue P,Guan L,Lai W

    更新日期:2016-09-01 00:00:00

  • FTIR spectroscopic and theoretical study of the photochemistry of matrix-isolated coumarin.

    abstract::The infrared spectrum of monomeric unsubstituted coumarin (C9H6O2; 2H-1-benzopyran-2-one), isolated in solid argon at 10 K is presented and assigned. The UV-induced (lambda>200 nm) unimolecular photochemistry of the matrix-isolated compound was studied experimentally. Three main photoreactions were observed: (a) decar...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/j.1751-1097.2007.00152.x

    authors: Kuş N,Breda S,Reva I,Tasal E,Ogretir C,Fausto R

    更新日期:2007-09-01 00:00:00

  • Alkali-labile photolesions mapping to purine sites in ultraviolet-irradiated DNA.

    abstract::Gel sequencing experiments with the 5'- and 3'-end-labeled oligonucleotides d(A3GA4GA5GA6GA3G) and d(AT)10 have demonstrated that dimeric adenine photoproducts and thymine-adenine photoadducts constitute alkali-labile lesions in UV-irradiated DNA. On treatment with hot piperidine, DNA strand breakage occurs predominan...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/j.1751-1097.1994.tb05022.x

    authors: Hejmadi V,Stevenson C,Kumar S,Davies RJ

    更新日期:1994-02-01 00:00:00

  • Asiatic Acid Glucosamine Salt Alleviates Ultraviolet B-induced Photoaging of Human Dermal Fibroblasts and Nude Mouse Skin.

    abstract::Herbal extracts including asiatic acid (AA) have become popular candidates of anti-photoaging agents due to their anti-inflammatory and antioxidant properties and minimal side effect. Nevertheless, low bioavailability due to poor solubility limits their practical application. In this study, a highly bioavailable form ...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/php.13160

    authors: Huang J,Tu T,Wang W,Zhou G,Zhang W,Wu X,Liu W

    更新日期:2020-01-01 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

  • Biologically effective doses of sunlight for immune suppression at various latitudes and their relationship to changes in stratospheric ozone.

    abstract::Using information on solar irradiance at different latitudes derived from a radiative transfer model and a detailed in vivo action spectrum for immune suppression in a murine system, we report here calculations of the "biologically effective" irradiance of sunlight for immune suppression. From 40 degrees N to 40 degre...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/j.1751-1097.1990.tb08686.x

    authors: De Fabo EC,Noonan FP,Frederick JE

    更新日期:1990-10-01 00:00:00

  • Cytotoxicity and mutagenicity of ophthalmic solution preservatives and UVA radiation in L5178Y cells.

    abstract::Four chemical preservatives commonly used in ophthalmic solutions were tested for their toxic and mutagenic potential in mouse lymphoma cells with and without exposure of the cells to ultraviolet A (UVA) radiation. The preservatives tested were benzalkonium chloride (BAK), chlorhexidine, thimerosal and ethylenediamine...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/j.1751-1097.1989.tb04174.x

    authors: Withrow TJ,Brown NT,Hitchins VM,Strickland AG

    更新日期:1989-09-01 00:00:00

  • Multispectral imaging autofluorescence microscopy for the analysis of lymph-node tissues.

    abstract::Although histochemical and immunohistochemical methods are the standard procedures in diagnosis of lymphoproliferative disorders, useful improvements in evidencing histopathologic manifestations can be obtained with the introduction of tissue autofluorescence analyses. We used microspectrofluorometry and a Multispectr...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1562/0031-8655(2000)071<0737:miamft>2.0.co;2

    authors: Rigacci L,Alterini R,Bernabei PA,Ferrini PR,Agati G,Fusi F,Monici M

    更新日期:2000-06-01 00:00:00

  • Protonation-state-Coupled Conformational Dynamics in Reaction Mechanisms of Channel and Pump Rhodopsins.

    abstract::Channel and pump rhodopsins use energy from light absorbed by a covalently bound retinal chromophore to transport ions across membranes of microbial cells. Ion transfer steps, including proton transfer, can couple to changes in protein conformational dynamics and water positions. Although general principles of how mic...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章,评审

    doi:10.1111/php.12790

    authors: Bondar AN,Smith JC

    更新日期:2017-11-01 00:00:00

  • Carotenohematoporphyrins as tumor-imaging dyes. Synthesis and in vitro photophysical characterization.

    abstract::Multichromophoric dyes for use in tumor imaging have been synthesized and photophysically characterized. Structurally, these dyes are dyads and triads that consist of one or two carotenoid polyenes covalently attached to hematoporphyrin (HP) or hematoporphyrin dimethyl ester (HPDME) moieties via ester linkages. The gr...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:

    authors: Tatman D,Liddell PA,Moore TA,Gust D,Moore AL

    更新日期:1998-10-01 00:00:00

  • Suberythemal Sun Exposures at Swedish Schools Depend on Sky Views of the Outdoor Environments - Possible Implications for Pupils' Health.

    abstract::More scheduled outdoor stay is increasingly advocated for school children. This study measured 2(nd) , 5(th) and 8(th) graders' erythemal UV-exposure in September, March and May at four Swedish schools. We related those exposures, as fractions of total available ambient radiation, to the schools outdoor environments d...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/php.12540

    authors: Pagels P,Wester U,Söderström M,Lindelöf B,Boldemann C

    更新日期:2016-01-01 00:00:00

  • On spectral relaxation in proteins.

    abstract::During the past several years there has been debate about the origins of nonexponential intensity decays of intrinsic tryptophan (trp) fluorescence of proteins, especially for single tryptophan proteins (STP). In this review we summarize the data from diverse sources suggesting that time-dependent spectral relaxation ...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章,评审

    doi:10.1562/0031-8655(2000)072<0421:OSRIP>2.0.CO;2

    authors: Lakowicz JR

    更新日期:2000-10-01 00:00:00