6-Nitro-Quinazolin-4(3H)-one Exhibits Photodynamic Effects and Photodegrades Human Melanoma Cell Lines. A Study on the Photoreactivity of Simple Quinazolin-4(3H)-ones.

Abstract:

:Photochemo and photodynamic therapies are minimally invasive approaches for the treatment of cancers and powerful weapons for competing bacterial resistance to antibiotics. Synthetic and naturally occurring quinazolinones are considered privileged anticancer and antibacterial agents, with several of them to have emerged as commercially available drugs. In the present study, applying a single-step green microwave irradiation mediated protocol we have synthesized eleven quinazolinon-4(3H)-ones, from cheap readily available anthranilic acids, in very good yields and purity. These products were irradiated in the presence of pBR322 plasmid DNA under UVB, UVA and visible light. Four of the compounds proved to be very effective DNA photocleavers, at low concentrations, being time and concentration dependent as well as pH independent. Participation of reactive oxygen species was related to the substitution of quinazolinone derivatives. 6-Nitro-quinazolinone in combination with UVA irradiation was found to be in vitro photodestructive for three cell lines; glioblastoma (U87MG and T98G) and mainly melanoma (A-375). Thus, certain appropriately substituted quinazolinones may serve as new lead photosensitizers for the development of promising biotechnological applications and as novel photochemo and photodynamic therapeutics.

journal_name

Photochem Photobiol

authors

Panagopoulos A,Balalas T,Mitrakas A,Vrazas V,Katsani KR,Koumbis AE,Koukourakis MI,Litinas KE,Fylaktakidou KC

doi

10.1111/php.13376

subject

Has Abstract

pub_date

2021-01-01 00:00:00

eissn

0031-8655

issn

1751-1097

pub_type

杂志文章
  • Synthesis, spectra and photophysics of some free base tetrafluoroalkyl and tetrafluoroaryl porphyrins with potential applications in imaging.

    abstract::The synthesis, characterization and photophysical properties of two perfluoroalkyl (5,10,15,20-tetrakis-[trifluoromethyl]- and [heptafluoropropyl]-porphyrin) and two perfluoroaryl (5,10,15,20-tetrakis-[2,6-difluorophenyl]- and [pentafluorophenyl]-porphyrin) are described, with reference to their potential in both phot...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1562/0031-8655(2002)075<0249:ssapos>2.0.co;2

    authors: Grancho JC,Pereira MM,Miguel Mda G,Rocha GA,Burrows HD

    更新日期:2002-03-01 00:00:00

  • Larval and adult emission spectra of bioluminescence in three European firefly species.

    abstract::We studied the spectral characteristics of the larvae of three sympatric Belgian species of fireflies, Lampyris noctiluca, Phosphaenus hemipterus and Lamprohiza splendidula. An in vivo spectral study was performed to compare bioluminescence spectra. The emission spectrum of a laboratory reared female L. noctiluca was ...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1562/2003-11-11-RA.1

    authors: De Cock R

    更新日期:2004-04-01 00:00:00

  • Ultraviolet B but not A radiation activates suppressor B cells in draining lymph nodes.

    abstract::Immunosuppressive doses of solar-simulated UV radiation activate lymph node B cells that can suppress primary immunity by inhibiting the function of dendritic cells. The aim of this study was to determine the waveband responsible for activation of these suppressor B cells. We exposed C57BL/6 mice to various doses of e...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1562/2005-04-20-RA-495

    authors: Byrne SN,Ahmed J,Halliday GM

    更新日期:2005-11-01 00:00:00

  • Slow solvent relaxation dynamics of nanometer sized reverse micellar systems through tryptophan metabolite, kynurenine.

    abstract::Exploration of environmental dynamics using intrinsic biological probe tryptophan is very important; however, it suffers from various difficulties. An alternative probe, kynurenine (KN), has been found to be an efficient probe for the ultrafast dynamics in the biological environment (Goswami et al., [2010] J. Phys. Ch...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/j.1751-1097.2011.01007.x

    authors: Rakshit S,Goswami N,Pal SK

    更新日期:2012-01-01 00:00:00

  • How do UV photomorphogenic responses confer water stress tolerance?

    abstract::Although ultraviolet-B (UV-B) radiation is potentially harmful, it is an important component of terrestrial radiation to which plants have been exposed since invading land. Since then, plants have evolved mechanisms to avoid and repair UV radiation damage; therefore, it is not surprising that photomorphogenic response...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章,评审

    doi:10.1562/0031-8655(2003)078<0529:hduprc>2.0.co;2

    authors: Gitz DC,Liu-Gitz L

    更新日期:2003-12-01 00:00:00

  • Cloning and Characterization of Luciferase from the Chinese Firefly Lamprigera yunnana.

    abstract::Lamprigera (Lampyridae) is a small genus with only 17 species distributing in Asian countries. Its larviform females and alate males can produce continuously strong yellow-green light at night. However, no luciferase gene was reported for this genus and its subfamily-level phylogenetic position still remains uncertain...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/php.13109

    authors: Liu GC,Zhang R,Hou QB,He JW,Dong ZW,Zhao RP,Wang W,Li XY

    更新日期:2019-09-01 00:00:00

  • Redox proteins as electron acceptors from chlorophyll triplet state in lipid bilayer vesicles: kinetics of reduction of membrane reconstituted cytochrome c oxidase mediated by 2,5-di-t-butyl benzoquinone and cytochrome c.

    abstract::Laser flash photolysis was used to determine the kinetics of electron transfer between membrane-bound triplet chlorophyll (3C), cytochrome c (cyt c) located in the external water phase, and vesicle-reconstituted cytochrome c oxidase (CCO). 2,5-Di-t-butyl benzoquinone (2,5 TBQ) was used as an electron transfer mediator...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/j.1751-1097.1990.tb08697.x

    authors: Chamupathi VG,Moezzi DM,Tollin G

    更新日期:1990-10-01 00:00:00

  • Photoinduced degradation of the herbicide clomazone model reactions for natural and technical systems.

    abstract::The photodegradation of the herbicide clomazone in the presence of S(2)O(8) (2-) or of humic substances of different origin was investigated. A value of (9.4 +/- 0.4) x 10(8) m(-1) s(-1) was measured for the bimolecular rate constant for the reaction of sulfate radicals with clomazone in flash-photolysis experiments. ...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/j.1751-1097.2008.00467.x

    authors: David Gara PM,Bosio GN,Arce VB,Poulsen L,Ogilby PR,Giudici R,Gonzalez MC,Mártire DO

    更新日期:2009-05-01 00:00:00

  • Irradiation-induced enhancement of Pc 4 fluorescence and changes in light scattering are potential dosimeters for Pc 4-PDT.

    abstract::Phthalocyanine 4 (Pc 4) is a promising photosensitizer currently in clinical trials. Photobiological responses to Pc 4 photodynamic therapy (Pc 4-PDT) have been characterized extensively, but relatively little has been done to evaluate dose metrics for this sensitizer. We describe an irradiation-induced increase in fl...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/j.1751-1097.2007.00128.x

    authors: Wang KK,Wilson JD,Kenney ME,Mitra S,Foster TH

    更新日期:2007-09-01 00:00:00

  • Photophysics of melatonin in different environments.

    abstract::Melatonin (N-acetyl-5-methoxytryptamine) is a naturally occurring hormone with a structural resemblance to tryptophan. Its fluorescence is solvent dependent and strongly quenched in the presence of oxygen. Fluorescence quenching in aqueous and organic solutions have been studied in the presence of different quenchers....

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1562/0031-8655(1999)069<0294:pomide>2.3.co;2

    authors: Rath MC,Mahal HS,Mukherjee T

    更新日期:1999-03-01 00:00:00

  • Comparative analysis of GPCR crystal structures.

    abstract::The phototransduction cascade is perhaps the best understood model system for G protein-coupled receptor (GPCR) signaling. Phototransduction links the absorption of a single photon of light to a decrease in cytosolic cGMP. Depletion of the cGMP pool induces closure of cGMP-gated cation channels resulting in the hyperp...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章,评审

    doi:10.1111/j.1751-1097.2008.00516.x

    authors: Lodowski DT,Angel TE,Palczewski K

    更新日期:2009-03-01 00:00:00

  • Effect of UV radiation on the neonatal skin immune system- implications for melanoma.

    abstract::The neonatal immune environment and the events that occur during this time have profound effects for the adult period. While protective immune responses can develop, the neonatal immune system, particularly the skin immune system (SIS), tends to promote tolerance. With this information we undertook a number of studies...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章,评审

    doi:10.1111/j.1751-1097.2007.00246.x

    authors: Muller HK,Malley RC,McGee HM,Scott DK,Wozniak T,Woods GM

    更新日期:2008-01-01 00:00:00

  • Potentiation of oxidative damage to proteins by ultraviolet-A and protection by antioxidants.

    abstract::We have studied the damage of alcohol dehydrogenase (ADH) and glyceraldehyde 3-phosphate dehydrogenase (GAPD) induced by Fe++/EDTA + H2O2 in combination with UV-A (main output at 365 nm). Enzyme inactivation, formation of hydroxyl radicals (measured in the absence of enzymes), increase in protein carbonyls, oxidation ...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/j.1751-1097.1992.tb02171.x

    authors: Hu ML,Tappel AL

    更新日期:1992-09-01 00:00:00

  • Effects of light energy and reducing agents on C60-mediated photosensitizing reactions.

    abstract::Many biomolecules contain photoactive reducing agents, such as reduced nicotinamide adenine dinucleotide (NADH) and 6-thioguanine (6-TG) incorporated into DNA through drug metabolism. These reducing agents may produce reactive oxygen species under UVA irradiation or act as electron donors in various media. The interac...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/php.12206

    authors: Quinones M,Zhang Y,Riascos P,Hwang HM,Aker WG,He X,Gao R

    更新日期:2014-03-01 00:00:00

  • Synchronous fluorescence spectroscopy for the detection and characterization of cervical cancers in vitro.

    abstract::The objective of this study was to assess the diagnostic potential of synchronous fluorescence (SF) spectroscopy (SFS) technique for the detection and characterization of normal and different malignancy stages of moderately differentiated squamous cell carcinoma (MDSCC), poorly differentiated squamous cell carcinoma (...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/j.1751-1097.2009.00628.x

    authors: Ebenezar J,Aruna P,Ganesan S

    更新日期:2010-01-01 00:00:00

  • Damage to UV-sensitive cells by short UV in photographic flashes.

    abstract::Light emitted by electronic photographic flash units is shown to damage bacteria and human skin fibroblasts deficient in repair systems, with survival curves very similar to those produced by 254 nm short UV. The lesions induced by these flashes are as photorepairable by the photolyase enzyme as those induced by 254 n...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/j.1751-1097.1996.tb03103.x

    authors: Menezes S,Monteiro C

    更新日期:1996-09-01 00:00:00

  • The effect of charge on cellular uptake and phototoxicity of polylysine chlorin(e6) conjugates.

    abstract::The effect of charge on the cellular uptake, localization and phototoxicity of conjugates between chlorin(e6) (ce6) and poly-L-lysine was studied in vitro. These conjugates (average MW 35-55 kDa) were synthesized to have polycationic, polyanionic or neutral charges. Two human cell lines (A431 epidermoid carcinoma cell...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/j.1751-1097.1997.tb01916.x

    authors: Soukos NS,Hamblin MR,Hasan T

    更新日期:1997-04-01 00:00:00

  • Wavelength dependence of DNA incision by a human ultraviolet endonuclease.

    abstract::The wavelength dependence of an ultraviolet irradiation of the DNA substrate for a human endonuclease was determined. Sites of DNA incision for all UVB and UVC wavelengths examined were at cytosines which were neither cyclobutane pyrimidine dimers nor 6-4'-(pyrimidin-2-one)pyrimidines. The optimal wavelengths for form...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/j.1751-1097.1989.tb04120.x

    authors: Gallagher PE,Weiss RB,Brent TP,Duker NJ

    更新日期:1989-03-01 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

  • Fluorescence lifetimes of protochlorophyllide in plants with different proportions of short-wavelength and long-wavelength protochlorophyllide spectral forms.

    abstract::Dark-grown leaves of maize (Zea mays), wheat (Triticum aestivum), wild-type pea (Pisum sativum) and its light-independent photomorphogenesis mutant (lip1) have different proportions of protochlorophyllide (Pchlide) forms as revealed by low-temperature fluorescence emission spectra. Four discrete spectral forms of Pchl...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1562/0031-8655(2003)078<0205:flopip>2.0.co;2

    authors: Myśliwa-Kurdziel B,Amirjani MR,Strzałka K,Sundqvist C

    更新日期:2003-08-01 00:00:00

  • Chelation with metal is not essential for antitumor photodynamic activity of sulfonated phthalocyanines.

    abstract::It is generally assumed that a central metal is essential for the efficiency of phthalocyanines in photodynamic therapy (PDT) of cancer. Contrary to the set opinion, the results of the present study indicate that the metal-free sulfonated phthalocyanines (H2PcSn, where n is the number of sulfonate groups per molecule)...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1562/0031-8655(2002)075<0527:cwmine>2.0.co;2

    authors: Feofanov A,Grichine A,Karmakova T,Kazachkina N,Pecherskih E,Yakubovskaya R,Luk'yanets E,Derkacheva V,Egret-Charlier M,Vigny P

    更新日期:2002-05-01 00:00:00

  • Solvothermal Synthesis of Cs0.33 WO3 /LDHs Composite as a Novel Visible-Light-Driven Photocatalyst.

    abstract::A novel Cs0.33 WO3 /LDHs (CWLDH) composite was synthesized by simple two steps solvothermal method and first investigated as the photocatalyst for tetracycline (TC) and Congo red (CR) degradation under visible light irradiation. The CWLDH heterostructures catalysts were characterized by XRD, UV-Vis, SEM, XPS and BET. ...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/php.12838

    authors: Zhang D,Ji T,Yu J,Jiang X,Jiao F

    更新日期:2018-03-01 00:00:00

  • Photochemical inactivation of Pseudomonas aeruginosa.

    abstract::Adaptability to a broad range of environments together with relatively high resistance to antibiotics and to disinfectants makes Pseudomonas aeruginosa a concern in hospitals and in public health. We investigated whether UVA-mediated photochemical inactivation of P. aeruginosa could be accomplished with high efficienc...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/j.1751-1097.2011.01029.x

    authors: Sagripanti JL,Grote G,Niederwöhrmeier B,Hülseweh B,Marschall HJ

    更新日期:2012-01-01 00:00:00

  • Phototoxicity of some bromine-substituted rhodamine dyes: synthesis, photophysical properties and application as photosensitizers.

    abstract::The synthesis of some bromine-substituted rhodamine derivatives viz., 4,5-dibromorhodamine methyl ester (dye 2) and 4,5-dibromorhodamine n-butyl ester (dye 3) are reported. These dyes were synthesized to promote a more efficient cancer cell photosensitizer for potential use in in vitro bone marrow purging in preparati...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/j.1751-1097.1996.tb03008.x

    authors: Pal P,Zeng H,Durocher G,Girard D,Li T,Gupta AK,Giasson R,Blanchard L,Gaboury L,Balassy A,Turmel C,Laperrière A,Villeneuve L

    更新日期:1996-02-01 00:00:00

  • Fluorescence polarization studies of B-phycoerythrin oriented in polymer film.

    abstract::Polarized steady-state fluorescence and fluorescence excitation spectra as well as time-resolved fluorescence for B-phycoerythrin (B-PE) from red algae, Porphyridium cruentum, embedded in polyvinyl stretched films were measured. The lifetimes of polarized fluorescence were analyzed using exponential components and fra...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:

    authors: Frackowiak D,Ptak A,Gryczynski Z,Gryczynski I,Targowski P,Zelent B

    更新日期:2004-01-01 00:00:00

  • Two new sterically hindered phthalocyanines: synthetic and photodynamic aspects.

    abstract::The synthesis and the properties of 1,4-dibutoxy-2,3-dicyanotriptycene, of a metal-free tetradibenzobarrelenooctabutoxyphthalocyanine, and of the corresponding zinc phthalocyanine are described. The two phthalocyanines do not aggregate when dissolved in benzene at concentrations up to 450 microM. For the metal-free an...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/j.1751-1097.1992.tb08510.x

    authors: Rihter BD,Bohorquez MD,Rodgers MA,Kenney ME

    更新日期:1992-05-01 00:00:00

  • Ultraviolet-C irradiation for prevention of central venous catheter-related infections: an in vitro study.

    abstract::Central venous catheters (CVC) are widely used in the United States and are associated with 250,000 to 500,000 CVC-related infections in hospitals annually. We used a catheter made from ultraviolet-C (UVC) transmissive material to test whether delivery of UVC from the lumen would allow inactivation of microorganisms o...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/j.1751-1097.2010.00819.x

    authors: Dai T,Tegos GP,St Denis TG,Anderson D,Sinofsky E,Hamblin MR

    更新日期:2011-01-01 00:00:00

  • The influence of ultraviolet-B radiation on growth, hydroxycinnamic acids and flavonoids of Deschampsia antarctica during Springtime ozone depletion in Antarctica.

    abstract::We examined the influence of solar ultraviolet-B radiation (UV-B; 280-320 nm) on the growth, biomass production and phenylpropanoid concentrations of Deschampsia antarctica during the springtime ozone depletion season at Palmer Station, along the Antarctic Peninsula. Treatments involved placing filters on frames over ...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1562/2004-09-18-RA-321

    authors: Ruhland CT,Xiong FS,Clark WD,Day TA

    更新日期:2005-09-01 00:00:00

  • Paraptosis and Photodynamic Therapy: A Progress Report.

    abstract::Photodamage to the endoplasmic reticulum (ER) can initiate a death pathway termed paraptosis. The "canonical" model of paraptosis, initiated by certain drugs and other stimuli, requires a brief interval of protein synthesis, involves the action of MAP kinases and can be followed by biochemical markers. The latter incl...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1111/php.13242

    authors: Kessel D

    更新日期:2020-09-01 00:00:00

  • Somatic-cell mutation induced by UVA and monochromatic UV radiation in repair-proficient and -deficient Drosophila melanogaster.

    abstract::Near-ultraviolet light (UVA: 320-400 nm) constitutes a major part of sunlight UV. It is important to know the effect of UVA on the biological activities of organisms on the earth. We have previously reported that black light induces somatic-cell mutation in Drosophila larvae. To investigate which wavelength of the UVA...

    journal_title:Photochemistry and photobiology

    pub_type: 杂志文章

    doi:10.1562/0031-8655(2001)073<0493:SCMIBU>2.0.CO;2

    authors: Negishi T,Nagaoka C,Hayatsu H,Suzuki K,Hara T,Kubota M,Watanabe M,Hieda K

    更新日期:2001-05-01 00:00:00