Abstract
Emissive features of flavins (Riboflavin/RF, Flavin MonoNucleotide/FMN and Flavin Adenine Dinucleotide/FAD) labeled native Deoxyribonucleic Acid (DNA) on Polyvinylpyrrolidone (PVP)-coated silver nanoparticles (SNPs), have been studied. The dual emission of flavins in DNA−PVP-coated SNPs systems is strongly influenced by the reaction time and temperature. Changes in the RF emissive features occur as a side effect when DNA is covalently linked hence, the RF destruction depends on DNA damage. Even if in an oxidation process, the FAD-DNA – PVP-coated SNPs system acts as a weak scavenger of reactive oxygen species, its antioxidant activity is approx. five times higher than that of RF-DNA−PVP-coated SNPs system. Destruction of RF by a riboflavin-mediated DNA photo-oxidation process that occurs on PVP-coated SNPs is suggested. Results have relevance in the redox process of riboflavin and provide valuable information for the further development of novel flavin-based SNPs systems as fluorescent antioxidant markers to solve several biological barriers in humans, such as protein-DNA interaction, cell binding.
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References
Bensasson RV, Land EJ, Truscott TG (1983) Flash photolysis and pulse radiolysis in biology and medicine. Pergamon Press, Oxford
Mc Cormick DB, Innis WSA, Merrill AH, Bowers-Komro DM, Oka M, Chastain JL (1988) An update on flavin metabolism in rats and humans. In: Edmondson DE, Mc Cormick DB (eds) Flavin and flavoproteins. Walter de Gruyter, New York
Ashoori M, Saedisomeolia A (2014) Riboflavin (vitamin B2) and oxidative stress: a review. Br J Nutr 111:1985–1991 (and refs herein)
Darguzyte M, Holm R, Baier J, Drude N, Schultze J, Koynov K, Schwiertz D, Dadfar SM, Lammers T, Barz M, Kiessling F (2020) Influence of Riboflavin Targeting on Tumor Accumulation and internalization of Peptostar Based Drug Delivery systems. Bioconjug Chem 31:2691–2696
Diaz M, Becker MI, De Ioannes AE, Silva E (1996) Development of monoclonal antibodies against a Riboflavin-Tryptophan Photoinduced Adduct: reactivity to Eye Lens Proteins, Photochem. Photobiol 63:762–767
Ito K, Inoue S, Yamamoto K, Kawanishi S (1993) S.8-Hydroxydeoxyguanosine formation at the 5′ site of 5′‐GG‐3′ sequences in double‐stranded DNA by UV radiation with riboflavin. J Biol Chem 268:13221–13227
Wu X, Guo LZ, Liu YH, Liu YC, Yang PL, Leung YS, Tai HC, Wang TD, LinjLai JCWCL, Chuang YH, Lin CH, Chou PT, Lai IR, Liu TM (2023) Plasma riboflavin fluorescence as a diagnostic marker of mesenteric ischemia-reperfusion injury in rats. Thromb Res 223:146–154
Wainwright M, Giddens RM (2003) Phenothiazinium photosensitizers: choices in synthesis and application. Dyes Pigm 57:245–257
Moreira LM, Lyon JP, Romani AP, Severino D, Rodrigues MR, de Oliveira HP(2012) Phenotiazinium Dyes as Photosensitizers (PS) in Photodynamic Therapy (PDT): Spectroscopic Properties and Photochemical Mechanisms, Chap. 14, Advanced Aspects of Spectroscopy. https://doi.org/10.5772/48087. and refs. herein
Mohr H, Knuver-Hopf J, Gravemann U, Redecker-Klein A, Muller TH (2004) West Nile virus in plasma is highly sensitive to methylene blue–light treatment. Transfusion 44:886–890
Tachibana K, Feril LB, Ikeda-Dantsuji Y (2008) Sonodynamic Therapy Ultrasonics 48:253–259
Moan J, Berg K (1991) The photodegradation of porphyrins in cells can be used to estimate the lifetime of singlet oxygen. Photochem Photobiol 53:549–553
Boye E, Moan J (1980) The photodynamic effect of hematoporphyrin on DNA. Photochem Photobiol 31:223–228
Watson JD, Crick FHC (1953) Molecular structure of nucleic acids: a structure for deoxyribose nucleic acid. Nature 171:737–738
Anderson RF, Amarsinghe C, Fisher LJ, Mak WB, Parker JE (2000) Reduction in free-radical-induced DNA strand breaks and base damage through fast chemical repair by flavonoids. Free Radical Res 33:91
Sengupta B, Pahari B, Blackmon L, Sengupta PK (2013) Prospect of Bioflavonoid Fisetin as a quadruplex DNA ligand: a Biophysical Approach. PLoSONE 8(6). https://doi.org/10.1371/journal.pone.0065383
Bhattacharjee S, Sengupta PK, Bhowmik S (2017) Exploring the preferential interaction of quercetin with VEGF promoter G-quadruplex DNA and construction of a pH-dependent DNA-based logic gate. RSC Adv 7:37230–37240
Bhattacharjee S, Chakraborty S, Chorell E, Sengupta PK, Bhowmik S(2018) Part A 629–639
Cao Y, He XW, Gao Z (1993) Fluorescence energy transfer between acridine orange and safranine T and its application in the determination of DNA. Talanta 49:377–383
Zhang GM, Pang YH, Shuang SM, Dong C, Choi MMF, Liu DS (2005) Spectroscopic studies on the interaction of safranine T with DNA in β-cyclodextrin and carboxymethyl-β-cyclodextrin. J Photochem Photobiol A 169:153–158
Bi S, Qiao C, Song D, Tian Y, Gao D, Sun Y, Zhang H (2006) Studies of interactions of flavonoids with DNA using acridine orange as a fluorescence probe, Sens. Actuators B Chem 119:199–208
Fisher AMR, Murphree AL, Gomer CJ (1995) Clinical and preclinical photodynamic therapy. Laser Surg Med 17:2–31 (and refs. herein)
A.Murza S, Sanchez-Cortes JV, Garcia-Ramos JM, Guisan C, Alfonso G, Rivas (2000) Interaction of the antitumor drug 9-aminoacridine with guanidinobenzoatase studied by spectroscopic methods: a possible Tumor marker probe based on the fluorescence exciplex emission. Biochemistry 39:10557–10565
Usacheva MN, Teichert MC, Biel MA (2003) The role of the methylene blue and toluidine blue monomers and dimers in the photoinactivation of bacteria. J Photochem Photobiol B 71:87–98
Wang Z, Li J, wang J, Zou M, Wang S, Li Y, Kong Y, Xia L (2012) Spectrometry researches on interaction and sonodynamic damage of riboflavin (RF) to bovine serum albumin (BSA). Spectrochim Acta A 87:1–10
Syafiuddin A, Salmiati MR, Salim ABH, Kueh T, Hadibarata H, Nur (2017) A review of silver nanoparticles: Research trends, global consumption, synthesis, properties, and future challenges. J Chin Chem Soc 64, 732–756. and references herein
Muhammad Z, Raza A, Ghafoor S, Naeem A, Naz SS, Riaz S, Ahmed W, Rana NF (2016) PEG capped methotrexate silver nanoparticles for efficient anticancer activity and biocompatibility. Eur J Pharm Sci 91:251–255
Panzarini E, Mariano S, Vergallo C, Carata E, Fimia GM, Mura F, Rossi M, Vergaro V, Ciccarella G, Corazzari M, Dini L (2017) Glucose capped silver nanoparticles induce cell cycle arrest in hela cells. Toxicol in Vitro 41:64–74
He H, Tao G, Wang Y, Cai R, Guo P, Chen L, Zuo H, Zhao P, Xia Q (2017) In situ green synthesis and characterization of sericin-silver nanoparticle composite with effective antibacterial activity and good biocompatibility. Mater Sci Eng C 80:509–516
Akter M, Sikder MT, Rahman MM, Ullah AKMA, Hossain KFB, Banik S, Hosokawa T, Saito T, Kurasaki M (2018) A systematic review on silver nanoparticles-induced cytotoxicity: physicochemical properties and perspectives. J Adv Res 9:1–16
Zheng K, Setyawati MI, Leong DT, Xie J (2018) Antimicrobial silver nanomaterials. Coord Chem Rev 357:1–17
Durán N, Durán M, de Jesus MB, Seabra AB, Fávaro WJ, Nakazato G (2016) Silver nanoparticles: a new view on mechanistic aspects on antimicrobial activity. Nanomed Nanotechnol Biol Med 12:789–799
Beztsinna N, Sole M, Taib N, Bestel I (2016) Bioengineered riboflavin in nanotechnology. Biomaterials 80:121–133 (and refs. herein)
Voicescu M, Angelescu DG, Ionescu S, Teodorescu VS (2013) Spectroscopic analysis of the riboflavin-serum albumins interaction on silver nanoparticles. J Nanopart Res 15:1–10
Voicescu M, Ionescu S, Calderon-Moreno JM, Teodorescu VS, Anastasescu M, Culita DC (2019) Tryptophan/Dextran70 based-fluorescent silver nanoparticles: synthesis and Physicochemical Properties. J Fluoresc 29:981–992
Voicescu M, Ionescu S, Manoiu VS, Anastasescu M, Craciunescu O, Moldovan L (2019) Syntehsis and biophysical characteristics of roboflavin/HSA protein system on silver nanoparticles. Mat Sci Eng C 96:30–40
Voicescu M, Craciunescu O, Calderon-Moreno JM, Anastasescu M, Manoiu VS, Tatia R, Culita DC, Moldovan L (2022) Fluorescent Flavin / PVP-Coated Silver Nanoparticles: Design and Biological Performance. J Fluoresc. https://doi.org/10.1007/s10895-022-02902-2
Voicescu M, Craciunescu O, Angelescu DG, Tatia R, Moldovan L (2021) Spectroscopic, molecular dynamics simulation and biological studies of Flavin MonoNucleotide and Flavin Adenine Dinucleotide in biomimetic systems, Spectrochim. Acta A 246:118997
Voicescu M, Ionita G, Constantinescu T, Vasilescu M (2006) The oxidative activity of Riboflavin studied by luminescence methods: the effect of cysteine, arginine, lysine and histidine amino acids. Rev Roum Chim 51(7–8):683–690
Voicescu M, Ion R, Meghea A (2010) Evaluation of the oxidative activity of some free base porphyrins by a chemiluminescence method. J Serb Chem Soc 75(3):333–341
Voicescu M, Nistor CL, Meghea A (2015) Insights into the antioxidant activity of some flavones on Silver nanoparticles using a chemiluminescence method. J Lumin 157:243–248
Gwinn E, Schultz D, Copp S, Swasey S (2015) DNA-protected silver clusters for nanophotonics. Nanomaterials 5:180–207
Speck WT, Rosenkranz S, Rosenkranz HS (1976) Further observations on the photo-oxidation of DNA in the presence of Riboflavin. Biochim Biophys Acta 435:79–44
Hirayama O, Takagi M, Hukumoto K, Katoh S (1997) Evaluation of antioxidant activity by chemiluminescence. Anal Biochem 247:237–241
Parejo I, Codina C, Petrakis C, Kefalas P (2000) Evaluation of scavenging activity assessed by Co(II)/EDTA-induced luminol chemiluminescnce and DPPH (2,2-diphenyl-1-picrylhydrazyl) free radical assay. J Pharmacol Toxicol Meth 44:507–512
Steenken S, Jovanovic SV (1997) How easily oxidizable is DNA? One-electron reduction potentials of adenosine and guanosine radicals in aqueous solution. J Am Chem Soc 119:617–618
Acknowledgements
This study was carried out within the research direction “Flavins – based BioNanoSystems Probed by Luminescence Methods” in the frame of the “Ilie Murgulescu” Institute of Physical Chemistry of the Romanian Academy.
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Voicescu, M. Preliminary Insights into the Fluorescence and Oxidative Characteristics of Flavin - DNA Systems on PVP - Coated Silver Nanoparticles. J Fluoresc (2024). https://doi.org/10.1007/s10895-023-03549-w
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DOI: https://doi.org/10.1007/s10895-023-03549-w