Cytotoxic and mutagenic potential of juglone: a comparison of free and nano-encapsulated form

1Aithal BK, Kumar MR, Rao BN, Udupa N, Rao BS. Juglone, a naphthoquinone from walnut, exerts cytotoxic and genotoxic effects against cultured melanoma tumor cells. Cell Biol Int 2009;33:1039–49. doi: 10.1016/j. cellbi.2009.06.018 Aithal BK Kumar MR Rao BN Udupa N Rao BS Juglone, a naphthoquinone from walnut, exerts cytotoxic and genotoxic effects against cultured melanoma tumor cells Cell Biol Int 2009331039 49 10.1016/j.cellbi.2009.06.018Open DOISearch in Google Scholar

2Coder KD. Black Walnut Allelopathy: Tree Chemical Warfare. Allelopathy Series. 2011;WSFNR11–10:1–13. Coder KD Black Walnut Allelopathy: Tree Chemical Warfare Allelopathy Series 2011WSFNR11–101 13Search in Google Scholar

3Lee K-C. Nature and occurrence of juglone in Juglans nigra L [master of science]. Manhattan, Kansas: Kansas State University, Department of Horticulture; 1967. Lee K-C Nature and occurrence of juglone in Juglans nigra L [master of science] Manhattan, Kansas Kansas State University, Department of Horticulture 1967Search in Google Scholar

4Kocacaliskan I, Terzi I. Allelopathic effects of walnut leaf extracts and juglone on seed germination and seedling growth. J Hortic Sci Biotechnol 2001;76:436–40. doi: 10.1080/14620316.2001.11511390 Kocacaliskan I Terzi I Allelopathic effects of walnut leaf extracts and juglone on seed germination and seedling growth J Hortic Sci Biotechnol 200176436 40 10.1080/14620316.2001.11511390Open DOISearch in Google Scholar

5Paulsen MT, Ljungman M. The natural toxin juglone causes degradation of p53 and induces rapid H2AX phosphorylation and cell death in human fibroblasts. Toxicol Appl Pharmacol 2005;209:1–9. doi: 10.1016/j.taap.2005.03.005 Paulsen MT Ljungman M The natural toxin juglone causes degradation of p53 and induces rapid H2AX phosphorylation and cell death in human fibroblasts Toxicol Appl Pharmacol 20052091 9 10.1016/j.taap.2005.03.005Open DOISearch in Google Scholar

6Hejl AM, Koster KL. Juglone disrupts root plasma membrane H⁺-ATPase activity and impairs water uptake, root respiration, and growth in soybean Glycine max and corn Zea mays J C he m Eco l 2 0 0 4 ; 3 0 : 4 5 3 – 7 1 . do i : 10.1023/b:joec.0000017988.20530.d5 Hejl AM Koster KL Juglone disrupts root plasma membrane H⁺-ATPase activity and impairs water uptake, root respiration, and growth in soybean Glycine max and corn Zea mays J C he m Eco l 2 0 0 4 ; 3 0 : 4 5 3 – 7 1 10.1023/b:joec.0000017988.20530.d5Open DOISearch in Google Scholar

7Inbaraj JJ, Chignell CF. Cytotoxic action of juglone and plumbagin: a mechanistic study using HaCaT keratinocytes. Chem Res Toxicol 2004;17:55–62. doi: 10.1021/tx034132s Inbaraj JJ Chignell CF Cytotoxic action of juglone and plumbagin: a mechanistic study using HaCaT keratinocytes Chem Res Toxicol 20041755 62 10.1021/tx034132sOpen DOISearch in Google Scholar

8Esterbauer H, Cheeseman KH. Determination of aldehydic lipid peroxidation products: Malonaldehyde and 4-hydroxynonenal. Methods Enzymol 1990;186:407–21. doi: 10.1016/0076-6879(90)86134-h Esterbauer H Cheeseman KH Determination of aldehydic lipid peroxidation products: Malonaldehyde and 4-hydroxynonenal Methods Enzymol 1990186407 21 10.1016/0076-6879(90)86134-hOpen DOISearch in Google Scholar

9Dama L, Poul B, Jadhav B. Antimicrobial activity of naphthoquinonic compounds. J Ecotoxicol Environ Monit 1998;8:213–5. Dama L Poul B Jadhav B Antimicrobial activity of naphthoquinonic compounds J Ecotoxicol Environ Monit 19988213 5Search in Google Scholar

10Arasoğlu T, Derman S, Mansuroğlu B, Uzunoğlu D, Koçyiğit BS, Gümüş B, Acar T, Tuncer B. Preparation, characterization, and enhanced antimicrobial activity: quercetin-loaded PLGA nanoparticles against foodborne pathogens. Turk J Biol 2017;41:127–40. doi: 10.3906/biy-1604-80 Arasoğlu T Derman S Mansuroğlu B Uzunoğlu D Koçyiğit BS Gümüş B Acar T Tuncer B Preparation, characterization, and enhanced antimicrobial activity: quercetin-loaded PLGA nanoparticles against foodborne pathogens Turk J Biol 201741127 40 10.3906/biy-1604-80Open DOISearch in Google Scholar

11Tan DTC, Osman H, Mohamad S, Kamaruddin AH. Synthesis and antibacterial activity of juglone derivatives. J Chem Chem Engin 2012;6:84–9. Tan DTC Osman H Mohamad S Kamaruddin AH Synthesis and antibacterial activity of juglone derivatives J Chem Chem Engin 2012684 9Search in Google Scholar

12Xu H, Yu X, Qu S, Sui D. Juglone, isolated from Juglans mandshurica Maxim induces apoptosis via down-regulation of AR expression in human prostate cancer LNCaP cells. Bioorg Med Chem Lett 2013;23:3631–4. doi: 10.1016/j. bmcl.2013.04.007 Xu H Yu X Qu S Sui D Juglone, isolated from Juglans mandshurica Maxim induces apoptosis via down-regulation of AR expression in human prostate cancer LNCaP cells Bioorg Med Chem Lett 2013233631 4 10.1016/j.bmcl.2013.04.00723643730Open DOISearch in Google Scholar

13Zakavi F, Golpasand Hagh L, Daraeighadikolaei A, Farajzadeh Sheikh A, Daraeighadikolaei A, Leilavi Shooshtari Z. Antibacterial effect of Juglans regia bark against oral pathologic bacteria. Int J Dent 2013;2013:854765. doi: 10.1155/2013/854765 Zakavi F Golpasand Hagh L Daraeighadikolaei A Farajzadeh Sheikh A Daraeighadikolaei A Leilavi Shooshtari Z Antibacterial effect of Juglans regia bark against oral pathologic bacteria Int J Dent 20132013854765 10.1155/2013/854765370844723878540Open DOISearch in Google Scholar

14Montenegro RC, Araújo AJ, Molina MT, Marinho Filho JDB, Rocha DD, Lopéz-Montero E, Goulart MO, Bento E, Alves APNN, Pessoa C, de Moraes MO, Costa-Lotufo LV. Cytotoxic activity of naphthoquinones with special emphasis on juglone and its 5-O-methyl derivative. Chem Biol Interact 2010;184:439–48. doi: 10.1016/j.cbi.2010.01.041 Montenegro RC Araújo AJ Molina MT Marinho Filho JDB Rocha DD Lopéz-Montero E Goulart MO Bento E Alves APNN Pessoa C de Moraes MO Costa-Lotufo LV Cytotoxic activity of naphthoquinones with special emphasis on juglone and its 5-O-methyl derivative Chem Biol Interact 2010184439 48 10.1016/j.cbi.2010.01.04120138029Open DOISearch in Google Scholar

15Shahidi Bonjar G, Aghighi S, Karimi Nik A. Antibacterial and antifungal survey in plants used in indigenous herbal-medicine of south east regions of Iran. J Biol Sci 2004;4:405–12. doi: 10.3923/jbs.2004.405.412 Shahidi Bonjar G Aghighi S Karimi Nik A Antibacterial and antifungal survey in plants used in indigenous herbal-medicine of south east regions of Iran J Biol Sci 20044405 12 10.3923/jbs.2004.405.412Open DOISearch in Google Scholar

16Arasoglu T, Mansuroglu B, Derman S, Gumus B, Kocyigit B, Acar T, Kocacaliskan I. Enhancement of antifungal activity of juglone (5-Hydroxy-1,4-naphthoquinone) using a Poly(D,L-lactic-co-glycolic acid) (PLGA) nanoparticle system. J Agric Food Chem 2016;64:7087–94. doi: 10.1021/acs.jafc.6b03309 Arasoglu T Mansuroglu B Derman S Gumus B Kocyigit B Acar T Kocacaliskan I Enhancement of antifungal activity of juglone (5-Hydroxy-1,4-naphthoquinone) using a Poly(D,L-lactic-co-glycolic acid) (PLGA) nanoparticle system J Agric Food Chem 2016647087 94 10.1021/acs.jafc.6b0330927600097Open DOISearch in Google Scholar

17Saling SC, Comar JF, Mito MS, Peralta RM, Bracht A. Actions of juglone on energy metabolism in the rat liver. Toxicol Appl Pharmacol 2011;257:319–27. doi: 10.1016/j. taap.2011.09.004 Saling SC Comar JF Mito MS Peralta RM Bracht A Actions of juglone on energy metabolism in the rat liver Toxicol Appl Pharmacol 2011257319 27 10.1016/j.taap.2011.09.00421945490Open DOISearch in Google Scholar

18Aithal KB, Kumar SM, Rao NB, Udupa N, Rao SB. Juglone, a naphthoquinone from walnut, exerts cytotoxic and genotoxic effects against cultured melanoma tumor cells. Cell Biol Int 2009;33:1039–49. doi: 10.1016/j. cellbi.2009.06.018 Aithal KB Kumar SM Rao NB Udupa N Rao SB Juglone, a naphthoquinone from walnut, exerts cytotoxic and genotoxic effects against cultured melanoma tumor cells Cell Biol Int 2009331039 49 10.1016/j.cellbi.2009.06.01819555768Open DOISearch in Google Scholar

19Strugstad M, Despotovski S. A summary of extraction, synthesis, properties, and potential uses of juglone: A literature review. J Ecosyst Management 2013;13(3):1–16. Strugstad M Despotovski S A summary of extraction, synthesis, properties, and potential uses of juglone: A literature review J Ecosyst Management 20131331 16Search in Google Scholar

20Aithal KB, Kumar S, Rao BN, Udupa N, Rao SBS. Tumor growth inhibitory effect of juglone and its radiation sensitizing potential: in vivo and in vitro studies. Integr Cancer Ther 2012;11:68–80. doi: 10.1177/1534735411403477 Aithal KB Kumar S Rao BN Udupa N Rao SBS Tumor growth inhibitory effect of juglone and its radiation sensitizing potential: in vivo and in vitro studies Integr Cancer Ther 20121168 80 10.1177/153473541140347721498474Open DOISearch in Google Scholar

21Abdollahi S, Lotfipour F. PLGA- and PLA-based polymeric nanoparticles for antimicrobial drug delivery. Biomed Int 2012;3:1–11. Abdollahi S Lotfipour F PLGA- and PLA-based polymeric nanoparticles for antimicrobial drug delivery Biomed Int 201231 11Search in Google Scholar

22Dinarvand R, Sepehri N, Manoochehri S, Rouhani H, Atyabi F. Polylactide-co-glycolide nanoparticles for controlled delivery of anticancer agents. Int J Nanomedicine 2011;6:877– 95. doi: 10.2147/IJN.S18905 Dinarvand R Sepehri N Manoochehri S Rouhani H Atyabi F Polylactide-co-glycolide nanoparticles for controlled delivery of anticancer agents Int J Nanomedicine 20116877–95 10.2147/IJN.S18905312439421720501Open DOISearch in Google Scholar

23Esmaeili F, Hosseini-Nasr M, Rad-Malekshahi M, Samadi N, Atyabi F, Dinarvand R. Preparation and antibacterial activity evaluation of rifampicin-loaded poly lactide-coglycolide nanoparticles. Nanomedicine 2007;3:161–7. doi: 10.1016/j.nano.2007.03.003 Esmaeili F Hosseini-Nasr M Rad-Malekshahi M Samadi N Atyabi F Dinarvand R Preparation and antibacterial activity evaluation of rifampicin-loaded poly lactide-coglycolide nanoparticles Nanomedicine 20073161 7 10.1016/j.nano.2007.03.00317468055Open DOISearch in Google Scholar

24Cheow WS, Chang MW, Hadinoto K. Antibacterial efficacy of inhalable levofloxacin-loaded polymeric nanoparticles against E. coli biofilm cells: the effect of antibiotic release profile. Pharmaceut Res 2010;27:1597–609. doi: 10.1007/ s11095-010-0142-6 Cheow WS Chang MW Hadinoto K Antibacterial efficacy of inhalable levofloxacin-loaded polymeric nanoparticles against E coli biofilm cells: the effect of antibiotic release profile. Pharmaceut Res 2010271597 609 10.1007/s11095-010-0142-620407918Open DOISearch in Google Scholar

25Kerimoglu O, Alarcin E. Poly(lactic-co-glycolic acid) based drug delivery devices for tissue engineering and regenerative medicine. ANKEM Derg 2012;26:86–98. doi: 10.5222/ankem.2012.086 Kerimoglu O Alarcin E Poly(lactic-co-glycolic acid) based drug delivery devices for tissue engineering and regenerative medicine ANKEM Derg 20122686 98 10.5222/ankem.2012.086Open DOISearch in Google Scholar

26Arasoglu T, Derman S, Mansuroglu B, Yelkenci G, Kocyigit B, Gumus B, Acar T, Kocacaliskan I. Synthesis, characterization and antibacterial activity of juglone encapsulated PLGA nanoparticles. J Appl Microbiol 2017;123:1407–19. doi: 10.1111/jam.13601 Arasoglu T Derman S Mansuroglu B Yelkenci G Kocyigit B Gumus B Acar T Kocacaliskan I Synthesis, characterization and antibacterial activity of juglone encapsulated PLGA nanoparticles J Appl Microbiol 20171231407 19 10.1111/jam.1360128980369Open DOISearch in Google Scholar

27Derman S. Caffeic acid phenethyl ester loaded PLGA nanoparticles: effect of various process parameters on reaction yield, encapsulation efficiency, and particle size. J Nanomater 2015;2015:ID341848. doi: 10.1155/2015/341848 Derman S Caffeic acid phenethyl ester loaded PLGA nanoparticles: effect of various process parameters on reaction yield, encapsulation efficiency, and particle size J Nanomater 20152015ID341848 10.1155/2015/341848Open DOISearch in Google Scholar

28Arasoglu T, Derman S, Mansuroglu B. Comparative evaluation of antibacterial activity of caffeic acid phenethyl ester and PLGA nanoparticle formulation by different methods. Nanotechnology 2015;27(2):025103. doi: 10.1088/0957-4484/27/2/025103 Arasoglu T Derman S Mansuroglu B Comparative evaluation of antibacterial activity of caffeic acid phenethyl ester and PLGA nanoparticle formulation by different methods Nanotechnology 2015272025103 10.1088/0957-4484/27/2/025103Open DOISearch in Google Scholar

29Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 1983;65:55–63. doi: 10.1016/0022-1759(83)90303-4 Mosmann T Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays J Immunol Methods 19836555 63 10.1016/0022-1759(83)90303-4Open DOISearch in Google Scholar

30Wallin RF, Arscott E. A practical guide to ISO 10993-5: Cytotoxicity, 1998 [displayed on 29 November 2019]. Available at https://www.namsa.com/wp-content/uploads/2015/10/A-Practical-Guide-to-ISO-10993-5_Cytotoxicity.pdf Wallin RF Arscott E A practical guide to ISO 10993-5: Cytotoxicity 1998 [displayed on 29 November 2019]. Available at https://www.namsa.com/wp-content/uploads/2015/10/A-Practical-Guide-to-ISO-10993-5_Cytotoxicity.pdfSearch in Google Scholar

31A be K , M a ts u k i N . Me a sure me n t of c e l l u l a r 3-(4,5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide (MTT) reduction activity and lactate dehydrogenase release using MTT. Neurosci Res 2000;38:325–9. doi: 10.1016/s0168-0102(00)00188-7 A be K M a ts u k i N Me a sure me n t of c e l l u l a r 3-(4,5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide (MTT) reduction activity and lactate dehydrogenase release using MTT Neurosci Res 200038325 9 10.1016/s0168-0102(00)00188-7Open DOISearch in Google Scholar

32Xenometrix. Ames MPF™ 98/100 Microplate Format Mutagenicity Assay. Stilwell (CA): Xenometrix; 2015. Xenometrix. Ames MPF™ 98/100 Microplate Format Mutagenicity Assay. Stilwell (CA): Xenometrix 2015Search in Google Scholar

33Hamel A, Roy M, Proudlock R. The bacterial reverse mutation test. In; Proudlock R, editor. Genetic toxicology testing. London: Academic Press Inc.; 2016. p. 79–138. Hamel A Roy M Proudlock R The bacterial reverse mutation test. In; Proudlock R, editor. Genetic toxicology testing London Academic Press Inc 2016 p 79–13810.1016/B978-0-12-800764-8.00004-5Search in Google Scholar

34Flückiger-Isler S, Kamber M. Direct comparison of the Ames microplate format (MPF) test in liquid medium with the standard Ames pre-incubation assay on agar plates by use of equivocal to weakly positive test compounds. Mutat Res 2012;747:36–45. doi: 10.1016/j.mrgentox.2012.03.014 Flückiger-Isler S Kamber M Direct comparison of the Ames microplate format (MPF) test in liquid medium with the standard Ames pre-incubation assay on agar plates by use of equivocal to weakly positive test compounds Mutat Res 201274736 45 10.1016/j.mrgentox.2012.03.01422579797Open DOISearch in Google Scholar

35Arasoglu T, Derman S. Assessment of the antigenotoxic activity of Poly(D,L-lactic-co-glycolic acid) nanoparticles loaded with caffeic acid phenethyl ester using the ames Salmonellamicrosome assay. J Agric Food Chem 2018;66:6196–204. doi: 10.1021/acs.jafc.8b01622 Arasoglu T Derman S Assessment of the antigenotoxic activity of Poly(D,L-lactic-co-glycolic acid) nanoparticles loaded with caffeic acid phenethyl ester using the ames Salmonellamicrosome assay J Agric Food Chem 2018666196 204 10.1021/acs.jafc.8b0162229799193Open DOISearch in Google Scholar

36Escobar P, Kemper R, Tarca J, Nicolette J, Kenyon M, Glowienke S, Sawant S, Christensen J, Johnson T, McKnight C, Ward G, Galloway SM, Custer L, Gocke E, O’Donovan MR, Braun K, Snyder RD, Mahadevan B. Bacterial mutagenicity screening in the pharmaceutical industry. Mutation Res 2013;752:99–118. doi: 10.1016/j. mrrev.2012.12.002 Escobar P Kemper R Tarca J Nicolette J Kenyon M Glowienke S Sawant S Christensen J Johnson T McKnight C Ward G Galloway SM Custer L Gocke E O’Donovan MR Braun K Snyder RD Mahadevan B Bacterial mutagenicity screening in the pharmaceutical industry Mutation Res 201375299 118 10.1016/j.mrrev.2012.12.00223262374Open DOISearch in Google Scholar

37Dutta D, Paul B, Mukherjee B, Mondal L, Sen S, Chowdhury C, Debnath MC. Nanoencapsulated betulinic acid analogue distinctively improves colorectal carcinoma in vitro and in vivo Sci Rep 2019;9(1):11506. doi: 10.1038/s41598-019-47743-y Dutta D Paul B Mukherjee B Mondal L Sen S Chowdhury C Debnath MC Nanoencapsulated betulinic acid analogue distinctively improves colorectal carcinoma in vitro and in vivo Sci Rep 20199111506 10.1038/s41598-019-47743-y668783131395908Open DOISearch in Google Scholar

38Ersoz M, Erdemir A, Duranoglu D, Uzunoglu D, Arasoglu T, Derman S, Mansuroglu B. Comparative evaluation of hesperetin loaded nanoparticles for anticancer activity against C6 glioma cancer cells. Artif Cells Nanomed Biotechnol 2019;47:319–29. doi: 10.1080/21691401.2018.1556213 Ersoz M Erdemir A Duranoglu D Uzunoglu D Arasoglu T Derman S Mansuroglu B Comparative evaluation of hesperetin loaded nanoparticles for anticancer activity against C6 glioma cancer cells Artif Cells Nanomed Biotechnol 201947319 29 10.1080/21691401.2018.155621330688095Open DOISearch in Google Scholar

39Bhattacharya S, Mondal L, Mukherjee B, Dutta L, Ehsan I, Debnath MC, Gaonkar RH, Pal MM, Majumdar S. Apigenin loaded nanoparticle delayed development of hepatocellular carcinoma in rats. Nanomedicine 2018;14:1905–17. doi: 10.1016/j.nano.2018.05.011 Bhattacharya S Mondal L Mukherjee B Dutta L Ehsan I Debnath MC Gaonkar RH Pal MM Majumdar S Apigenin loaded nanoparticle delayed development of hepatocellular carcinoma in rats Nanomedicine 2018141905 17 10.1016/j.nano.2018.05.011Open DOISearch in Google Scholar

40Ramirez O, Motta-Mena LB, Cordova A, Garza KM. A small library of synthetic di-substituted 1,4-naphthoquinones induces ROS-mediated cell death in murine fibroblasts. PloS One 2014;9(9):e106828. doi: 10.1371/journal.pone.0106828 Ramirez O Motta-Mena LB Cordova A Garza KM A small library of synthetic di-substituted 1,4-naphthoquinones induces ROS-mediated cell death in murine fibroblasts PloS One 201499e106828 10.1371/journal.pone.0106828Open DOISearch in Google Scholar

41Kumari A, Yadav SK, Yadav SC. Biodegradable polymeric nanoparticles based drug delivery systems. Colloids and Surf B Biointerfaces 2010;75:1–18. doi: 10.1016/j. colsurfb.2009.09.001 Kumari A Yadav SK Yadav SC Biodegradable polymeric nanoparticles based drug delivery systems Colloids and urf B Biointerfaces 2010751 18 10.1016/j.colsurfb.2009.09.001Open DOISearch in Google Scholar

42Terzi I. Allelopathic effects of juglone and walnut leaf and fruit hull extracts on seed germination and seedling growth in muskmelon and cucumber. Asian J Chem 2009;21:1840–6. Terzi I Allelopathic effects of juglone and walnut leaf and fruit hull extracts on seed germination and seedling growth in muskmelon and cucumber Asian J Chem 2009211840 6Search in Google Scholar

43Kocaçalişkan I, Ceylan M, Terzi I. Effects of juglone on seedling growth in intact and coatless seeds of cucumber Cucumis sativus cv. Beith Alpha). Sci Res Essays 2009;4:039–41. Kocaçalişkan I Ceylan M Terzi I Effects of juglone on seedling growth in intact and coatless seeds of cucumber Cucumis sativus cv Beith Alpha). Sci Res Essays 20094039 41Search in Google Scholar

44Topal S, Kocaçalişkan I, Arslan O, Tel AZ. Herbicidal effects of juglone as an allelochemical. Phyton 2007;46:259–69. Topal S Kocaçalişkan I Arslan O Tel AZ Herbicidal effects of juglone as an allelochemical Phyton 200746259 69Search in Google Scholar

45Terzi I, Kocaçalişkan I, Benlioğlu O, Solak K. Effects of juglone on growth of cucumber seedlings with respect to physiological and anatomical parameters. Acta Physiol Plant 2003;25:353–6. doi: 10.1007/s11738-003-0016-1 Terzi I Kocaçalişkan I Benlioğlu O Solak K Effects of juglone on growth of cucumber seedlings with respect to physiological and anatomical parameters Acta Physiol Plant 200325353 6 10.1007/s11738-003-0016-1Open DOISearch in Google Scholar

46Babula P, Adam V, Havel L, Kizek R. Noteworthy secondary metabolites naphthoquinones-their occurrence, pharmacological properties and analysis. Curr Pharmaceut Anal 2009;5:47–68. doi: 10.2174/157341209787314936 Babula P Adam V Havel L Kizek R Noteworthy secondary metabolites naphthoquinones-their occurrence, pharmacological properties and analysis Curr Pharmaceut Anal 2009547 68 10.2174/157341209787314936Open DOISearch in Google Scholar

47Babula P, Vaverkova V, Poborilova Z, Ballova L, Masarik M, Provaznik I. Phytotoxic action of naphthoquinone juglone demonstrated on lettuce seedling roots. Plant Physiol Biochem 2014;84:78–86. doi: 10.1016/j.plaphy.2014.08. 02748 Babula P Vaverkova V Poborilova Z Ballova L Masarik M Provaznik I Phytotoxic action of naphthoquinone juglone demonstrated on lettuce seedling roots Plant Physiol Biochem 20148478 86 10.1016/j.plaphy.2014.08.02748Open DOISearch in Google Scholar

48Tikkanen L, Matsushima T, Natori S, Yoshihira K. Mutagenicity of natural naphthoquinones and benzoquinones in the Salmonella/microsome test. Mutat Res 1983;124:25– 34. doi: 10.1016/0165-1218(83)90182-9 Tikkanen L Matsushima T Natori S Yoshihira K Mutagenicity of natural naphthoquinones and benzoquinones in the Salmonella/microsome test Mutat Res 198312425–34 10.1016/0165-1218(83)90182-9Open DOISearch in Google Scholar

49Gaivão I, Sierra LM, Comendador MA. The w/w⁺ SMART assay of Drosophila melanogaster detects the genotoxic effects of reactive oxygen species inducing compounds. Mutat Res 1999;440:139–45. doi: 10.1016/s1383-5718(99)00020-0 Gaivão I Sierra LM Comendador MA The w/w⁺ SMART assay of Drosophila melanogaster detects the genotoxic effects of reactive oxygen species inducing compounds Mutat Res 1999440139 45 10.1016/s1383-5718(99)00020-0Open DOISearch in Google Scholar

50Krucińska I, Żywicka B, Komisarczyk A, Szymonowicz M, Kowalska S, Zaczyńska E, Struszczyk M, Czarny A, Jadczyk P, Umińska-Wasiluk B. Biological properties of low-toxicity PLGA and PLGA/PHB fibrous nanocomposite implants for osseous tissue regeneration. Part I: Evaluation of potential biotoxicity. Molecules 2017;22:pii:E2092. doi: 10.3390/ molecules22122092 Krucińska I Żywicka B Komisarczyk A Szymonowicz M Kowalska S Zaczyńska E Struszczyk M Czarny A Jadczyk P Umińska-Wasiluk B Biological properties of low-toxicity PLGA and PLGA/PHB fibrous nanocomposite implants for osseous tissue regeneration. Part I: Evaluation of potential biotoxicity Molecules 201722piiE2092 10.3390/molecules22122092Open DOISearch in Google Scholar

51Yoo HS, Lee KH, Oh JE, Park TG. In vitro and in vivo anti-tumor activities of nanoparticles based on doxorubicin-PLGA conjugates. J Control Release 2000;68:419–31. doi: 10.1016/s0168-3659(00)00280-7 Yoo HS Lee KH Oh JE Park TG In vitro and in vivo anti-tumor activities of nanoparticles based on doxorubicin-PLGA conjugates J Control Release 200068419 31 10.1016/s0168-3659(00)00280-7Open DOISearch in Google Scholar