Preliminary evaluation of acute cytogenotoxicity of a novel phenylboronic acid derivative; 2-(bromoacetamido) phenylboronic acid using the Allium cepa chromosome aberrations assay

References

• Abdel-Rahman HHM, Abdel Migid HM, Attia SA, Rizkalla AA. 2015. Cytogenetical, biochemical and chemical analytical studies for assessment of the water quality of Nile water using three bioassays. Middle East J Appl Sci. 5(5):112–124.
   Google Scholar
• Akinboro A, Mohamed KB, Asmawi MZ, Sulaiman SF, Sofiman OA. 2011. Antioxidants in aqueous extract of Myristica fragrans (Houtt.) suppress mitosis and cyclophosphamide-induced chromosomal aberrations in Allium cepa L. cells. J Zhejiang Univ Sci B. 12(11):915–922. 10.5897/AJB
   Google Scholar
• Alexander B, Browse DJ, Reading SJ, Benjamin IS. 1999. A simple and accurate mathematical method for calculation of the EC50. J Pharmacol Toxicol Methods. 41:55–58. 10.1016/S1056-8719(98)00038-0
   PubMed Web of Science ®Google Scholar
• Al-Qaoud KM, Shihab PA, Abu-Qatouseh LF, Lowe CR, Rawashdeh AM, Alkhayyat YA, Ratrout SS, Naser SM 2014. Phenylboronic acid. Patent N0. : US 8,877,980 B2. 2014.
   Google Scholar
• Al-Zoubi RM. 2011. Mild, green and catalytic: Ortho-iodoarylboronic acids for direct amide bond formation at room temperature [ Ph. D. Thesis]. University of Alberta: Edmonton, Alberta.
   Google Scholar
• Arslan M, Topaktas M, Rencuzogullari E. 2008. The effects of boric acid on sister chromatid exchanges and chromosome aberrations in cultured human lymphocytes. Cytotechnology. 56:91–96. 10.1007/s10616-007-9094-z
   PubMed Web of Science ®Google Scholar
• Barranco WT, Eckhert CD. 2006. Cellular changes in boric acid-treated DU-145 prostate cancer cells. Br J Cancer. 94:884–890. 10.1038/sj.bjc.6603009
   PubMed Web of Science ®Google Scholar
• Bradke TM, Hall C, Carper SW, Plopper GE. 2008. Phenylboronic acid selectively inhibits human prostate and breast cancer cell migration and decreases viability. Cell Adh Migr. 2:153–160. 10.4161/cam.2.3.6484
   PubMed Web of Science ®Google Scholar
• Cambre NJ, Sumerlin SB. 2011. Biomedical applications of boronic acid polymers. Polymer. 52:4631–4643. 10.1016/j.polymer.2011.07.057
   Web of Science ®Google Scholar
• Ceyhunc B, Atamanalp M. 2016. The effects of acute boric acid treatment on gill, kidney and muscle tissues in juvenile rainbow trout. J Appl Anim Res. 44:297–302.
   Web of Science ®Google Scholar
• Christopher HB, Kapoor MB. 1988. The cytogenetic effects of sodium salicylate on the root meristem cells of Allium sativa L. Cytologia. 54:203–209.
   Web of Science ®Google Scholar
• Doi Y, Paterson DL 2007. Detection of plasmid-mediated class C β-lactamases. Int J Infect Dis. 11: 191–197.
   PubMed Web of Science ®Google Scholar
• Dunetz JR, Magano J, Weisenburger GA. 2016. Large-Scale applications of amide coupling reagents for the synthesis of pharmaceuticals. Org Process Res Dev. 20:140–177. 10.1021/op500305s
   Web of Science ®Google Scholar
• Fenech M, Kirsch-Volders M, Natarajan AT, Surralles J, Crott JW, Parry J, Norppa H, Eastmond DA, Tucker JD, Thomas P. 2011. Molecular mechanisms of micronucleus, nucleoplasmic bridge and nuclear bud formation in mammalian and human cells. Mutagenesis. 26:125–132. 10.1093/mutage/geq052
   PubMed Web of Science ®Google Scholar
• Fiskesjö G. 1993. The Allium test in waste-water monitoring. Environ Toxicol Water Qual. 8:291–298. 10.1002/(ISSN)1098-2256
   Google Scholar
• Fusconi A, Gallo C, Camusso W. 2007. Effects of cadmium on root apical meristem of Pisumsativum L: cell viability, cell proliferation and microtubule pattern as suitable markers for assessment of stress pollution. Mutat Res. 632:9–19. 10.1016/j.mrgentox.2007.03.012
   PubMed Web of Science ®Google Scholar
• Gallardo-Williams MT, Chapin RE, King PE, Moser GJ, Goldsworthy TL, Morrison JP, Maronpot RR. 2004. Boron supplementation inhibits the growth and local expression of IGF-1 in human prostate adenocarcinoma (LNCaP) tumors in nude mice. Toxicol Pathol. 32:73–78. 10.1080/01926230490260899
   PubMed Web of Science ®Google Scholar
• Gupta AK, Simpson FC. 2014. Investigational drugs for onychomycosis. Expert Opin Investig Drugs. 23:97–106. 10.1517/13543784.2013.840289
   PubMed Web of Science ®Google Scholar
• Hall DG, Lee JCH, Ding J. 2012. Catalytic enantioselective transformations of borylated substrates: preparation and synthetic applications of chiral alkylboronates. Pure Appl Chem. 84:2263–2277.
   Web of Science ®Google Scholar
• Hidalgo A, Gonzales JA, Navas P, Garcia-Herdugo G. 1989. Abnormal mitosis and growth inhibition in Allium cepa roots induced by propham and chlorpropham. Cytobios. 57:7–17.
   Google Scholar
• Ji M, Li P, Sheng N, Liu L, Pan H, Wang C, Cai L, Ma Y. 2016. Sialic acid-targeted nanovectors with phenylboronic acid-grafted polyethylenimine robustly enhance siRNA-based cancer therapy. ACS Appl. Mater. Interfaces. 8:9565–9576. 10.1021/acsami.5b11866
   PubMed Web of Science ®Google Scholar
• Kahraman E, Gürhan ID, Korkmaz M. 2013. Investigation of possible genotoxic and cytotoxic effects of differential boron compounds in CCL 62 (Hela contaminant) human amniotic epithelial cell line. Med Sci. 2:454–468.
   Google Scholar
• Khalil A, Maslat A, Hafez A, Mizyed S, Ashram M. 2009. Genotoxicity of different tert-butyl calyx [4] crowns. Zeitschrift für Naturforschung C. 63:167–175.
   Google Scholar
• Lee DY, Choe K, Jeong YJ, Yoo J, Lee SM, Park JH, Kim P, Kim YC. 2015. Establishment of a controlled insulin delivery system using a glucose-responsive double-layered nanogel. RSC Adv. 5:14482–14491. 10.1039/C4RA16656F
   Web of Science ®Google Scholar
• Leme DM, Marin-Morales MA. 2009. Allium cepa test in environmental monitoring: a review on its application. Mutat Res. 682:71–81. 10.1016/j.mrrev.2009.06.002
   PubMed Web of Science ®Google Scholar
• McAuley EM, Bradke TA, Plopper GE. 2011. Phenylboronic acid is a more potent inhibitor than boric acid of key signaling networks involved in cancer cell migration. Cell Adh Migr. 5:382–386. 10.4161/cam.5.5.18162
   PubMed Web of Science ®Google Scholar
• Mercykutty VC, Stephen J. 1980. Adriamycin induced genetic toxicity as demonstrated by the Allium test. Cytologia. 45:769–777. 10.1508/cytologia.45.769
   Web of Science ®Google Scholar
• Mustafa Y, Arikan ES. 2008. Genotoxicity testing of quizalofop-P-ethyl herbicide using the Allium cepa anaphase-telophase chromosome aberration assay. Caryologia. 61:45–52. 10.1080/00087114.2008.10589608
   Web of Science ®Google Scholar
• Namita K, Sonia S. 2013. Allium cepa root chromosomal aberration assay: a review. Indian J Pharm Biol Res. 1:105–119.
   Google Scholar
• National Toxicology Program. 1987. Toxicology and carcinogenesis studies of boric acid. Natl Toxicol Program Tech Rep Ser. 324:1–126.
   PubMedGoogle Scholar
• Nefic H, Musanovic J, Metovic A, Kurteshi K. 2013. Chromosomal and nuclear alterations in root tip cells of Allium cepa L. induced by alprazolam. Med Arh. 67:388–392.10.5455/medarh
   Google Scholar
• O’Donovan MR, Mee CD, Fenner S, Teasdale A, Phillips DH. 2011. Boronic acids—a novel class of bacterial mutagen. Mutat Res. 724:1–6. 10.1016/j.mrgentox.2011.05.006
   PubMed Web of Science ®Google Scholar
• Osman AGM. 2014. Genotoxicity tests and their contributions in aquatic environmental research. J Environ Prot. 05:1391–1399. 10.4236/jep.2014.514132
   Google Scholar
• Ping KY, Darah I, Yusuf UK, Yeng C, Sasidharan S. 2012. Genotoxicity of Euphorbia hirta: an Allium cepa assay. Molecules. 17:7782–7791. 10.3390/molecules17077782
   PubMed Web of Science ®Google Scholar
• Pundir CS, Chawla S. 2014. Determination of glycated hemoglobin with special emphasis on biosensing methods. Anal Biochem. 444:47–56. 10.1016/j.ab.2013.09.023
   PubMed Web of Science ®Google Scholar
• Qureshi S, Al-Shabanah OA, Al-Harbi MM, Al-Bekairi AM, Raza M. 2001. Boric acid enhances in vivo Ehrlich ascites carcinoma cell proliferation in Swiss albino mice. Toxicology. 165:1–11. 10.1016/S0300-483X(01)00396-1
   PubMed Web of Science ®Google Scholar
• Sarıkayaa R, Erciyasb K, Karac MI, Sezer U, Erciyas AF, Ay S. 2016. Evaluation of genotoxic and antigenotoxic effects of boron by the somatic mutation and recombination test (SMART) on Drosophila. Drug Chem Toxicol. 12:1–7.
   Google Scholar
• Seth CS, Chaturvedi PK, Misra V. 2007. Toxic effect of arsenate and cadmium alone and in combination on giant duckweed (Spirodela polyrrhiza L.) in response to its accumulation. Environ Toxicol. 22:539–549. 10.1002/(ISSN)1522-7278
   PubMed Web of Science ®Google Scholar
• Sudhakar R, Gowda N, Venu G. 2001. Mitotic abnormalities induced by silk dyeing industry effluents in the cells of Allium cepa. Cytologia. 66:235–239. 10.1508/cytologia.66.235
   Google Scholar
• Türkoğlu, Ș. 2012. Determination of genotoxic effects of chlorfenvinphos and fenbuconazole in Allium cepa root cells by mitotic activity, chromosome aberration, DNA content, and comet assay. Pest Biochem Physiol. 103:224–23025.
   Web of Science ®Google Scholar
• Wang X, Xia N, Liu L. 2013. Boronic acid-based approach for separation and immobilization of glycoproteins and its application in sensing. Int J Mol Sci. 14:20890–20912. 10.3390/ijms141020890
   PubMed Web of Science ®Google Scholar
• Zhang C, Losego MD, Braun PV. 2013. Hydrogel-based glucose sensors: effects of phenylboronic acid chemical structure on response. Chem Mater. 25:3239–3250. 10.1021/cm401738p
   Web of Science ®Google Scholar