Journal of Korean Neurosurgical Society

  • 제64권6호
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  • Pages.864-872
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  • 2021
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  • 2005-3711(pISSN)
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  • 1598-7876(eISSN)
대한신경외과학회 (The Korean Neurosurgical Society)
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Synthesis of New Boron Derived Compounds; Anticancer, Antioxidant and Antimicrobial Effect in Vitro Glioblastoma Tumor Model

  • 투고 : 2021.02.03
  • 심사 : 2021.03.26
  • 발행 : 2021.11.01
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초록

Objective : The aim of our study is to investigate the cytotoxic, antioxidant, and antimicrobial effects of newly synthesized boron compounds in U87MG glioblastoma cell treatment. Methods : We synthesized boron glycine monoester (BGM) and boron glycine diester (BGD) structures containing boron atoms and determined their cytotoxic activities on glioblastoma by the MTT method. The inhibitory concentration 50 (IC50) value was calculated with GraphPad Prism 5.0 program. The IC50 values were administered 48 hours on U87MG glioblastoma cell. Catalase (CAT), acid phosphatase (ACP) and alkaline phosphatase (ALP) enzyme activity, malondialdehyde (MDA), total glutathione (GSH), and total protein levels were detected using spectrophotometric methods. We determined the antimicrobial activities of BGM and BGD with the disc diffusion method. Results : After 48 hours of BGM and BGD application to U87MG glioblastoma cells, we found the IC50 value as 6.6 mM and 26 mM, respectively. CAT and ACP enzyme activities were decreased in BGM and BGD groups. MDA which is a metabolite of lipid peroxidation was increased in both boron compounds groups. GSH level was reduced especially in BGD group. BGM and BGD have been found to be antimicrobial effects. Conclusion : Boron compounds, especially the BGM, can provide a new therapeutic approach for the treatment of glioblastoma with their anticancer, antioxidant, and antimicrobial effects.

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참고문헌

  1. Aebi H : Catalase in vitro in Bergmeyer HU (ed) : Methods of Enzymatic Analysis, ed 2. London : Academic Press, 1974, pp121-126
  2. Ahmad S, Haque MM, Ashraf SM, Ahmad S : Urethane modified boron filled polyesteramide: a novel anti-microbial polymer from a sustainable resource. Eur Polym J 40 : 2097-2104, 2004 https://doi.org/10.1016/j.eurpolymj.2004.05.013
  3. Ali F, Hosmane NS, Zhu Y : Boron chemistry for medical applications. Molecules 25 : 828, 2020 https://doi.org/10.3390/molecules25040828
  4. Axtell JC, Saleh LMA, Qian EA, Wixtrom AI, Spokoyny AM : Synthesis and applications of perfunctionalized boron clusters. Inorg Chem 57 : 2333-2350, 2018 https://doi.org/10.1021/acs.inorgchem.7b02912
  5. Aydin HE, Koldemir-Gunduz M, Kizmazoglu C, Kandemir T, Arslantas A : Cytotoxic effect of boron application on glioblastoma cells. Turk Neurosurg 31 : 206-210, 2021
  6. Backos DS, Franklin CC, Reigan P : The role of glutathione in brain tumor drug resistance. Biochem Pharmacol 83 : 1005-1012, 2012 https://doi.org/10.1016/j.bcp.2011.11.016
  7. Barth RF, Zhang Z, Liu T : A realistic appraisal of boron neutron capture therapy as a cancer treatment modality. Cancer Commun (Lond) 38 : 36, 2018 https://doi.org/10.1186/s40880-018-0280-5
  8. Beutler E : Glutathione in Red Cell Metabolism: A Manual of Biochemical Methods, ed 2. New York : Grune & Stratton, 1975, pp112-114
  9. Bradford MM : A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72 : 248-254, 1976 https://doi.org/10.1006/abio.1976.9999
  10. Canturk Z, Tunali Y, Korkmaz S, Gulbas Z : Cytotoxic and apoptotic effects of boron compounds on leukemia cell line. Cytotechnology 68 : 87-93, 2016 https://doi.org/10.1007/s10616-014-9755-7
  11. Celik B, Ersoz E, Korkmaz M : Investigation of the therapy potential of borax pentahydrate in glioblastoma multiforme cell line. J Boron 5 : 56-61, 2020
  12. Celik SY, Demir N, Demir Y : The in-vitro effect of lisonopril on serum alkaline phosphatase and acid phosphatase enzymes activity. CBU J Sci 13 : 233-237, 2017
  13. Ciftci N : The role of oxidative stress in cancer: could antioxidants fuel the progression of cancer? Ahi Evran Tip Dergisi 1 : 8-13, 2017
  14. Clinical and Laboratory Standards Institute (CLSI). Performance standards for antimicrobial disk susceptibility tests; approved standard, eleventh edition. Wayne : CLSI, 2012
  15. Fojo T, Bates S : Strategies for reversing drug resistance. Oncogene 22 : 7512-7523, 2003 https://doi.org/10.1038/sj.onc.1206951
  16. Gunduz MK, Bolat M, Kaymak G, Berikten D, Kose DA : Therapeutic effects of newly synthesized boron compounds (BGM and BGD) on hepatocellular carcinoma. Biol Trace Elem Res, 2021 [Epub ahead of print]
  17. Halliwell B : Oxidative stress and neurodegeneration: where are we now? J Neurochem 97 : 1634-1658, 2006 https://doi.org/10.1111/j.1471-4159.2006.03907.x
  18. Hawthorne MF : The role of chemistry in the development of boron neutron capture therapy of cancer. Angew Chem Int Ed Engl 32 : 950-984, 1993 https://doi.org/10.1002/anie.199309501
  19. Hawthorne MF, Maderna A : Applications of radiolabeled boron clusters to the diagnosis and treatment of cancer. Chem Rev 99 : 3421-3434, 1999 https://doi.org/10.1021/cr980442h
  20. Kachadourian R, Brechbuhl HM, Ruiz-Azuara L, Gracia-Mora I, Day BJ : Casiopeina IIgly-induced oxidative stress and mitochondrial dysfunction in human lung cancer A549 and H157 cells. Toxicology 268 : 176-183, 2010 https://doi.org/10.1016/j.tox.2009.12.010
  21. Kaynar H, Meral M, Turhan H, Keles M, Celik G, Akcay F : Glutathione peroxidase, glutathione-S-transferase, catalase, xanthine oxidase, CuZn superoxide dismutase activities, total glutathione, nitric oxide, and malondialdehyde levels in erythrocytes of patients with small cell and non-small cell lung cancer. Cancer Lett 227 : 133-139, 2005 https://doi.org/10.1016/j.canlet.2004.12.005
  22. Kose DA : Preparation and structure investigation of biopotent boron compounds with hydroxy-functionalized organic molecules. Ankara : Hacettepe University, Science Institute, 2008
  23. Kose DA, Karan Zumreoglu B, Hokelek T, Sahin E : Boric acid complexes with organic biomolecules: mono-chelate complexes with salicylic and glucuronic acids. Inorganica Chimica Acta 363 : 4031-4037, 2010 https://doi.org/10.1016/j.ica.2010.08.001
  24. Kose DA, Zumreoglu-Karan B : Mixed ligand complexes of boric acid with organic biomolecules. Chemical Papers 66 : 54-60, 2012 https://doi.org/10.2478/s11696-011-0108-0
  25. Kose DA, Zumreoglu-Karan B, Hokelek T : A comparative examination of mono- and Bis-chelate salicylatoborate complexes and the crystal structure of layered magnesium Bis-salicylatoborate. Inorganica Chimica Acta 375 : 236-241, 2011 https://doi.org/10.1016/j.ica.2011.05.012
  26. Ledwozyw A, Michalak J, Stepien A, Kadziolka A : The relationship between plasma triglycerides, cholesterol, total lipids and lipid peroxidation products during human atherosclerosis. Clin Chim Acta 155 : 275-283, 1986 https://doi.org/10.1016/0009-8981(86)90247-0
  27. Meiyanto E, Susidarti RA, Jenie RI, Utomo RY, Novitasari D, Wulandari F, et al. : Synthesis of new boron containing compound (CCB-2) based on curcumin structure and its cytotoxic effect against cancer cells. J Appl Pharm Sci 10 : 060-066, 2020 https://doi.org/10.7324/japs.2020.102010
  28. Ostrom QT, Bauchet L, Davis FG, Deltour I, Fisher JL, Langer CE, et al. : The epidemiology of glioma in adults: a "state of the science" review. Neuro Oncol 16 : 896-913, 2014 https://doi.org/10.1093/neuonc/nou087
  29. Pointer BR, Boyer MP, Schmidt M : Boric acid destabilizes the hyphal cytoskeleton and inhibits invasive growth of Candida albicans. Yeast 32 : 389-398, 2015 https://doi.org/10.1002/yea.3066
  30. Qian EA, Wixtrom AI, Axtell JC, Saebi A, Jung D, Rehak P, et al. : Atomically precise organomimetic cluster nanomolecules assembled via perfluoroaryl-thiol SNAr chemistry. Nat Chem 9 : 333-340, 2017 https://doi.org/10.1038/nchem.2686
  31. Rajneesh CP, Manimaran A, Sasikala KR, Adaikappan P : Lipid peroxidation and antioxidant status in patients with breast cancer. Singapore Med J 49 : 640-643, 2008
  32. Ray G, Batra S, Shukla NK, Deo S, Raina V, Ashok S, et al. : Lipid peroxidation, free radical production and antioxidant status in breast cancer. Breast Cancer Res Treat 59 : 163-170, 2000 https://doi.org/10.1023/A:1006357330486
  33. Rock K, McArdle O, Forde P, Dunne M, Fitzpatrick D, O'Neill B, et al. : A clinical review of treatment outcomes in glioblastoma multiforme--the validation in a non-trial population of the results of a randomised phase III clinical trial: has a more radical approach improved survival? Br J Radiol 85 : e729-e733, 2012 https://doi.org/10.1259/bjr/83796755
  34. Sarac N. Ugur A, Boran R, Elgin ES : The use of boron compounds for stabilization of lipase from pseudomonas aeruginosa ES3 for the detergent industry. J Surfactants Deterg 18 : 275-285, 2015 https://doi.org/10.1007/s11743-014-1653-7
  35. Sari P : Investigation of the biochemical effects of epigallocatechin gallate and resveratrol in cultured C6 glioma cells. Saglik Bilimleri Enstitusu : Istanbul Science University, 2011
  36. Sayin Z, Ucan US, Sakmanoglu A : Antibacterial and antibiofilm effects of boron on different bacteria. Biol Trace Elem Res 173 : 241-246, 2016 https://doi.org/10.1007/s12011-016-0637-z
  37. Schumacker PT : Reactive oxygen species in cancer: a dance with the devil. Cancer Cell 27 : 156-157, 2015 https://doi.org/10.1016/j.ccell.2015.01.007
  38. Uysal N, Gonenc S, SonmeZ A, Aksu I, Topcu A, Kayatekin BM, et al. : Antioxidant enzyme activities and lipid peroxidation levels in adolescent rat brain. Ege Tip Dergisi 44 : 75-79, 2005
  39. Walter K, Schult C : Acid and alkaline phosphatase in serum (two point method) in Bergmeyer HU (ed) : Methods of Enzymatic Analysis, ed 2. Cambridge : Academic Press, 1974, Vol 2, pp856-886
  40. Yerlikaya A, Okur E, Eker S, Erin N : Combined effects of the proteasome inhibitor bortezomib and Hsp70 inhibitors on the B16F10 melanoma cell line. Mol Med Rep 3 : 333-339, 2010 https://doi.org/10.3892/mmr_00000262
  41. Yilmaz MT : Minimum inhibitory and minimum bactericidal concentrations of boron compounds against several bacterial strains. Turk J Med Sci 42 : 1423-1429, 2012
  42. Zablocka-Slowinska K, Placzkowska S, Skorska K, Prescha A, Pawelczyk K, Porebska I, et al. : Oxidative stress in lung cancer patients is associated with altered serum markers of lipid metabolism. PLoS One 14 : e0215246, 2019 https://doi.org/10.1371/journal.pone.0215246
  43. Zanders ED, Svensson F, Bailey DS : Therapy for glioblastoma: is it working? Drug Discov Today 24 : 1193-1201, 2019 https://doi.org/10.1016/j.drudis.2019.03.008
  44. Zavjalov E, Zaboronok A, Kanygin V, Kasatova A, Kichigin A, Mukhamadiyarov R, et al. : Accelerator-based boron neutron capture therapy for malignant glioma: a pilot neutron irradiation study using boron phenylalanine, sodium borocaptate and liposomal borocaptate with a heterotopic U87 glioblastoma model in SCID mice. Int J Radiat Biol 96 : 868-878, 2020 https://doi.org/10.1080/09553002.2020.1761039
  45. Zhu Y, Gao S, Hosmane NS : Boron-enriched advanced energy materials. Inorg Chim 471 : 577-586, 2018 https://doi.org/10.1016/j.ica.2017.11.037
  46. Zhu Y, Hosmane NS : Ionic liquids: recent advances and applications in boron chemistry. Eur J Inorg Chem 2017 : 4369-4377, 2017 https://doi.org/10.1002/ejic.201700553
  47. Zhu Y, Hosmane NS : Nanostructured boron compounds for cancer therapy. Pure Appl Chem 90 : 653-663, 2018 https://doi.org/10.1515/pac-2017-0903
  48. Zumreoglu-Karan B, Kose DA : Boric acid: a simple molecule of physiologic, therapeutic and prebiotic significance. Pure Appl Chem 87 : 155-162, 2015 https://doi.org/10.1515/pac-2014-0909