Research Article
BibTex RIS Cite

BISBENZOXAZOLE DERIVATIVES HAD ANTI-PROLIFERATIVE EFFECT ON HUMAN CANCER CELLS

Year 2019, , 203 - 211, 31.07.2019
https://doi.org/10.18036/estubtdc.598863

Abstract



ABSTRACT



 



A series of symmetric bis-benzoxazole derivatives
were synthesized using one-pot cyclisation reaction between 4-fluoro
substituted 2-aminophenol and suitable carboxylic acids. Synthesized compounds’
anticancer activities were tested by using MTT assay on human prostate (DU145)
and breast (MCF7) cancer cells. Screening results revealed that all compounds
possessed a high level anti-cancer potential by significantly decreasing the
cell proliferation in prostate and breast cancer cell lines. Our compounds
exerted their anti-proliferative effects in a dose and time dependent manner.
Our results suggest that they can be highly potent since they were biologically
active even at low concentration ranges. Our study presents a series of new
bis-benzoxazole based
compounds with potential therapeutic effects
against tumor cells. Therefore, characterization of new generation
bis-benzoxazole derivatives will have a significant contribution on the
development of new era anti-cancer drug candidates.

References

  • [1] Williams GH, Stoeber K. Cell cycle markers in clinical oncology. CurrOpin Cell Biol 2007; 19: 1- 6.
  • [2] Bower JJ et al. Topoisomerase IIalpha maintains genomic stability through decatenationG(2) checkpoint signaling. Oncogene 2010; 29: 4787–4799.
  • [3] Hartwell LH, Kastan MB. Cell cycle control and cancer. Science1994; 266: 1821–1828.
  • [4] Marie Classon EH. The retinoblastoma tumor suppressor in development and cancer. Nat Rev Cancer 2002; 2: 910–917.
  • [5] Xu B, Kim ST, Kastan MB. Involvement of Brca1 in S-Phase and G2-Phase checkpoints after ionizing irradiation. Mol Cell Biol 2001; 21: 3445–3450.
  • [6] Rui-Hong Wang HY, Chu-Xia Deng. A requirement for breast-cancer-associated gene 1 (BRCA1) in the spindle checkpoint. Proc Natl Acad Sci 2004; 101: 17108–17113.
  • [7] Santarpia L, et al. DNA repair gene patters as prognostic and predictive factors in molecular breast cancer subtypes. Oncologist 2013; 18: 1063–1073.
  • [8] Sorlie T, et al. Gene expression patterns of breast carcinomas distinguish tumor subclasses with clinical implications. Proc Natl Acad Sci 2001; 98: 10869–10874.
  • [9] Nakagawa T, et al. Identification of decatenation G2 checkpoint impairment independently of DNA damage G2 checkpoint in human lung cancer cell lines. Cancer Res 2004; 64: 4826–4832.
  • [10] Hinck L, Näthke I. Changes in cell and tissue organization in cancer of the breast and colon. Curr Opin Cell Biol 2014;0:87–95.
  • [11] Cho EH, et al. Characterization of circulating tumor cell aggregates identified in patients with epithelial tumors. Phys Biol 2012; 9: 016001.
  • [12] De Smedt L, Palmans S, Sagaert X. Tumour budding in colorectal cancer: what do we know and what can we do?. Virchows Archiv 2016; 468: (397).
  • [13] Gustavsson B, et al. A Review of the Evolution of Systemic Chemotherapy in the Management of Colorectal Cancer. Clin Col Canc 2015; 14: 1.
  • [14] Huang CY, Ju DT, Chang CF, Muralidhar Reddy P, Velmurugan BK. A review on the effects of current chemotherapy drugs and natural agents in treating non–small cell lung cancer. BioMedicine 2017; 7(4): 23.
  • [15] Longo DL, Fauci AS, Kasper DL, Hauser SL, Jameson JL, Loscalzo J. Harrison’s Principles of internal medicine. 18th ed. New York: McGraw-Hill Companies, 2011.
  • [16] Andreae S. Lexikon der Krankheiten und Untersuchungen. Stuttgart: Thieme, 2008.
  • [17] Hu Q, Sun W, Wang C, Gu Z. Recent Advances of Cocktail Chemotherapy by Combination Drug Delivery Systems. Adv. Drug Deliv. Rev. 2016; 98: 19–34.
  • [18] Hoelder S, Clarke PA, Workman P. Discovery of small molecule cancer drugs: Successes, challenges and opportunities. Mol Oncol 2012; 6: 2.
  • [19] Pearce A, Haas M, Viney R, Pearson SA, Haywood P, Brown C, et al. Incidence and severity of self-reported chemotherapy side effects in routine care: A prospective cohort study. PLoS ONE 2017; 12(10): e0184360. [20] Ihbe-Heffinger A, Ehlken B, Bernard R, Berger K, Peschel C, Eichler HG, et al. The impact of delayed chemotherapy-induced nausea and vomiting on patients, health resource utilization and costs in German cancer centers. Ann Oncol 2004; 15(3):1.
  • [21] Khoshbin AR, et al. The effect of radiotherapy and chemotherapy on osmotic fragility of red blood cells and plasma levels of malondialdehyde in patients with breast cancer. Rep Pract Oncol Radiother 2015; 20(4): 305–308.
  • [22] Global Burden of Disease Cancer Collaboration. The Global Burden of Cancer 2013. JAMA Oncology 2015; 1(4): 505–527.
  • [23] Ayaz F, Kheeree R, Isse QA, Ersan RH, Algul O. DNA Base Bioisosteres, Bis-benzoxazoles, Exert Anti-proliferative Effect on Human Prostate and Breast Cancer Cells JOTCSA 2018; 5(3): 1145-1152.
  • [24] Kumar D, Jacob MR, Reynolds MB, Kerwin SM. Synthesis and evaluation of anticancer benzoxazoles and benzimidazoles related to UK-1. Bioorg Med Chem 2002; 10(12):3997-4004.

BISBENZOXAZOLE DERIVATIVES HAD ANTI-PROLIFERATIVE EFFECT ON HUMAN CANCER CELLS

Year 2019, , 203 - 211, 31.07.2019
https://doi.org/10.18036/estubtdc.598863

Abstract



ABSTRACT



 



A series of symmetric bis-benzoxazole derivatives
were synthesized using one-pot cyclisation reaction between 4-fluoro
substituted 2-aminophenol and suitable carboxylic acids. Synthesized compounds’
anticancer activities were tested by using MTT assay on human prostate (DU145)
and breast (MCF7) cancer cells. Screening results revealed that all compounds
possessed a high level anti-cancer potential by significantly decreasing the
cell proliferation in prostate and breast cancer cell lines. Our compounds
exerted their anti-proliferative effects in a dose and time dependent manner.
Our results suggest that they can be highly potent since they were biologically
active even at low concentration ranges. Our study presents a series of new
bis-benzoxazole based
compounds with potential therapeutic effects
against tumor cells. Therefore, characterization of new generation
bis-benzoxazole derivatives will have a significant contribution on the
development of new era anti-cancer drug candidates.

References

  • [1] Williams GH, Stoeber K. Cell cycle markers in clinical oncology. CurrOpin Cell Biol 2007; 19: 1- 6.
  • [2] Bower JJ et al. Topoisomerase IIalpha maintains genomic stability through decatenationG(2) checkpoint signaling. Oncogene 2010; 29: 4787–4799.
  • [3] Hartwell LH, Kastan MB. Cell cycle control and cancer. Science1994; 266: 1821–1828.
  • [4] Marie Classon EH. The retinoblastoma tumor suppressor in development and cancer. Nat Rev Cancer 2002; 2: 910–917.
  • [5] Xu B, Kim ST, Kastan MB. Involvement of Brca1 in S-Phase and G2-Phase checkpoints after ionizing irradiation. Mol Cell Biol 2001; 21: 3445–3450.
  • [6] Rui-Hong Wang HY, Chu-Xia Deng. A requirement for breast-cancer-associated gene 1 (BRCA1) in the spindle checkpoint. Proc Natl Acad Sci 2004; 101: 17108–17113.
  • [7] Santarpia L, et al. DNA repair gene patters as prognostic and predictive factors in molecular breast cancer subtypes. Oncologist 2013; 18: 1063–1073.
  • [8] Sorlie T, et al. Gene expression patterns of breast carcinomas distinguish tumor subclasses with clinical implications. Proc Natl Acad Sci 2001; 98: 10869–10874.
  • [9] Nakagawa T, et al. Identification of decatenation G2 checkpoint impairment independently of DNA damage G2 checkpoint in human lung cancer cell lines. Cancer Res 2004; 64: 4826–4832.
  • [10] Hinck L, Näthke I. Changes in cell and tissue organization in cancer of the breast and colon. Curr Opin Cell Biol 2014;0:87–95.
  • [11] Cho EH, et al. Characterization of circulating tumor cell aggregates identified in patients with epithelial tumors. Phys Biol 2012; 9: 016001.
  • [12] De Smedt L, Palmans S, Sagaert X. Tumour budding in colorectal cancer: what do we know and what can we do?. Virchows Archiv 2016; 468: (397).
  • [13] Gustavsson B, et al. A Review of the Evolution of Systemic Chemotherapy in the Management of Colorectal Cancer. Clin Col Canc 2015; 14: 1.
  • [14] Huang CY, Ju DT, Chang CF, Muralidhar Reddy P, Velmurugan BK. A review on the effects of current chemotherapy drugs and natural agents in treating non–small cell lung cancer. BioMedicine 2017; 7(4): 23.
  • [15] Longo DL, Fauci AS, Kasper DL, Hauser SL, Jameson JL, Loscalzo J. Harrison’s Principles of internal medicine. 18th ed. New York: McGraw-Hill Companies, 2011.
  • [16] Andreae S. Lexikon der Krankheiten und Untersuchungen. Stuttgart: Thieme, 2008.
  • [17] Hu Q, Sun W, Wang C, Gu Z. Recent Advances of Cocktail Chemotherapy by Combination Drug Delivery Systems. Adv. Drug Deliv. Rev. 2016; 98: 19–34.
  • [18] Hoelder S, Clarke PA, Workman P. Discovery of small molecule cancer drugs: Successes, challenges and opportunities. Mol Oncol 2012; 6: 2.
  • [19] Pearce A, Haas M, Viney R, Pearson SA, Haywood P, Brown C, et al. Incidence and severity of self-reported chemotherapy side effects in routine care: A prospective cohort study. PLoS ONE 2017; 12(10): e0184360. [20] Ihbe-Heffinger A, Ehlken B, Bernard R, Berger K, Peschel C, Eichler HG, et al. The impact of delayed chemotherapy-induced nausea and vomiting on patients, health resource utilization and costs in German cancer centers. Ann Oncol 2004; 15(3):1.
  • [21] Khoshbin AR, et al. The effect of radiotherapy and chemotherapy on osmotic fragility of red blood cells and plasma levels of malondialdehyde in patients with breast cancer. Rep Pract Oncol Radiother 2015; 20(4): 305–308.
  • [22] Global Burden of Disease Cancer Collaboration. The Global Burden of Cancer 2013. JAMA Oncology 2015; 1(4): 505–527.
  • [23] Ayaz F, Kheeree R, Isse QA, Ersan RH, Algul O. DNA Base Bioisosteres, Bis-benzoxazoles, Exert Anti-proliferative Effect on Human Prostate and Breast Cancer Cells JOTCSA 2018; 5(3): 1145-1152.
  • [24] Kumar D, Jacob MR, Reynolds MB, Kerwin SM. Synthesis and evaluation of anticancer benzoxazoles and benzimidazoles related to UK-1. Bioorg Med Chem 2002; 10(12):3997-4004.
There are 23 citations in total.

Details

Primary Language English
Subjects Structural Biology
Journal Section Articles
Authors

Furkan Ayaz 0000-0003-0271-0594

Qadar Ahmed Isse This is me 0000-0002-7391-2014

Rusmeenee Kheeree This is me 0000-0002-4301-5443

Ronak Haj Ersan This is me 0000-0001-6651-5910

Oztekin Algul 0000-0001-5685-7511

Publication Date July 31, 2019
Published in Issue Year 2019

Cite

APA Ayaz, F., Isse, Q. A., Kheeree, R., Ersan, R. H., et al. (2019). BISBENZOXAZOLE DERIVATIVES HAD ANTI-PROLIFERATIVE EFFECT ON HUMAN CANCER CELLS. Eskişehir Teknik Üniversitesi Bilim Ve Teknoloji Dergisi - C Yaşam Bilimleri Ve Biyoteknoloji, 8(2), 203-211. https://doi.org/10.18036/estubtdc.598863
AMA Ayaz F, Isse QA, Kheeree R, Ersan RH, Algul O. BISBENZOXAZOLE DERIVATIVES HAD ANTI-PROLIFERATIVE EFFECT ON HUMAN CANCER CELLS. Eskişehir Teknik Üniversitesi Bilim ve Teknoloji Dergisi - C Yaşam Bilimleri Ve Biyoteknoloji. July 2019;8(2):203-211. doi:10.18036/estubtdc.598863
Chicago Ayaz, Furkan, Qadar Ahmed Isse, Rusmeenee Kheeree, Ronak Haj Ersan, and Oztekin Algul. “BISBENZOXAZOLE DERIVATIVES HAD ANTI-PROLIFERATIVE EFFECT ON HUMAN CANCER CELLS”. Eskişehir Teknik Üniversitesi Bilim Ve Teknoloji Dergisi - C Yaşam Bilimleri Ve Biyoteknoloji 8, no. 2 (July 2019): 203-11. https://doi.org/10.18036/estubtdc.598863.
EndNote Ayaz F, Isse QA, Kheeree R, Ersan RH, Algul O (July 1, 2019) BISBENZOXAZOLE DERIVATIVES HAD ANTI-PROLIFERATIVE EFFECT ON HUMAN CANCER CELLS. Eskişehir Teknik Üniversitesi Bilim ve Teknoloji Dergisi - C Yaşam Bilimleri Ve Biyoteknoloji 8 2 203–211.
IEEE F. Ayaz, Q. A. Isse, R. Kheeree, R. H. Ersan, and O. Algul, “BISBENZOXAZOLE DERIVATIVES HAD ANTI-PROLIFERATIVE EFFECT ON HUMAN CANCER CELLS”, Eskişehir Teknik Üniversitesi Bilim ve Teknoloji Dergisi - C Yaşam Bilimleri Ve Biyoteknoloji, vol. 8, no. 2, pp. 203–211, 2019, doi: 10.18036/estubtdc.598863.
ISNAD Ayaz, Furkan et al. “BISBENZOXAZOLE DERIVATIVES HAD ANTI-PROLIFERATIVE EFFECT ON HUMAN CANCER CELLS”. Eskişehir Teknik Üniversitesi Bilim ve Teknoloji Dergisi - C Yaşam Bilimleri Ve Biyoteknoloji 8/2 (July 2019), 203-211. https://doi.org/10.18036/estubtdc.598863.
JAMA Ayaz F, Isse QA, Kheeree R, Ersan RH, Algul O. BISBENZOXAZOLE DERIVATIVES HAD ANTI-PROLIFERATIVE EFFECT ON HUMAN CANCER CELLS. Eskişehir Teknik Üniversitesi Bilim ve Teknoloji Dergisi - C Yaşam Bilimleri Ve Biyoteknoloji. 2019;8:203–211.
MLA Ayaz, Furkan et al. “BISBENZOXAZOLE DERIVATIVES HAD ANTI-PROLIFERATIVE EFFECT ON HUMAN CANCER CELLS”. Eskişehir Teknik Üniversitesi Bilim Ve Teknoloji Dergisi - C Yaşam Bilimleri Ve Biyoteknoloji, vol. 8, no. 2, 2019, pp. 203-11, doi:10.18036/estubtdc.598863.
Vancouver Ayaz F, Isse QA, Kheeree R, Ersan RH, Algul O. BISBENZOXAZOLE DERIVATIVES HAD ANTI-PROLIFERATIVE EFFECT ON HUMAN CANCER CELLS. Eskişehir Teknik Üniversitesi Bilim ve Teknoloji Dergisi - C Yaşam Bilimleri Ve Biyoteknoloji. 2019;8(2):203-11.