314
Views
5
CrossRef citations to date
0
Altmetric
Research Articles

Exploring the binding mechanism of saccharin and sodium saccharin to promoter of human p53 gene by theoretical and experimental methods

, , , &
Pages 548-564 | Received 17 Nov 2018, Accepted 09 Feb 2019, Published online: 11 Mar 2019

References

  • Amatya, V. J., Naumann, U., Weller, M., & Ohgaki, H. (2005). TP53 promoter methylation in human gliomas. Acta Neuropathologica, 110(2), 178–184. doi:10.1007/s00401-005-1041-5
  • Andreatta, M., Munoz, S., Lantieri, M., Eynard, A., & Navarro, A. (2008). Artificial sweetener consumption and urinary tract tumors in Cordoba, Argentina. Preventive Medicine, 47(1), 136–139. doi:10.1016/j.ypmed.2008.03.015
  • Arnold, D. L. (1984). Toxicology of saccharin. Fundamental and Applied Toxicology: Official Journal of the Society of Toxicology, 4(5), 674–685.
  • Bell, R. P., & Higginson, W. (1949). The catalyzed dehydration of acetaldehyde hydrate, and the effect of structure on the velocity of protolytic reactions. Proceedings of the Royal Society of London A, 197(1049), 141–159.
  • Berendsen, H. J., Postma, J. V., van Gunsteren, W. F., DiNola, A., & Haak, J. (1984). Molecular dynamics with coupling to an external bath. The Journal of Chemical Physics, 81(8), 3684–3690. doi:10.1063/1.448118
  • Bienz-Tadmor, B., Zakut‐Houri, R., Libresco, S., Givol, D., & Oren, M. (1985). The 5′ region of the p53 gene: Evolutionary conservation and evidence for a negative regulatory element. The EMBO Journal, 4(12), 3209–3213. doi:10.1002/j.1460-2075.1985.tb04067.x
  • Birdsall, C. K., & Langdon, A. B. (2004). Plasma physics via computer simulation. Boca Raton, FL: CRC Press.
  • Bosetti, C., Gallus, S., Talamini, R., Montella, M., Franceschi, S., Negri, E., & La Vecchia, C. (2009). Artificial sweeteners and the risk of gastric, pancreatic, and endometrial cancers in Italy. Cancer Epidemiology and Prevention Biomarkers, 18(8), 2235–2238. doi:10.1158/1055-9965.EPI-09-0365
  • Cesarone, C., Bolognesi, C., & Santi, L. (1980). Renal and hepatic toxicity studies in mice treated with sodium saccharin: Breaks in single-stranded DNA. Bollettino Della Società Italiana di Biologia Sperimentale, 56(23), 2486–2491.
  • Cheatham, T. E., III, Srinivasan, J., Case, D. A., & Kollman, P. A. (1998). Molecular dynamics and continuum solvent studies of the stability of polyG–polyC and polyA–polyT DNA duplexes in solution. Journal of Biomolecular Structure and Dynamics, 16(2), 265–280. doi:10.1080/07391102.1998.10508245
  • Cohen, S. M., Cano, M., Earl, R. A., Carson, S. D., & Garland, E. M. (1991). A proposed role for silicates and protein in the proliferative effects of saccharin on the male rat urothelium. Carcinogenesis, 12(9), 1551–1555. doi:10.1093/carcin/12.9.1551
  • Cohen, S. M., Garland, E. M., Cano, M., John, M. K. S., Khachab, M., Wehner, J. M., & Arnold, L. L. (1995). Effects of sodium ascorbate, sodium saccharin and ammonium chloride on the male rat urinary bladder. Carcinogenesis, 16(11), 2743–2750. doi:10.1093/carcin/16.11.2743
  • Darden, T., York, D., & Pedersen, L. (1993). Particle mesh Ewald: An N⋅ log (N) method for Ewald sums in large systems. The Journal of Chemical Physics, 98(12), 10089–10092. doi:10.1063/1.464397
  • Ellwein, L. B., & Cohen, S. M. (1990). The health risks of saccharin revisited. Critical Reviews in Toxicology, 20(5), 311–326. doi:10.3109/10408449009089867
  • Fahlberg, C., & Remsen, I. (1879). Ueber die oxydation des orthotoluolsulfamids. Berichte Der Deutschen Chemischen Gesellschaft, 12(1), 469–473. doi:10.1002/cber.187901201135
  • Findikli, Z., & Turkoglu, S. (2014). Determination of the effects of some artificial sweeteners on human peripheral lymphocytes using the comet assay. Journal of Toxicology and Environmental Health Sciences, 6(8), 147–153.
  • Frisch, M. J. (1998). Gaussian 98. Revision A.9. Wallingford, CT: Gaussian Inc.
  • Goodsell, D. S., Morris, G. M., & Olson, A. J. (1996). Automated docking of flexible ligands: Applications of AutoDock. Journal of Molecular Recognition, 9(1), 1–5. doi:10.1002/(SICI)1099-1352(199601)9:1<1::AID-JMR241>3.0.CO;2-6
  • Hasegawa, R., & Cohen, S. M. (1986). The effect of different salts of saccharin on the rat urinary bladder. Cancer Letters, 30(3), 261–268.
  • Hess, B., Bekker, H., Berendsen, H. J., & Fraaije, J. G. (1997). LINCS: A linear constraint solver for molecular simulations. Journal of Computational Chemistry, 18(12), 1463–1472. doi:10.1002/(SICI)1096-987X(199709)18:12<1463::AID-JCC4>3.3.CO;2-L
  • Hess, B., Kutzner, C., Van Der Spoel, D., & Lindahl, E. (2008). GROMACS 4: Algorithms for highly efficient, load-balanced, and scalable molecular simulation. Journal of Chemical Theory and Computation, 4(3), 435–447. doi:10.1021/ct700301q
  • Humans and Organization. (1987). Overall evaluations of carcinogenicity: An updating of IARC monographs (Vol. 1–42), Lyon. Geneva, Switzerland: World Health Organization.
  • Humphrey, W., Dalke, A., & Schulten, K. (1996). VMD: Visual molecular dynamics. Journal of Molecular Graphics, 14(1), 33–38.
  • Icsel, C., & Yilmaz, V. T. (2014). In vitro DNA binding studies of the sweetening agent saccharin and its copper(II) and zinc(II) complexes. Journal of Photochemistry and Photobiology. B, Biology, 130, 115–121. doi:10.1016/j.jphotobiol.2013.11.001
  • Jesionek-Kupnicka, D., Szybka, M., Malachowska, B., Fendler, W., Potemski, P., Piaskowski, S., … Zawlik, I. (2014). TP53 promoter methylation in primary glioblastoma: Relationship with TP53 mRNA and protein expression and mutation status. DNA and Cell Biology, 33(4), 217–226. doi:10.1089/dna.2013.2201
  • Jorgensen, W. L., Chandrasekhar, J., Madura, J. D., Impey, R. W., & Klein, M. L. (1983). Comparison of simple potential functions for simulating liquid water. The Journal of Chemical Physics, 79(2), 926–935. doi:10.1063/1.445869
  • Kang, J. H., Kim, S. J., Noh, D.-Y., Park, I. A., Choe, K. J., Yoo, O. J., & Kang, H.-S. (2001). Methylation in the p53 promoter is a supplementary route to breast carcinogenesis: Correlation between CpG methylation in the p53 promoter and the mutation of the p53 gene in the progression from ductal carcinoma in situ to invasive ductal carcinoma. Laboratory Investigation, 81(4), 573–579. doi:10.1038/labinvest.3780266
  • Kashanian, S., Khodaei, M. M., & Kheirdoosh, F. (2013). In vitro DNA binding studies of aspartame, an artificial sweetener. Journal of Photochemistry and Photobiology B: Biology, 120, 104–110. doi:10.1016/j.jphotobiol.2013.01.001
  • Khan, S. (2015). Artificial sweeteners: Safe or unsafe? JPMA. The Journal of the Pakistan Medical Association, 65(2), 225–227.
  • Krowech, G., Faust, J., Endlich, B., & Sandy, M. S. (2003). Evidence on the carcinogenicity of sodium saccharin. Reproductive and Cancer Hazard Assessment Section, Office of Environmental Health Hazard Assessment. Sacramento, CA: California Environmental Protection Agency.
  • Kumari, R., Kumar, R., Consortium, O. S. D. D., & Lynn, A. (2014). g_mmpbsa – A GROMACS tool for high-throughput MM-PBSA calculations. Journal of Chemical Information and Modeling, 54(7), 1951–1962. doi:10.1021/ci500020m
  • Lavery, R., Zakrzewska, K., Beveridge, D., Bishop, T. C., Case, D. A., Cheatham III, T., Laughton, C. (2009). A systematic molecular dynamics study of nearest-neighbor effects on base pair and base pair step conformations and fluctuations in B-DNA. Nucleic Acids Research, 38(1), 299–313. doi:10.1093/nar/gkp834
  • Leach, A. R. (2001). Molecular modelling: Principles and applications. London, England: Pearson Education.
  • Lin, J., Gao, C., & Liu, R. (2013). Interaction mechanism of Trp–Arg dipeptide with calf thymus DNA. Journal of Fluorescence, 23(5), 921–927. doi:10.1007/s10895-013-1217-7
  • Lohani, N., Singh, H. N., & Moganty, R. R. (2016). Structural aspects of the interaction of anticancer drug Actinomycin-D to the GC rich region of hmgb1 gene. International Journal of Biological Macromolecules, 87, 433–442. doi:10.1016/j.ijbiomac.2016.02.060
  • Lutz, W. K., & Schlatter, C. (1977). Saccharin does not bind to DNA of liver or bladder in the rat. Chemico-Biological Interactions, 19(2), 253–257.
  • Mahnam, K., & Raisi, F. (2017). A theoretical and experimental study of calcium, iron, zinc, cadmium, and sodium ions absorption by aspartame. Journal of Biological Physics, 43(1), 87–103. doi:10.1007/s10867-016-9435-2
  • Majumdar, R., Railkar, R., & Dighe, R. R. (2011). Docking and free energy simulations to predict conformational domains involved in hCG–LH receptor interactions using recombinant antibodies. Proteins: Structure, Function, and Bioinformatics, 79(11), 3108–3122. doi:10.1002/prot.23138
  • Mansourian, M., Fassihi, A., Saghaie, L., Madadkar-Sobhani, A., Mahnam, K., & Abbasi, M. (2015). QSAR and docking analysis of A2B adenosine receptor antagonists based on non-xanthine scaffold. Medicinal Chemistry Research, 24(1), 394–407. doi:10.1007/s00044-014-1133-7
  • Mansourian, M., Madadkar-Sobhani, A., Mahnam, K., Fassihi, A., & Saghaie, L. (2012). Characterization of adenosine receptor in its native environment: Insights from molecular dynamics simulations of palmitoylated/glycosylated, membrane-integrated human A 2B adenosine receptor. Journal of Molecular Modeling, 18(9), 4309–4324. doi:10.1007/s00894-012-1427-y
  • Mansourian, M., Mahnam, K., Madadkar-Sobhani, A., Fassihi, A., & Saghaie, L. (2015). Insights into the human A1 adenosine receptor from molecular dynamics simulation: Structural study in the presence of lipid membrane. Medicinal Chemistry Research, 24(10), 3645–3659. doi:10.1007/s00044-015-1409-6
  • Martin, A., Kanetsky, P., Amirimani, B., Colligon, T., Athanasiadis, G., Shih, H., … Weber, B. (2003). Germline TP53 mutations in breast cancer families with multiple primary cancers: Is TP53 a modifier of BRCA1? Journal of Medical Genetics, 40(4), e34–e34.
  • Mokhtaruddin, N. S. M., Yusof, E. N. M., Ravoof, T. B., Tiekink, E. R., Veerakumarasivam, A., & Tahir, M. I. M. (2017). Unusual saccharin-N, O (carbonyl) coordination in mixed-ligand copper (II) complexes: Synthesis, X-ray crystallography and biological activity. Journal of Molecular Structure, 1139, 1–9. doi:10.1016/j.molstruc.2017.03.037
  • Moradi, S. Z., Nowroozi, A., Sadrjavadi, K., Moradi, S., Mansouri, K., Hosseinzadeh, L., & Shahlaei, M. (2018). Direct evidences for the groove binding of the Clomifene to double stranded DNA. International Journal of Biological Macromolecules, 114, 40–53. doi:10.1016/j.ijbiomac.2018.03.040
  • Morris, G. M., Goodsell, D. S., Halliday, R. S., Huey, R., Hart, W. E., Belew, R. K., & Olson, A. J. (1998). Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. Journal of Computational Chemistry, 19(14), 1639–1662. doi:10.1002/(SICI)1096-987X(19981115)19:14<1639::AID-JCC10>3.0.CO;2-B
  • Morris, G. M., Huey, R., Lindstrom, W., Sanner, M. F., Belew, R. K., Goodsell, D. S., & Olson, A. J. (2009). AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility. Journal of Computational Chemistry, 30(16), 2785–2791. doi:10.1002/jcc.21256
  • No, D. C. R. (1987). Saccharin and its salts. Lyon, France: IARC.
  • Pearlman, D. A., Case, D. A., Caldwell, J. W., Ross, W. S., Cheatham, T. E., DeBolt, S., … Kollman, P. (1995). AMBER, a package of computer programs for applying molecular mechanics, normal mode analysis, molecular dynamics and free energy calculations to simulate the structural and energetic properties of molecules. Computer Physics Communications, 91(1-3), 1–41. doi:10.1016/0010-4655(95)00041-D
  • Petitjean, A., Achatz, M., Borresen-Dale, A., Hainaut, P., & Olivier, M. (2007). TP53 mutations in human cancers: Functional selection and impact on cancer prognosis and outcomes. Oncogene, 26(15), 2157–2165. doi:10.1038/sj.onc.1210302
  • Rahimipour, M., Talebi, A. R., Anvari, M., Sarcheshmeh, A. A., & Omidi, M. (2014). Saccharin consumption increases sperm DNA fragmentation and apoptosis in mice. Iranian Journal of Reproductive Medicine, 12(5), 307–312.
  • Saad, A., Khan, F. A., Hayee, A., & Nazir, M. S. (2014). A review on potential toxicity of artificial sweeteners vs safety of stevia: A natural biosweetener. Journal of Biology, Agriculture and Healthcare, 4(15), 1–12.
  • Sasaki, Y. F., Kawaguchi, S., Kamaya, A., Ohshita, M., Kabasawa, K., Iwama, K., … Tsuda, S. (2002). The comet assay with 8 mouse organs: Results with 39 currently used food additives. Mutation Research/Genetic Toxicology and Environmental Mutagenesis, 519(1-2), 103–119. doi:10.1016/S1383-5718(02)00128-6
  • Schernhammer, E. S., Bertrand, K. A., Birmann, B. M., Sampson, L., Willett, W. C., & Feskanich, D. (2012). Consumption of artificial sweetener–and sugar-containing soda and risk of lymphoma and leukemia in men and women. The American Journal of Clinical Nutrition, 96(6), 1419–1428. doi:10.3945/ajcn.111.030833
  • Sharan, R. (2007). Analysis of Biological Networks: Transcriptional Networks – Promoter Sequence Analysis (pp. 1–5). Tel Aviv, Israel: Tel Aviv University.
  • Smith, M. L., & Seo, Y. R. (2002). p53 regulation of DNA excision repair pathways. Mutagenesis, 17(2), 149–156.
  • Sturgeon, S. R., Hartge, P., Silverman, D. T., Kantor, A. F., Linehan, W. M., Lynch, C., & Hoover, R. N. (1994). Associations between bladder cancer risk factors and tumor stage and grade at diagnosis. Epidemiology, 5(2), 218–225. doi:10.1097/00001648-199403000-00012
  • Suzuki, H., & Suzuki, N. (1988). Mutagenicity of saccharin in a human cell strain. Mutation Research, 209(1-2), 13–16.
  • Suzuki, H., & Suzuki, N. (1993). Detection of K-RAS codon 12 mutation by polymerase chain reaction and differential dot-blot hybridization in sodium saccharin-treated human RSA cell. Biochemical and Biophysical Research Communications, 196(2), 956–961. doi:10.1006/bbrc.1993.2342
  • Tomasetti, C., Li, L., & Vogelstein, B. (2017). Stem cell divisions, somatic mutations, cancer etiology, and cancer prevention. Science, 355(6331), 1330–1334. doi:10.1126/science.aaf9011
  • Tuck, S. P., & Crawford, L. (1989). Characterization of the human p53 gene promoter. Molecular and Cellular Biology, 9(5), 2163–2172.
  • van Eyk, A. D. (2015). The effect of five artificial sweeteners on Caco-2, HT-29 and HEK-293 cells. Drug and Chemical Toxicology, 38(3), 318–327. doi:10.3109/01480545.2014.966381
  • Wallace, A. C., Laskowski, R. A., & Thornton, J. M. (1995). LIGPLOT: A program to generate schematic diagrams of protein–ligand interactions. Protein Engineering, Design and Selection, 8(2), 127–134. doi:10.1093/protein/8.2.127
  • Wang, J., Wolf, R. M., Caldwell, J. W., Kollman, P. A., & Case, D. A. (2004). Development and testing of a general AMBER force field. Journal of Computational Chemistry, 25(9), 1157–1174. doi:10.1002/jcc.20035
  • Wang, Y., Xu, Z.-L., Xie, Y.-Y., Tian, Y.-X., Shen, Y.-D., Young, G. M., … Sun, Y.-M. (2011). Development of polyclonal antibody-based indirect competitive enzyme-linked immunosorbent assay for sodium saccharin residue in food samples. Food Chemistry, 126(2), 815–820. doi:10.1016/j.foodchem.2010.11.076
  • Weihrauch, M., & Diehl, V. (2004). Artificial sweeteners-do they bear a carcinogenic risk?. Annals of Oncology: Official Journal of the European Society for Medical Oncology, 15(10), 1460–1465. doi:10.1093/annonc/mdh256
  • Whitehouse, C. R., Boullata, J., & McCauley, L. A. (2008). The potential toxicity of artificial sweeteners. AAOHN Journal, 56(6), 251–261. doi:10.3928/08910162-20080601-02
  • Whysner, J., & Williams, G. M. (1996). Saccharin mechanistic data and risk assessment: Urine composition, enhanced cell proliferation, and tumor promotion. Pharmacology & Therapeutics, 71(1-2), 225–252. doi:10.1016/0163-7258(96)00069-1
  • Wolff, S., & Rodin, B. (1978). Saccharin-induced sister chromatid exchanges in Chinese hamster and human cells. Science, 200(4341), 543–545. doi:10.1126/science.644315
  • Yadav, R. K., & Yadava, U. (2014). Molecular dynamics simulation of DNA duplex, analog of PPT (polypurine tract), its conformation and hydration: A theoretical study. Medicinal Chemistry Research, 23(1), 280–286. doi:10.1007/s00044-013-0631-3
  • Yadava, U., Shukla, B. K., & Roychoudhury, M. (2015). Pyrazolo [3, 4-d] pyrimidines as the inhibitors of mycobacterial β-oxidation trifunctional enzyme. Medicinal Chemistry Research, 24(12), 4002–4015. doi:10.1007/s00044-015-1441-6
  • Yadava, U., Yadav, S. K., & Yadav, R. K. (2017). Electronic structure, vibrational assignments and simulation studies with A/T rich DNA duplex of an aromatic bis-amidine derivative. DNA Repair, 60, 9–17. doi:10.1016/j.dnarep.2017.10.005
  • Yang, J., & Duerksen-Hughes, P. (1998). A new approach to identifying genotoxic carcinogens: p53 induction as an indicator of genotoxic damage. Carcinogenesis, 19(6), 1117–1125. doi:10.1093/carcin/19.6.1117
  • Zhang, G., Wang, L., Zhou, X., Li, Y., & Gong, D. (2014). Binding characteristics of sodium saccharin with calf thymus DNA in vitro. Journal of Agricultural and Food Chemistry, 62(4), 991–1000. doi:10.1021/jf405085g

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.