Nuclear Medicine and Biology
Volume 35, Issue 4 , Pages 481-492 , May 2008

Metabolic comparison of radiolabeled aniline- and phenol-phthaleins with 131I

  • Uğur Avcıbaşı

      Affiliations

    • Department of Chemistry, Faculty of Art and Science, Celal Bayar University, 45030 Manisa, Turkey
    • Corresponding Author InformationCorresponding author. Tel.: +90 236 2412151 158; fax: +90 236 2412158.
    • ,
  • Nesibe Avcıbaşı

      Affiliations

    • Ege Vocational Training School, Ege University, Bornova, 35100 Izmir, Turkey
    • ,
  • Turan Ünak

      Affiliations

    • Division of Nuclear Chemistry, Department of Chemistry, Ege University, Faculty of Science, Bornova, 35100 Izmir, Turkey
    • ,
  • Perihan Ünak

      Affiliations

    • Department of Nuclear Applications, Ege University, Institute of Nuclear Sciences, Bornova, 35100 Izmir, Turkey
    • ,
  • Fazilet Zümrüt Müftüler

      Affiliations

    • Department of Nuclear Applications, Ege University, Institute of Nuclear Sciences, Bornova, 35100 Izmir, Turkey
    • ,
  • Yeliz Yıldırım

      Affiliations

    • Division of Nuclear Chemistry, Department of Chemistry, Ege University, Faculty of Science, Bornova, 35100 Izmir, Turkey
    • ,
  • Haluk Dinçalp

      Affiliations

    • Department of Chemistry, Faculty of Art and Science, Celal Bayar University, 45030 Manisa, Turkey
    • ,
  • Fikriye Gül Gümüşer

      Affiliations

    • Department of Nuclear Medicine, Celal Bayar University, School of Medicine, 45030 Manisa, Turkey
    • ,
  • Ebru Rükşen Dursun

      Affiliations

    • Department of Nuclear Medicine, Celal Bayar University, School of Medicine, 45030 Manisa, Turkey

Received 11 May 2007 ,Revised 7 February 2008 ,Accepted 14 February 2008.

References 

  1. Ravdin PM, Van Beurden M, Jordan VC. Estrogenic effects of phenolphthalein on human breast cancer cells in vitro. Breast Cancer Res Treat. 1987;9:151–154
  2. Tsutsui T, Tamura Y, Yagi E, Hasegawa K, Tanaka Y, Uehama A, et al. Cell-transforming activity and genotoxicity of phenolphthalein in cultured Syrian hamster embryo cell. Int J Cancer. 1997;73:697–701
  3. Dunnick JK, Hailey JR. Phenolphthalein exposure causes multiple carcinogenic effects in experimental model system. Cancer Res. 1996;56:4922–4926
  4. Herbert JS, Corbett JT, Mason RP. In vitro free radical metabolism of phenolphthalein by peroxidase. Drug Metab Dispos. 1997;25(4):468–480
  5. Starkey DE, Han A, Bao JJ, Ahn CH, Wehmeyer KR, Prenger MC, et al. Fluorogenic assay for b-glucuronidase using microchip-based capillary electrophoresis. J Chromatogr B. 2001;762:33–41
  6. Ünak T, Avcıbaşı U, Yıldırım Y, Çetinkaya B. Attempts to develop a new nuclear measurement technique of b-glucuronidase levels in biological samples. Czech J Phys Suppl A. 2003;53:A797–A802
  7. Ünak T, Avcıbaşı U, Yıldırım Y. A radioanalytical technique for measurement of beta-glucuronidase activity. J Radioanal Nucl Chem. 2005;266(3):503–506
  8. Mostafa MH, Sheweita SA, O'connor PJ. Relationship between schistosomiasis and bladder cancer. Clin Microbiol Rev. 1999;12:97–111
  9. Liu CS, Liou SH, Loh CH, Yu YC, Uang SN, Shih TS, et al. Occupational bladder cancer in a 4,4′-methylenebis(2-chloroaniline) (MBOCA)-exposed worker. Environ Health Persp. 2005;113(6):771–774
  10. Robert A, Ducos P, Francin JM. Biological monitoring of workers exposed to 4,4′-methylene-bis-(2-orthochloroaniline). I. A new and easy determination of “free” and “total” MOCA in urine. Int Arch Occup Environ Health. 1999;72:223–237
  11. Lamm DL, Torti FM. Bladder cancer. Cancer J Clin. 1996;49:103–112
  12. Rubino GF, Scansett G, Pioltto G. The carcinogenic effects of aromatic amines: an epidemiological study on the role of o-toluidine and 4,49-methylene bis(2-methylaniline) in inducing bladder cancer in man. Environ Res. 1982;27:241–245
  13. Ward E, Carpenter A, Markowitz S, Halpering D. Excess number of bladder cancer in workers exposed to orthotoluidine and aniline. J Natl Cancer Inst. 1991;83:501–506
  14. Ferlin MG, Dalla Via L, Gia OM. Synthesis and antiproliferative activity of some new DNA-targeted alkylating pyrroloquinolines. Bioorgan Med Chem. 2004;12(4):771–774
  15. Connors TA, Whisson ME. Cure of mice bearing advanced plasma cell tumours with Aniline Mustard: the relationship between glucuronidase activity and tumour sensitivity. Nature,. 1966;210:866–867
  16. Ferguson LR, Liu AP, Denny WA, Cullinane C, Talarico T, Phillips DR. Transcriptional blockages in a cell-free system by sequence-selective DNA alkylating agents. Chem-Biol Interact. 2000;126(1):15–31
  17. Ünak T, Akgun Z, Duman Y, Yıldırım Y, Avcıbaşı U, Çetinkaya B. Radioiodination and preliminary biological tests of aniline-mustard and its glucuronide conjugate as a potential anticancer prodrug. J Radioanal Nucl Chem. 2003;256(3):529–534
  18. Hubacher MH. Anilinephthalein. Notes 1951;73:5885–5886.
  19. Zihnioglu F. 1992. Doctorate Thesis. E.U. Graduate school of natural and applied sciences chemistry department biochemistry, Section Code, p. 169.
  20. Bradford MM. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem. 1976;72:248–254
  21. Alkharfy KM, Frye RF. Sensitive liquid chromatographic method using fluorescence detection for the determination of estradiol 3- and 17-glucuronides in rat and human liver microsomal incubations: formation kinetics. J Chromatogr B Analyt Technol Biomed Life Sci. 2002;1:33–38
  22. Stevenson DE. Optimisation of UDP-glucuronyl transferase-catalysed synthesis of testosterone-b-d-glucuronide by inhibition of contaminating b-glucuronidase. Biotech Techn. 1999;13:17–21
  23. Stevenson DE, Hubl U. Optimization of b-D-glucuronide synthesis using UDP-glucurnoyl transferase. Enzyme and Microbial Technology. 1999;24:388–396
  24. Ünak T, Ünak P. Synkavit and its direct labelling with iodine-125, as a potential anti-cancer drug. Nucl Med Biol. 1993;20(7):889–894
  25. Green MD, Tephly TR. N-Glucuronidation of carcinogenic aromatic amines catalyzed by rat hepatic microsomal preparations and purified rat liver uridine 5′-diphosphate-glucuronosyltransferase. Cancer Res. 1987;47:2028–2031
  26. Miller EC, Miller JA, Hartmann HA. N-Hydroxy-2-acetylaminofluorence: a metabolite of 2-acethylaminofluorene with increased carcinogen activity in the rat. Cancer Res. 1961;21:815–824
  27. Garner RC, Martin CN, Clayson DB. Carcinogenic aromatic amines and related compounds. In:  Searle CE editors. Chemical carcinogens. 2nd edition. Washington, DC: American Chemical Society; 1984;p. 175–276
  28. Kadlubar FF, Miller JA, Miller EC. Hepatic microsomal N-glucuronidation and nucleic acid binding of N-hydroxy arylamines in relation to urinary bladder carcinogenesis. Cancer Res. 1977;37:805–814
  29. Poupko JM, Hearn WL, Radomski JL. N-glucuronidation of N-hydroxy aromatic amines: A mechanism for their transport and bladder-specific carcinogenicity. Toxicol Appl Pharmacol. 1979;50:479–484
  30. Kadlubar FF, Unruh LE, Flammang TJ, Sparks D, Mitchum RK, Mulder GJ. Alteration of urinary levels of the carcinogen, N-hydroxy-2-naphthylamine, and its N-glucuronide in the rat by control of urinary pH, inhibition of metabolic sulfation, and changes in biliary excretion. Chem-Biol Interact. 1981;33:129–147
  31. Biber FZ, Ünak P, Ertay T, Medine EI, Zihnioğlu F, Taşçi C, et al. Synthesis of an estradiol glucuronide derivative and investigation of its radiopharmaceutical potential. Appl. Radiat. Isot. 2006;64(7):778–788
  32. Anghileri LJ, Miller ES. b-Glucuronidase activity in tumors accumulation of radioiodinated phenolphthalein. Oncology,. 1971;25:19–32

PII: S0969-8051(08)00069-3

doi: 10.1016/j.nucmedbio.2008.02.003

Nuclear Medicine and Biology
Volume 35, Issue 4 , Pages 481-492 , May 2008

Article Tools

* Image Usage & Resolution