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Investigation of Radiopharmaceutical Potential of an Unsymmetrical Perylene diimide DMANPER Radiolabeled with 131I ​

Year 2011, Volume: 39 Issue: 3, 289 - 296, 01.08.2011

Abstract

The aim of this study was to investigate the radiopharmaceutical potential of N- 2,6-diisopropylphenyl -N’- [4- N,N-dimethylaminophenyl ]-perylene-3,4,9,10-tetra carboxylic diimide DMANPER radiolabeled with 131I using scintigraphic imaging and biodistributional techniques. Radiolabeled DMANPER 131I-DMANPER was intravenously injected into an adult male Albino rabbit via its ear vein anesthetizing with a mixture of Alfazyne and Alfamine Serva to determine dynamic and static situations of radiolabeled compound in the rabbit metabolism. Three rats were used for biodistribution studies corresponding to different time intervals. The animals were sacrificed by heart puncture under ether anesthesia within post-injection time intervals ranging from 30 to 300 min. Results were expressed as % of the injected dose per gram tissue % ID/g . TLRC analysis showed that DMANPER was successfully radioiodinated with 131I with a yield of practically 100 %. According to scintigraphy studies, 131I-DMANPER was completely accumulated in the stomach in 30 min. In the biodistributional data for 131I-DMANPER in rats, a significant amount of activity is seen in the stomach between 30-60 min. It can be concluded that 131I-DMANPER may be an alternative imaging agent like N- 2,6- diisopropylphenyl -N`- 4-pyridyl -perylene-3,4,9,10-tetracarboxylic diimide PYPER to be a potential agent for diagnosis and perhaps therapy of stomach cancer.

References

  • N.W. Kim, M.A. Piatyszek, K.R. Prowse, C.B. Harley, M.D. West, P.L.C. Ho, Specific association of human telomerase activity with immortal cells and cancer Science, 266 (1994) 2011.
  • J. Lingner, T.R. Hughes, A. Shevchenko, M. Mann, V. Lundblad, Cech TR, Reverse transcriptase motifs in the catalytic subunit of telomerase, Science, 276 (1997) 561.
  • T.M. Nakamura, G.B. Morin, K.B. Chapman, S.L. Weinrich, W.H. Andrews, J. Lingner, Telomerase catalytic subunit homologs from fission yeast and human, Science, 277 (1997) 955.
  • D. Sun, B. Thompson, B.E. Cathers, M. Salazar, S.M. Kerwin, J.O. Trent, Inhibition of human telomerase by a G-quadruplex-interactive compound, J. Med. Chem, 40 (1997) 2113.
  • G. Laughlan, A.I.H. Murchie, D.G. Norman, M.H. Moore, P.C.E. Moody, D.M.J. Lilley, The high- resolution crystal structure of a parallel-stranded guanine tetraplex, Science, 265 (1994) 520.
  • D.E. Gilbert, J. Feigon, Multi-stranded DNA structures, Curr. Opin. Struct. Biol., 9 (1999) 305. 7. H. Arthanari, S. Basu, T.L. Kawano, P.H. Bolton, Fluorescent dyes specific for quadruplex DNA, Nucleic. Acids Res, 26 (1998) 3724.
  • I. Haq, J.O. Trent, B.Z. Chowdhry, T.C. Jenkins, intercalative G-tetraplex stabilization of telomeric DNA by a cationic porphyrin, J. Am. Chem. Soc, 121 (1999) 1768.
  • M.A. Read, S. Neidle, Structural characterization of a guanine-quadruplex ligand complex, Biochemistry, 39 (2000) 13422.
  • S.M. Kerwin, D. Sun, J.T. Kern, A. Rangan, P.W. Thomas, G-quadruplex DNA binding by a series of carbocyanine dyes, Bioorg. Med. Chem. Lett, 11
  • P. Alberti, P. Schmitt, C.H. Nguyen, C. Rivalle, M. Hoarau, D.S. Grierson, Benzoindoloquinolines interact with DNA tetraplexes and inhibit telomerase, Bioorg. Med. Chem. Lett, 12 (2002) 1071.
  • T. Ünak, Potential use of radiolabeled glucuronide prodrugs with auger and/or alpha emitters in combined chemo- and radio-therapy of cancer, Curr. Pharm. Design, 6 (2000) 1127.
  • H. Dinçalp, N. Avcıbaşı, S. Içli, Spectral properties and G-quadruplex DNA binding selectivities of a series of unsymmetrical perylene diimides, J. Photoch. Photobio. A, 185 (2007) 1.
  • U. Avcıbaşı, H. Dinçalp, T. Ünak, Y. Yıldırım, N. Avcıbaşı, Y. Duman, Preliminary tests of the radiopharmaceutical potential of N-(2,6- diisopropylphenyl)-N ’-(4-pyridyl)-per ylene- 3,4,9,10-tetracarboxylic diimide radiolabeled with iodine-131, J. Radioanal. Nucl. Ch, 273(3) (2007) 669.
  • E. Protozanova, R.B. Macgregor, Kinetic footprinting of DNA triplex formation, Anal. Biochem, 243 (1996) 92.
  • W. Guschlbauer, J.F. Chantot, D. Thiele, Four- stranded nucleic acid structures 25 years later: From guanosine gels to telomer DNA, J. Biomol. Struct. Dyn, 8 (1990) 491.
  • R. Samudrala, X. Zhang, R.M. Wadkins, D.L. Mattern, Synthesis of a non-cationic, water-soluble perylenetetracarboxylic diimide and its interactions with G-quadruplex-forming DNA, Anal. Biochem, 15 (2007) 186.
  • L. Ma, H. Tai, C. Li, Y. Zhang, Z. Wang, W.Z. Ji, Photodynamic inhibitory effects of three perylenequinones on human colorectal carcinoma cell line and primate embryonic stem cell line, World J. Gastroenterol., 9(3) (2003) 485.
  • J.S. Ma, F. Yan, C.Q. Wang, J.Y. An, Hypocrellin-A sensitized photooxidation of bilirubin, Photochem. Photobiol., 50 (1989) 827.
  • G.G. Miller, K. Brown, A.M. Ballangrud, O. Barajas, Z. Xiao, J. Tulip, J.W. Lown, J.M. Leithoff, M.J. Allalunis- Turner, R.D. Mehta and R.B. Moore, Preclinical assessment of hypocrellin B and hypocrellin B derivatives as sensitizers for photodynamic therapy of cancer: progress update, Photochem Photobiol, 65 (1997) 714.
  • Y.Y. He, J.Y. An, L.J. Jiang, Glycoconjugated hypocrellin: synthesis of [(b-D-glucosyl)ethylthiyl] hypocrellins and photosensitized generation of singlet oxygen, Biochim. Biophys. Acta, 1472 (1999) 232.
  • Z.Diwu, Novel therapeutic and diagnostic application of Photobiol., 61 (1995) 529. hypericins, Photochem.
  • C. Schleger, N. Krebsfaenger, A. Kalkuhl, R. Bader, T. Singer, Innovative cell culture methods in drug development, ALTEX, 18 (2001) 8.
  • J. Rohwedel, K. Guan, C. Hegert, A.M. Wobus, Embryonic stem cells as an in vitro model for mutagenicity, cytotoxicity and embryotoxicity studies: present state and future prospects, Toxicol. in vitro, 15 (2001) 741.
  • Z.J. Diwu, R.P. Haugland, J.X. Liu, J.W. Lown, G.G. Miller, R.B. Moore, K. Brown, J. Tulip and M.S. McPhee, Photosensitization by anticancer agents 21: New perylene- and aminonaphthoquinones, Free Radic Biol Med, 20 (1996) 589.
  • Z.J. Wang, Y.Y. He, C.G. Huang, J.S. Huang, Y.C. Huang, J.Y. An, Y. Gu, L.J. Jiang, Pharmacokinetics, tissue distribution and photodynamic therapy efficacy of liposomal-delivered hypocrellin A, a potential photosensitizer for tumor therapy, Photochem. Photobiol., 70 (1999) 773.
  • J. Hirayama, K. Ikebuchi, H. Abe, K.W. Kwon, Y. Ohnishi, M. Horiuchi, M. Shinagawa, K. Ikuta, N. Kamo and S. Sekiguchi, Photoinactivation of virus infectivity by hypocrellin A, Photochem. Photobiol.
  • J.B. Hudson, J. Zhou, J. Chen, L. Harris, L. Yip, G.H. Towers, Hypocrellin, from Hypocrella bambuase, is phototoxic to human immunodeficiency virus, Photochem. Photobiol., 60 (1994) 253.

Radyoaktif 131I ile İşaretli Asimetrik Bir Perilen diimid’in DMANPER Radyofarmösitik Potansiyelinin İncelenmesi

Year 2011, Volume: 39 Issue: 3, 289 - 296, 01.08.2011

Abstract

B u çalışmanın amacı sintigrafik görüntüleme ve biyodağılım teknikleri kullanılarak, 131I ile işaretlenmiş N- 2,6diizopropilfenil -N’-[4- N,N-dimetillaminofenil ]-perilen-3,4,9,10-tetra karboksilik diimid’in DMANPER radyofarmösitik potansiyelini incelemektir. Radyo işaretli DMANPER 131I-DMANPER , tavşan metabolizmasında radyoaktif olarak işaretlenmiş bileşiğin dinamik ve statik durumunu belirlemek için, Alfazin ve Alfamin karışımı ile anestezi verilmiş yetişkin bir erkek Albino tavşana kulak veni yoluyla enjekte edilmiştir. Biyodağılım çalışmalarında farklı zaman aralıkları için üç adet sıçan kullanılmıştır. Enjeksiyondan sonra 30 ile 300 dakika arasında değişen bir zaman aralığı içerisinde, hayvanların eter anestezisi ile kalplerinin durdurulmasıyla hayatlarına son verdirilmiştir. Sonuçlar, gram doku başına enjekte edilen dozun %’si olarak ifade edilmiştir % ID/g . İnce tabaka radyo-kromatografi analizleri TLRC , DMANPER’in 131I ile başarılı bir biçimde, yaklaşık % 100 verimle işaretlendiğini göstermiştir. 131I-DMANPER 30 dakikalık süre içerisinde tamamen midede birikmiştir. 131I-DMANPER için farelerde yapılan biyodağılım sonuçlarında, 30 ile 60 dakika arasında en fazla aktivite midede görülmüştür. 131I-DMANPER’in mide kanserinin teşhisi ve tedavisi için N- 2,6-diizopropilfenilN`- 4-piridil -perilen-3,4,9,10-tetrakarboksilik diimid PYPER gibi bir alternatif görüntüleme ajanı olabileceği sonucuna varılabilir

References

  • N.W. Kim, M.A. Piatyszek, K.R. Prowse, C.B. Harley, M.D. West, P.L.C. Ho, Specific association of human telomerase activity with immortal cells and cancer Science, 266 (1994) 2011.
  • J. Lingner, T.R. Hughes, A. Shevchenko, M. Mann, V. Lundblad, Cech TR, Reverse transcriptase motifs in the catalytic subunit of telomerase, Science, 276 (1997) 561.
  • T.M. Nakamura, G.B. Morin, K.B. Chapman, S.L. Weinrich, W.H. Andrews, J. Lingner, Telomerase catalytic subunit homologs from fission yeast and human, Science, 277 (1997) 955.
  • D. Sun, B. Thompson, B.E. Cathers, M. Salazar, S.M. Kerwin, J.O. Trent, Inhibition of human telomerase by a G-quadruplex-interactive compound, J. Med. Chem, 40 (1997) 2113.
  • G. Laughlan, A.I.H. Murchie, D.G. Norman, M.H. Moore, P.C.E. Moody, D.M.J. Lilley, The high- resolution crystal structure of a parallel-stranded guanine tetraplex, Science, 265 (1994) 520.
  • D.E. Gilbert, J. Feigon, Multi-stranded DNA structures, Curr. Opin. Struct. Biol., 9 (1999) 305. 7. H. Arthanari, S. Basu, T.L. Kawano, P.H. Bolton, Fluorescent dyes specific for quadruplex DNA, Nucleic. Acids Res, 26 (1998) 3724.
  • I. Haq, J.O. Trent, B.Z. Chowdhry, T.C. Jenkins, intercalative G-tetraplex stabilization of telomeric DNA by a cationic porphyrin, J. Am. Chem. Soc, 121 (1999) 1768.
  • M.A. Read, S. Neidle, Structural characterization of a guanine-quadruplex ligand complex, Biochemistry, 39 (2000) 13422.
  • S.M. Kerwin, D. Sun, J.T. Kern, A. Rangan, P.W. Thomas, G-quadruplex DNA binding by a series of carbocyanine dyes, Bioorg. Med. Chem. Lett, 11
  • P. Alberti, P. Schmitt, C.H. Nguyen, C. Rivalle, M. Hoarau, D.S. Grierson, Benzoindoloquinolines interact with DNA tetraplexes and inhibit telomerase, Bioorg. Med. Chem. Lett, 12 (2002) 1071.
  • T. Ünak, Potential use of radiolabeled glucuronide prodrugs with auger and/or alpha emitters in combined chemo- and radio-therapy of cancer, Curr. Pharm. Design, 6 (2000) 1127.
  • H. Dinçalp, N. Avcıbaşı, S. Içli, Spectral properties and G-quadruplex DNA binding selectivities of a series of unsymmetrical perylene diimides, J. Photoch. Photobio. A, 185 (2007) 1.
  • U. Avcıbaşı, H. Dinçalp, T. Ünak, Y. Yıldırım, N. Avcıbaşı, Y. Duman, Preliminary tests of the radiopharmaceutical potential of N-(2,6- diisopropylphenyl)-N ’-(4-pyridyl)-per ylene- 3,4,9,10-tetracarboxylic diimide radiolabeled with iodine-131, J. Radioanal. Nucl. Ch, 273(3) (2007) 669.
  • E. Protozanova, R.B. Macgregor, Kinetic footprinting of DNA triplex formation, Anal. Biochem, 243 (1996) 92.
  • W. Guschlbauer, J.F. Chantot, D. Thiele, Four- stranded nucleic acid structures 25 years later: From guanosine gels to telomer DNA, J. Biomol. Struct. Dyn, 8 (1990) 491.
  • R. Samudrala, X. Zhang, R.M. Wadkins, D.L. Mattern, Synthesis of a non-cationic, water-soluble perylenetetracarboxylic diimide and its interactions with G-quadruplex-forming DNA, Anal. Biochem, 15 (2007) 186.
  • L. Ma, H. Tai, C. Li, Y. Zhang, Z. Wang, W.Z. Ji, Photodynamic inhibitory effects of three perylenequinones on human colorectal carcinoma cell line and primate embryonic stem cell line, World J. Gastroenterol., 9(3) (2003) 485.
  • J.S. Ma, F. Yan, C.Q. Wang, J.Y. An, Hypocrellin-A sensitized photooxidation of bilirubin, Photochem. Photobiol., 50 (1989) 827.
  • G.G. Miller, K. Brown, A.M. Ballangrud, O. Barajas, Z. Xiao, J. Tulip, J.W. Lown, J.M. Leithoff, M.J. Allalunis- Turner, R.D. Mehta and R.B. Moore, Preclinical assessment of hypocrellin B and hypocrellin B derivatives as sensitizers for photodynamic therapy of cancer: progress update, Photochem Photobiol, 65 (1997) 714.
  • Y.Y. He, J.Y. An, L.J. Jiang, Glycoconjugated hypocrellin: synthesis of [(b-D-glucosyl)ethylthiyl] hypocrellins and photosensitized generation of singlet oxygen, Biochim. Biophys. Acta, 1472 (1999) 232.
  • Z.Diwu, Novel therapeutic and diagnostic application of Photobiol., 61 (1995) 529. hypericins, Photochem.
  • C. Schleger, N. Krebsfaenger, A. Kalkuhl, R. Bader, T. Singer, Innovative cell culture methods in drug development, ALTEX, 18 (2001) 8.
  • J. Rohwedel, K. Guan, C. Hegert, A.M. Wobus, Embryonic stem cells as an in vitro model for mutagenicity, cytotoxicity and embryotoxicity studies: present state and future prospects, Toxicol. in vitro, 15 (2001) 741.
  • Z.J. Diwu, R.P. Haugland, J.X. Liu, J.W. Lown, G.G. Miller, R.B. Moore, K. Brown, J. Tulip and M.S. McPhee, Photosensitization by anticancer agents 21: New perylene- and aminonaphthoquinones, Free Radic Biol Med, 20 (1996) 589.
  • Z.J. Wang, Y.Y. He, C.G. Huang, J.S. Huang, Y.C. Huang, J.Y. An, Y. Gu, L.J. Jiang, Pharmacokinetics, tissue distribution and photodynamic therapy efficacy of liposomal-delivered hypocrellin A, a potential photosensitizer for tumor therapy, Photochem. Photobiol., 70 (1999) 773.
  • J. Hirayama, K. Ikebuchi, H. Abe, K.W. Kwon, Y. Ohnishi, M. Horiuchi, M. Shinagawa, K. Ikuta, N. Kamo and S. Sekiguchi, Photoinactivation of virus infectivity by hypocrellin A, Photochem. Photobiol.
  • J.B. Hudson, J. Zhou, J. Chen, L. Harris, L. Yip, G.H. Towers, Hypocrellin, from Hypocrella bambuase, is phototoxic to human immunodeficiency virus, Photochem. Photobiol., 60 (1994) 253.
There are 27 citations in total.

Details

Primary Language English
Journal Section Research Article
Authors

Uğur Avcıbaşı This is me

Haluk Dinçalp This is me

Nesibe Avcıbaşı This is me

Publication Date August 1, 2011
Published in Issue Year 2011 Volume: 39 Issue: 3

Cite

APA Avcıbaşı, U., Dinçalp, H., & Avcıbaşı, N. (2011). Investigation of Radiopharmaceutical Potential of an Unsymmetrical Perylene diimide DMANPER Radiolabeled with 131I ​. Hacettepe Journal of Biology and Chemistry, 39(3), 289-296.
AMA Avcıbaşı U, Dinçalp H, Avcıbaşı N. Investigation of Radiopharmaceutical Potential of an Unsymmetrical Perylene diimide DMANPER Radiolabeled with 131I ​. HJBC. August 2011;39(3):289-296.
Chicago Avcıbaşı, Uğur, Haluk Dinçalp, and Nesibe Avcıbaşı. “Investigation of Radiopharmaceutical Potential of an Unsymmetrical Perylene Diimide DMANPER Radiolabeled With 131I ​”. Hacettepe Journal of Biology and Chemistry 39, no. 3 (August 2011): 289-96.
EndNote Avcıbaşı U, Dinçalp H, Avcıbaşı N (August 1, 2011) Investigation of Radiopharmaceutical Potential of an Unsymmetrical Perylene diimide DMANPER Radiolabeled with 131I ​. Hacettepe Journal of Biology and Chemistry 39 3 289–296.
IEEE U. Avcıbaşı, H. Dinçalp, and N. Avcıbaşı, “Investigation of Radiopharmaceutical Potential of an Unsymmetrical Perylene diimide DMANPER Radiolabeled with 131I ​”, HJBC, vol. 39, no. 3, pp. 289–296, 2011.
ISNAD Avcıbaşı, Uğur et al. “Investigation of Radiopharmaceutical Potential of an Unsymmetrical Perylene Diimide DMANPER Radiolabeled With 131I ​”. Hacettepe Journal of Biology and Chemistry 39/3 (August 2011), 289-296.
JAMA Avcıbaşı U, Dinçalp H, Avcıbaşı N. Investigation of Radiopharmaceutical Potential of an Unsymmetrical Perylene diimide DMANPER Radiolabeled with 131I ​. HJBC. 2011;39:289–296.
MLA Avcıbaşı, Uğur et al. “Investigation of Radiopharmaceutical Potential of an Unsymmetrical Perylene Diimide DMANPER Radiolabeled With 131I ​”. Hacettepe Journal of Biology and Chemistry, vol. 39, no. 3, 2011, pp. 289-96.
Vancouver Avcıbaşı U, Dinçalp H, Avcıbaşı N. Investigation of Radiopharmaceutical Potential of an Unsymmetrical Perylene diimide DMANPER Radiolabeled with 131I ​. HJBC. 2011;39(3):289-96.

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