The Korean Journal of Nuclear Medicine (대한핵의학회지)

The Korean Society of Nuclear Medicine (대한핵의학회)
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Tc-99m Labeling of Dione Bisoxime Compounds

Dione Bisoxime 계통의 화합물에 대한 테크네슘표지 원리에 관한 연구

  • Jeong, Jae-Min (Department of Nuclear Medicine, Seoul National University Hospital) ;
  • Cho, Jung-Hyuk (Laboratory of Organic Synthesis, Korea Institute of Science and Technology) ;
  • Oh, Seung-Joon (Laboratory of Organic Synthesis, Korea Institute of Science and Technology) ;
  • Lee, Myung-Chul (Department of Nuclear Medicine, Seoul National University Hospital) ;
  • Chung, Soo-Wook (Department of Nuclear Medicine, Seoul National University Hospital) ;
  • Chung, June-Key (Department of Nuclear Medicine, Seoul National University Hospital) ;
  • Lee, Dong-Soo (Department of Nuclear Medicine, Seoul National University Hospital) ;
  • Kwark, Cheol-Eun (Department of Nuclear Medicine, Seoul National University Hospital) ;
  • Lee, Kyung-Han (Department of Nuclear Medicine, Seoul National University Hospital) ;
  • Koh, Chang-Soon (Department of Nuclear Medicine, Seoul National University Hospital)
  • 정재민 (서울대학교병원 핵의학과) ;
  • 조정혁 (한국과학기술연구소 유기합성실) ;
  • 오승준 (한국과학기술연구소 유기합성실) ;
  • 이명철 (서울대학교병원 핵의학과) ;
  • 정수욱 (서울대학교병원 핵의학과) ;
  • 정준기 (서울대학교병원 핵의학과) ;
  • 이동수 (서울대학교병원 핵의학과) ;
  • 곽철은 (서울대학교병원 핵의학과) ;
  • 이경한 (서울대학교병원 핵의학과) ;
  • 고창순 (서울대학교병원 핵의학과)
  • Published : 1995.03.31
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Abstract

Tc-99m Labeled hexamethylenepropyleneamineoxime ([$^{99m}Tc$]-HMPAO) is a famous amino-oxime compound and is widely used to construct SPECT images of cerebral blood flow. To investigate the relationship between chemical structure and radiolabeling in these kind of diamine-oxime compounds, we synthesized seven compounds by Schiff's base formation and successive reduction with sodium borohydride. They were (RR/SS )-4,8-diaza-3,6,6,9-tetramethylundecane-2,10-dione bisoxime (2), (RR/SS/meso)-4,8-diaza-3,9-dimethy-lundecane-2,10-dione bisoxime (4), (RR/SS/meso)-4,8-diaza-3,10-dimethyldodecane-2,11-dione bisoxime (5), (RR/SS/meso)-4,7-diaza-3,6,6,8-tetramethyldecane-2,9-dione bisoxime (8), (RR/SS/meso)-4,7-diaza-5,6-cyclohexyl-3,8-dimethyldecane-2,9-dione bisoxime (10), (RR/SS/meso)-3,4-bis(1-aza-2-methyl-3-oxime-1-butyl)-benzoic acid (12), and (RR/SS/ meso)-2,3-bis(1-aza-2-methyl-3-oxime-1-butyl) benzophenone (14). Chemical structures of all the synthesized compounds were identified by taking $^1H$ spectrum. Among them, 2 and 4 are propyleneamine oxime (PnAO), 6 is butyleneamine oxime (BnAO) and 8, 10, 12 and 14 are ethyleneamine oxime (EnAO). Each compound (0.5 mg) was incubated with stannous chloride (0.5 g - 8 g), carbonate-bicarbonate buffer (final concentration = 0.1 M, pH 7 - pH 10) and Tc-99m-pertechenate (1 ml). Tc-99m labeling of these compounds were checked by ITLC (acetone), ITLC (normal saline), reverse phase TLC (50 % acetonitrile) and ITLC (ethyl acetate). According to the results, EnAO's were not labeled by Tc-99m in any of above condition. About 11 % of maximum labeling efficiency was obtained with BnAO. However, 4 (PnAO) was labeled with Tc-99m to 85 % which is similar to the labeling efficiency of 2 (HMPAO). Hydrophilic impurity (9 % ) was the most significant problem with the labeling of 4, however, pertechnetate (3 % ) and colloid (3 %) were minor problem. In conclusion, we synthesized seven diamine blsoxlme compounds. Among them, four EnAO compounds were not labeled by Tc-99m. A BnAO was labeled poorly and two PnAO's were labeled well. These labeling can be explained by tertiary structure of their Tc-99m chelate.

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