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제109회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Refinement of the electrophilic DMSO/POCl3 reaction with meso-aryl BODIPY systems: implications for biological ROS sensing and neurodegenerative disease research

등록일
2012년 2월 23일 11시 17분 58초
접수번호
1404
발표코드
INOR.P-257 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
발표시간
4월 25일 (수요일) 18:00~21:00
발표형식
포스터
발표분야
무기화학
저자 및
공동저자
전태홍, D.G.Churchill
KAIST 화학과, Korea
We report a synthetic, optical, biological, structural, study where ROS fluorescent/optical probing capacity in sulfur containing 4,4-difluoro-1,3,5,7-tetramethyl-8-(2/3-thienyl/furyl)-4-bora-3a,4a-diaza-s-indacene-based systems is elucidated. Importantly, a recently published POCl3/DMSO reaction mentioned the 2-chloro-6-methylsulfide derivative as the exclusive product (Kim, T. I.; Park, S,; Choi, Y.; Kim, Y. Chem. Asian J. 2011, 6, 1358-61). However, here, via the same protocol, related co-products were isolated and characterized including the 2,6-disulfido and 2,6-dichloro species. The 8-meso tail group modifies product type and distribution slightly. MeS-containing products undergo a time-dependent “off-on” response with NaOCl (10 equiv), etc. This was reported previously by Kim et. al. for the 2-chloro-6-methylsulfide species. Compounds 4b and 2b enter the cytosol of SH-SY5Y neuroblastoma and accumulate in the juxtanuclear region; cell toxicity was determined to be very low. Cheminformatics c log p values were obtained on all species including ones where the sulfur is oxidized. Compounds were characterized by NMR spectroscopy and X-ray diffraction.

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