A fluorescent redox sensor with tuneable oxidation potential

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 4, 2010, Pages 1457-1459

  Kierat, Radoslaw M ^a   Thaler, Birgit M B ^a   Krämer, Roland ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORESCENT DYE; HYDROQUINONE DERIVATIVE; RHODAMINE B;

ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; FLUORESCENCE MICROSCOPY; HUMAN; HUMAN CELL; MOLECULAR PROBE; MOLECULAR SENSOR; OXIDATION REDUCTION REACTION;

FLUORESCENT DYES; HYDROQUINONES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; RHODAMINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 75449115233     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.03.171     Document Type: Article

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19. Synthetic procedures for 1: 2,5-Dihydroxybenzoic acid (141 mg, 0.91 mmol), HBTU (345 mg, 0.91 mmol) and N,N-diisopropylethylamine (145 μl, 1.14 mmol) were dissolved in dry N,N-dimethylformamide. The reaction mixture was stirred in an atmosphere of nitrogen for 30 min, then rhodamine B-piperazineamide (500 mg, 0.91 mmol) was added and the mixed solution stirred over night. The reaction mixture was quenched with water, saturated with potassium chloride, extracted with chloroform, dried with magnesium sulfate and evaporated under reduced pressure. The crude product was purified by flash column chromatography on silica with chloroform-methanol (7:1) as the eluent to give 1 (0.16 g, 25%) as pink solid.
20. Synthetic procedures for 2: Synthesis according to Ref. 13 gives 2 (61 mg, 9%) as pink solid.
21. 5 requires 647.3233).
22. 6 requires 677.3258).