Russian Journal of Bioorganic Chemistry, Vol. 29, No. 1, 2003, р . 80

New Fluorescent Bichromophoric Probes for the Donor Donor Energy Migration (DDEM) Studies

L. B.-Å. Johansson*, S. V. Kalinin*, K. A. Filatova**, and Jul. G. Molotkovsky** ¹

* Umeå University , Umeå, Sweden , **Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, ul. Miklukho-Maklaya 16/10, GSP Moscow , 117997 Russia

Abstract: Three fluorescent probes were synthesized for studying the excitation energy migration between two identical fluorophores. Each probe has two identical fluorescent groups (dansyl, 7-nitrobenzo-2-oxa-1,3-diazole-4-yl, or fluoresceinyl) linked by the rigid bis-(8-aminooctyl)amide of 4,4'-biphenyldicarbonic acid or flexible dotriacontanedioic acid spacer, which enables the intramolecular energy migration through the distance of 3.2–3.5 nm.

Key words: donor–donor energy migration (DDEM), fluorescent bichromophoric probes, synthesis

Russian Journal of Bioorganic Chemistry, Vol. 29, No. 1, 2003, р . 94

Unusual Fluorescent Properties of N -(9-Anthroyl) Derivatives of Aromatic Amines

Jul. G. Molotkovsky ¹

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, ul. Miklukho-Maklaya 16/10, GSP Moscow , 117997 Russia

Abstract: 9-Anthroyl derivatives of some aromatic amines exhibit unusual fluorescence characteristics. In solvents of low and medium polarity (hexane, chloroform, DMF, and tert-butanol), their emission maxima are shifted to longer wavelengths as compared to the spectra recorded in polar solvents (ethanol and methanol); the red shift is accompanied by an increase in the fluorescence quantum yield. Possible reasons of such an anomalous spectral shift are discussed.

Key words: aromatic amines, N-(9-anthroyl) derivatives; fluorescent properties; fluorescence

Russian Journal of Bioorganic Chemistry, Vol. 29, No. 2, 2003, р . 168

Synthesis and Characteristics of Fluorescent BODIPY-Labeled Gangliosides

I. I. Mikhalyov ¹ and Jul. G. Molotkovsky

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, ul. Miklukho-Maklaya 16/10, Moscow , 117997 Russia

Abstract: A series of new fluorescent-labeled gangliosides bearing the residues of acids labeled by 4,4-diflu-oro-4-bora-3a,4a-diaza-s-indacene(BODIPY) in the polar or/and apolar moiety were synthesized. These are ganglioside GM1 labeled with the residue of 4,4-difluoro-4-bora-3a,4a-diaza-5,7-dimethyl-s-indacenyl-3-propanoic (BODIPY-FL-propanoic) and -indacenyl-5-pentanoic (BODIPY-FL-pentanoic) acid in the oligosaccharide moiety of the molecule, and ganglioside GD1a labeled with two residues of BODIPY-FL-pentanoic acid in the oligosaccharide moiety and also with the residue of BODIPY-FL-pentanoic acid and the residue of 4,4difluoro-4-bora-3a,4a-diaza-5-octyl-s-indacenyl-5-pentanoic acid in the ceramide part of the molecule. Some spectral characteristics and the behavior in the model membrane systems of the synthesized probes were studied. In their emission spectra, the BODIPY-labeled gangliosides included into phosphatidylcholine liposomes at high concentrations (>1 mol %) exhibit a long-wavelength maximum (at ~630 nm) in addition to the usual maximum (at 510–515 nm).

Key words: BODIPY fluorophore, fluorescence spectra, fluorescent gangliosides, membrane probes, synthesis