85559-46-2Relevant academic research and scientific papers
SMALL MOLECULE MODULATORS OF PCSK9 AND METHODS OF USE THEREOF
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Paragraph 0363; 0373, (2016/02/22)
A compound of Formula (I): or a pharmaceutically acceptable salt, hydrate, solvate, or racemic mixture or stereoisomer thereof, and methods for preventing or treating an LDL-cholesterol-related disease or disorder using such compound(s), and kits and comp
Alternative one-pot synthesis of (trifluoromethyl)phenyldiazirines from tosyloxime derivatives: Application for new synthesis of optically pure diazirinylphenylalanines for photoaffinity labeling
Wang, Lei,Murai, Yuta,Yoshida, Takuma,Ishida, Akiko,Masuda, Katsuyoshi,Sakihama, Yasuko,Hashidoko, Yasuyuki,Hatanaka, Yasumaru,Hashimoto, Makoto
, p. 616 - 619 (2015/03/04)
Alternative one-pot synthesis of 3-(trifluoromethyl)-3-phenyldiazirine derivatives from corresponding tosyloximes is developed. The deprotonation of intermediate diaziridine by NH2- is a new approach for construction of diazirine. Moreover, a novel synthesis of optically pure (trifluoromethyl)diazirinylphenylalanine derivatives was attempted involving these methods.
Tri- and tetravalent photoactivable cross-linking agents
Welle, Alexandre,Billard, Francois,Marchand-Brynaert, Jacqueline
supporting information; experimental part, p. 2249 - 2254 (2012/10/08)
A modular synthesis of photoactivable cross-linking agents is described, using an aromatic core, di- or triethyleneglycol spacers and photoaffinity labeling synthons that feature either perfluorophenyl azide or aryl(trifluoromethyl)diazirine motifs. Symmetrical and nonsymmetrical trivalent structures were obtained from phloroglucinol and dopamine, respectively. Symmetrical tetravalent structures resulted from the coupling of two dopamine derivatives with oxalyl chloride. Georg Thieme Verlag Stuttgart New York.
Comparing lipid photo-cross-linking efficacy of penetratin analogues bearing three different photoprobes: Dithienyl ketone, benzophenone, and trifluoromethylaryldiazirine
Jiao, Chen-Yu,Alves, Isabel D.,Point, Vanessa,Lavielle, Solange,Sagan, Sandrine,Chassaing, Gérard
experimental part, p. 352 - 359 (2011/01/04)
Photoactivatable penetratin analogues bearing three different photoprobes, which do not disturb the membranotropic properties of the peptides, have been tested for their photo-cross-linking efficacy in glycerol and lipid media. In the case of glycerol, photo-cross-linking was observed, whereas in the case of SDS (used as a membrane model system), the dynamics of the SDS/penetratin assemblies and the photosensitizer properties of the probes prevented the cross-linking between the peptide and SDS. Bilayers of DMPG were partially photo-cross-linked by the penetratin analogues containing either a benzophenone or a trifluoromethylaryl-diazirine, whereas dithienyl ketone acted exclusively as a photosensitizer. The characterization by MALDI-TOF mass spectrometry of the photoadducts formed after irradiation required basic hydrolysis of DMPG for an efficient capture of the biotinylated peptide analogues with streptavidin-coated magnetic beads. MALDI-TOF analysis of the photoadducts between the photoactivatable penetratin and DMPG allowed an unambiguous identification of the covalent bond formed with the lipids. Altogether, we show herein that the efficacy of the lipid photo-cross-linking depends on the environment, the dynamics of the supramolecular assembly, and the physicochemical properties of the photoprobe.
Convenient synthesis of a [1-14C]diazirinylbenzoic acid as a photoaffinity label for binding studies of V-ATPase inhibitors
Bender, Tobias,Huss, Markus,Wieczorek, Helmut,Grond, Stephanie,Von Zezschwitz, Paultheo
, p. 3870 - 3878 (2008/02/13)
Diazirine-tagged systems are considered reliable compounds for photoaffinity labeling (PAL) in biochemical studies as they enable investigation and understanding of biological mechanisms through covalent bonding to the target and subsequent detection. 14C-labeled 4-(3-trifluoromethyl-3H- diazirin-3-yl)benzoic acid (11) was prepared by a lithium-bromide exchange on the bis-silylated 4-bromophenyldiaziridine 19 with subsequent transformations with electrophiles as key steps of the synthesis. Using 14CO 2, which was generated from rather inexpensive Ba14CO 3, the desired diaziridinylbenzoic acid 21 was obtained in 78% yield based on the employed radioactive material. Oxidation under mild conditions then yielded diazirine 11 in a 100 mg scale. This versatile photoaffinity label was selectively attached to the tetrahydropyrane ring of bafilomycin A1 (2) and concanamycin A-derived 3, which both specifically inhibit the V-ATPases. Inhibition assays were performed and revealed that the inhibitory capacities of the labeled derivatives are suitable for PAL studies on this important group of enzymes to elucidate the as yet unknown binding sites. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Grafting organic and biomolecules on H-terminated porous silicon from a diazirine
Wei, Shuai,Wang, Jing,Guo, Dong-Jie,Chen, Ya-Qing,Xiao, Shou-Jun
, p. 1172 - 1173 (2007/10/03)
A diazirine compound, 1,4-(1-azi-2,2,2-trifluoroethyl)benzoic acid, was used as a stable carbene precursor to react with Si-H terminated porous silicon (PSi) under microwave irradiation. After formation of a molecular monolayer, the end carboxyl group was
Synthesis and tritium labeling of new aromatic diazirine building blocks for photoaffinity labeling and cross-linking
Ambroise, Yves,Pillon, Florence,Mioskowski, Charles,Valleix, Alain,Rousseau, Bernard
, p. 3961 - 3964 (2007/10/03)
The synthesis of three bifunctional 3-phenyl-3-(trifluoromethyl)diazirinyl building blocks is described. These compounds were designed for their potential chemical reactivity toward a wide range of functional groups occurring in proteins and small molecul
Photoaffinity radioligand for NADH:ubiquinone oxidoreductase: [S- C3H2] (Trifluoromethyl)diazirinyl-pyridaben
Latli, Bachir,Morimoto, Hiromi,Williams, Philip G.,Casida, John E.
, p. 191 - 199 (2007/10/03)
Pyridaben is a new and very potent insecticide and miticide that acts by inhibiting the activity of NADH:ubiquinone oxidoreductase (the most complex of all the respiratory enzymes). The binding site, presumed to be the same as that of rotenone and fenazaq
Photoaffinity labeling of the ligand-interacting helix of the retinoic acid receptor alpha
Sasaki, Toru,Morisaki, Naoko,Iwasaki, Shigeo,Kagechika, Hiroshi,Fukasawa, Hiroshi,Shudo, Koichi,Shida, Yasuo,Hashimoto, Yuichi
, p. 913 - 916 (2007/10/03)
Two photoaffinity-labeling probes for retinoic acid receptor (RAR) α, 4-[(3-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenyl)carboxamido]benzoic acid (3DIAM) and its para-isomer (4DIAM), were designed and synthesized. Both compounds possess high affinity for
Synthesis and characterization of novel photoreactive naltrexone analogs as isomeric carbene-generating probes for opioid receptors
Hatanaka, Yasumaru,Nakamura, Norio,Wakabayashi, Miwa,Fujioka, Toshiyuki,Kikuchi, Tohru
, p. 519 - 522 (2007/10/03)
A convenient synthesis of m- and p-CF3-diazirinylbenzoic acid was developed. A pair of novel photoaffinity probes bearing these diazirines on a naltrexyl framework bind reversibly with high affinity at μ-, δ-, and κ- receptors.
