Preparation and properties of 3-(O-(2-carboxyethyl))oxime derivatives of steroid hormones

Pouzar, Vladimı́r; Černý, Ivan

doi:10.1016/0039-128x(95)00198-y

Cited by 7 publications

(1 citation statement)

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“…The 3-oxime 12 showed no correlation peak of the H-4 or H-2 and the proton 3-oxime group in the COSY spectrum. To support the configuration of the 3-oxime, it should be noted that the suggestions about anisotropic influence of N-O bond in E - an Z -isomeric 3-steroidal oxime on chemical shifts differences of 4-H signal were experimentally confirmed in this study [ 27 , 28 ]. The chemical shift of H-4 peak (6.15 ppm) of 12 was shifted further downfield than H-4 peak (5.87 ppm) of 11 , thus confirming the E -configuration of the 3-oxime group.…”

Section: Resultssupporting

confidence: 56%

Synthesis and 5α-Reductase Inhibitory Activity of C21 Steroids Having 1,4-diene or 4,6-diene 20-ones and 4-Azasteroid 20-Oximes

2011

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PurposeA connectome is a comprehensive description of synaptic connectivity for a neural domain. Our goal was to produce a connectome data set for the inner plexiform layer of the mammalian retina. This paper describes our first retinal connectome, validates the method, and provides key initial findings.MethodsWe acquired and assembled a 16.5 terabyte connectome data set RC1 for the rabbit retina at ≈2 nm resolution using automated transmission electron microscope imaging, automated mosaicking, and automated volume registration. RC1 represents a column of tissue 0.25 mm in diameter, spanning the inner nuclear, inner plexiform, and ganglion cell layers. To enhance ultrastructural tracing, we included molecular markers for 4-aminobutyrate (GABA), glutamate, glycine, taurine, glutamine, and the in vivo activity marker, 1-amino-4-guanidobutane. This enabled us to distinguish GABAergic and glycinergic amacrine cells; to identify ON bipolar cells coupled to glycinergic cells; and to discriminate different kinds of bipolar, amacrine, and ganglion cells based on their molecular signatures and activity. The data set was explored and annotated with Viking, our multiuser navigation tool. Annotations were exported to additional applications to render cells, visualize network graphs, and query the database.ResultsExploration of RC1 showed that the 2 nm resolution readily recapitulated well known connections and revealed several new features of retinal organization: (1) The well known AII amacrine cell pathway displayed more complexity than previously reported, with no less than 17 distinct signaling modes, including ribbon synapse inputs from OFF bipolar cells, wide-field ON cone bipolar cells and rod bipolar cells, and extensive input from cone-pathway amacrine cells. (2) The axons of most cone bipolar cells formed a distinct signal integration compartment, with ON cone bipolar cell axonal synapses targeting diverse cell types. Both ON and OFF bipolar cells receive axonal veto synapses. (3) Chains of conventional synapses were very common, with intercalated glycinergic-GABAergic chains and very long chains associated with starburst amacrine cells. Glycinergic amacrine cells clearly play a major role in ON-OFF crossover inhibition. (4) Molecular and excitation mapping clearly segregates ultrastructurally defined bipolar cell groups into different response clusters. (5) Finally, low-resolution electron or optical imaging cannot reliably map synaptic connections by process geometry, as adjacency without synaptic contact is abundant in the retina. Only direct visualization of synapses and gap junctions suffices.ConclusionsConnectome assembly and analysis using conventional transmission electron microscopy is now practical for network discovery. Our surveys of volume RC1 demonstrate that previously studied systems such as the AII amacrine cell network involve more network motifs than previously known. The AII network, primarily considered a scotopic pathway, clearly derives ribbon synapse input from photopic ON and OFF cone bipol...

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Section: Resultssupporting

confidence: 56%

Synthesis and 5α-Reductase Inhibitory Activity of C21 Steroids Having 1,4-diene or 4,6-diene 20-ones and 4-Azasteroid 20-Oximes

2011

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Hydroxylamine Analogs and Derivatives of Amino Acids. Aminooxy Acids

Zvilichovsky

2010

Patai's Chemistry of Functional Groups

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This chapter provides a review of researches in the field of aminooxy acids and related compounds. The first syntheses of aminooxy acids were described about 120 years ago. The first natural aminooxy acids and their derivatives, like canaline, canavanine and the antibiotic cycloserine, were discovered in the thirties and fifties of last century. Their first peptides were prepared in the sixties. In recent years this field gained increasing interest due to the special properties of peptides glycosides and glycopeptides containing aminooxy acids. These biomimetic compounds include aminooxy acids incorporated in biologically active macromolecules, either inside the chains or in terminal positions. The latter derivatives are used for ligation of functional groups resulting in biological probes, biosensors and and other useful devices. The free aminooxy group in such chains enables the facile prepration of bioconjugates, attachment to solid surfaces, modifications of recombinant proteins, preparing various vaccines and more. Peptides, proteins and glycopeptides containing an amidooxy bond exhibit interesting secondary, tertiary and quaternary structures. They reveal new folding properties, resulting in useful biomimetic foldamers for various applications. This chapter includes up to date information on the synthesis, chemical and biological properties of aminooxy acids and their derivatives.

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3- and 19-Oximes of 16α,17α-cyclohexanoprogesterone derivatives: Synthesis and interactions with progesterone receptor and other proteins

et al. 2008

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Preparation and properties of 3-(O-(2-carboxyethyl))oxime derivatives of steroid hormones

Cited by 7 publications

References 6 publications

Synthesis and 5α-Reductase Inhibitory Activity of C21 Steroids Having 1,4-diene or 4,6-diene 20-ones and 4-Azasteroid 20-Oximes

Synthesis and 5α-Reductase Inhibitory Activity of C21 Steroids Having 1,4-diene or 4,6-diene 20-ones and 4-Azasteroid 20-Oximes

Hydroxylamine Analogs and Derivatives of Amino Acids. Aminooxy Acids

3- and 19-Oximes of 16α,17α-cyclohexanoprogesterone derivatives: Synthesis and interactions with progesterone receptor and other proteins

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