Synthesis and transport applications of 3-aminobicyclo[3,2,1]octane-3-carboxylic acids

Hn, Christensen; Me, Handlogten; Jv, Vadgama; E, de la Cuesta; Ballesteros, Paloma; Gg, Trigo; Avendaño, Carlos

doi:10.1021/jm00364a008

Cited by 41 publications

(4 citation statements)

References 4 publications

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“…. 3,5-DHPG was synthesized from 3,5-dihydroxybenzaldehyde by reaction with potassium cyanide and ammonium carbonate (Christensen et al ., 1983), J. Neurochem., Vol.…”

Section: Methodsmentioning

confidence: 99%

3,5‐Dihydroxyphenylglycine Is a Highly Selective Agonist for Phosphoinositide‐Linked Metabotropic Glutamate Receptors in the Rat Hippocampus

Schoepp

Goldsworthy²,

Johnson

et al. 1994

Journal of Neurochemistry

261

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Metabotropic glutamate receptors (mGluRs) are a heterogeneous family of G protein‐coupled glutamate receptors that are linked to multiple second messenger systems in the CNS. In this study the selectivity of mGluR agonists for different mGluR second messenger effects was characterized in slices of the rat hippocampus. The mGluR agonists (1S,3R)‐1‐aminocyclopentane‐1,3‐dicarboxylic acid and (2S,3S,4S)α‐(carboxycyclopropyl)glycine produced multiple effects on second messengers that included enhanced phosphoinositide hydrolysis in both adult and neonatal rat hippocampus, inhibition of forskolin‐stimulated cyclic AMP (cAMP) formation in adult tissue, and increases in basal cAMP formation in the neonatal hippocampus. In contrast, 3,5‐dihydroxyphenylglycine was potent and effective in increasing phosphoinositide hydrolysis in both adult and neonatal hippocampus but unlike the other mGluR agonists did not inhibit forskolin‐stimulated cAMP formation (in the adult) or substantially enhance basal cAMP formation (in the neonate). Thus, in the rat hippocampus mGluR agonist‐mediated increases or decreases in cAMP formation are not secondary to mGluR‐mediated changes in phosphoinositide hydrolysis. Furthermore, 3,5‐dihydroxyphenylglycine can be used to activate subpopulations of mGluRs coupled to phosphoinositide hydrolysis with minimal effects on cAMP‐mGluR second messenger systems.

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“…. 3,5-DHPG was synthesized from 3,5-dihydroxybenzaldehyde by reaction with potassium cyanide and ammonium carbonate (Christensen et al ., 1983), J. Neurochem., Vol.…”

Section: Methodsmentioning

confidence: 99%

3,5‐Dihydroxyphenylglycine Is a Highly Selective Agonist for Phosphoinositide‐Linked Metabotropic Glutamate Receptors in the Rat Hippocampus

Schoepp

Goldsworthy²,

Johnson

et al. 1994

Journal of Neurochemistry

261

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“…3,5-DHPG was synthesized from 3,5-dihydroxybenzaldehyde by reaction with potassium cyanide and ammonium carbonate (20) followed by hydrolysis of the resulting hydantoin in 2M NaOH at reflux under nitrogen.…”

Section: Synthesis and Chemistrymentioning

confidence: 99%

(S)‐3,5‐DHPG: A Review

Wiśniewski

Car

2002

CNS Drug Reviews

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3,5-dihydroxyphenylglycine (3,5-DHPG) was the first agonist shown to be group I metabotropic glutamate receptor selective with its agonist effects residing exclusively in the S-isomer. Some results suggest that (S)-3,5-DHPG may be a partial agonist of mGluR 1a and mGluR 5a in neurons and astrocytes. It has been reported that (S)-3,5-DHPG can, under certain conditions, interact with NMDA receptors. (S)-3,5-DHPG exerts different effects on second messengers in adult and neonatal tissues. It stimulates phosphoinositide hydrolysis in a dose-dependent manner in both the adult and neonate hippocampus, inhibits stimulated cAMP levels in the adult and enhances the cAMP in the neonate. It is an effective antagonist of mGluRs linked to phospholipase D (PLD) in the adult and an agonist in the neonate brain or astrocyte cultures. (S)-3,5-DHPG induces elevation of [Ca 2+ ] i and regulates multiple subtypes of Ca 2+ channels. This agonist of group I mGluRs may modulate neurotransmitters release, reflecting the diversity of mechanisms involved. Depending on the dose, (S)-3,5-DHPG enhances or decreases excitatory postsynaptic potentials (EPSPs) and under appropriate conditions it can induce long-term depression (LTD) and long-term potentiation (LTP). Some studies suggested a therapeutic role for (S)-3,5-DHPG in neuronal injury, regulation of intestinal motility and secretion, learning and memory processes and in cardiovascular system.(S)-3,5-DHPG may be useful as a cognitive enhancing agent in memory impairment associated with ischemia or hypoxia. Recent investigations suggested possible beneficial effects of (S)-3,5-DHPG in Alzheimer's disease.

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“…[29] The most recent and complete compilation of enantioselective in small peptides, [9Ϫ12] to increased lipophilicity, [13] as well as to higher resistance towards both enzymatic and chemi-syntheses of β-amino acids can be found in JuaristiЈs book. [30] However, among all the available methods for the cal hydrolysis.…”

Section: Introductionmentioning

confidence: 99%

Preparation of Achiral and of Enantiopure Geminally Disubstituted β-Amino Acids for β-Peptide Synthesis

2000

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Synthesis and transport applications of 3-aminobicyclo[3,2,1]octane-3-carboxylic acids

Cited by 41 publications

References 4 publications

3,5‐Dihydroxyphenylglycine Is a Highly Selective Agonist for Phosphoinositide‐Linked Metabotropic Glutamate Receptors in the Rat Hippocampus

3,5‐Dihydroxyphenylglycine Is a Highly Selective Agonist for Phosphoinositide‐Linked Metabotropic Glutamate Receptors in the Rat Hippocampus

(S)‐3,5‐DHPG: A Review

Preparation of Achiral and of Enantiopure Geminally Disubstituted β-Amino Acids for β-Peptide Synthesis

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