Radical methylation and radical hydroxymethylation of nicotine and quinine.

Itokawa, Hideji; Inaba, Toshiharu; Haruta, R.; Kameyama, Shoji

doi:10.1248/cpb.26.1295

Cited by 11 publications

(1 citation statement)

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“…The preparation of 6-hydroxymethylnicotine was based on a modification of the synthesis of Itokawa et al (8), involving radical hydroxymethylation of (-)-nicotine. To a mixture containing 0.5 g of(-)-nicotine dissolved in 50 ml of methanol containing The publication costs of this article were defrayed in part by page charge payment.…”

Section: Methodsmentioning

confidence: 99%

Characterization of a purified nicotinic receptor from rat brain by using idiotypic and anti-idiotypic antibodies.

Abood¹,

Langone²,

Bjercke³

et al. 1987

Proc. Natl. Acad. Sci. U.S.A.

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The availability of an anti-nicotine monoclonal antibody has made it possible to further establish the nature of the nicotine recognition proteins purified from rat brain by affinity chromatography and to provide a highly sensitive assay for determining [ H]nicotine binding to the purified material.An enantiomeric analogue of nicotine, (-)-6-hydroxymethylnicotine, was used to prepare the affinity column. In addition, with the use of an anti-idiotypic monoclonal antibody, it was confirmed that the recognition site for nicotine resides on a protein complex composed of two components with molecular masses of 62 and 57 kDa. It was also demonstrated that the same two proteins could be purified by immunoaffinity chro- Although the nicotinic cholinergic receptors of the Torpedo electric organ and mammalian neuromuscular junction are similar in their molecular characteristics (see ref. 1 for review), the nature of the nicotinic site in mammalian brain and its relationship to the peripheral receptor remains problematical. A number of studies have described limited crossreactivity between antibodies against the electric organ and an a-bungarotoxin-binding site in rat brain (2-4); however, neither receptor-binding studies using [3H]nicotine and 3H-labeled cholinergic agents as ligands nor behavioral and electrophysiological studies indicate any similarity in the a-bungarotoxin and nicotine sites in rat brain. Recently, a monoclonal antibody (mAb) prepared against purified nicotinic receptors from chicken brain has been used to isolate, by immunoaffinity chromatography, a nicotinic receptor from rat brain (4). The receptor complex, which was composed of two proteins having molecular masses of 51 and 79 kDa, differs somewhat from a nicotine-binding complex purified by affinity chromatography using a nicotine analogue conjugated to epoxy-Sepharose (5).The present communication describes further studies on the characterization of the nicotinic receptor purified by affinity chromatography by making use of idiotypic mAbs (6) to nicotine as well as their anti-idiotypes. MATERIALS AND METHODSPreparation of Rat Brain Membranes. After adult male Sprague-Dawley rats were sacrificed by spinal dislocation, the whole brains were removed, washed, and homogenized with a Brinkmann Polytron in 20 vol of ice-cold 0.05 M sodium phosphate, pH 7.5. The membrane pellet obtained after centrifugation at 50,000 x g for 30 min was washed once, recentrifuged, and stored at -

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Section: Methodsmentioning

confidence: 99%

Characterization of a purified nicotinic receptor from rat brain by using idiotypic and anti-idiotypic antibodies.

Abood¹,

Langone²,

Bjercke³

et al. 1987

Proc. Natl. Acad. Sci. U.S.A.

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ChemInform Abstract: RADICAL METHYLATION AND RADICAL HYDROXYMETHYLATION OF NICOTINE AND QUININE

Itokawa¹,

Inaba²,

Haruta³

et al. 1978

Chemischer Informationsdienst

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Synthesis and binding activity of 4‐azanicotine

Howell¹,

Martin²,

Sloan³

et al. 1991

Journal of Heterocyclic Chem

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4‐Azanicotine (1) has been synthesized by the cyclopropylimine rearrangement. A study of several Lewis acids as possible catalysts for the NMF‐mediated cyclopropyl imine rearrangement of cyclopropyl‐2‐pyrazinylmethanone (4) indicated that both aluminum chloride and magnesium chloride are suitable catalysts, lithium bromide shows only a trace of activity and zinc chloride, titanium tetrachloride, and titanium tetra‐isopropoxide show no activity. Compound 1, in which the aromatic ring is less basic than in nicotine, and 6‐aminonicotine (5), in which the aromatic ring is more basic, have been compared with the binding properties of nicotine in the P2 rat brain preparation. Compound 1 binds with an affinity very similar to that of nicotine at two of the receptor sites, 5 binds at these sites but with a lower affinity. Unlike nicotine, 1 and 5 do not bind at the very high affinity ‘upregulatory’ site.

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Radical methylation and radical hydroxymethylation of nicotine and quinine.

Cited by 11 publications

References 0 publications

Characterization of a purified nicotinic receptor from rat brain by using idiotypic and anti-idiotypic antibodies.

Characterization of a purified nicotinic receptor from rat brain by using idiotypic and anti-idiotypic antibodies.

ChemInform Abstract: RADICAL METHYLATION AND RADICAL HYDROXYMETHYLATION OF NICOTINE AND QUININE

Synthesis and binding activity of 4‐azanicotine

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