Alkaloids in mammalian tissues. 3. Condensation of L-tryptophan and L-5-hydroxytryptophan with formaldehyde and acetaldehyde

Brossi, Arnold; Focella, A.; Teitel, S.

doi:10.1021/jm00262a027

Cited by 102 publications

(47 citation statements)

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“…4). To discriminate between the two possible orientations of the LTrp side chain, we synthesized a conformationally constrained analogue of 10 by means of the PicteteSpengler reaction [30], where the L-Trp moiety is forced to assume a X 1 value of À60 by means of a methylene group connecting position 2 of the indole nucleus to the a-nitrogen of the amino acid (Fig. 5).…”

Section: Resultsmentioning

confidence: 99%

Δ5-Cholenoyl-amino acids as selective and orally available antagonists of the Eph–ephrin system

Castelli

Tognolini

Vacondio

et al. 2015

European Journal of Medicinal Chemistry

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The Eph receptor-ephrin system is an emerging target for the development of novel anti-angiogenic therapies. Research programs aimed at developing small-molecule antagonists of the Eph receptors are still in their initial stage as available compounds suffer from pharmacological drawbacks, limiting their application in vitro and in vivo. In the present work, we report the design, synthesis and evaluation of structure-activity relationships of a class of Δ(5)-cholenoyl-amino acid conjugates as Eph-ephrin antagonists. As a major achievement of our exploration, we identified N-(3β-hydroxy-Δ(5)-cholen-24-oyl)-L-tryptophan (UniPR1331) as the first small molecule antagonist of the Eph-ephrin system effective as an anti-angiogenic agent in endothelial cells, bioavailable in mice by the oral route and devoid of biological activity on G protein-coupled and nuclear receptors targeted by bile acid derivatives.

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Section: Resultsmentioning

confidence: 99%

Δ5-Cholenoyl-amino acids as selective and orally available antagonists of the Eph–ephrin system

Castelli

Tognolini

Vacondio

et al. 2015

European Journal of Medicinal Chemistry

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“…A plausible explanation of this finding can be given by considering the following. Tpi is formed by Pictet-Spengler condensation of Trp with one equivalent of formaldehyde in dilute acid (39). The less stable N-acyl-D-Tpi, present in AN-253, can be expected to undergo decomposition to yield formaldehyde and N-acyl-D-Trp.…”

Section: Discussionmentioning

confidence: 99%

Design, synthesis, and in vitro evaluation of cytotoxic analogs of bombesin-like peptides containing doxorubicin or its intensely potent derivative, 2-pyrrolinodoxorubicin

Nagy

Armatis

Cai

et al. 1997

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

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“…MTCA was a 12:1 diastereoisomeric mixture of (-)-(1S,3S)-MTCA (SS-MTCA) and (-)-(1R,3S)-MTCA (RS-MTCA) of known absolute configuration (Yamaria and Akimoto 1969) based on 1H-NMR spectrum analysis . An internal standard, 1-ethyl-tetrahydro-[3-carboline-3-carboxylic acid, was synthesized from L-tryptophan and propionaldehyde using a previously published procedure (Brossi et al 1973). The methanol was of HPLC grade (Wako Pure Chemical Industries Ltd, Osaka, Japan).…”

Section: Methodsmentioning

confidence: 99%

Accumulation of 1-methyl-tetrahydro-Β-carboline-3-carboxylic acid in blood and organs of rat. A possible causative substance of eosinophilia-myalgia syndrome associated with ingestion ofl-tryptophan

1993

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1-Methyl-tetrahydro-beta-carboline-3-carboxylic acid (MTCA) may cause eosinophilia-myalgia syndrome (EMS) associated with ingestion of L-tryptophan. The distribution and excretion of MTCA were studied in rats which had received perorally a single 1.6 mg/kg dose of MTCA. MTCA concentrations in blood, kidney, liver, brain, heart, spleen, lung and gastrocnemius muscle were measured by HPLC combined with fluorometric detection. The concentration of MTCA in each organ reached a maximum at 1 h and then gradually declined. However, a significant level of MTCA still remained at 5 h, when 52% of ingested MTCA remained in the contents of the large intestine. Twenty-nine percent of the ingested MTCA was excreted in urine over the course of 24 h. A higher dose (10 mg/kg) of MTCA resulted in significant elevations in the concentrations and amounts of MTCA in the various organs. In addition, chronic treatment with a 10 mg/kg dose of MTCA for 6 weeks further increased the concentrations and amounts of MTCA in each organ. However, no histological changes were observed in any of the organs after chronic treatment. This is the first report which demonstrates accumulation of MTCA in the blood and various organs, including muscle, of rats.

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Alkaloids in mammalian tissues. 3. Condensation of L-tryptophan and L-5-hydroxytryptophan with formaldehyde and acetaldehyde

Cited by 102 publications

References 1 publication

Δ5-Cholenoyl-amino acids as selective and orally available antagonists of the Eph–ephrin system

Δ5-Cholenoyl-amino acids as selective and orally available antagonists of the Eph–ephrin system

Design, synthesis, and in vitro evaluation of cytotoxic analogs of bombesin-like peptides containing doxorubicin or its intensely potent derivative, 2-pyrrolinodoxorubicin

Accumulation of 1-methyl-tetrahydro-Β-carboline-3-carboxylic acid in blood and organs of rat. A possible causative substance of eosinophilia-myalgia syndrome associated with ingestion ofl-tryptophan

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