Synthesis of Novel and Stable 5-Aminolevulinic Acid Derivatives for the Efficient Synthesis of 5-Aminolevulinic Acid Based Prodrugs

Vallinayagam, Ramakrishnan; Bertschy, Hugo; Berger, Yann; Wenger, Virginie; Neier, Reinhard

doi:10.1055/s-2007-990825

Cited by 3 publications

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“…The latter, having the nucleophilicity of the δ-position silenced, presented a completely straightforward precursor to 1 and proved to be amenable to coupling with 4 under various reaction conditions. Briefly [14], 8 was prepared from levulinic acid ( 5 ) through δ-bromination and concomitant methyl ester formation (compound 6 ), followed by azidation to 7 . Finally, enzymatic cleavage of the ester [15] resulted in liberation of the carboxylic acid functionality that is required for the coupling to the CD (Scheme 2, compound 8 , Figure S1, Figure S2 in Supporting Information File 1).…”

Section: Resultsmentioning

confidence: 99%

A versatile δ-aminolevulinic acid (ΑLA)-cyclodextrin bimodal conjugate-prodrug for PDT applications with the help of intracellular chemistry

Aggelidou¹,

Theodossiou²,

Gonçalves³

et al. 2014

Beilstein J. Org. Chem.

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SummaryGrafting of δ-aminolevulinic acid (1) moieties on the narrow periphery of a β-cyclodextrin (β-CD) derivative through hydrolysable bonds was implemented, in order to generate a water-soluble, molecular/drug carrier with the capacity to undergo intracellular transformation into protoporphyrin IX (PpIX), an endogenous powerful photosensitizer for photodynamic therapy (PDT). The water-soluble derivative 2 was prepared by esterifying δ-azidolevulinic acid with heptakis(6-hydroxyethylamino-6-deoxy)-β-cyclodextrin, with an average degree of substitution, DS = 3. Delivery of water-soluble, colorless 2 to cells resulted in intense red fluorescence registered by confocal microscopy, evidently due to the engagement of the intracellular machinery towards formation of PpIX. Conjugate 2 was further complexed with a fluorescein-labeled model guest molecule which was successfully transported into the cells, thereby demonstrating the bimodal action of the derivative. The present work shows the versatility of CDs in smart applications and constitutes advancement to our previously shown PpIX-β-CD conjugation both in terms of water solubility and lack of aggregation.

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Section: Resultsmentioning

confidence: 99%

A versatile δ-aminolevulinic acid (ΑLA)-cyclodextrin bimodal conjugate-prodrug for PDT applications with the help of intracellular chemistry

Aggelidou¹,

Theodossiou²,

Gonçalves³

et al. 2014

Beilstein J. Org. Chem.

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Solid‐Phase Synthesis of Structurally Diverse Heterocycles by an Amide–Ketone Condensation/N‐Acyliminium Pictet–Spengler Sequence

Komnatnyy

Givskov

Nielsen

2012

Chemistry A European J

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An efficient approach for the solid-phase synthesis of structurally diverse heterocyclic compounds is presented. Under acidic reaction conditions, peptidic levulinamides undergo intramolecular ketone-amide condensation reactions to form cyclic N-acyliminium intermediates. In the presence of a tethered nucleophile, a second cyclization reaction results in the formation of a fused bicyclic ring system. The scope of the methodology was demonstrated by several combinations of substituted ketones and nucleophiles, the latter conveniently originating from amino acids with functionalized side chains, such as tryptophan, substituted phenylalanines, and cysteine. The cyclization sequence provides diastereomerically pure products in high yields. In one extension of the methodology, the resulting relative stereochemistry of the products enables the formation of bridged ring systems by a unique cyclative release mechanism.

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4-Ketovalero lactone (KVL): A gateway molecule for diversification of the furanic platform

Durão,

Marinova,

Ravutsov

et al. 2024

Sustainable Chemistry and Pharmacy

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Synthesis of Novel and Stable 5-Aminolevulinic Acid Derivatives for the Efficient Synthesis of 5-Aminolevulinic Acid Based Prodrugs

Abstract: The efficient synthesis of two stable, easily handled precursors of 5-aminolevulinate is reported. These precursors are stable to the chemical transformation needed for the synthesis of bioconjugates and can be readily deprotected in good yields.

Cited by 3 publications

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A versatile δ-aminolevulinic acid (ΑLA)-cyclodextrin bimodal conjugate-prodrug for PDT applications with the help of intracellular chemistry

A versatile δ-aminolevulinic acid (ΑLA)-cyclodextrin bimodal conjugate-prodrug for PDT applications with the help of intracellular chemistry

Solid‐Phase Synthesis of Structurally Diverse Heterocycles by an Amide–Ketone Condensation/N‐Acyliminium Pictet–Spengler Sequence

4-Ketovalero lactone (KVL): A gateway molecule for diversification of the furanic platform

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