Synthesis of amino acid derivatives of 5-alkoxy-3,4-dihalo-2(5H)-furanones and their preliminary bioactivity investigation as linkers

Novel phosphoramidate derivatives of the anti-HIV nucleoside analogue d4T were designed to act as labile membrane-soluble prodrugs of the bio-active free nucleotide d4TMP. We herein reveal the very marked dependence of the antiviral activity of these phosphoramidates upon the stereochemistry of the amino acid attached to the phosphate centre; with a strong preference for the L-stereochemistry. These phosphate triesters were shown to liberate amino acid derivatives of the nucleotide intracellularly. These novel analogues, typified by alaninyl d4T monophosphate, may act as intracellular sources of the free nucleotides. The alaninyl d4T adducts themselves exert an antiviral effect when administered extracellularly, but again with clear distinctions between the L- and D-series. This evidence indicates that extracellularly administered blocked triesters derived from L-amino acids can generate d4TMP intracellularly, by a new pathway which is highly dependent on the amino acid stereochemistry.

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Some N-acyl-D-amino acid derivatives having antibotulinal properties

Canadian Journal of Microbiology ◽

10.1139/m87-100 ◽

1987 ◽

Vol 33 (7) ◽

pp. 577-582 ◽

Cited By ~ 16

Author(s):

A. Paquet ◽

K. Rayman

Keyword(s):

Amino Acids ◽

Amino Acid ◽

Aspartic Acid ◽

Sodium Nitrite ◽

Amino Acid Derivatives ◽

Ester Method ◽

Succinimidyl Ester ◽

High Yields ◽

Derivatives Of ◽

Acyl Derivatives

Several N-acyl derivatives of D-tryptophan, D-alanine, D-methionine, D-valine, and D-aspartic acid were synthesized in high yields using the succinimidyl ester method and examined for their antibotulinal properties. In conjunction with 60 ppm of sodium nitrite, sorbyl-D-tryptophan, sorbyl-D-alanine, myristoyl-D-aspartic acid, and glycyl-D-alanine were highly inhibitory. In the absence of sodium nitrite, the N-acyl derivatives of the D-amino acids were not inhibitory. On its own, 60 ppm of sodium nitrite was only slightly inhibitory. Sorbyl-L-tryptophan and sorbyl-L-alanine had no effect in the presence or absence of 60 ppm of sodium nitrite.

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Piezoactive amino acid derivatives containing fragments of planar-chiral ortho-carboranes

Journal of Materials Chemistry C ◽

10.1039/c8tc02266f ◽

2018 ◽

Vol 6 (32) ◽

pp. 8638-8645 ◽

Cited By ~ 2

Author(s):

Dmitry A. Gruzdev ◽

Alla S. Nuraeva ◽

Pavel A. Slepukhin ◽

Galina L. Levit ◽

Pavel S. Zelenovskiy ◽

...

Keyword(s):

Amino Acids ◽

Amino Acid ◽

Amino Acid Derivatives ◽

Piezoelectric Activity ◽

Derivatives Of

Compounds possessing a high piezoelectric activity have been found among enantio pure ortho-carboranyl derivatives of amino acids.

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Amino acid derivatives of natural chlorins as a platform for the creation of targeted photosensitizers in oncology

Тонкие химические технологии ◽

10.32362/2410-6593-2020-15-6-16-33 ◽

2021 ◽

Vol 15 (6) ◽

pp. 16-33

Author(s):

A. F. Mironov ◽

P. V. Ostroverkhov ◽

S. I. Tikhonov ◽

V. A. Pogorilyy ◽

N. S. Kirin ◽

...

Keyword(s):

Amino Acids ◽

Amino Acid ◽

Tumor Cells ◽

Targeted Delivery ◽

Methionine Sulfoximine ◽

Amino Acid Derivatives ◽

Resonance Spectroscopy ◽

Biochemical Processes ◽

Derivatives Of

Objectives. This study aims to obtain the amino acid derivatives of chlorophyll a and bacteriochlorophyll a for the targeted delivery of pigments to tumor foci. This will increase biocompatibility and, as a result, reduce toxic side effects. In addition to photodynamic efficiency, an additional cytotoxic effect is expected for the obtained conjugates of photosensitizers (PSs) with amino acids. This is owing to the participation of the latter in intracellular biochemical processes, including interaction with the components of the glutathione antioxidant system, leading to the vulnerability of tumor cells to oxidative stress.Methods. In this work, we have implemented the optimization of the structure of a highly efficient infrared PS based on O-propyloxim-N-propoxybacteriopurpurinimide (DPBP), absorbing at 800 nm and showing photodynamic efficacy for the treatment of deep-seated and pigmented tumors, by introducing L-lysine, L-arginine, methionine sulfoximine (MSO), and buthionine sulfoximine (BSO) methyl esters. The structure of the obtained compounds was proved by mass spectrometry and nuclear magnetic resonance spectroscopy, and the photoinduced cytotoxicity was studied in vitro on the HeLa cell line.Results. Conjugates of DPBP with amino acids and their derivatives, such as lysine, arginine, MSO, and BSO have been prepared. The chelating ability of DPBP conjugate with lysine was shown, and its Sn(IV) complex was obtained.Conclusions. Biological testing of DPBP with MSO and BSO showed a 5–6-fold increase in photoinduced cytotoxicity compared to the parent DPBP PS. Additionally, a high internalization of pigments by tumor cells was found, and the dark cytotoxicity (in the absence of irradiation) of DPBP-MSO and DPBP-BSO increased fourfold compared to the initial DPBP compound. This can be explained by the participation of methionine derivatives in the biochemical processes of the tumor cell.

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Reversed-phase chromatography of phenylthiocarbamyl amino acid derivatives of physiological amino acids: an evaluation and a comparison with analysis by ion-exchange chromatography

Journal of Chromatography B Biomedical Sciences and Applications ◽

10.1016/0378-4347(92)80094-7 ◽

1992 ◽

Vol 574 (1) ◽

pp. 23-34 ◽

Cited By ~ 36

Author(s):

Andrew S. Feste

Keyword(s):

Amino Acids ◽

Amino Acid ◽

Ion Exchange ◽

Reversed Phase ◽

Ion Exchange Chromatography ◽

Exchange Chromatography ◽

Amino Acid Derivatives ◽

Reversed Phase Chromatography ◽

Derivatives Of

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Catalytic asymmetric propargyl- and allylboration of hydrazonoesters: a metal-free approach to sterically encumbered chiral α-amino acid derivatives

Chemical Communications ◽

10.1039/c8cc07908k ◽

2018 ◽

Vol 54 (91) ◽

pp. 12852-12855 ◽

Cited By ~ 8

Author(s):

Sybrand J. T. Jonker ◽

Colin Diner ◽

Göran Schulz ◽

Hiroaki Iwamoto ◽

Lars Eriksson ◽

...

Keyword(s):

Amino Acids ◽

Amino Acid ◽

Asymmetric Catalysis ◽

Amino Acid Derivatives ◽

Metal Free ◽

Catalytic Asymmetric

Metal-free asymmetric catalysis for the synthesis of sterically encumbered amino-acids was developed using allyl- and allenylboronic acid reagents.

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A new double-labelling procedure for determination of amino acid composition: Application to bacteriorhodopsin

Canadian Journal of Biochemistry ◽

10.1139/o78-079 ◽

1978 ◽

Vol 56 (6) ◽

pp. 517-520 ◽

Cited By ~ 3

Author(s):

H. Kaplan ◽

D. C. H. Cheng ◽

G. Oda ◽

M. Kates

Keyword(s):

Amino Acids ◽

Amino Acid ◽

Amino Acid Mixture ◽

Acid Mixture ◽

Amino Acid Derivatives ◽

Double Labelling ◽

Tryptophan Residues ◽

Labelling Procedure ◽

Derivatives Of

A new double-labelling procedure for amino acid analysis which requires only routine chromatographic equipment is described. When 1-fluoro-2,4-dinitro[3H]benzene is reacted with a mixture of 14C-labelled amino acids followed by reaction with the same 14C-labelled amino acid mixture diluted with an unlabelled sample of amino acids, the 3H: 14C ratio in the resulting 2,4-dinitrophenyl (DNP) amino acid derivatives of the diluted sample will be increased in proportion to the quantity of unlabelled amino acid in the diluted sample. This procedure gave reliable results when applied to the known proteins insulin and lysozyme. The procedure is most advantageous when applied to amino acids which are unstable during acid hydrolysis or present in low molar fractions.When applied to the analysis of the bacteriorhodopsin in Halobacterium cutirubrum, this procedure showed the presence of one histidine residue and four tryptophan residues per mole protein but no cystine or cysteine; in general, the analyses obtained were consistent with those originally reported by Oesterhelt, D. and Stoeckenius, W. (1971) (Nature (London) New Biol. 233, 149–152) for bacteriorhodopsin of H. halobium.

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The preparation of dimedone derivatives of amino acids and their use in peptide synthesis

Australian Journal of Chemistry ◽

10.1071/ch9650417 ◽

1965 ◽

Vol 18 (3) ◽

pp. 417 ◽

Cited By ~ 10

Author(s):

B Halpern

Keyword(s):

Amino Acids ◽

Amino Acid ◽

Peptide Synthesis ◽

Catalytic Hydrogenation ◽

Amino Acid Derivatives ◽

Alkyl Esters ◽

Benzyl Esters ◽

Derivatives Of

The preparation of dimedone derivatives of amino acids has been effected by saponification of the corresponding alkyl esters, and also by catalytic hydrogenation of the respective benzyl esters. The amino acid derivatives have been used to synthesize peptides in excellent yields, employing dicyclohexyl carbodiimide as the condensing agent.

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