Synthesis, protonation constants and biological activity determination of amino acid-salicylaldehyde-derived Schiff bases.

Abstract:

:Schiff bases represent a class of molecules widely studied for their importance in organic and coordination chemistry. Despite the large amount of studies on the chemical and biological properties of the Schiff bases, the different experimental conditions prevent a useful comparison to search for a correlation structure-activity. Moreover, literature is lacking in comprehensive data on the spectroscopic characterization of these compounds. For this reason, six Schiff bases, derived from salicylaldehyde and natural amino acids were fully characterized by nuclear magnetic resonance and infrared spectroscopy, and their aqueous solution equilibria, antiproliferative activity and DNA-binding activity were examined. All experimental conditions were kept constants to achieve comparable information and useful insights about their structure-activity correlation. The synthesized compounds showed DNA binding constants in the 101-102 M-1 range, depending on the substituent present in the amino acid side-chain, and resulted devoid of significant cytotoxic activity against the different human tumor cell lines showing IC50 values higher than 100 µM.

journal_name

Amino Acids

journal_title

Amino acids

authors

Fattuoni C,Vascellari S,Pivetta T

doi

10.1007/s00726-019-02816-0

subject

Has Abstract

pub_date

2020-03-01 00:00:00

pages

397-407

issue

3

eissn

0939-4451

issn

1438-2199

pii

10.1007/s00726-019-02816-0

journal_volume

52

pub_type

杂志文章
  • The neuronal differentiation process involves a series of antioxidant proteins.

    abstract::Involvement of individual antioxidant proteins (AOXP) and antioxidants in the differentiation process has been already reported. A systematic search strategy for detecting differentially regulated AOXP in neuronal differentiation, however, has not been published so far. The aim of this study was to provide an analytic...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-005-0214-9

    authors: Oh JE,Karlmark Raja K,Shin JH,Hengstschläger M,Pollak A,Lubec G

    更新日期:2005-11-01 00:00:00

  • Transglutaminases: future perspectives.

    abstract::This is the third special issue focused on "Transglutaminases" that is now available on this journal and dedicated to one of the pioneers of these enzymes, John Edward Folk, who died December 2010 [see in this issue Beninati et al. 2012a]. The first edition, "Polyamines and Transglutaminases" was published in Amino Ac...

    journal_title:Amino acids

    pub_type: 社论

    doi:10.1007/s00726-012-1431-7

    authors: Beninati S,Facchiano F,Piacentini M

    更新日期:2013-01-01 00:00:00

  • Expression of ABC-1 transporter is elevated in human glioma cells under irradiation and temozolomide treatment.

    abstract:OBJECTIVE:Chemo-therapeutic treatment of glioma patients has minor success. Little is known about mechanisms of a pronounced resistance of gliomas towards actual therapies, yet. ABC-1 belongs to the group of transporters known to be involved in the export of hydrophobic substances and vascular regulation. This study in...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-005-0171-3

    authors: Trog D,Moenkemann H,Haertel N,Schüller H,Golubnitschaja O

    更新日期:2005-03-01 00:00:00

  • A proteomic analysis of PKCε targets in astrocytes: implications for astrogliosis.

    abstract::Astrocytes are glial cells in the central nervous system (CNS) that play key roles in brain physiology, controlling processes, such as neurogenesis, brain energy metabolism and synaptic transmission. Recently, immune functions have also been demonstrated in astrocytes, influencing neuronal survival in the course of ne...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-010-0691-3

    authors: Burgos M,Fradejas N,Calvo S,Kang SU,Tranque P,Lubec G

    更新日期:2011-02-01 00:00:00

  • Effects of phenylalanine and phenylpyruvate on ATP-ADP hydrolysis by rat blood serum.

    abstract::The nucleotide (ATP-ADP)/nucleoside (adenosine) ratio in the circulation can modulate the processes of vasoconstriction, vasodilatation and platelet aggregation. The main objective of the present study with rat blood serum was to evaluate the possibility of changes in nucleotide hydrolysis by phenylalanine (Phe) and p...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-002-0345-1

    authors: Rücker B,Oses JP,Kirst IB,Berti SL,Bonan CD,Battastini AM,Sarkis JJ

    更新日期:2003-06-01 00:00:00

  • A synthetic peptide derived of the β2-β3 loop of the plant defensin from Vigna unguiculata seeds induces Leishmania amazonensis apoptosis-like cell death.

    abstract::For medical use of proteins and peptide-based drugs, it is desirable to have small biologically active sequences because they improve stability, reduce side effects, and production costs. Several plant defensins have their biological activities imparted by a sequence named γ-core. Vu-Def, a Vigna unguiculata defensin,...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-019-02800-8

    authors: Souza GS,de Carvalho LP,de Melo EJT,da Silva FCV,Machado OLT,Gomes VM,de Oliveira Carvalho A

    更新日期:2019-11-01 00:00:00

  • Comparison of amino acids interaction with gold nanoparticle.

    abstract::The study of nanomaterial/biomolecule interface is an important emerging field in bionanoscience, and additionally in many biological processes such as hard-tissue growth and cell-surface adhesion. To have a deeper understanding of the amino acids/gold nanoparticle assemblies, the adsorption of these amino acids on th...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-013-1642-6

    authors: Ramezani F,Amanlou M,Rafii-Tabar H

    更新日期:2014-04-01 00:00:00

  • Design, synthesis and biological evaluation of non-peptide PAR1 thrombin receptor antagonists based on small bifunctional templates: arginine and phenylalanine side chain groups are keys for receptor activity.

    abstract::In the present study, we report the synthesis and biological evaluation of a series of new non-peptide PAR(1) mimetic receptor antagonists, based on conformational analysis of the S(42)FLLR(46) tethered ligand (TL) sequence of PAR(1). These compounds incorporate the key pharmacophore groups in the TL sequence, guanidy...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-009-0306-z

    authors: Androutsou ME,Saifeddine M,Hollenberg MD,Matsoukas J,Agelis G

    更新日期:2010-04-01 00:00:00

  • Protein-polyamine conjugates by transglutaminase 2 as potential markers for antineoplastic screening of natural compounds.

    abstract::The role of post-translational modification of cell proteins with polyamines, a reaction catalyzed by a tissue tranglutaminase (TG, EC 2.3.2.13), in the induction of cell differentiation, represents an intriguing strategy to control cell proliferation and metastatic ability of different tumor cell lines. In this revie...

    journal_title:Amino acids

    pub_type: 杂志文章,评审

    doi:10.1007/s00726-008-0157-z

    authors: Lentini A,Provenzano B,Tabolacci C,Beninati S

    更新日期:2009-04-01 00:00:00

  • Mapping surface residues of eIF5A that are important for binding to the ribosome using alanine scanning mutagenesis.

    abstract::The translation elongation factor eIF5A is conserved through evolution and is necessary to rescue the ribosome during translation elongation of polyproline-containing proteins. Although the site of eIF5A binding to the ribosome is known, no systematic analysis has been performed so far to determine the important resid...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-016-2279-z

    authors: Barbosa NM,Boldrin PE,Rossi D,Yamamoto PA,Watanabe TF,Serrão VH,Hershey JW,Fraser CS,Valentini SR,Zanelli CF

    更新日期:2016-10-01 00:00:00

  • Transport mechanism and regulatory properties of the human amino acid transporter ASCT2 (SLC1A5).

    abstract::The kinetic mechanism of the transport catalyzed by the human glutamine/neutral amino acid transporter hASCT2 over-expressed in P. pastoris was determined in proteoliposomes by pseudo-bi-substrate kinetic analysis of the Na(+)-glutamineex/glutaminein transport reaction. A random simultaneous mechanism resulted from th...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-014-1808-x

    authors: Scalise M,Pochini L,Panni S,Pingitore P,Hedfalk K,Indiveri C

    更新日期:2014-11-01 00:00:00

  • Novel insights into nucleoamino acids: biomolecular recognition and aggregation studies of a thymine-conjugated L-phenyl alanine.

    abstract::This article deals with the synthesis in solid phase and characterization of a nucleoamino amide, based on a phenylalaninamide moiety which was N-conjugated to a thymine nucleobase. In analogy to the natural nucleobase-amino acid conjugates, endowed with a wide range of biological properties, the nucleoamino amide int...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-018-2562-2

    authors: Roviello GN

    更新日期:2018-07-01 00:00:00

  • Relationship between protein folding kinetics and amino acid properties.

    abstract::The successful prediction of protein-folding rates based on the sequence-predicted secondary structure suggests that the folding rates might be predicted from sequence alone. To pursue this question, we directly predict the folding rates from amino acid sequences, which do not require any information on secondary or t...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-011-1189-3

    authors: Huang JT,Xing DJ,Huang W

    更新日期:2012-08-01 00:00:00

  • Solution structure of a novel α-conotoxin with a distinctive loop spacing pattern.

    abstract::α-Pharmacological conotoxins are among the most selective ligands of nicotinic acetylcholine receptors with typical cysteine frameworks. They are characterized by the intercysteine loop and classified into various subfamilies, such as α3/5 and α4/7 conotoxins. A novel α-conotoxin, Pu14a (DCPPHPVPGMHKCVCLKTC), with a d...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-011-1093-x

    authors: Zhang B,Huang F,Du W

    更新日期:2012-07-01 00:00:00

  • The inhibitory effect of various indolyl amino acid derivatives on arginase activity in macrophages.

    abstract::Numerous indolyl amino acids and their derivatives inhibited arginase activity. The inhibition was found to be non-competitive, - at least partly - allosteric, and independent on manganese ions in the active site, and it cannot be explained by the dissociation of arginase homotrimers. Indole alone is weakly inhibitory...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-006-0470-3

    authors: Hrabák A,Bajor T,Mészáros G

    更新日期:2008-02-01 00:00:00

  • Principal component analysis of the relationship between the D-amino acid concentrations and the taste of the sake.

    abstract::We performed sensory evaluations on 141 bottles of sake and analyzed the relationship between the D-amino acid concentrations, and the taste of the sake using principal component analysis, which yielded seven principal components (PC1-7) that explained 100 % of the total variance in the data. PC1, which explains 33.6 ...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-012-1359-y

    authors: Okada K,Gogami Y,Oikawa T

    更新日期:2013-02-01 00:00:00

  • Expression of the kynurenine enzymes in macrophages and microglial cells: regulation by immune modulators.

    abstract::The regulation of the expression of indoleamine 2,3-dioxygenase (IDO) was studied in cloned murine macrophages (MT2) and microglial (N11) cells. Both cell lines express IDO and inducible nitric oxide synthase activity after interferon-gamma (IFN-gamma) stimulation. The regulation of IDO expression appears to differ in...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/BF01345271

    authors: Alberati-Giani D,Cesura AM

    更新日期:1998-01-01 00:00:00

  • Lysine transporters in human trypanosomatid pathogens.

    abstract::In previous studies we characterized arginine transporter genes from Trypanosoma cruzi and Leishmania donovani, the etiological agents of chagas disease and kala azar, respectively, both fatal diseases in humans. Unlike arginine transporters in higher eukaryotes that transport also lysine, these parasite transporters ...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-010-0812-z

    authors: Inbar E,Canepa GE,Carrillo C,Glaser F,Suter Grotemeyer M,Rentsch D,Zilberstein D,Pereira CA

    更新日期:2012-01-01 00:00:00

  • Site-specific pegylation of an antimicrobial peptide increases resistance to Pseudomonas aeruginosa elastase.

    abstract::M33 is a branched peptide currently under preclinical characterization for the development of a new antibacterial drug against gram-negative bacteria. Here, we report its pegylation at the C-terminus of the three-lysine-branching core and the resulting increase in stability to Pseudomonas aeruginosa elastase. This pro...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-014-1686-2

    authors: Falciani C,Lozzi L,Scali S,Brunetti J,Bracci L,Pini A

    更新日期:2014-05-01 00:00:00

  • Effect of hyperprolinemia on acetylcholinesterase and butyrylcholinesterase activities in rat.

    abstract::We observed here that acute proline (Pro) administration provoked a decrease (32%) of acetylcholinesterase (AChE) activity in cerebral cortex and an increase (22%) of butyrylcholinesterase (BuChE) activity in the serum of 29-day-old rats. In contrast, chronic administration of Pro did not alter AChE or BuChE activitie...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-005-0186-9

    authors: Delwing D,Chiarani F,Wannmacher CM,Wajner M,Wyse AT

    更新日期:2005-05-01 00:00:00

  • A comparative SAR study of thrombin receptor derived non peptide mimetics: importance of phenyl/guanidino proximity for activity.

    abstract::Thrombin, the most potent physiological platelet agonist interacts with cells through a specific G protein-coupled receptor which has been cloned and sequenced. Synthetic thrombin receptor peptides (TRAPs) comprising the first 5 amino acids (SFLLR and SFLLR-NH2) of the new N-terminus tethered ligand of the thrombin re...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/BF01318860

    authors: Alexopoulos K,Matsoukas J,Tselios T,Roumelioti P,Mavromoustakos T,Holada K

    更新日期:1998-01-01 00:00:00

  • Use ofα-aminoisobutyric acid and isovaline as marker amino acids for the detection of fungal polypeptide antibiotics. Screening ofHypocrea.

    abstract::Filamentous fungi of the genusHypocrea were grown on malt extract/peptone agar, the mycelia were extracted with dichloromethane/methanol, and the extracts were totally hydrolyzed with 6 N HCl (110°C, 24 h). The amino acids (AA) released from peptides were converted into theirN(O)-pen-tafluoropropionyl 1-propyl esters ...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/BF00806923

    authors: Brückner H,Maisch J,Reinecke C,Kimonyo A

    更新日期:1991-06-01 00:00:00

  • Exploring pitfalls of 64Cu-labeled EGFR-targeting peptide GE11 as a potential PET tracer.

    abstract::The epidermal growth factor receptor (EGFR) represents an important molecular target for both radiotracer-based diagnostic imaging and radionuclide therapy of various cancer entities. For the delivery of radionuclides to the tumor, peptides hold great potential as a transport vehicle. With respect to EGFR, the peptide...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-018-2616-5

    authors: Striese F,Sihver W,Gao F,Bergmann R,Walther M,Pietzsch J,Steinbach J,Pietzsch HJ

    更新日期:2018-10-01 00:00:00

  • Asymmetric hydrogenation of dehydrodipeptides bearing different protecting groups.

    abstract::N-[(Z)-N-Benzoyl- or N-boc-(2-fluorophenyl)dehydroalanyl]-(R)- or (S)-phenyl-alanines 1,2,5 and 6 were hydrogenated in the presence of chiral and achiral rhodium complexes. The optical induction is compared to the results obtained using the corresponding esters as substrates. ...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s007260200018

    authors: Döbler C,Kreuzfeld HJ,Fischer C,Michalik M

    更新日期:2002-06-01 00:00:00

  • Inducible nitric oxide synthase activity in colon biopsies from inflammatory areas: correlation with inflammation intensity in patients with ulcerative colitis but not with Crohn's disease.

    abstract::Nitric oxide synthase (NOS) activities are responsible for the enzymatic conversion of L-arginine into NO and L-citrulline. Relatively low amounts of NO are produced in intestinal epithelial cells or are released from nerve endings. The effects of NO production are related to the maintenance of epithelial integrity an...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s007260050020

    authors: Guihot G,Guimbaud R,Bertrand V,Narcy-Lambare B,Couturier D,Duée PH,Chaussade S,Blachier F

    更新日期:2000-01-01 00:00:00

  • Multi-omic approach decodes paradoxes of the triple-negative breast cancer: lessons for predictive, preventive and personalised medicine.

    abstract::Breast cancer epidemic in the early twenty-first century results in around two million new cases and half-a-million of the disease-related deaths registered annually worldwide. A particularly dramatic situation is attributed to some specific patient subgroups such as the triple-negative breast cancer (TNBC). TNBC is a...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-017-2524-0

    authors: Golubnitschaja O,Filep N,Yeghiazaryan K,Blom HJ,Hofmann-Apitius M,Kuhn W

    更新日期:2018-04-01 00:00:00

  • Potent effects of amino acid scanned antimicrobial peptide Feleucin-K3 analogs against both multidrug-resistant strains and biofilms of Pseudomonas aeruginosa.

    abstract::Pseudomonas aeruginosa is particularly difficult to treat because it possesses a variety of resistance mechanisms and because it often forms biofilms. Antimicrobial peptides represent promising candidates for future templates of antibiotic-resistant bacterial infections due to their unique mechanism of antimicrobial a...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-018-2625-4

    authors: Xie J,Li Y,Li J,Yan Z,Wang D,Guo X,Zhang J,Zhang B,Mou L,Yang W,Jiang X

    更新日期:2018-10-01 00:00:00

  • Non-covalent binding of azo compound to peptide chain: interactions of biebrich scarlet and naphthochrome green with four model proteins.

    abstract::We studied the non-specific interactions of two azo compounds: biebrich scarlet (BS) and naphthochrome green (NG), with four model proteins: bovine serum albumin, ovalbumin, poly-L-lysine and hemoglobin by UV-VIS spectrometry, fluorophotometry and circular dichroism melting technique. The optimal acidities of NG and B...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-008-0058-1

    authors: Gao HW,Liu XH,Qiu Z,Tan L

    更新日期:2009-02-01 00:00:00

  • Protection from hypoxic injury in cultured hepatocytes by glycine, alanine, and serine.

    abstract::Isolated hepatocytes from rat liver in primary culture rapidly lost viability under hypoxic conditions. In the presence of glycine, L-alanine or L-serine loss of viability under hypoxic conditions was greatly retarded. Glycine and L-serine already showed significant protection from hypoxic injury at a concentration of...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/BF00808120

    authors: Brecht M,de Groot H

    更新日期:1994-02-01 00:00:00

  • A mechanistic role for polypeptide hormone receptor lateral mobility in signal transduction.

    abstract::Lateral diffusion of membrane-integral receptors within the plane of the membrane has been postulated to be mechanistically important for signal transduction. Direct measurement of polypeptide hormone receptor lateral mobility using fluorescence photobleaching recovery techniques indicates that tyrosine kinase recepto...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/BF00805831

    authors: Jans DA,Pavo I

    更新日期:1995-06-01 00:00:00