Abstract:
:This work proposes a strategy that uses solid-phase peptide synthesis associated with copper(I)-catalyzed azide alkyne cycloaddition reaction to promote the glycosylation of an antimicrobial peptide (HSP1) containing a carboxyamidated C-terminus (HSP1-NH2). Two glycotriazole-peptides, namely [p-Glc-trz-G1]HSP1-NH2 and [p-GlcNAc-trz-G1]HSP1-NH2, were prepared using per-O-acetylated azide derivatives of glucose and N-acetylglucosamine in the presence of copper(II) sulfate pentahydrate (CuSO4·5H2O) and sodium ascorbate as a reducing agent. In order to investigate the synergistic action of the carbohydrate motif linked to the triazole-peptide structure, a triazole derivative [trz-G1]HSP1-NH2 was also prepared. A set of biophysical approaches such as DLS, Zeta Potential, SPR and carboxyfluorescein leakage from phospholipid vesicles confirmed higher membrane disruption and lytic activities as well as stronger peptide-LUVs interactions for the glycotriazole-peptides when compared to HSP1-NH2 and to its triazole derivative, which is in accordance with the performed biological assays: whereas HSP1-NH2 presents relatively low and [trz-G1]HSP1-NH2 just moderate fungicidal activity, the glycotriazole-peptides are significantly more effective antifungal agents. In addition, the glycotriazole-peptides and the triazole derivative present strong inhibition effects on ergosterol biosynthesis in Candida albicans, when compared to HSP1-NH2 alone. In conclusion, the increased fungicidal activity of the glycotriazole-peptides seems to be the result of (A) more pronounced membrane-disruptive properties, which is related to the presence of a saccharide ring, together with (B) the inhibition of ergosterol biosynthesis, which seems to be related to the presence of both the monosaccharide and the triazole rings.
journal_name
Amino Acidsjournal_title
Amino acidsauthors
Junior EFC,Guimarães CFRC,Franco LL,Alves RJ,Kato KC,Martins HR,de Souza Filho JD,Bemquerer MP,Munhoz VHO,Resende JM,Verly RMdoi
10.1007/s00726-017-2441-2subject
Has Abstractpub_date
2017-08-01 00:00:00pages
1389-1400issue
8eissn
0939-4451issn
1438-2199pii
10.1007/s00726-017-2441-2journal_volume
49pub_type
杂志文章相关文献
AMINO ACIDS文献大全abstract::Glioma is the most common type of brain tumor, and has the worst prognosis in human malignancy. Experimental evidence suggests that the use of high concentrations of various amino acids may perturb neoplastic cell growth. Thus, the aim of this study was to investigate whether essential amino acids can alter the growth...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s00726-011-1122-9
更新日期:2012-08-01 00:00:00
abstract::Lamin A/C proteins are the major components of a thin proteinaceous filamentous meshwork, the lamina, that underlies the inner nuclear membrane. A few specific mutations in the lamin A/C gene cause a disease with remarkably different clinical features: FPLD, or familial partial lipodystrophy (Dunnigan-type), which mai...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s00726-011-1108-7
更新日期:2012-08-01 00:00:00
abstract::This work deals with the Dakin-West synthesis, starting from the nucleoamino acid 1-thyminyl acetic acid, as well the NMR, ESI MS, and X-ray characterization of a heteroaromatic compound denominated by us T(2)CO, comprising two thymine moieties anchored to a 2-propanonic unit, the spectroscopic properties of which wer...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s00726-012-1237-7
更新日期:2012-10-01 00:00:00
abstract::In the postgenomic era new technologies are emerging for global analysis of protein function. The introduction of active site-directed chemical probes for enzymatic activity profiling in complex mixtures, known as activity-based proteomics has greatly accelerated functional annotation of proteins. Here we review probe...
journal_title:Amino acids
pub_type: 杂志文章,评审
doi:10.1007/s00726-006-0305-2
更新日期:2006-06-01 00:00:00
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
更新日期:2018-10-01 00:00:00
abstract::Relaxin family peptides perform a variety of biological functions by binding and activating relaxin family peptide receptor 1-4 (RXFP1-4), four A-class G protein-coupled receptors. In the present work, we developed a novel ligand binding assay for RXFP3 and RXFP4 based on NanoLuc complementation technology (NanoBiT). ...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s00726-018-2588-5
更新日期:2018-08-01 00:00:00
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
更新日期:2018-07-01 00:00:00
abstract::L-tryptophan is an essential amino acid in food, but is also widely used as a drug on the basis of several physiological actions. Lately, tryptophan's uses as a drug and as a food supplement have been discontinued in several countries due to its severe side-effects.In the present study, the distribution of tryptophan ...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/BF00806494
更新日期:1995-06-01 00:00:00
abstract::Methionine (Met) is an essential amino acid for all organisms. In plants, Met also functions as a precursor of plant hormones, polyamines, and defense metabolites. The regulatory mechanism of Met biosynthesis is highly complex and, despite its great importance, remains unclear. To investigate how accumulation of Met i...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s00726-010-0562-y
更新日期:2010-10-01 00:00:00
abstract::Over the last few years, consistent data have demonstrated that creatine (Cr) supplementation prevents the accumulation of fat in rat liver as well as the progression of fatty liver disease in different situations. Studies have demonstrated that Cr is effective and prevents fatty liver in high-fat and choline-deficien...
journal_title:Amino acids
pub_type: 杂志文章,评审
doi:10.1007/s00726-016-2183-6
更新日期:2016-08-01 00:00:00
abstract::Taurine is found in bone tissue, but its function in skeletal tissue is not fully understood. The present study was undertaken to investigate regulation of gene expression of connective tissue growth factor (CTGF), and the roles of mitogen-activated protein kinases (MAPKs) in murine osteoblast MC3T3-E1 cells treated w...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s00726-006-0380-4
更新日期:2007-01-01 00:00:00
abstract::Among the available protocols, chemically driven approaches to oxidize cysteine may not be required for molecules that, under the native-like conditions, naturally fold in conformations ensuring an effective pairing of the right disulfide bridge pattern. In this contest, we successfully prepared the distinctin, a natu...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s00726-015-1983-4
更新日期:2015-08-01 00:00:00
abstract::The relationship between taurine concentrations of plasma, whole blood, serum and skeletal muscle during taurine depletion and repletion was investigated in cats, to identify the most useful indicators of taurine status. Sixteen cats were fed a purified diet containing either 0 or 0.15 g/kg taurine for 5 months. Treat...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s007260170006
更新日期:2001-12-01 00:00:00
abstract::A fast and efficient microwave-assisted solid phase peptide synthesis (MW-SPPS) of a 51mer peptide, the main heparin-binding site (60-110) of human pleiotrophin (hPTN), using 2-chlorotrityl chloride resin (CLTR-Cl) following the 9-fluorenylmethyloxycarbonyl/tert-butyl (Fmoc/tBu) methodology and with the standard N,N'-...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s00726-010-0753-6
更新日期:2011-05-01 00:00:00
abstract::The present research has been carried out to elicit the mechanism of antiangiogenic activity of a fusion peptide P2. Peptide P2 was designed by the connection of a heptapeptide MMP inhibitor to ES-2, a fragment of Endostatin. In a previous study, P2 demonstrated strong antiangiogenic and antitumor effect, and the curr...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s00726-018-2589-4
更新日期:2018-08-01 00:00:00
abstract::Angiotensin-(1-7) [Ang-(1-7)], a heptapeptide hormone of the renin-angiotensin-aldosterone system, is a promising candidate as a treatment for cancer that reflects its anti-proliferative and anti-angiogenic properties. However, the peptide's therapeutic potential is limited by the short half-life and low bioavailabili...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s00726-017-2471-9
更新日期:2017-10-01 00:00:00
abstract::eIF5A is highly conserved from archaea to mammals, essential for cell viability and the only protein known to contain the essential amino acid residue hypusine, generated by a unique posttranslational modification. eIF5A was originally identified as a translation initiation factor due to its ability to stimulate the f...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s00726-011-0985-0
更新日期:2012-02-01 00:00:00
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
更新日期:2005-03-01 00:00:00
abstract::The enhancing effect on the water structure has been confirmed for most of the osmolytes exhibiting both stabilizing and destabilizing properties in regard to proteins. The presented work concerns osmolytes, which should be classified as "structure breaking" solutes: taurine and N,N,N-trimethyltaurine (TMT). Here, we ...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s00726-017-2499-x
更新日期:2018-01-01 00:00:00
abstract::The aim of this study was to determine the contribution of dietary amino acids (AA) to energy metabolism under high protein (HP) diets, using a double tracer method to follow simultaneously the metabolic fate of α-amino groups and carbon skeletons. Sixty-seven male Wistar rats were fed a normal (NP) or HP diet for 14 ...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s00726-010-0756-3
更新日期:2011-05-01 00:00:00
abstract::In the absence of exogenous Ca(2+) and Mg(2+) and in the presence of EGTA, which favours the release of endogenous Ca(2+), the polyamine spermine is able to stimulate the activity of pyruvate dehydrogenase complex (PDC) of energized rat liver mitochondria (RLM). This stimulation exhibits a gradual concentration-depend...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s00726-008-0099-5
更新日期:2009-03-01 00:00:00
abstract::The sulfur-containing excitatory amino acid (EAA) L-cysteine sulfinic acid (CSA), a neurotransmitter candidate, is endogenously synthesized from L-cysteine (Cys). Exogenous Cys administration into the brain produces cardiovascular effects; these effects likely occur via synaptic stimulation of central nervous system (...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s00726-014-1733-z
更新日期:2014-07-01 00:00:00
abstract::Formalin-fixed paraffin-embedded (FFPE) tissues are a real treasure for retrospective analysis considering the amount of samples present in hospital archives, combined with pathological, clinical, and outcome information available for every sample. Although unlocking the proteome of these tissues is still a challenge,...
journal_title:Amino acids
pub_type: 杂志文章,评审
doi:10.1007/s00726-013-1494-0
更新日期:2013-08-01 00:00:00
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
更新日期:1998-01-01 00:00:00
abstract::Chiral dehydroamino acid building blocks are versatile starting materials for the preparation of optically active unusual amino acids and other compounds of pharmacological interest. Herein we disclose the expedient preparation of dehydroalanines (ΔAla) equipped with oxazolidin-2-one (Oxd) chiral auxiliaries, Ts-Oxd-Δ...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s00726-014-1839-3
更新日期:2014-12-01 00:00:00
abstract::Dopa and related catecholamines and their degradation products have been demonstrated to have neurotoxic potential in a number of cellular and in vivo experiments. Several mechanisms have been hypothesized to be involved including generation of prooxidant products that subsequently oxidize membrane lipids and exposed ...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/BF01345261
更新日期:1998-01-01 00:00:00
abstract::We have developed the first operationally simple and environmentally benign protocol for the aqueous asymmetric Michael addition reaction of chiral nickel(II) glycinate with nitroalkenes. The reactions proceeded smoothly in the presence of TBAB (tetrabutyl ammonium bromide) in neat water at room temperature and provid...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s00726-011-0870-x
更新日期:2012-05-01 00:00:00
abstract::The specific function of putative cut2 protein (or CFP25), encoded by the Rv2301 gene from Mycobacterium tuberculosis H37Rv, has not been identified yet. The aim of this study was to assess some of CFP25 characteristics and its possible biological role in Mycobacterium tuberculosis H37Rv invasion process to target cel...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s00726-011-0938-7
更新日期:2012-06-01 00:00:00
abstract::The cross-linking of protein molecules to form stable supramolecular aggregates capable of acting as protective and supporting structures is a common feature of organisms coping with the stresses of life. These new polymeric forms range from thick rigid structures to thin flexible membranes. The formation of such cros...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/BF00813999
更新日期:1991-10-01 00:00:00
abstract::3-Fluorotyrosine fluorescence is quenched effectively by phosphate ions not only by a dynamic but also by a static mechanism owing to H-bond complex formation in ground state. 3-Fluorotyrosine pKa values both in the ground and first excited state (8.3 and 4, respectively) are appreciably lower than those of tyrosine, ...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/BF00805830
更新日期:1993-10-01 00:00:00