Stabilization of Angiotensin-(1-7) by key substitution with a cyclic non-natural amino acid.

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 bioavailability resulting from rapid enzymatic metabolism by peptidases including angiotensin-converting enzyme (ACE) and dipeptidyl peptidase 3 (DPP 3). We report the facile assembly of three novel Ang-(1-7) analogues by solid-phase peptide synthesis which incorporates the cyclic non-natural δ-amino acid ACCA. The analogues containing the ACCA substitution at the site of ACE cleavage exhibit complete resistance to human ACE, while substitution at the DDP 3 cleavage site provided stability against DPP 3 hydrolysis. Furthermore, the analogues retain the anti-proliferative properties of Ang-(1-7) against the 4T1 and HT-1080 cancer cell lines. These results suggest that ACCA-substituted Ang-(1-7) analogues which show resistance against proteolytic degradation by peptidases known to hydrolyze the native heptapeptide may be novel therapeutics in the treatment of cancer.

journal_name

Amino Acids

journal_title

Amino acids

authors

Wester A,Devocelle M,Tallant EA,Chappell MC,Gallagher PE,Paradisi F

doi

10.1007/s00726-017-2471-9

subject

Has Abstract

pub_date

2017-10-01 00:00:00

pages

1733-1742

issue

10

eissn

0939-4451

issn

1438-2199

pii

10.1007/s00726-017-2471-9

journal_volume

49

pub_type

杂志文章
  • Glutamine, arginine, and leucine signaling in the intestine.

    abstract::Glutamine and leucine are abundant constituents of plant and animal proteins, whereas the content of arginine in foods and physiological fluids varies greatly. Besides their role in protein synthesis, these three amino acids individually activate signaling pathway to promote protein synthesis and possibly inhibit auto...

    journal_title:Amino acids

    pub_type: 杂志文章,评审

    doi:10.1007/s00726-008-0225-4

    authors: Marc Rhoads J,Wu G

    更新日期:2009-05-01 00:00:00

  • The effect of lysine deprivation on leukemic blood.

    abstract::Studies have shown that specific amino acids are required for optimal growth of leukemic versus normal cells, and it is believed that the depletion of selected amino acids can abrogate tumor growth. We have developed a technique for studying the effect of amino acid deprivation on leukemic cell proliferation. The tech...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/BF00805995

    authors: Reiken SR,Briedis DM

    更新日期:1992-10-01 00:00:00

  • Prediction of protein structural classes by Chou's pseudo amino acid composition: approached using continuous wavelet transform and principal component analysis.

    abstract::A prior knowledge of protein structural classes can provide useful information about its overall structure, so it is very important for quick and accurate determination of protein structural class with computation method in protein science. One of the key for computation method is accurate protein sample representatio...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-008-0170-2

    authors: Li ZC,Zhou XB,Dai Z,Zou XY

    更新日期:2009-07-01 00:00:00

  • Effect of repetitive lysine-tryptophan motifs on the bactericidal activity of antimicrobial peptides.

    abstract::Previous studies identified lysine- and tryptophan-rich sequences within various cationic antimicrobial peptides. In the present study, we synthesized a series of peptides composed of lysine (K)-tryptophan (W) repeats (KW)( n ) (where n equals 2, 3, 4 or 5) with amida...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-012-1388-6

    authors: Gopal R,Seo CH,Song PI,Park Y

    更新日期:2013-02-01 00:00:00

  • A new method to synthesize creatine derivatives.

    abstract::Creatine is an amino acid that has a pivotal role in energy metabolism of cells. Creatine acts as an "ATP shuttle", carrying ATP to the sites where it is utilized, through its reversible phosphorylation by creatine kinase. Moreover, the creatine-phosphocreatine system delays ATP depletion during anoxia or ischemia, th...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-013-1525-x

    authors: Garbati P,Salis A,Adriano E,Galatini A,Damonte G,Balestrino M,Millo E

    更新日期:2013-10-01 00:00:00

  • Cysteine enhances activity and stability of immobilized papain.

    abstract::Immobilization of papain on Sepharose 6B in the presence of different concentrations of cysteine affected the enzyme activity depending on cysteine concentration. The maximum specific activity was observed when papain was immobilized with 200 mM cysteine. The immobilization process brought significant enhancement of s...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-009-0302-3

    authors: Homaei AA,Sajedi RH,Sariri R,Seyfzadeh S,Stevanato R

    更新日期:2010-03-01 00:00:00

  • Peptide analogues of 1811-1818 loop of the A3 subunit of the light chain A3-C1-C2 of FVIII of blood coagulation: biological evaluation.

    abstract::Factor VIII, the plasma protein deficient or defective in individuals with hemophilia A, is a critical member of the blood coagulation cascade. Recent studies have identified the FVIII light chain region Glu1811-Lys1818 as being involved in FIXa binding and in the assembly of the FX-activating FIXaz-FVIIIa complex. Ba...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-009-0464-z

    authors: Patsialas K,Koutsas C,Makris P,Liakopoulou-Kyriakides M

    更新日期:2010-07-01 00:00:00

  • Intramuscular adaptations to eccentric exercise and antioxidant supplementation.

    abstract::Prophylactic supplementation of N-acetyl-cysteine (NAC) and epigallocatechin gallate (EGCG) was studied for physiological and cellular changes in skeletal muscle after eccentric muscle contractions. Thirty healthy, active males (20.0 +/- 1.8 years, 160 +/- 7.1 cm, 76.1 +/- 17.0 kg) ingested for 14 days either 1,800 mg...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-009-0432-7

    authors: Kerksick CM,Kreider RB,Willoughby DS

    更新日期:2010-06-01 00:00:00

  • Pharmacological approaches to counter the toxicity of Dopa.

    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

    authors: VonVoigtlander PF,Fici GJ,Althaus JS

    更新日期:1998-01-01 00:00:00

  • Biosynthesis and metabolic engineering of glucosinolates.

    abstract::Glucosinolates are amino acid-derived natural plant products found throughout the Capparales order. Glucosinolates and their degradation products have a wide range of biological activities, e.g. in plant defense as deterrents against insect and fungi. The conversion of amino acids to aldoximes is a key step in glucosi...

    journal_title:Amino acids

    pub_type: 杂志文章,评审

    doi:10.1007/s007260200014

    authors: Mikkelsen MD,Petersen BL,Olsen CE,Halkier BA

    更新日期:2002-01-01 00:00:00

  • O-GlcNAc in cancer biology.

    abstract::O-linked β-N-actylglucosamine (O-GlcNAc) is a carbohydrate post-translational modification on hydroxyl groups of serine and/or threonine residues of cytosolic and nuclear proteins. Analogous to phosphorylation, O-GlcNAcylation plays crucial regulatory roles in a variety of cellular processes. O-GlcNAc was termed a nut...

    journal_title:Amino acids

    pub_type: 杂志文章,评审

    doi:10.1007/s00726-013-1543-8

    authors: Ma Z,Vosseller K

    更新日期:2013-10-01 00:00:00

  • L-Leucine induces growth arrest and persistent ERK activation in glioma cells.

    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

    authors: Takeuchi S,Nawashiro H,Wada K,Nomura N,Toyooka T,Otani N,Osada H,Matsuo H,Shinomiya N

    更新日期:2012-08-01 00:00:00

  • The relation between glutamine and the immunodepression observed in exercise.

    abstract::Glutamine is the most abundant amino acid in the body. It is an important fuel for some key cells of the immune system. Both the plasma concentration of glutamine and the functional ability of immune cells in the blood are decreased after prolonged, exhaustive exercise. Glutamine feeding has had beneficial effects in ...

    journal_title:Amino acids

    pub_type: 杂志文章,评审

    doi:10.1007/s007260170065

    authors: Castell LM,Newsholme EA

    更新日期:2001-01-01 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

  • 4-[18F]Fluoro-N-methyl-N-(propyl-2-yn-1-yl)benzenesulfonamide ([18F]F-SA): a versatile building block for labeling of peptides, proteins and oligonucleotides with fluorine-18 via Cu(I)-mediated click chemistry.

    abstract::Cu(I)-mediated [3+2]cycloaddition between azides and alkynes has evolved into a valuable bioconjugation tool in radiopharmaceutical chemistry. We have developed a simple, convenient and reliable radiosynthesis of 4-[18F]fluoro-N-methyl-N-(propyl-2-yn-1-yl)benzenesulfonamide ([18F]F-SA) as a novel aromatic sulfonamide-...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-012-1450-4

    authors: Ramenda T,Steinbach J,Wuest F

    更新日期:2013-04-01 00:00:00

  • Co-regulation of mitochondrial respiration by proline dehydrogenase/oxidase and succinate.

    abstract::Proline dehydrogenase/oxidase (PRODH/POX) is a mitochondrial protein critical to multiple stress pathways. Because of the roles of PRODH/POX in signaling, and its shared localization to the mitochondrial inner membrane with the electron transport chain (ETC), we investigated whether there was a direct relationship bet...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-015-2134-7

    authors: Hancock CN,Liu W,Alvord WG,Phang JM

    更新日期:2016-03-01 00:00:00

  • On the segregation of protein ionic residues by charge type.

    abstract::Based on ubiquitous presence of large ionic motifs and clusters in proteins involved in gene transcription and protein synthesis, we analyzed the distribution of ionizable sidechains in a broad selection of proteins with regulatory, metabolic, structural and adhesive functions, in agonist, antagonist, toxin and antimi...

    journal_title:Amino acids

    pub_type: 杂志文章,评审

    doi:10.1007/s00726-012-1418-4

    authors: Parker MS,Balasubramaniam A,Parker SL

    更新日期:2012-12-01 00:00:00

  • The many faces of interferon tau.

    abstract::Interferon tau (IFNT) was discovered as the pregnancy recognition signal in ruminants, but is now known to have a plethora of physiological functions in the mammalian uterus. The mammalian uterus includes, from the outer surface to the lumen, the serosa, myometrium and endometrium. The endometrium consists of the lumi...

    journal_title:Amino acids

    pub_type: 杂志文章,评审

    doi:10.1007/s00726-014-1905-x

    authors: Bazer FW,Ying W,Wang X,Dunlap KA,Zhou B,Johnson GA,Wu G

    更新日期:2015-03-01 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

  • Piceatannol attenuates homocysteine-induced endoplasmic reticulum stress and endothelial cell damage via heme oxygenase-1 expression.

    abstract::A growing body of evidence implicates endoplasmic reticulum (ER)-induced cellular dysfunction and apoptosis as important factors to a variety of diseases. In endothelial cells (ECs), the sulfur-containing amino acid homocysteine (Hcy) causes EC apoptosis and reactive oxygen species (ROS) generation through induction o...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-016-2375-0

    authors: Kil JS,Jeong SO,Chung HT,Pae HO

    更新日期:2017-04-01 00:00:00

  • Loss ofHindIII cleavage sites in theD-amino acid oxidase gene in some inbred strains of mice.

    abstract::D-Amino acid oxidase cDNA was amplified by a polymerase chain reaction using RNA extracted from the mouse kidney. When digested withHindIII, the cDNAs of the BALB/c and ddY/DAO(-) mice were cleaved into two fragments whereas the cDNA of the ddY/DAO(+) mice was not. Sequencing revealed that nucleotide-471 of the cDNAs ...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/BF00806548

    authors: Konno R,Sasaki M,Enami J,Niwa A

    更新日期:1995-03-01 00:00:00

  • The effect of acute taurine ingestion on 4-km time trial performance in trained cyclists.

    abstract::Taurine (TAU) has been shown to improve exercise time to exhaustion and 3-km running performance; however, no studies have considered the effect of acute TAU ingestion on short duration cycling time trial (TT) performance. The aim of this study was to determine the effects of a single oral acute dose of 1000 mg of TAU...

    journal_title:Amino acids

    pub_type: 杂志文章,随机对照试验

    doi:10.1007/s00726-016-2282-4

    authors: Ward R,Bridge CA,McNaughton LR,Sparks SA

    更新日期:2016-11-01 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

  • Homocysteine and oxidative stress.

    abstract::Hyperhomocysteinemia is an independent risk factor for cardiovascular disease (ischemic disease, such as stroke and myocardial infarction, and arterial and venous thrombotic events) in the general population. We can assume that the association is causal, based on the example of homocystinuria, and on the evidence put ...

    journal_title:Amino acids

    pub_type: 杂志文章,评审

    doi:10.1007/s00726-003-0026-8

    authors: Perna AF,Ingrosso D,De Santo NG

    更新日期:2003-12-01 00:00:00

  • PaleAle 5.0: prediction of protein relative solvent accessibility by deep learning.

    abstract::Predicting the three-dimensional structure of proteins is a long-standing challenge of computational biology, as the structure (or lack of a rigid structure) is well known to determine a protein's function. Predicting relative solvent accessibility (RSA) of amino acids within a protein is a significant step towards re...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-019-02767-6

    authors: Kaleel M,Torrisi M,Mooney C,Pollastri G

    更新日期:2019-09-01 00:00:00

  • No peptide left behind: the "out of range" recovery in IPG-IEF fractionation.

    abstract::IEF is often used in multidimensional shotgun proteomics and the narrow range of 3.5-4.5 is the recommended pH interval for the fractionation of tryptic peptides. Usually, even if IEF is performed in IPG strip with a narrow range pH, the entire sample must be loaded onto the strip, including the "out of IPG range" pep...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-014-1720-4

    authors: Iori E,Rattazzi M,Millioni R

    更新日期:2014-05-01 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

  • 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

  • Activity-based proteomics: enzymatic activity profiling in complex proteomes.

    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

    authors: Schmidinger H,Hermetter A,Birner-Gruenberger R

    更新日期:2006-06-01 00:00:00

  • Synthesis of a bicyclic delta-amino acid as a constrained Gly-Asn dipeptide isostere.

    abstract::Delta-amino acids are very attractive in drug discovery, especially in the peptidomimetic area, because of their capability to act as dipeptide isosteres and reverse turn mimetics. Herein we report the synthesis of a rigid delta-amino acid constrained by a 3-aza-6,8-dioxabicyclo[3.2.1]octane-based scaffold, which can ...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-007-0636-7

    authors: Trabocchi A,Menchi G,Danieli E,Guarna A

    更新日期:2008-06-01 00:00:00