Cyclodidepsipeptides with a promising scaffold in medicinal chemistry.

Abstract:

:Among the large family of cyclodepsipeptides, the simplest members are the cyclodidepsipeptides which have an ester group and an amide group in the same six-membered ring. To point out the pharmacological potential of this class of compounds, the present article reviews structure, isolation, synthesis and biological properties of the known cyclodidepsipeptides. Synthesis of cyclodidepsipeptides is achieved by two general approaches--by initial formation of the amide bond, or initial formation of the ester bond; and subsequent intermolecular cyclization to cyclodidepsipeptide structure. It is closely related to the condensation and ring-closure strategies applied in the preparation of the larger members of the cyclodepsipeptide family. However, due to synthesis of the smaller heretocycles it allows for the use of more versatile building blocks. There are data on antimicrobial, antioxidant and immunomodulatory activities of cyclodidepsipeptides as well as their inhibitory activities toward α-glucosidase, acyl-CoA:cholesterol acyltransferase, xanthine oxidase and platelet aggregation. Because we have recently found that two 6-(propan-2-yl)-4-methyl-morpholine-2,5-diones, as novel non-purine xanthine oxidase inhibitors, may give promise to be used in the treatment of gout, in this review we have included a study of molecular interactions of the selected cyclodidepsipeptides with xanthine oxidase using idTarget web server. Cyclodidepsipeptides showed promising pharmacological activities and meet all criteria for good solubility and permeability. However, further research of their medical application is necessary. In addition to this, the diversity of natural cyclodidepsipeptides, simplicity for synthesis and convenience for rational drug design indicate the cyclodidepsipeptide as promising scaffold in medicinal chemistry.

journal_name

Amino Acids

journal_title

Amino acids

authors

Smelcerovic A,Dzodic P,Pavlovic V,Cherneva E,Yancheva D

doi

10.1007/s00726-014-1666-6

subject

Has Abstract

pub_date

2014-04-01 00:00:00

pages

825-40

issue

4

eissn

0939-4451

issn

1438-2199

journal_volume

46

pub_type

杂志文章,评审
  • 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

  • Age-related salivary polyamine increase in adolescents wearing orthodontic Ni-Ti archwires.

    abstract::Until now information about the influence of puberty on gingival tissue responses to Ni-Ti alloy haven't been available. Since our previous researches have demonstrated that Ni-Ti appliances have an influence on hyperplastic gingivopathy and data has pointed out a possible hormonal influence on the susceptibility of g...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s007260200001

    authors: Venza M,Visalli M,Ruggeri P,Cicciù D,Teti D

    更新日期:2002-01-01 00:00:00

  • Antidepressant-like effect of MPEP, a potent, selective and systemically active mGlu5 receptor antagonist in the olfactory bulbectomized rats.

    abstract::Using the olfactory bulbectomy model of depression, we examined the antidepressant-like activity of 2-methyl-6-(phenylethynyl)-pyridine (MPEP) in rats. Bulbectomized rats required a significantly greater number of trials to acquire the response similar to sham-operated controls in the passive avoidance model. Both the...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-001-0131-5

    authors: Wieronska JM,Szewczyk B,Branski P,Palucha A,Pilc A

    更新日期:2002-01-01 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

  • Metabolism and function in animal tissues of agmatine, a biogenic amine formed from arginine.

    abstract::Recently agmatine, decarboxylated arginine, has been shown to be an important biological compound in several animal tissues. This paper summarizes the known information regarding the transport of arginine, its decarboxylation and the effects of the agmatine formed mainly on NO and polyamine synthesis. ...

    journal_title:Amino acids

    pub_type: 杂志文章,评审

    doi:10.1007/s00726-003-0030-z

    authors: Grillo MA,Colombatto S

    更新日期:2004-02-01 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

  • Central regulation of feeding behavior through neuropeptides and amino acids in neonatal chicks.

    abstract::Animals at the neonatal stage have to eat more to support better growth and health. However, it is difficult to understand the mechanism of feeding during an early stage of life in the brain of the rodent model. Chickens are precocial and they can look for their food by themselves right after hatching. Neonatal chicks...

    journal_title:Amino acids

    pub_type: 杂志文章,评审

    doi:10.1007/s00726-019-02762-x

    authors: Tran PV,Chowdhury VS,Furuse M

    更新日期:2019-08-01 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

  • 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

  • Synthesis and structural studies of new analogues of PTH(1-11) containing Cα-tetra-substituted amino acids in position 8.

    abstract::The N-terminal 1-34 fragment of parathyroid hormone (PTH) is fully active in vitro and in vivo and it can reproduce all biological responses characteristic of the native intact PTH. Recently, analogues of PTH(1-11) fragments with helicity-enhancing substitutions have been demonstrated to yield potent analogues of PTH(...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-010-0591-6

    authors: Caporale A,Sturlese M,Schievano E,Mammi S,Peggion E

    更新日期:2010-11-01 00:00:00

  • Glycotriazole-peptides derived from the peptide HSP1: synergistic effect of triazole and saccharide rings on the antifungal activity.

    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...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-017-2441-2

    authors: Junior EFC,Guimarães CFRC,Franco LL,Alves RJ,Kato KC,Martins HR,de Souza Filho JD,Bemquerer MP,Munhoz VHO,Resende JM,Verly RM

    更新日期:2017-08-01 00:00:00

  • Mitochondrial nitric oxide inhibits ATP synthesis. Effect of free calcium in rat heart.

    abstract::Nitric oxide is a small potentially toxic molecule and a diatomic free radical. We report the interaction of L-arginine, oxygen and calcium with the synthesis of nitric oxide in heart mitochondria. Nitric oxide synthesis is increased in broken rat heart mitochondria compared with intact and permeabilized mitochondria....

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-002-0331-7

    authors: Saavedra-Molina A,Ramírez-Emiliano J,Clemente-Guerrero M,Pérez-Vázquez V,Aguilera-Aguirre L,González-Hernández JC

    更新日期:2003-01-01 00:00:00

  • ω-Amidase: an underappreciated, but important enzyme in L-glutamine and L-asparagine metabolism; relevance to sulfur and nitrogen metabolism, tumor biology and hyperammonemic diseases.

    abstract::In mammals, two major routes exist for the metabolic conversion of L-glutamine to α-ketoglutarate. The most widely studied pathway involves the hydrolysis of L-glutamine to L-glutamate catalyzed by glutaminases, followed by the conversion of L-glutamate to α-ketoglutarate by the action of an L-glutamate-linked aminotr...

    journal_title:Amino acids

    pub_type: 杂志文章,评审

    doi:10.1007/s00726-015-2061-7

    authors: Cooper AJ,Shurubor YI,Dorai T,Pinto JT,Isakova EP,Deryabina YI,Denton TT,Krasnikov BF

    更新日期:2016-01-01 00:00:00

  • Asymmetric synthesis of α-amino acids via homologation of Ni(II) complexes of glycine Schiff bases. Part 3: Michael addition reactions and miscellaneous transformations.

    abstract::The major goal of this review is a critical discussion of the literature data on asymmetric synthesis of α-amino acids via Michael addition reactions involving Ni(II)-complexes of amino acids. The material covered is divided into two conceptually different groups dealing with applications of: (a) Ni(II)-complexes of g...

    journal_title:Amino acids

    pub_type: 杂志文章,评审

    doi:10.1007/s00726-014-1764-5

    authors: Aceña JL,Sorochinsky AE,Soloshonok V

    更新日期:2014-09-01 00:00:00

  • Molecular imaging of fibrosis using a novel collagen-binding peptide labelled with 99mTc on SPECT/CT.

    abstract::Fibrosis, closely related to chronic various diseases, is a pathological process characterised by the accumulation of collagen (largely collagen type I). Non-invasive methods are necessary for the diagnosis and follow-up of fibrosis. This study aimed to develop a collagen-targeted probe for the molecular imaging of fi...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-016-2328-7

    authors: Zheng L,Ding X,Liu K,Feng S,Tang B,Li Q,Huang D,Yang S

    更新日期:2017-01-01 00:00:00

  • Widely targeted metabolomics and coexpression analysis as tools to identify genes involved in the side-chain elongation steps of aliphatic glucosinolate biosynthesis.

    abstract::Amino acid and glucosinolate biosynthesis are two interdependent pathways; amino acid synthesis as a part of primary metabolism provides the precursors for glucosinolate biosynthesis in secondary metabolism. In our previous studies, the combination of coexpression analysis and metabolite profiling led to the identific...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-010-0681-5

    authors: Albinsky D,Sawada Y,Kuwahara A,Nagano M,Hirai A,Saito K,Hirai MY

    更新日期:2010-10-01 00:00:00

  • Real-time heterogeneous protein-protein interaction between αA-crystallin N-terminal mutants and αB-crystallin using quartz crystal microbalance (QCM).

    abstract::The lens transparency depends on higher concentration of lens proteins and their interactions. α-Crystallin is one of the predominant lens proteins, responsible for proper structural and functional architecture of the lens microenvironment, and any alteration of which results in cataract formation. The R12C, R21L, R49...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-015-1935-z

    authors: Ramkumar S,Fujii N,Sakaue H,Fujii N,Thankappan B,kumari RP,Natarajaseenivasan K,Anbarasu K

    更新日期:2015-05-01 00:00:00

  • Plasma levels and urinary excretion of amino acids by subjects with renal calculi.

    abstract::Plasma levels and urinary amino acid excretions were estimated by high-performance liquid chromatography in 15 control subjects and 36 stone formers (SFs) classified according to the stone type: (1) 22 cases with calcium oxalate stones; (2) four cases with pure uric acid stones; (3) 10 cases with magnesium-ammonium ph...

    journal_title:Amino acids

    pub_type: 杂志文章,评审

    doi:10.1007/s00726-009-0359-z

    authors: Atanassova SS,Panchev P,Ivanova M

    更新日期:2010-05-01 00:00:00

  • Reduced muscle carnosine content in type 2, but not in type 1 diabetic patients.

    abstract::Carnosine is present in high concentrations in skeletal muscle where it contributes to acid buffering and functions also as a natural protector against oxidative and carbonyl stress. Animal studies have shown an anti-diabetic effect of carnosine supplementation. High carnosinase activity, the carnosine degrading enzym...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-011-1165-y

    authors: Gualano B,Everaert I,Stegen S,Artioli GG,Taes Y,Roschel H,Achten E,Otaduy MC,Junior AH,Harris R,Derave W

    更新日期:2012-07-01 00:00:00

  • Branched chain amino acid metabolism profiles in progressive human nonalcoholic fatty liver disease.

    abstract::Nonalcoholic fatty liver disease (NAFLD) is a globally widespread disease of increasing clinical significance. The pathological progression of the disease from simple steatosis to nonalcoholic steatohepatitis (NASH) has been well defined, however, the contribution of altered branched chain amino acid metabolomic profi...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-014-1894-9

    authors: Lake AD,Novak P,Shipkova P,Aranibar N,Robertson DG,Reily MD,Lehman-McKeeman LD,Vaillancourt RR,Cherrington NJ

    更新日期:2015-03-01 00:00:00

  • Glycine metabolism in animals and humans: implications for nutrition and health.

    abstract::Glycine is a major amino acid in mammals and other animals. It is synthesized from serine, threonine, choline, and hydroxyproline via inter-organ metabolism involving primarily the liver and kidneys. Under normal feeding conditions, glycine is not adequately synthesized in birds or in other animals, particularly in a ...

    journal_title:Amino acids

    pub_type: 杂志文章,评审

    doi:10.1007/s00726-013-1493-1

    authors: Wang W,Wu Z,Dai Z,Yang Y,Wang J,Wu G

    更新日期:2013-09-01 00:00:00

  • Folding properties of the hepatitis B core as a carrier protein for vaccination research.

    abstract::The hepatitis B core (HBc) protein has been used successfully in numerous experiments as a carrier for heterologous peptides. Folding and capsid formation of the chimeric proteins is not always achieved easily. In silico analyses were performed to provide further comprehension of the feasibility for predicting success...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-009-0365-1

    authors: Janssens ME,Geysen D,Broos K,De Goeyse I,Robbens J,Van Petegem F,Timmermans JP,Guisez Y

    更新日期:2010-05-01 00:00:00

  • Proteomic and metabolomic changes driven by elevating myocardial creatine suggest novel metabolic feedback mechanisms.

    abstract::Mice over-expressing the creatine transporter have elevated myocardial creatine levels [Cr] and are protected against ischaemia/reperfusion injury via improved energy reserve. However, mice with very high [Cr] develop cardiac hypertrophy and dysfunction. To investigate these contrasting effects, we applied a non-biase...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-016-2236-x

    authors: Zervou S,Yin X,Nabeebaccus AA,O'Brien BA,Cross RL,McAndrew DJ,Atkinson RA,Eykyn TR,Mayr M,Neubauer S,Lygate CA

    更新日期:2016-08-01 00:00:00

  • Effects of glutamate antagonists on the activity of aromatic L-amino acid decarboxylase.

    abstract::This study examines the hypothesis that glutamate tonically suppresses the activity of the enzyme aromatic L-amino acid decarboxylase (AADC), and hence the biosynthesis of dopamine, to explain how antagonists of glutamate receptors might potentiale the motor actions of L-DOPA in animal models of Parkinson's disease. A...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/BF01345241

    authors: Fisher A,Biggs CS,Starr MS

    更新日期:1998-01-01 00:00:00

  • Knockdown of ornithine decarboxylase antizyme 1 causes loss of uptake regulation leading to increased N1, N11-bis(ethyl)norspermine (BENSpm) accumulation and toxicity in NCI H157 lung cancer cells.

    abstract::Ornithine decarboxylase antizyme 1 (AZ1) is a major regulatory protein responsible for the regulation and degradation of ornithine decarboxylase (ODC). To better understand the role of AZ1 in polyamine metabolism and in modulating the response to anticancer polyamine analogues, a small interfering RNA strategy was use...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-011-1030-z

    authors: Fraser AV,Goodwin AC,Hacker-Prietz A,Sugar E,Woster PM,Casero RA Jr

    更新日期:2012-02-01 00:00:00

  • Oxidative degradation of N(ε)-fructosylamine-substituted peptides in heated aqueous systems.

    abstract::Glycation, or non-enzymatic glycosylation, is a common protein modification formed by reactions between reducing sugars (i.e. aldoses and ketoses) with protein amino groups. Resulting Amadori and Heyns compounds, respectively, can be oxidatively degraded yielding a structurally heterogeneous group of advanced glycatio...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-015-1940-2

    authors: Greifenhagen U,Frolov A,Hoffmann R

    更新日期:2015-05-01 00:00:00

  • Characterization of calmodulin binding domains in TRPV2 and TRPV5 C-tails.

    abstract::The transient receptor potential channels TRPV2 and TRPV5 belong to the vanilloid TRP subfamily. TRPV2 is highly similar to TRPV1 and shares many common properties with it. TRPV5 (and also its homolog TRPV6) is a rather distinct member of the TRPV subfamily. It is distant for being strictly Ca(2+)-selective and featur...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-010-0712-2

    authors: Holakovska B,Grycova L,Bily J,Teisinger J

    更新日期:2011-02-01 00:00:00

  • Membrane phosphoinositides and protein-membrane interactions.

    abstract::Proteins with polybasic clusters bind to negatively charged phosphoinositides at the cell membrane. In this review, I have briefly discussed the types of phosphoinositides naturally found on membrane surfaces and how they recruit protein complexes for carrying out the process of signal transduction. A large number of ...

    journal_title:Amino acids

    pub_type: 杂志文章,评审

    doi:10.1007/s00726-013-1512-2

    authors: Gokhale NA

    更新日期:2013-10-01 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

  • Dietary L-leucine and L-alanine supplementation have similar acute effects in the prevention of high-fat diet-induced obesity.

    abstract::High-protein diets have been shown to alleviate detrimental effects of high-fat diets and this effect can be partially mimicked by dietary L-leucine supplementation. Here, we aimed to elucidate the early mechanisms and the specificity of leucine effects. We performed a 1-week trial with male C57BL/6 mice fed ad libitu...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-012-1363-2

    authors: Freudenberg A,Petzke KJ,Klaus S

    更新日期:2013-02-01 00:00:00