Design and synthesis of mono and bicyclic tetrapeptides thioester as potent inhibitor of histone deacetylases.

Abstract:

:Inhibitors of histone deacetylases (HDACs) are a promising class of anticancer agents that have an effect on gene regulation. The naturally occurring cyclic depsipeptide FK228 containing disulfide and Largazole possessing thioester functionalities act as pro-drugs and share the same HDAC inhibition mechanism in cell. Inspired from these facts, we have reported bicyclic tetrapeptide disulfide HDAC inhibitors resembling FK228 with potent activity and enhanced selectivity. In the present study, we report the design and synthesis of several mono and bicyclic tetrapeptide thioester HDAC inhibitors that share the inhibition mechanism similar to Largazole. Most of the compounds showed HDAC1 and HDAC4 inhibition and p21 promoting activity in nanomolar ranges. Among these the monocyclic peptides 1, 2 and bicyclic peptide, 4 are notable demanding more advanced research to be promising anticancer drug candidates.

journal_name

Amino Acids

journal_title

Amino acids

authors

Hoque MA,Islam MS,Islam MN,Kato T,Nishino N,Ito A,Yoshida M

doi

10.1007/s00726-014-1800-5

subject

Has Abstract

pub_date

2014-10-01 00:00:00

pages

2435-44

issue

10

eissn

0939-4451

issn

1438-2199

journal_volume

46

pub_type

杂志文章
  • 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

  • Central L-arginine reduced stress responses are mediated by L-ornithine in neonatal chicks.

    abstract::Recently, we observed that central administration of L-arginine attenuated stress responses in neonatal chicks, but the contribution of nitric oxide (NO) to this response was minimal. The sedative and hypnotic effects of L-arginine may be due to L-arginine itself and/or its metabolites, excluding NO. To clarify the me...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-007-0617-x

    authors: Suenaga R,Yamane H,Tomonaga S,Asechi M,Adachi N,Tsuneyoshi Y,Kurauchi I,Sato H,Denbow DM,Furuse M

    更新日期:2008-06-01 00:00:00

  • Expression and function of arginine-producing and consuming-enzymes in the kidney.

    abstract::The kidney plays a key role in arginine metabolism. Arginine production is controlled by argininosuccinate synthetase (ASS) and argininosuccinate lyase (ASL) which metabolize citrulline and aspartate to arginine and fumarate whereas arginine consumption is dependent on arginine:glycine amidinotransferase (GAT), which ...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-011-0897-z

    authors: Levillain O

    更新日期:2012-04-01 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

  • In silico investigation of molecular mechanism of laminopathy caused by a point mutation (R482W) in lamin A/C protein.

    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

    authors: Rajendran V,Purohit R,Sethumadhavan R

    更新日期:2012-08-01 00:00:00

  • Nucleobase-containing peptides: an overview of their characteristic features and applications.

    abstract::Reports on nucleobase-containing chiral peptides (both natural and artificial) and achiral pseudopeptides are reviewed. Their synthesis, structural features, DNA and RNA-binding ability, as well as some other interesting applications which make them promising diagnostic/therapeutic agents of great importance in many a...

    journal_title:Amino acids

    pub_type: 杂志文章,评审

    doi:10.1007/s00726-010-0567-6

    authors: Roviello GN,Benedetti E,Pedone C,Bucci EM

    更新日期:2010-06-01 00:00:00

  • A potential estrogen mimetic effect of a bis(ethyl)polyamine analogue on estrogen receptor positive MCF-7 breast cancer cells.

    abstract::BE-3-3-3-3 (1,15-(ethylamino)4,8,12-triazapentadecane) is a bis(ethyl)polyamine analogue under investigation as a therapeutic agent for breast cancer. Since estradiol (E(2)) is a critical regulatory molecule in the growth of breast cancer, we examined the effect of BE-3-3-3-3 on estrogen receptor α (ERα) positive MCF-...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-011-1005-0

    authors: Nayvelt I,John S,Hsu HC,Yang P,Liu W,Das G,Hyvönen MT,Alhonen L,Keinänen TA,Shirahata A,Patel R,Thomas T,Thomas TJ

    更新日期:2012-02-01 00:00:00

  • Physiological and therapeutic effects of carnosine on cardiometabolic risk and disease.

    abstract::Obesity, type 2 diabetes (T2DM) and cardiovascular disease (CVD) are the most common preventable causes of morbidity and mortality worldwide. They represent major public health threat to our society. Increasing prevalence of obesity and T2DM contributes to escalating morbidity and mortality from CVD and stroke. Carnos...

    journal_title:Amino acids

    pub_type: 杂志文章,评审

    doi:10.1007/s00726-016-2208-1

    authors: Baye E,Ukropcova B,Ukropec J,Hipkiss A,Aldini G,de Courten B

    更新日期:2016-05-01 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

  • 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

  • Differential regulation of protein synthesis by amino acids and insulin in peripheral and visceral tissues of neonatal pigs.

    abstract::The high efficiency of protein deposition during the neonatal period is driven by high rates of protein synthesis, which are maximally stimulated after feeding. In the current study, we examined the individual roles of amino acids and insulin in the regulation of protein synthesis in peripheral and visceral tissues of...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-008-0149-z

    authors: Suryawan A,O'Connor PM,Bush JA,Nguyen HV,Davis TA

    更新日期:2009-05-01 00:00:00

  • Protein and non-protein biomarkers in melanoma: a critical update.

    abstract::Melanoma is the most malignant type of all skin neoplasms. Its worldwide incidence has steadily increased during the past decades, suggesting a probable melanoma 'epidemic'. Although current clinical, morphologic, and histopathologic methods provide insights into disease behavior and outcome, melanoma is still an unpr...

    journal_title:Amino acids

    pub_type: 杂志文章,评审

    doi:10.1007/s00726-012-1409-5

    authors: Tandler N,Mosch B,Pietzsch J

    更新日期:2012-12-01 00:00:00

  • CCK and NPY as anti-anxiety treatment targets: promises, pitfalls, and strategies.

    abstract::Short CCK peptides elicit panic attacks in humans and anxiogenic-like effects in some animal models, but CCK receptor antagonists have not been found clinically effective. Yet CCK overactivity appears to be involved in submissive behaviour, and CCKB receptor expression and binding are increased in suicide victims and ...

    journal_title:Amino acids

    pub_type: 杂志文章,评审

    doi:10.1007/s00726-006-0334-x

    authors: Harro J

    更新日期:2006-10-01 00:00:00

  • Antimicrobial activity and membrane-active mechanism of tryptophan zipper-like β-hairpin antimicrobial peptides.

    abstract::Antimicrobial peptides (AMPs) with amphipathic β-hairpin structures have been demonstrated to possess potent antimicrobial activities and great cell selectivities. However, our understanding of β-hairpin antimicrobial peptides lags behind that of α-helices, mainly because it is difficult for short peptides to form rob...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-015-2029-7

    authors: Xu L,Chou S,Wang J,Shao C,Li W,Zhu X,Shan A

    更新日期:2015-11-01 00:00:00

  • Applications and current challenges of proteomic approaches, focusing on two-dimensional electrophoresis.

    abstract::Since the formulation of the concept of "proteomics" in 1995, a plethora of proteomic technologies have been developed in order to study proteomes of tissues, cells and organelles. The powerful new technologies enabled by proteomic approaches have lead to the application of these methods to an exponentially increasing...

    journal_title:Amino acids

    pub_type: 杂志文章,评审

    doi:10.1007/s00726-006-0460-5

    authors: Vercauteren FG,Arckens L,Quirion R

    更新日期:2007-09-01 00:00:00

  • Synthesis and biological activity of oxytocin analogues containing unnatural amino acids in position 9: structure activity study.

    abstract::We report the solid phase synthesis and some pharmacological properties of 24 oxytocin (OT) analogues. Basic modifications at position 9 (introduction of L- or D-beta-(2-thienyl)-alanine [L- or D-Thi], or L- or D-3-Pyridylalanine [L- or D-3-Pal]) were combined with D-tyrosine(OEthyl) [D-Tyr(Et)] or D-1-naphthylalanine...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-009-0372-2

    authors: Magafa V,Borovicková L,Slaninová J,Cordopatis P

    更新日期:2010-05-01 00:00:00

  • Margatoxin and iberiotoxin, two selective potassium channel inhibitors, induce c-fos like protein and mRNA in rat organotypic dorsal striatal slices.

    abstract::The isolated single organotypic slice model allows to investigate the effects of drugs and toxins on the expression of transcription factors in the striatum without dopaminergic and glutamatergic interactions. In this study the effects of margatoxin and iberiotoxin on the expression of c-fos mRNA by in situ hybridizat...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s007260070030

    authors: Saria A,Fischer HS,Humpel C,Pfattner A,Schatz DS,Schuligoi R

    更新日期:2000-01-01 00:00:00

  • Immunohistochemical localization of D-aspartate oxidase in porcine peripheral tissues.

    abstract::D-Aspartate (D-Asp) is an endogenous substance in mammals. Degradation of D-Asp is carried out only by D-aspartate oxidase (DDO). We measured DDO activity in porcine tissues, and produced an anti-porcine DDO antibody to examine the cellular localization of DDO. All the tissues examined showed DDO activities, whereas t...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-010-0785-y

    authors: Yamamoto A,Tanaka H,Ishida T,Horiike K

    更新日期:2011-07-01 00:00:00

  • A dual action of taurine on the delayed rectifier K(+) current in embryonic chick cardiomyocytes.

    abstract::Effects of taurine on the delayed rectifier K(+) channel in isolated 10-day-old embryonic chick ventricular cardiomyocytes were examined at different intracellular Ca(2+) concentrations ([Ca]i), using whole-cell voltage and current clamp techniques. Experiments were performed at room temperature (22°C). Test pulses we...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/BF00805955

    authors: Satoh H

    更新日期:1995-09-01 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

  • Simultaneous stable-isotope dilution GC-MS measurement of homoarginine, guanidinoacetate and their common precursor arginine in plasma and their interrelationships in healthy and diseased humans.

    abstract::Low concentrations of L-homoarginine (hArg) in plasma or serum and urine have recently emerged as a novel cardiovascular risk factor. Previously, we reported gas chromatography-mass spectrometry (GC-MS) and GC-tandem MS (GC-MS/MS) methods for the quantitative determination of hArg and Arg in plasma, serum, urine and o...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-015-2120-0

    authors: Hanff E,Kayacelebi AA,Yanchev GR,Maassen N,Haghikia A,Tsikas D

    更新日期:2016-03-01 00:00:00

  • Taurine supplementation induces long-term beneficial effects on glucose homeostasis in ob/ob mice.

    abstract::The sulfur-containing amino acid, taurine (Tau), regulates glucose and lipid homeostasis under normal, pre- and diabetic conditions. Here, we aimed to verify whether Tau supplementation exerts its beneficial effects against obesity, hyperglycemia and alterations in islet functions, in leptin-deficient obese (ob/ob), o...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-018-2553-3

    authors: Borck PC,Vettorazzi JF,Branco RCS,Batista TM,Santos-Silva JC,Nakanishi VY,Boschero AC,Ribeiro RA,Carneiro EM

    更新日期:2018-06-01 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

  • Antizyme inhibitor 2: molecular, cellular and physiological aspects.

    abstract::Polyamines are small organic polycations essential for cell proliferation and survival. Antizymes (AZs) are small proteins regulated by polyamines that inhibit polyamine biosynthesis and uptake in mammalian cells. In addition, antizyme functions are also regulated by antizyme inhibitors, homologue proteins of ornithin...

    journal_title:Amino acids

    pub_type: 杂志文章,评审

    doi:10.1007/s00726-009-0419-4

    authors: López-Contreras AJ,Ramos-Molina B,Cremades A,Peñafiel R

    更新日期:2010-02-01 00:00:00

  • The effect of heat shock on amino acid transport and cell volume in 3T3 cells.

    abstract::In 3T3 cells temperatures higher than physiological stimulated amino acid transport activity in a dose-dependent manner up to 44 degrees C. However, the temperature increase did not induce widespread transport increase of all other nutrients tested. The activities of both amino acid transport systems A and ASC were en...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s007260170033

    authors: Petronini PG,Caccamo AE,Alfieri RR,Bonelli MA,Borghetti AF

    更新日期:2001-01-01 00:00:00

  • Creatine supplementation as a possible new therapeutic approach for fatty liver disease: early findings.

    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

    authors: Deminice R,de Castro GS,Brosnan ME,Brosnan JT

    更新日期:2016-08-01 00:00:00

  • Differential protein expression profile in gastrointestinal stromal tumors.

    abstract::Gastrointestinal stromal tumors (GISTs) arise from the interstitial cells of Cajal through gain of function mutations of the oncogene KIT. Imatinib offers the first effective treatment for patients with GISTs, but the therapeutic outcome strongly depends on the type of KIT mutation. We used ProteinChip technology to i...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-004-0140-2

    authors: Landuyt B,Prenen H,Debiec-Rychter M,Sciot R,de Bruijn EA,van Oosterom AT

    更新日期:2004-12-01 00:00:00

  • Differential responses to anxiogenic drugs in a mouse model of panic disorder as revealed by Fos immunocytochemistry in specific areas of the fear circuitry.

    abstract::Sensitivity to pharmacological challenges has been reported in patients with panic disorder. We have previously validated transgenic mice overexpressing the neurotrophin-3 (NT-3) receptor, TrkC (TgNTRK3), as an engineered murine model of panic disorder. We could determine that TgNTRK3 mice presented increased cellular...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-006-0464-1

    authors: Sahún I,Gallego X,Gratacòs M,Murtra P,Trullás R,Maldonado R,Estivill X,Dierssen M

    更新日期:2007-11-01 00:00:00

  • Studies on the synthesis and stability of α-ketoacyl peptides.

    abstract::Oxidative stress, an excess of reactive oxygen species (ROS), may lead to oxidative post-translational modifications of proteins resulting in the cleavage of the peptide backbone, known as α-amidation, and formation of fragments such as peptide amides and α-ketoacyl peptides (α-KaP). In this study, we first compared d...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-020-02902-8

    authors: Sajapin J,Hellwig M

    更新日期:2020-10-01 00:00:00

  • Isolation and antiproliferation of tumor cells by a novel peptide (TC22) from the beetle Tribolium castaneum.

    abstract::Anticancer peptides (ACPs) are biologically anticancer active molecules that are produced by mammals, plants, insects and microorganisms. Here, a new peptide (TC22) with the amino acid sequence MTVVLLLIVLPLLGGVHSSGIL was identified and characterized from the beetle Tribolium castaneum. We found it inhibited the growth...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-018-2666-8

    authors: Liu XD,Zhang FX,Qin ZH,Shan H

    更新日期:2019-02-01 00:00:00