Cytotoxic T lymphocyte epitope analogues containing cis- or trans-4-aminocyclohexanecarboxylic acid residues.

Abstract:

:In order to improve the immunotherapeutical potential of H-Cys-Leu-Gly-Gly-Leu-Leu-Thr-Met-Val-OH (CLG) peptide, an Epstein-Barr virus (EBV) subdominant epitope derived from the membrane protein LMP2, we have synthesized and tested CLG analogues containing cis- and/or trans-4-aminocyclohexanecarboxylic acid (ACCA) replacing Gly-Gly and/or Thr-Met dipeptide units. All pseudopeptides were tested for metabolic stability and for their capacity to bind HLA-A2 molecules and to sensitize target cells to lysis. All new compounds exhibited higher enzymatic resistance compared to the original CLG and some trans-ACCA-derivatives were able to associate HLA-A2 and to efficiently stimulate CTL responses directed against the CLG natural epitope.

journal_name

Bioorg Med Chem

authors

Marastoni M,Bazzaro M,Micheletti F,Gavioli R,Tomatis R

doi

10.1016/s0968-0896(02)00033-0

subject

Has Abstract

pub_date

2002-09-01 00:00:00

pages

3061-6

issue

9

eissn

0968-0896

issn

1464-3391

pii

S0968089602000330

journal_volume

10

pub_type

杂志文章
  • An approach to identifying novel substrates of bacterial arylamine N-acetyltransferases.

    abstract::Arylamine N-acetyltransferases (NATs) catalyse the acetylation of arylamine, arylhydrazine and arylhydroxylamine substrates by acetyl Coenzyme A. NAT has been discovered in a wide range of eukaryotic and prokaryotic species. Although prokaryotic NATs have been implicated in xenobiotic metabolism, to date no endogenous...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(02)00642-9

    authors: Brooke EW,Davies SG,Mulvaney AW,Pompeo F,Sim E,Vickers RJ

    更新日期:2003-04-03 00:00:00

  • Identification of selective inhibitors of sphingosine kinases 1 and 2 through a structure-activity relationship study of 4-epi-jaspine B.

    abstract::We recently reported that 4-epi-jaspine B exhibits potent inhibitory activity towards sphingosine kinases (SphKs). In this study, we investigated the effects of modifying the 2-alkyl group, as well as the functional groups on the THF ring of 4-epi-jaspine B using a diversity-oriented synthesis approach based on a late...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2017.03.059

    authors: Ohno H,Honda M,Hamada N,Miyagaki J,Iwata A,Otsuki K,Maruyama T,Nakamura S,Nakanishi I,Inuki S,Fujii N,Oishi S

    更新日期:2017-06-15 00:00:00

  • A continuous flow synthesis and derivatization of 1,2,4-thiadiazoles.

    abstract::A continuous flow process is presented that enables the efficient synthesis and derivatization of 1,2,4-thiadiazole heterocycles. Special attention was given to the safe handling of the versatile yet hazardous trichloromethane sulfenylchloride reagent including its in-line quenching in order to eliminate malodourous a...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2017.01.022

    authors: Baumann M,Baxendale IR

    更新日期:2017-12-01 00:00:00

  • Factors that influence T box riboswitch efficacy and tRNA affinity.

    abstract::The T box riboswitch is an intriguing potential target for antibacterial drug discovery. Found primarily in Gram-positive bacteria, the riboswitch regulates gene expression by selectively responding to uncharged tRNA to control transcription readthrough. Polyamines and molecular crowding are known to specifically affe...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2015.07.018

    authors: Zeng C,Zhou S,Bergmeier SC,Hines JV

    更新日期:2015-09-01 00:00:00

  • Design of a pyrene-containing fluorescence probe for labeling of RNA poly(A) tracts.

    abstract::A labeling probe containing a pyrenecarboxamide-tethered modified DNA base, (Py)U, has been developed for fluorometric detection of RNA poly(A) tracts, in which the fluorescence emission intensity was controlled by the microstructural change around (Py)U caused by binding with the target RNA. ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2007.09.024

    authors: Tanaka K,Okamoto A

    更新日期:2008-01-01 00:00:00

  • Protein linear indices of the 'macromolecular pseudograph alpha-carbon atom adjacency matrix' in bioinformatics. Part 1: prediction of protein stability effects of a complete set of alanine substitutions in Arc repressor.

    abstract::A novel approach to bio-macromolecular design from a linear algebra point of view is introduced. A protein's total (whole protein) and local (one or more amino acid) linear indices are a new set of bio-macromolecular descriptors of relevance to protein QSAR/QSPR studies. These amino-acid level biochemical descriptors ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2005.01.062

    authors: Marrero-Ponce Y,Medina-Marrero R,Castillo-Garit JA,Romero-Zaldivar V,Torrens F,Castro EA

    更新日期:2005-04-15 00:00:00

  • Syntheses and evaluation of a homologous series of aza-vesamicol as improved radioiodine-labeled probes for sigma-1 receptor imaging.

    abstract::Sigma-1 receptor imaging probes for determining the expression levels are desirable for diagnoses of various diseases and companion diagnoses of therapeutic agents targeting the sigma-1 receptor. In this study, we aimed to develop probes with higher affinity for the sigma-1 receptor. For this purpose, we synthesized a...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2019.03.054

    authors: Ogawa K,Masuda R,Mishiro K,Wang M,Kozaka T,Shiba K,Kinuya S,Odani A

    更新日期:2019-05-15 00:00:00

  • Characterization of novel furan compounds on the basis of their radical scavenging activity and cytoprotective effects against glutamate- and lipopolysaccharide-induced insults.

    abstract::There is increasing evidence indicating that free radicals and oxygenases such as cyclooxygenase (COX) and lipoxygenase (LOX) are related to the onset and development of neurodegenerative diseases. In order to prevent and/or delay these diseases, the use of radical-scavenging antioxidants and inhibitors against oxygen...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.10.038

    authors: Nishio K,Fukuhara A,Omata Y,Saito Y,Yamaguchi S,Kato H,Yoshida Y,Niki E

    更新日期:2008-12-15 00:00:00

  • A novel QSAR model for predicting induction of apoptosis by 4-aryl-4H-chromenes.

    abstract::A linear quantitative structure-activity relationship (QSAR) model is presented for modeling and predicting induction of apoptosis by 4-aryl-4H-chromenes. The model was produced by using the multiple linear regression (MLR) technique on a database that consists of 43 recently discovered 4-aryl-4H-chromenes. Among the ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2006.05.061

    authors: Afantitis A,Melagraki G,Sarimveis H,Koutentis PA,Markopoulos J,Igglessi-Markopoulou O

    更新日期:2006-10-01 00:00:00

  • Directed evolution of N-acetylneuraminic acid aldolase to catalyze enantiomeric aldol reactions.

    abstract::Expanding the scope of substrate specificity and stereoselectivity is of current interest in enzyme catalysis. Using error-prone PCR for in vitro directed evolution, the Neu5Ac aldolase from Escherichia coli has been altered to improve its catalytic activity toward enantiomeric substrates including N-acetyl-L-mannosam...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(03)00052-x

    authors: Wada M,Hsu CC,Franke D,Mitchell M,Heine A,Wilson I,Wong CH

    更新日期:2003-05-01 00:00:00

  • NMR study into the mechanism of recognition of the degree of polymerization by oligo/polysialic acid antibodies.

    abstract::Oligo/polysialic acids consisting of consecutive α(2,8)-linkages on gangliosides and glycoproteins play a role in cell adhesion and differentiation events in a manner that is dependent on the degree of polymerization (DP). Anti-oligo/polysialic acid antibodies often have DP-dependent antigenic specificity, and such un...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2013.07.023

    authors: Hanashima S,Sato C,Tanaka H,Takahashi T,Kitajima K,Yamaguchi Y

    更新日期:2013-10-01 00:00:00

  • New carbocyclic nucleoside analogues with a bicyclo[2.2.1]heptane fragment as sugar moiety; synthesis, X-ray crystallography and anticancer activity.

    abstract::An amine group was synthesized starting from an optically active bicyclo[2.2.1]heptane compound, which was then used to build the 5 atoms ring of a key 6-chloropurine intermediate. This was then reacted with ammonia and selected amines obtaining new adenine- and 6-substituted adenine conformationally constrained carbo...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2013.10.056

    authors: Tănase CI,Drăghici C,Căproiu MT,Shova S,Mathe C,Cocu FG,Enache C,Maganu M

    更新日期:2014-01-01 00:00:00

  • Synthesis and elastase-inhibiting activity of 2-pyridinyl-isothiazol-3(2H)-one 1,1-dioxides.

    abstract::The synthesis of a series of new isothiazol-3(2H)-one 1,1-dioxides with halogenated (mostly fluorinated) pyridinyl and pentafluorophenyl substituents at 2-position is reported. These compounds (18-24) became easily accessible from 2-thiocyanato-1-carboxaldehydes and aminopyridines, pentafluoroaniline, respectively, by...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.07.049

    authors: Eilfeld A,González Tanarro CM,Frizler M,Sieler J,Schulze B,Gütschow M

    更新日期:2008-09-01 00:00:00

  • Structure-activity relationship studies of manzamine A: amidation of positions 6 and 8 of the beta-carboline moiety.

    abstract::Twenty manzamine amides were synthesized and evaluated for in vitro antimalarial and antimicrobial activities. The amides of manzamine A (1) showed significantly reduced cytotoxicity against Vero cells, although were less active than 1. The structure-activity analysis showed that linear, short alkyl groups adjacent to...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2009.09.026

    authors: Wahba AE,Peng J,Kudrimoti S,Tekwani BL,Hamann MT

    更新日期:2009-11-15 00:00:00

  • Investigation into the influence of an acrylic acid acceptor in organic D-π-A sensitizers against phototoxicity.

    abstract::Photodynamic therapy (PDT) is a non-invasive, selective, and cost-effective cancer therapy. We previously reported that thiophene-based organic D-π-A sensitizers consist of an electron-donating (D) moiety, a π-conjugated bridge (π) moiety, and an electron-accepting (A) moiety, and are readily accessible and stable tem...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2020.115558

    authors: Fuse S,Moriya W,Sato S,Nakamura H

    更新日期:2020-07-01 00:00:00

  • Carbonic anhydrases as targets for medicinal chemistry.

    abstract::Carbonic anhydrases (CAs, EC 4.2.1.1) are zinc enzymes acting as efficient catalysts for the reversible hydration of carbon dioxide to bicarbonate. 16 different alpha-CA isoforms were isolated in mammals, where they play crucial physiological roles. Some of them are cytosolic (CA I, CA II, CA III, CA VII, CA XIII), ot...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.bmc.2007.04.020

    authors: Supuran CT,Scozzafava A

    更新日期:2007-07-01 00:00:00

  • Design, synthesis, and structure-activity relationships of potent GPIIb/IIIa antagonists: discovery of FK419.

    abstract::The discovery of the non-peptide antiplatelet injectable agent FK419 is reported. Based on the beta-turn structure of RGD peptide sequences in the alpha chain of fibrinogen, which binds the glycoprotein IIb/IIIa (GPIIb/IIIa) on the surface of platelets to induce platelet aggregation, the prototype 2 was designed. Afte...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2005.03.056

    authors: Yamanaka T,Ohkubo M,Kuroda S,Nakamura H,Takahashi F,Aoki T,Mihara K,Seki J,Kato M

    更新日期:2005-07-01 00:00:00

  • Bromo-deaza-SAH: a potent and selective DOT1L inhibitor.

    abstract::Chemical inhibition of proteins involved in chromatin-mediated signaling is an emerging strategy to control chromatin compaction with the aim to reprogram expression networks to alter disease states. Protein methyltransferases constitute one of the protein families that participate in epigenetic control of gene expres...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2013.01.049

    authors: Yu W,Smil D,Li F,Tempel W,Fedorov O,Nguyen KT,Bolshan Y,Al-Awar R,Knapp S,Arrowsmith CH,Vedadi M,Brown PJ,Schapira M

    更新日期:2013-04-01 00:00:00

  • One-pot enzymatic glycan remodeling of a therapeutic monoclonal antibody by endoglycosidase S (Endo-S) from Streptococcus pyogenes.

    abstract::A facile, one-pot enzymatic glycan remodeling of antibody rituximab to produce homogeneous high-mannose and hybrid type antibody glycoforms is described. This method was based on the unique substrate specificity of the endoglycosidase S (Endo-S) from Streptococcus pyogenes. While Endo-S efficiently hydrolyzes the bi-a...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2017.07.053

    authors: Tong X,Li T,Orwenyo J,Toonstra C,Wang LX

    更新日期:2018-04-01 00:00:00

  • Syntheses, activity and modeling studies of 3- and 4-(sulfo- and sulfonamidoalkyl)pyridine and piperidine-2-carboxylic acid derivatives as analogs of NMDA receptor antagonists.

    abstract::A series of 3- and 4-(sulfo- and sulfonamidoalkyl)pyridine and piperidine-2-carboxylic acid derivatives as analogs of NMDA receptor antagonists was prepared. Affinity for the NMDA receptor was determined by binding assays using the specific radioligand [3H] (2SR,4RS)-4-(phosphonomethyl)piperidine-2-carboxylic acid (CG...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/0968-0896(95)00087-w

    authors: el Hadri A,Maldivi P,Leclerc G,Rocher JP

    更新日期:1995-09-01 00:00:00

  • Dose dependent actions of LCL521 on acid ceramidase and key sphingolipid metabolites.

    abstract::The function of acid ceramidase (ACDase), whose congenital deficiency leads to Farber disease, has been recognized to be vital to tumor cell biology, and inhibition of its activity may be beneficial in cancer therapy. Therefore, manipulation of the activity of this enzyme may have significant effect, especially on can...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2018.11.012

    authors: Bai A,Bielawska A,Rahmaniyan M,Kraveka JM,Bielawski J,Hannun YA

    更新日期:2018-12-15 00:00:00

  • Synthesis of imidazo[1,5,4-de]quinoxalin-9-ones, benzimidazole analogues of pyrroloiminoquinone marine natural products.

    abstract::The imidazoquinoxalinones 1 and 2 are benzimidazole analogues of indole-based marine natural products called makaluvamins. The stabilized cation 1 and the zwitterion 2 were prepared in approximately 9 steps from readily available starting materials. Compound 1 is more cytostatic and cytotoxic than 2 and also shows act...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2004.10.016

    authors: Labarbera DV,Skibo EB

    更新日期:2005-01-17 00:00:00

  • A strategy for dual inhibition of the proteasome and fatty acid synthase with belactosin C-orlistat hybrids.

    abstract::The proteasome, a validated cellular target for cancer, is central for maintaining cellular homeostasis, while fatty acid synthase (FAS), a novel target for numerous cancers, is responsible for palmitic acid biosynthesis. Perturbation of either enzymatic machine results in decreased proliferation and ultimately cellul...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2017.01.020

    authors: Zhu M,Harshbarger WD,Robles O,Krysiak J,Hull KG,Cho SW,Richardson RD,Yang Y,Garcia A,Spiegelman L,Ramirez B,Wilson CT,Yau JA,Moore JT,Walker CB,Sacchettini JC,Liu WR,Sieber SA,Smith JW,Romo D

    更新日期:2017-06-01 00:00:00

  • Three-dimensional molecular-field analyses of octopaminergic agonists for the cockroach neuronal octopamine receptor.

    abstract::The quantitative structure-activity relationship of a set of 40 octopaminergic agonists against receptor 2 in cockroach nervous tissue, was analyzed using molecular-field analysis (MFA). MFA on the study set of those compounds evaluated effectively the energy between a probe and a molecular model at a series of points...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(03)00313-4

    authors: Hirashima A,Morimoto M,Kuwano E,Eto M

    更新日期:2003-08-15 00:00:00

  • 1,2,3-triazole-, arylamino- and thio-substituted 1,4-naphthoquinones: potent antitumor activity, electrochemical aspects, and bioisosteric replacement of C-ring-modified lapachones.

    abstract::1,2,3-Triazole-, arylamino- and thio-substituted naphthoquinones (24, 8, and 2 representatives, respectively) were synthesized in moderate yields and evaluated against several human cancer cell lines (blood, ovarian, breast, central nervous system, colon, and prostate cancers and melanoma), showing, for some of them, ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2014.01.033

    authors: da Cruz EH,Hussene CM,Dias GG,Diogo EB,de Melo IM,Rodrigues BL,da Silva MG,Valença WO,Camara CA,de Oliveira RN,de Paiva YG,Goulart MO,Cavalcanti BC,Pessoa C,da Silva Júnior EN

    更新日期:2014-03-01 00:00:00

  • Synthesis and antitumor activity of novel per-butyrylated glycosides of podophyllotoxin and its derivatives.

    abstract::A series of perbutyrylated glycosides of podophyllotoxin and its derivatives were synthesized and evaluated for their antitumor activity in vitro. Most of them exhibit cytotoxic activity against a panel of five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7, SW480) using MTT assays. Among the synthesized comp...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2015.02.021

    authors: Zi CT,Yang D,Dong FW,Li GT,Li Y,Ding ZT,Zhou J,Jiang ZH,Hu JM

    更新日期:2015-04-01 00:00:00

  • Novel 3,6-bis(imidazolidine)acridines as effective photosensitizers for photodynamic therapy.

    abstract::The photoeffect of new proflavine derivatives with DNA-binding and antitumour activities, 3,6-bis((1-alkyl-5-oxo-imidazolidin-2-yliden)imino)acridine hydrochlorides (AcrDIMs), was studied to evaluate them as potential photosensitizers for photodynamic antitumor therapy. EPR measurements showed that superoxide radical ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2014.07.013

    authors: Cižeková L,Grolmusová A,Ipóthová Z,Barbieriková Z,Brezová V,Hunáková L,Imrich J,Janovec L,Dovinová I,Paulíková H

    更新日期:2014-09-01 00:00:00

  • Synthesis of egonol derivatives and their antimicrobial activities.

    abstract::Eighteen derivatives of egonol (A-R) were synthesized and evaluated for their antimicrobial activities against Staphylococcus aureus ATCC 29213, Bacillus subtilis ATCC 6633, Candida albicans ATCC 10231 and Escherichia coli ATCC 8739 microorganisms comparing with egonol. The obtained data reported that compound B exhib...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2010.12.044

    authors: Emirdağ-Öztürk S,Karayildirim T,Anil H

    更新日期:2011-02-01 00:00:00

  • Preparation of yuanhuacine and relative daphne diterpene esters from Daphne genkwa and structure-activity relationship of potent inhibitory activity against DNA topoisomerase I.

    abstract::Two new daphne diterpene esters Yuanhuajine (2) and Yuanhuagine (4), together with three known daphne diterpene esters yuanhuacine (1), yuanhuadine (3), and yuanhuapine (5), were isolated and identified from Daphne genkwa, a traditional Chinese medicine. Their structures were elucidated by a combination of UV, IR, MS ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2006.01.055

    authors: Zhang S,Li X,Zhang F,Yang P,Gao X,Song Q

    更新日期:2006-06-01 00:00:00

  • Chemical synthesis and biochemical characterization of cyclic oligonucleotides containing acyl groups at both 5'- and 3'-terminal positions.

    abstract::Modified oligonucleotides, whose ON-OFF switch of hybridization can be controlled by an external stimulus, are important to understanding life phenomena and efficient treatment of diseases. The ON-OFF switch can be completely controlled by chemical modification of the oligonucleotide such as cyclization. However, thei...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2020.115799

    authors: Nishizawa S,Ohkubo A

    更新日期:2020-12-01 00:00:00