Synthesis of novel sulfide-based cyclic peptidomimetic analogues to solonamides

被引：4

作者：

Vanegas, Jose Brango ^{[1
]}

Martinho, Luan A. ^{[1
]}

Bessa, Lucinda Janete ^{[2
]}

Vasconcelos, Andreanne G. ^{[3
]}

Placido, Alexandra ^{[4
,5
]}

Pereira, Alex L. ^{[6
]}

Leite, Jose Roberto S. A. ^{[3
]}

Machado, Angelo ^{[1
]}

机构：

[1] Univ Brasilia, Inst Quim, Campus Univ Darcy Ribeiro, BR-70910900 Brasilia, DF, Brazil

[2] Univ Porto, Fac Ciencias, LAQV REQUIMTE, Dept Quim & Bioquim, P-4169007 Porto, Portugal

[3] Univ Brasilia, Area Morfol, Fac Med, BR-70910900 Brasilia, DF, Brazil

[4] Univ Porto, Glial Cell Biol Lab, i3S, P-420013 Porto, Portugal

[5] UPTEC, Bioprospectum Lda, P-4200135 Porto, Portugal

[6] Univ Brasilia, Ctr Metropolitano, Campus Ceilandia, BR-72220275 Ceilandia Sul, DF, Brazil

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 15卷

关键词：

antivirulence drug; bacteria; macrocyclization; pathoblocker; quorum quenching; NATIVE AUTOINDUCING PEPTIDES; SOLID-PHASE SYNTHESES; STAPHYLOCOCCUS-AUREUS; MACRO-HETEROCYCLES; THIOETHER PEPTIDE; AGRC; MACROCYCLIZATION; RECEPTOR; POTENT; CYCLODEPSIPEPTIDES;

D O I：

10.3762/bjoc.15.247

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Eight new sulfide-based cyclic peptidomimetic analogues of solonamides A and B have been synthesized via solid-phase peptide synthesis and S(N)2' reaction on a Morita-Baylis-Hillman (MBH) residue introduced at the N-terminal of a tetrapeptide. This last step takes advantage of the electrophilic feature of the MBH residue and represents a new cyclization strategy occurring. The analogues were prepared in moderate overall yields and did not show toxic effects on Staphylococcus aureus growth and were not toxic to human fibroblasts. Two of them inhibited the hemolytic activity of S. aureus, suggesting an interfering action in the bacterial quorum sensing similar to the one already reported for solonamides.

引用

页码：2544 / 2551

页数：8

共 45 条

[1]

[Anonymous], AUR ROS ATCC 29213

[2] The agr Inhibitors Solonamide B and Analogues Alter Immune Responses to Staphylococccus aureus but Do Not Exhibit Adverse Effects on Immune Cell Functions [J].

Baldry, Mara ;

Kitir, Betul ;

Frokiaer, Hanne ;

Christensen, Simon B. ;

Taverne, Nico ;

Meijerink, Marjolein ;

Franzyk, Henrik ;

Olsen, Christian A. ;

Wells, Jerry M. ;

Ingmer, Hanne .

PLOS ONE, 2016, 11 (01)

[3] Surface Coatings that Promote Rapid Release of Peptide-Based AgrC Inhibitors for Attenuation of Quorum Sensing in Staphylococcus aureus [J].

Broderick, Adam H. ;

Stacy, Danielle M. ;

Tal-Gan, Yftah ;

Kratochvil, Michael J. ;

Blackwell, Helen E. ;

Lynn, David M. .

ADVANCED HEALTHCARE MATERIALS, 2014, 3 (01) :97-105

[4] Solid-phase syntheses of β-turn analogues to mimic or disrupt protein-protein interactions [J].

Burgess, K .

ACCOUNTS OF CHEMICAL RESEARCH, 2001, 34 (10) :826-835

[5] Bacterial small-molecule signaling pathways [J].

Camilli, A ;

Bassler, BL .

SCIENCE, 2006, 311 (5764) :1113-1116

[6] Parallel synthesis of 19-membered ring macro-heterocycles via intramolecular thioether formation [J].

Derbel, Safa ;

Ghedira, Kamel ;

Nefzi, Adel .

TETRAHEDRON LETTERS, 2010, 51 (28) :3607-3609

[7]

European Centre for Disease Prevention and Control, 2019, Surveillance of antimicrobial resistance in Europe Annual report of the European Antimicrobial Resistance Surveillance Network (EARS-Net), DOI [10.2900/230516, DOI 10.2900/230516]

[8]

Feng YB, 2000, BIOTECHNOL BIOENG, V71, P3, DOI 10.1002/(SICI)1097-0290(200024)71:1<3::AID-BIT2>3.0.CO

[9]

2-K

[10] Solid-phase SN2 macrocyclization reactions to form β-turn mimics [J].

Feng, YB ;

Pattarawarapan, M ;

Wang, ZC ;

Burgess, K .

ORGANIC LETTERS, 1999, 1 (01) :121-124

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