New coumarin-based fluorescent melatonin ligands. Design, synthesis and pharmacological characterization

被引：17

作者：

de la Fuente Revenga, Mario ^{[1
]}

Herrera-Arozamena, Clara ^{[1
]}

Fernandez-Saez, Nerea ^{[1
]}

Barco, Gema ^{[1
]}

Garcia-Orue, Itxaso ^{[1
]}

Sugden, David ^{[2
]}

Rivara, Silvia ^{[3
]}

Isabel Rodriguez-Franco, Maria ^{[1
]}

机构：

[1] Consejo Super Invest Cient IQM CSIC, Inst Quim Med, Madrid 28006, Spain

[2] Kings Coll London, Div Womens Hlth, London SE1 1UL, England

[3] Univ Parma, Dipartimento Farm, I-43124 Parma, Italy

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2015年 / 103卷

关键词：

Melatonin; GPCRs fluorescent probes; Coumarins; Bioisosterism; DERIVATIVES; RECEPTORS;

D O I：

10.1016/j.ejmech.2015.09.003

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The design and synthesis of a series of new fluorescent coumarin-containing melatonin analogues is presented. The combination of high-binding affinities for human melatonergic receptors (h-MT1R and h-MT2R) and fluorescent properties, derived from the inclusion of melatonin pharmacophoric elements in the coumarin scaffold, yielded suitable candidates for the development of MT1R and MT2R fluorescent probes for imaging in biological media. (C) 2015 Elsevier Masson SAS. All rights reserved.

引用

页码：370 / 373

页数：4

共 15 条

[1]

[Anonymous], HUM MT1 MT2 REC AG R

[2] Original Fluorescent Ligand-Based Assays Open New Perspectives in G-Protein Coupled Receptor Drug Screening [J].

Cottet, Martin ;

Faklaris, Orestis ;

Zwier, Jurriaan M. ;

Trinquet, Eric ;

Pin, Jean-Philippe ;

Durroux, Thierry .

PHARMACEUTICALS, 2011, 4 (01) :202-214

[3] Novel N-Acetyl Bioisosteres of Melatonin: Melatonergic Receptor Pharmacology, Physicochemical Studies, and Phenotypic Assessment of Their Neurogenic Potential [J].

de la Fuente Revenga, Mario ;

Fernandez-Saez, Nerea ;

Herrera-Arozamena, Clara ;

Morales-Garcia, Jose A. ;

Alonso-Gil, Sandra ;

Perez-Castillo, Ana ;

Caignard, Daniel-Henri ;

Rivara, Silvia ;

Isabel Rodriguez-Franco, Maria .

JOURNAL OF MEDICINAL CHEMISTRY, 2015, 58 (12) :4998-5014

[4] Neurogenic Potential Assessment and Pharmacological Characterization of 6-Methoxy-1,2,3,4-tetrahydro-β-carboline (Pinoline) and Melatonin-Pinoline Hybrids [J].

de la Fuente Revenga, Mario ;

Perez, Concepcion ;

Morales-Garcia, Jose A. ;

Alonso-Gil, Sandra ;

Perez-Castillo, Ana ;

Caignard, Daniel-Henri ;

Yanez, Matilde ;

Gamo, Ana M. ;

Isabel Rodriguez-Franco, Maria .

ACS CHEMICAL NEUROSCIENCE, 2015, 6 (05) :800-810

[5] SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF NOVEL NAPHTHALENIC AND BIOISOSTERIC RELATED AMIDIC DERIVATIVES AS MELATONIN RECEPTOR LIGANDS [J].

DEPREUX, P ;

LESIEUR, D ;

MANSOUR, HA ;

MORGAN, P ;

HOWELL, HE ;

RENARD, P ;

CAIGNARD, DH ;

PFEIFFER, B ;

DELAGRANGE, P ;

GUARDIOLA, B ;

YOUS, S ;

DEMARQUE, A ;

ADAM, G ;

ANDRIEUX, J .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (20) :3231-3239

[6] Melatonin-A pleiotropic, orchestrating regulator molecule [J].

Hardeland, Ruediger ;

Cardinali, Daniel P. ;

Srinivasan, Venkatramanujam ;

Spence, D. Warren ;

Brown, Gregory M. ;

Pandi-Perumal, Seithikurippu R. .

PROGRESS IN NEUROBIOLOGY, 2011, 93 (03) :350-384

[7] Design, synthesis and pharmacological characterization of coumarin-based fluorescent analogs of excitatory amino acid transporter subtype 1 selective inhibitors, UCPH-101 and UCPH-102 [J].

Huynh, Tri H. V. ;

Abrahamsen, Bjarke ;

Madsen, Karsten K. ;

Gonzalez-Franquesa, Alba ;

Jensen, Anders A. ;

Bunch, Lennart .

BIOORGANIC & MEDICINAL CHEMISTRY, 2012, 20 (23) :6831-6839

[8] Bright Building Blocks for Chemical Biology [J].

Lavis, Luke D. ;

Raines, Ronald T. .

ACS CHEMICAL BIOLOGY, 2014, 9 (04) :855-866

[9] Toward Fluorescent Probes for G-Protein-Coupled Receptors (GPCRs) [J].

Ma, Zhao ;

Du, Lupei ;

Li, Minyong .

JOURNAL OF MEDICINAL CHEMISTRY, 2014, 57 (20) :8187-8203

[10] Melatonin receptor ligands: Synthesis of new melatonin derivatives and comprehensive comparative molecular field analysis (CoMFA) study [J].

Mor, M ;

Rivara, S ;

Silva, C ;

Bordi, F ;

Plazzi, PV ;

Spadoni, G ;

Diamantini, G ;

Balsamini, C ;

Tarzia, G ;

Fraschini, F ;

Lucini, V ;

Nonno, R ;

Stankov, BM .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (20) :3831-3844

← 1 2 →