Novel 2-[(benzylamino)methyl]pyrrolidine-3,4-diol derivatives as α-mannosidase inhibitors and with antitumor activities against hematological and solid malignancies

被引：21

作者：

Bello, Claudia ^{[1
]}

Cea, Michele ^{[3
]}

Dal Bello, Giovanna ^{[2
]}

Garuti, Anna ^{[3
]}

Rocco, Ilaria ^{[3
]}

Cirmena, Gabriella ^{[3
]}

Moran, Eva ^{[3
]}

Nahimana, Aimable ^{[5
]}

Duchosal, Michel A. ^{[5
]}

Fruscione, Floriana ^{[4
]}

Pronzato, Paolo ^{[2
]}

Grossi, Francesco ^{[2
]}

Patrone, Franco ^{[3
]}

Ballestrero, Alberto ^{[3
]}

Dupuis, Marc ^{[1
]}

Sordat, Bernard ^{[1
]}

Nencioni, Alessio ^{[3
]}

Vogel, Pierre ^{[1
]}

机构：

[1] Ecole Polytech Fed Lausanne, Lab Glycochem & Asymmetr Synth LGSA, CH-1015 Lausanne, Switzerland

[2] Natl Inst Canc Res, I-16132 Genoa, Italy

[3] Univ Genoa, Dept Internal Med, I-16126 Genoa, Italy

[4] Univ Genoa, Dept Expt Med, I-16126 Genoa, Italy

[5] Univ Hosp CHUV, Serv Hematol, Lausanne, Switzerland

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2010年 / 18卷 / 09期

基金：

瑞士国家科学基金会;

关键词：

Glycosylation; alpha-Mannosidase inhibitors; Antiproliferative effects; Cell cycle; Haematological malignances; ENDOPLASMIC-RETICULUM; HUMAN GLIOBLASTOMA; CELL SURVIVAL; CANCER; GLYCOSYLATION; SWAINSONINE; LYMPHOMA; GROWTH; BCL-2; CYTOTOXICITY;

D O I：

10.1016/j.bmc.2010.03.009

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Novel alpha-mannosidase inhibitors of the type (2R,3R,4S)-2-({[(1R)-2- hydroxy-1-arylethyl]amine}methyl) pyrrolidine-3,4-diol have been prepared and assayed for their anticancer activities. Compound 30 with the aryl group = 4-trifluoromethylbiphenyl inhibits the proliferation of primary cells and cell lines of different origins, irrespective of Bcl-2 expression levels, inducing a G2/Mcell cycle arrest and by modification of genes involved in cell cycle progression and survival. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：3320 / 3334

页数：15

共 57 条

[1] Glycosidase inhibitors: update and perspectives on practical use
Asano, N
[J]. GLYCOBIOLOGY, 2003, 13 (10) : 93R - 104R
[2] Ballestrero A, 2001, CANCER-AM CANCER SOC, V92, P2030, DOI 10.1002/1097-0142(20011015)92:8<2030::AID-CNCR1541>3.0.CO
[3] 2-G
[4] Rapid access to N-Boc phenylglycine derivatives via benzylic lithiation reactions
Barberis, C
Voyer, N
Roby, J
Chénard, S
Tremblay, M
Labrie, P
[J]. TETRAHEDRON, 2001, 57 (15) : 2965 - 2972
[5] Sensitization of resistant lymphoma cells to irradiation-induced apoptosis by the death ligand TRAIL
Belka, C
Schmid, B
Marini, P
Durand, E
Rudner, J
Faltin, H
Bamberg, M
Schulze-Osthoff, K
Budach, W
[J]. ONCOGENE, 2001, 20 (17) : 2190 - 2196
[6] ASSIGNMENT OF THE ABSOLUTE-CONFIGURATION OF NATURAL LENTIGINOSINE BY SYNTHESIS AND ENZYMATIC ASSAYS OF OPTICALLY PURE (+)-ENANTIOMERS AND (-)-ENANTIOMERS
BRANDI, A
CICCHI, S
CORDERO, FM
FRIGNOLI, R
GOTI, A
PICASSO, S
VOGEL, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) : 6806 - 6812
[7] Altered glycosylation of proteins in cancer: What is the potential for new anti-tumour strategies
Brooks, S. A.
Carter, T. M.
Royle, L.
Harvey, D. J.
Fry, S. A.
Kinch, C.
Dwek, R. A.
Rudd, P. M.
[J]. ANTI-CANCER AGENTS IN MEDICINAL CHEMISTRY, 2008, 8 (01) : 2 - 21
[8] Synthesis and glycosidase inhibitory activities of 2-(aminoalkyl)pyrrolidine-3,4-diol derivatives
Carmona, AT
Popowycz, F
Gerber-Lemaire, S
Rodríguez-García, E
Schütz, C
Vogel, P
Robina, I
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (23) : 4897 - 4911
[9] Glycoprotein glycosylation and cancer progression
Dennis, JW
Granovsky, M
Warren, CE
[J]. BIOCHIMICA ET BIOPHYSICA ACTA-GENERAL SUBJECTS, 1999, 1473 (01): : 21 - 34
[10] INHIBITION OF LYSOSOMAL ALPHA-MANNOSIDASE BY SWAINSONINE, AN INDOLIZIDINE ALKALOID ISOLATED FROM SWAINSONA-CANESCENS
DORLING, PR
HUXTABLE, CR
COLEGATE, SM
[J]. BIOCHEMICAL JOURNAL, 1980, 191 (02) : 649 - 651

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