Recent advances in the synthesis of spermine and spermidine analogs of the shark aminosterol squalamine

被引：37

作者：

Brunel, JM ^{[1
]}

Letourneux, Y ^{[1
]}

机构：

[1] Fac Sci & Tech St Jerome, INRA, IMRN, UMR 1111, F-13397 Marseille 20, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 2003卷 / 20期

关键词：

amines; antiangiogenesis; antimicrobial agents; natural products; squalamine; steroids;

D O I：

10.1002/ejoc.200300167

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Great attention has recently been focused on the shark aminosterol squalamine (1) because of its important antimicrobial and antiangiogenic activities. Herein, we present the different series of spermine and spermidine analogs that have been synthesized. Many of the squalamine mimics demonstrate a broad spectrum activity against microorganisms. Squalamine is currently undergoing Phase 11 clinical trials in cancer patients. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).

引用

页码：3897 / 3907

页数：11

共 29 条

[1] Squalamine, a novel cationic steroid, specifically inhibits the brush-border Na+/H+ exchanger isoform NHE3 [J].

Akhter, S ;

Nath, SK ;

Tse, CM ;

Williams, J ;

Zasloff, M ;

Donowitz, M .

AMERICAN JOURNAL OF PHYSIOLOGY-CELL PHYSIOLOGY, 1999, 276 (01) :C136-C144

[2] Synthesis of 25-aminosterols, new antifungal agents [J].

Beuchet, P ;

Dherbomez, M ;

Elkiel, L ;

Charles, G ;

Letourneux, Y .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (11) :1599-1600

[3]

Bhargava P, 2001, CLIN CANCER RES, V7, P3912

[4] ANTIBACTERIAL PEPTIDES - KEY COMPONENTS NEEDED IN IMMUNITY [J].

BOMAN, HG .

CELL, 1991, 65 (02) :205-207

[5] Synthesis and bioactivities of steroid derivatives as antifungal agents [J].

Chung, SK ;

Ryoo, CH ;

Yang, HW ;

Shim, JY ;

Kang, MG ;

Lee, KW ;

Kang, HI .

TETRAHEDRON, 1998, 54 (52) :15899-15914

[6] A synthetic ionophore that recognizes negatively charged phospholipid membranes [J].

Deng, G ;

Dewa, T ;

Regen, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (37) :8975-8976

[7] Stereoselective synthesis of 7α- and 7β-aminocholestanol as potent fungicidal drugs [J].

Fouace, S ;

El kihel, L ;

Dherbomez, M ;

Letourneux, Y .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (23) :3011-3014

[8] The synthesis and characterization of analogs of the antimicrobial compound squalamine: 6 beta-hydroxy-3-aminosterols synthesized from hyodeoxycholic acid [J].

Jones, SR ;

Kinney, WA ;

Zhang, XH ;

Jones, LM ;

Selinsky, BS .

STEROIDS, 1996, 61 (10) :565-571

[9] Squalamine analogues as potential anti-trypanosomal and anti-leishmanial compounds [J].

Khabnadideh, S ;

Tan, CL ;

Croft, SL ;

Kendrick, H ;

Yardley, V ;

Gilbert, IH .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (11) :1237-1239

[10] Synthesis and antimicrobial activity of squalamine analogue [J].

Kim, HS ;

Choi, BS ;

Kwon, KC ;

Lee, SO ;

Kwak, HJ ;

Lee, CH .

BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (08) :2059-2065

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