C2-symmetrical sterol-polyether conjugates as highly efficient synthetic ionophores

被引：15

作者：

Avallone, E

Izzo, I

Vuolo, G

Costabile, M

Garrisi, D

Pasquato, L

Scrimin, P

Tecilla, P

De Riccardis, F

机构：

[1] Univ Salerno, Dept Chem, I-84081 Baronissi, Salerno, Italy

[2] Univ Padua, Dept Organ Chem, I-35131 Padua, Italy

[3] ITM CNR, Padova Sect, I-35131 Padua, Italy

[4] Univ Trieste, Dept Chem Sci, I-34127 Trieste, Italy

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 32期

关键词：

ionophore; steroid; amphiphiles;

D O I：

10.1016/S0040-4039(03)01454-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new class of artificial ionophores has been rationally designed and synthesized linking to a tetrafunctionalized L-treitol spacer two rigid hydrophobic 3beta-hydroxy-5alpha-23,24-bisnorcholanic units and two flexible hydrophilic oligo(ethylene glycol) chains. Compounds 1a and 1b were incorporated into phospholipid vesicles and shown to facilitate Na+-transport. (C) 2003 Elsevier Ltd. All rights reserved.

引用

收藏

页码：6121 / 6124

页数：4

相关论文

共 44 条

[1] SYNTHETIC PEPTIDES AS MODELS FOR ION CHANNEL PROTEINS [J].

AKERFELDT, KS ;

LEAR, JD ;

WASSERMAN, ZR ;

CHUNG, LA ;

DEGRADO, WF .

ACCOUNTS OF CHEMICAL RESEARCH, 1993, 26 (04) :191-197

[2]

[Anonymous], TOP CURR CHEM

[3] Self-assembling cyclic β3-peptide nanotubes as artificial transmembrane ion channels [J].

Clark, TD ;

Buehler, LK ;

Ghadiri, MR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (04) :651-656

[4] A biosensor that uses ion-channel switches [J].

Cornell, BA ;

BraachMaksvytis, VLB ;

King, LG ;

Osman, PDJ ;

Raguse, B ;

Wieczorek, L ;

Pace, RJ .

NATURE, 1997, 387 (6633) :580-583

[5] POLYOXYGENATED STEROIDS OF MARINE ORIGIN [J].

DAURIA, MV ;

MINALE, L ;

RICCIO, R .

CHEMICAL REVIEWS, 1993, 93 (05) :1839-1895

[6] An artificial ionophore based on a polyhydroxylated steroid dimer [J].

De Riccardis, F ;

Di Filoppo, M ;

Garrisi, D ;

Izzo, I ;

Mancin, F ;

Pasquato, L ;

Scrimin, P ;

Tecilla, P .

CHEMICAL COMMUNICATIONS, 2002, (24) :3066-3067

[7] A general method for the synthesis of the N2- and N6- carcinogenic amine adducts of 2′-deoxyguanosine and 2′-deoxyadenosine [J].

De Riccardis, F ;

Bonala, RR ;

Johnson, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (45) :10453-10460

[8] ESTERIFICATION OF N-PROTECTED ALPHA-AMINO-ACIDS WITH ALCOHOL/CARBODIIMIDE/4-(DIMETHYLAMINO)-PYRIDINE - RACEMIZATION OF ASPARTIC AND GLUTAMIC-ACID DERIVATIVES [J].

DHAON, MK ;

OLSEN, RK ;

RAMASAMY, K .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (10) :1962-1965

[9] Synthesis of a transmembrane ionophore based on a C2-symmetric polyhydroxysteroid derivative [J].

Di Filippo, M ;

Izzo, I ;

Savignano, L ;

Tecilla, P ;

De Riccardis, F .

TETRAHEDRON, 2003, 59 (10) :1711-1717

[10] Ion conductors that favor passive transport in ergosterol-rich over cholesterol-rich phospholipid membranes [J].

DiGiorgio, AF ;

Otto, S ;

Bandyopadhyay, P ;

Regen, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (44) :11029-11030

← 1 2 3 4 5 →