Improving the membrane permeability of sialic acid derivatives

被引：22

作者：

Altamore, TM

Duggan, PJ ^{[1
]}

Krippner, GY

机构：

[1] Monash Univ, Sch Chem, Melbourne, Vic 3800, Australia

[2] CSIRO Mol & Hlth Technol, Clayton, Vic 3169, Australia

[3] Monash Univ, Sch Chem, Biota Chem Lab, Melbourne, Vic 3800, Australia

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2006年 / 14卷 / 04期

基金：

澳大利亚研究理事会;

关键词：

membrane transport; boronic acids; sialic acid; anti-virals;

D O I：

10.1016/j.bmc.2005.09.028

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：

The potential of boronic acids to improve the bioavailability of carbohydrate derived drugs was investigated through the study of the transport of four sialic acid derivatives through a lipophilic Supported liquid membrane at departure phase pH's of 7.4, 8.5 and 10.0. It was found that facilitated transport did occur in most cases, but interestingly, and in contrast to that observed with monosaccharides such as D-fructose, the lipophilic ammonium salt, Aliquat (R) 336, promoted higher fluxes than those of the boronic acid. The triol side chain of the sialic acid derivatives, combined with the amide at C5. appears to represent a previously unrecognised chloride binding domain which promotes extraction of these compounds into membranes containing Aliquat (R) 336, leading to fluxes greater than those produced by boronic acids. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：1126 / 1133

页数：8

共 40 条

[21] 2-DEOXY-2.3-DEHYDRO-SIALIC ACIDS .I. SYNTHESIS AND PROPERTIES OF 2-DEOXY-2.3-DEHYDRO-N-ACYL-NEURAMINIC ACIDS AND THEIR METHYL ESTERS
MEINDL, P
TUPPY, H
[J]. MONATSHEFTE FUR CHEMIE, 1969, 100 (04): : 1295 - &
[22] BORONIC ACIDS MEDIATE GLYCOSIDE TRANSPORT THROUGH A LIQUID ORGANIC MEMBRANE VIA REVERSIBLE FORMATION OF TRIGONAL BORONATE ESTERS
MORIN, GT
PAUGAM, MF
HUGHES, MP
SMITH, BD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (10) : 2724 - 2728
[23] TRANSPORT OF GLYCOSIDES THROUGH LIQUID ORGANIC MEMBRANES MEDIATED BY REVERSIBLE BORONATE FORMATION IS A DIFFUSION-CONTROLLED PROCESS
MORIN, GT
HUGHES, MP
PAUGAM, MF
SMITH, BD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (20) : 8895 - 8901
[24] MUNRO TA, 1997, J CHEM SOC CHEM COMM, P2167
[25] Anomalous binding profile of phenylboronic acid with N-acetylneuraminic acid (Neu5Ac) in aqueous solution with varying pH
Otsuka, H
Uchimura, E
Koshino, H
Okano, T
Kataoka, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (12) : 3493 - 3502
[26] Tuning the affinity of a synthetic sialic acid receptor using combinatorial chemistry
Patterson, S
Smith, BD
Taylor, RE
[J]. TETRAHEDRON LETTERS, 1998, 39 (20) : 3111 - 3114
[27] Facilitated transport of small carbohydrates through plasticized cellulose triacetate membranes. Evidence for fixed-site jumping transport mechanism
Riggs, JA
Smith, BD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (11) : 2765 - 2766
[28] Nucleotide carrier mixture with transport selectivity for ribonucleoside-5'-phosphates
Riggs, JA
Hossler, KA
Smith, BD
Karpa, MJ
Griffin, G
Duggan, PJ
[J]. TETRAHEDRON LETTERS, 1996, 37 (35) : 6303 - 6306
[29] Liquid membrane transport using boronic acid carriers
Smith, BD
[J]. SUPRAMOLECULAR CHEMISTRY, 1996, 7 (01) : 55 - 60
[30] Smith BD, 1999, ADV SUPR CH, V5, P157

← 1 2 3 4 →