Synthesis of a novel 'smart' bifunctional chelating agent 1-(2-[β,D-galactopyranosyloxylethyl)-7-(1-carboxy-3-[4-aminophenyllpropyl)-4,10-bis(carboxymethyl)-1,4,7,10-tetraazacyclododecane (Gal-PA-DO3A-NH2) and its Gd(III) complex

被引：10
作者：
Wardle, Nick J.
Herlihy, Amy H.
So, Po-Wah
Bell, Jimmy D.
Bligh, S. W. Annie
机构：
[1] London Metropolitan Univ, Inst Hlth Res & Policy, London N7 8DB, England
[2] Univ London Imperial Coll Sci Technol & Med, MRC Clin Sci Ctr, Dept Imaging Sci, Mol Imaging Grp, London, England
来源：
BIOORGANIC & MEDICINAL CHEMISTRY | 2007年 / 15卷 / 14期
基金：
英国医学研究理事会;
关键词：
DO3A; MRI; Gd(III) complex; contrast agents;
D O I：
10.1016/j.bmc.2007.05.004
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：
A new synthetic pathway to 1-(2-[beta,D-galactopyranosyloxy]ethyl)-7-(1-carboxy-3-[4-aminophenyl]propyl)-4,10-bis(carboxymethyl)-1,4,7,10-tetraazacyclododecane (Gal-PA-DO3A-NH2) and 1-(2-[beta,D-galactopyranosyloxy]ethyl)-4,7,10-tris(carboxymethyl)-1, 4,7,10-tetraazacyclododecane (Gal-DO3A) chelating agents was developed involving full hydroxyl- and carboxyl-group protection in precursors to product. Two sequences of cyclen-N-functionalisation were subsequently investigated, one successfully, towards synthesis of the novel 'smart' bifunctional Gal-PA-DO3A-NH2 chelate. The longitudinal proton relaxivities of the neutral [Gd-(Gal-PA-DO3A-NH2)] and [Gd-(Gal-DO(3)A)] complexes were increased by 28% and 37% in the presence of beta-galactosidase, respectively. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4714 / 4721
页数：8
相关论文
共 30 条
[1]   Intraperitoneal radioimmunotherapy of ovarian cancer with Lu-177-CC49: A phase I/II study [J].
Alvarez, RD ;
Partridge, EE ;
Khazaeli, MB ;
Plott, G ;
Austin, M ;
Kilgore, L ;
Russell, CD ;
Liu, TP ;
Grizzle, WE ;
Schlom, J ;
LoBuglio, AF ;
Meredith, RF .
GYNECOLOGIC ONCOLOGY, 1997, 65 (01) :94-101
[2]  
BERG A, 1996, Patent No. 5531978
[3]   Macrocyclic chelators with paramagnetic cations are internalized into mammalian cells via a HIV-tat derived membrane translocation peptide [J].
Bhorade, R ;
Weissleder, R ;
Nakakoshi, T ;
Moore, A ;
Tung, CH .
BIOCONJUGATE CHEMISTRY, 2000, 11 (03) :301-305
[4]   NMR IMAGING OF FOREARMS IN HEALTHY-VOLUNTEERS AND PATIENTS WITH GIANT-CELL TUMOR OF BONE [J].
BRADY, TJ ;
GEBHARDT, MC ;
PYKETT, IL ;
BUONANNO, FS ;
NEWHOUSE, JH ;
BURT, CT ;
SMITH, RJ ;
MANKIN, HJ ;
KISTLER, JP ;
GOLDMAN, MR ;
HINSHAW, WS ;
POHOST, GM .
RADIOLOGY, 1982, 144 (03) :549-552
[5]   HYDROXYETHYLATION OF MACROCYCLIC POLYAMINES, INHIBITION BY PARTIAL PROTONATION [J].
BUOEN, S ;
DALE, J ;
KRANE, J .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1984, 38 (09) :773-778
[6]   A MILD PROCEDURE FOR ETHERIFICATION OF ALCOHOLS WITH PRIMARY ALKYL-HALIDES IN THE PRESENCE OF SILVER TRIFLATE [J].
BURK, RM ;
GAC, TS ;
ROOF, MB .
TETRAHEDRON LETTERS, 1994, 35 (44) :8111-8112
[7]   The interaction of MS-325 with human serum albumin and its effect on proton relaxation rates [J].
Caravan, P ;
Cloutier, NJ ;
Greenfield, MT ;
McDermid, SA ;
Dunham, SU ;
Bulte, JWM ;
Amedio, JC ;
Looby, RJ ;
Supkowski, RM ;
Horrocks, WD ;
McMurry, TJ ;
Lauffer, RB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (12) :3152-3162
[8]   GADOLINIUM-DTPA AS A CONTRAST AGENT IN MRI - INITIAL CLINICAL-EXPERIENCE IN 20 PATIENTS [J].
CARR, DH ;
BROWN, J ;
BYDDER, GM ;
STEINER, RE ;
WEINMANN, HJ ;
SPECK, U ;
HALL, AS ;
YOUNG, IR .
AMERICAN JOURNAL OF ROENTGENOLOGY, 1984, 143 (02) :215-224
[9]  
CARR DH, 1984, LANCET, V1, P484
[10]   Improved synthesis of the bifunctional chelating agent 1,4,7,10-tetraaza-N-(1-carboxy-3-(4-nitrophenyl)propyl)-N′,N",N′"-tris(acetic acid)cyclododecane (PA-DOTA) [J].
Chappell, LL ;
Rogers, BE ;
Khazaeli, MB ;
Mayo, MS ;
Buchsbaum, DJ ;
Brechbiel, MW .
BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (11) :2313-2320
123