Lipophilicity coefficients of [11C]Me-Halo-CGS 27023A analogs determined by HPLC

被引:16
作者
Fei, XS [1 ]
Zheng, QH [1 ]
机构
[1] Indiana Univ, Sch Med, Dept Radiol, Indianapolis, IN 46202 USA
基金
美国国家卫生研究院;
关键词
lipophilicity coefficients; C-11]Me-Halo-CGS 27023A; positron emission; tomography; tumor imaging agents; HPLC;
D O I
10.1081/JLC-200051486
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
New radiolabeled matrix metalloproteinase inhibitors (MMPIs) [C-11]Me-Halo-CGS 27023A analogs have been synthesized for evaluation as potential novel positron emission tomography (PET) tumor imaging agents. Their lipophilicity coefficients (log P) were determined by C-18 reversed-phase HPLC method. These logP values were compared, and the correlations between lipophilicity and biological activity of selected analogs were made. The results suggest the appropriate level of lipophilic character in this class of compounds as useful imaging agents appears to be in the range of 2.00-2.67.
引用
收藏
页码:939 / 945
页数:7
相关论文
共 10 条
[1]   Synthesis of radiolabeled biphenylsulfonamide matrix metalloproteinase inhibitors as new potential PET cancer imaging agents [J].
Fei, XS ;
Zheng, QH ;
Liu, XA ;
Wang, JQ ;
Sun, HB ;
Mock, BH ;
Stone, KL ;
Miller, KD ;
Sledge, GW ;
Hutchins, GD .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (13) :2217-2222
[2]   Synthesis of MMP inhibitor radiotracer [11C]CGS 25966, a new potential PET tumor imaging agent [J].
Fei, XS ;
Zheng, QH ;
Liu, X ;
Wang, JQ ;
Stone, KL ;
Miller, KD ;
Sledge, GW ;
Hutchins, GD .
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2003, 46 (04) :343-351
[3]   Synthesis of MMP inhibitor radiotracers [11C]methyl-CGS 27023A and its analogs, new potential PET breast cancer imaging agents [J].
Fei, XS ;
Zheng, QH ;
Hutchins, GD ;
Liu, X ;
Stone, KL ;
Carlson, KA ;
Mock, BH ;
Winkle, WL ;
Glick-Wilson, BE ;
Miller, KD ;
Fife, RS ;
Sledge, GW ;
Sun, HB ;
Carr, RE .
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2002, 45 (06) :449-470
[4]   EVALUATION OF A SIMPLE HPLC CORRELATION METHOD FOR THE ESTIMATION OF THE OCTANOL-WATER PARTITION-COEFFICIENTS OF ORGANIC-COMPOUNDS [J].
HAKY, JE ;
YOUNG, AM .
JOURNAL OF LIQUID CHROMATOGRAPHY, 1984, 7 (04) :675-689
[5]   In vivo activity and hydrophobicity of cytostatic aziridinyl quinones [J].
Moret, EE ;
deBoer, M ;
Hilbers, HW ;
Tollenaere, JP ;
Janssen, LHM ;
Holthuis, JJM ;
Driebergen, RJ ;
Verboom, W ;
Reinhoudt, DN .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (03) :720-728
[6]   DESIGN OF 5-(3,5-DI-TERT-BUTYL-4-HYDROXYPHENYL)-1,3,4-THIADIAZOLES, 5-(3,5-DI-TERT-BUTYL-4-HYDROXYPHENYL)-1,3,4-OXADIAZOLES, AND 5-(3,5-DI-TERT-BUTYL-4-HYDROXYPHENYL)-1,2,4-TRIAZOLES AS ORALLY-ACTIVE, NONULCEROGENIC ANTIINFLAMMATORY AGENTS [J].
MULLICAN, MD ;
WILSON, MW ;
CONNOR, DT ;
KOSTLAN, CR ;
SCHRIER, DJ ;
DYER, RD .
JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (08) :1090-1099
[7]   Hydrophilic, pro-drug analogues of T138067 are efficacious in controlling tumor growth in vivo and show a decreased ability to cross the blood brain barrier [J].
Rubenstein, SM ;
Baichwal, V ;
Beckmann, H ;
Clark, DL ;
Frankmoelle, W ;
Roche, D ;
Santha, E ;
Schwender, S ;
Thoolen, M ;
Ye, QP ;
Jaen, JC .
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (22) :3599-3605
[8]   Comparative studies of potential cancer biomarkers carbon-11 labeled MMP inhibitors (S)-2-(4′-[11C]methoxybiphenyl-4-sulfonylamino)-3-methylbutyric acid and N-hydroxy-(R)-2-[[(4′-[11C]methoxyphenyl)sulfonyl]benzylamino]-3-methylbutanamide [J].
Zheng, QH ;
Fei, XS ;
Liu, X ;
Wang, JQ ;
Stone, KL ;
Martinez, TD ;
Gay, DJ ;
Baity, WL ;
Miller, KD ;
Sledge, GW ;
Hutchins, GD .
NUCLEAR MEDICINE AND BIOLOGY, 2004, 31 (01) :77-85
[9]   Synthesis, biodistribution and micro-PET imaging of a potential cancer biomarker carbon-11 labeled MMP inhibitor (2R)-2-[[4-(6-fluorohex-1-ynyl)phenyl]sulfonylamino]-3-methylbutyric acid [11C]methyl ester [J].
Zheng, QH ;
Fei, XS ;
DeGrado, TR ;
Wang, JQ ;
Stone, KL ;
Martinez, TD ;
Gay, DJ ;
Baity, WL ;
Mock, BH ;
Glick-Wilson, BE ;
Sullivan, ML ;
Miller, KD ;
Sledge, GW ;
Hutchins, GD .
NUCLEAR MEDICINE AND BIOLOGY, 2003, 30 (07) :753-760
[10]   Synthesis and preliminary biological evaluation of MMP inhibitor radiotracers [11C]methyl-halo-CGS 27023A analogs, new potential PET breast cancer imaging agents [J].
Zheng, QH ;
Fei, XS ;
Liu, X ;
Wang, JQ ;
Sun, HB ;
Mock, BH ;
Stone, KL ;
Martinez, TD ;
Miller, KD ;
Sledge, GW ;
Hutchins, GD .
NUCLEAR MEDICINE AND BIOLOGY, 2002, 29 (07) :761-770