Bo-Li Liu

Name: 刘伯里; Liu, BoLi

Organization: Beijing Normal University , China

Department: College of Chemistry

Title: Professor(PhD)

Chemicals
References

Novel Cyclopentadienyl Tricarbonyl Complexes of 99mTc Mimicking Chalcone as Potential Single-Photon Emission Computed Tomography Imaging Probes for β-Amyloid Plaques in Brain

Co-reporter:Zijing Li ; Mengchao Cui ; Jiapei Dai ; Xuedan Wang ; Pingrong Yu ; Yanping Yang ; Jianhua Jia ; Hualong Fu ; Masahiro Ono ; Hongmei Jia ; Hideo Saji ;Boli Liu

Journal of Medicinal Chemistry 2013 Volume 56(Issue 2) pp:471-482

Publication Date(Web):December 14, 2012

DOI:10.1021/jm3014184

Rhenium and technetium-99m cyclopentadienyl tricarbonyl complexes mimicking the chalcone structure were prepared. These complexes were proved to have affinity to β-amyloid (Aβ) in fluorescent staining on brain sections of Alzheimer’s Disease (AD) patient and binding assay using Aβ1–42 aggregates, with Ki values ranging from 899 to 108 nM as the extension of conjugated π system. In vitro autoradiograpy on sections of transgenic mouse brain confirmed the affinity of [99mTc]5 (Ki = 108 nM). In biodistribution, all compounds showed good initial uptakes into the brain and fast blood clearance, while the decreasing of initial brain uptakes correspond to increasing of conjugation length, from 4.10 ± 0.38% ID/g ([99mTc]3) to 1.11 ± 0.34% ID/g ([99mTc]5). These small technetium-99m complexes (<500 Da) designed by an integrated approach provide encouraging evidence that development of a promising 99mTc-labeled agent for imaging Aβ plaques in the brain may be feasible.

Synthesis and biological evaluation of 18F-labled 2-phenylindole derivatives as PET imaging probes for β-amyloid plaques

Co-reporter:Hualong Fu, Lihai Yu, Mengchao Cui, Jinming Zhang, Xiaojun Zhang, Zijing Li, Xuedan Wang, Jianhua Jia, Yanping Yang, Pingrong Yu, Hongmei Jia, Boli Liu

Bioorganic & Medicinal Chemistry 2013 Volume 21(Issue 13) pp:3708-3714

Publication Date(Web):1 July 2013

DOI:10.1016/j.bmc.2013.04.028

A novel series of fluorinated 2-phenylindole derivatives were synthesized and evaluated as β-amyloid imaging probes for PET. The in vitro inhibition assay demonstrated that their binding affinities for Aβ1–42 aggregates ranged from 28.4 to 1097.8 nM. One ligand was labeled with 18F ([18F]1a) for its high affinity (Ki = 28.4 nM), which was also confirmed by in vitro autoradiography experiments on brain sections of transgenic mouse (C57BL6, APPswe/PSEN1, 11 months old, male). In vivo biodistribution experiments in normal mice showed that this radiotracer displayed high initial uptake (5.82 ± 0.51% ID/g at 2 min) into and moderate washout (2.77 ± 0.31% ID/g at 60 min) from the brain. [18F]1a could be developed as a promising new PET imaging probe for Aβ plaques although necessary modifications are still needed.

Synthesis and Evaluation of Novel 18F Labeled 2-Pyridinylbenzoxazole and 2-Pyridinylbenzothiazole Derivatives as Ligands for Positron Emission Tomography (PET) Imaging of β-Amyloid Plaques

Co-reporter:Mengchao Cui ; Xuedan Wang ; Pingrong Yu ; Jinming Zhang ; Zijing Li ; Xiaojun Zhang ; Yanping Yang ; Masahiro Ono ; Hongmei Jia ; Hideo Saji ;Boli Liu

Journal of Medicinal Chemistry 2012 Volume 55(Issue 21) pp:9283-9296

Publication Date(Web):September 13, 2012

DOI:10.1021/jm300973k

A series of fluoro-pegylated (FPEG) 2-pyridinylbenzoxazole and 2-pyridinylbenzothiazole derivatives were synthesized and evaluated as novel β-amyloid (Aβ) imaging probes for PET. They displayed binding affinities for Aβ1–42 aggregates that varied from 2.7 to 101.6 nM. Seven ligands with high affinity were selected for 18F labeling. In vitro autoradiography results confirmed the high affinity of these radiotracers. In vivo biodistribution experiments in normal mice indicated that the radiotracers with a short FPEG chain (n = 1) displayed high initial uptake into and rapid washout from the brain. One of the 2-pyridinylbenzoxazole derivatives, [18F]-5-(5-(2-fluoroethoxy)benzo[d]oxazol-2-yl)-N-methylpyridin-2-amine ([18F]32) (Ki = 8.0 ± 3.2 nM) displayed a brain2min/brain60min ratio of 4.66, which is highly desirable for Aβ imaging agents. Target specific binding of [18F]32 to Aβ plaques was validated by ex vivo autoradiographic experiment with transgenic model mouse. Overall, [18F]32 is a promising Aβ imaging agent for PET and merits further evaluation in human subjects.

18F-Labeled 2-phenylquinoxaline derivatives as potential positron emission tomography probes for in vivo imaging of β-amyloid plaques

Co-reporter:Pingrong Yu, Mengchao Cui, Xuedan Wang, Xiaojun Zhang, Zijing Li, Yanping Yang, Jianhua Jia, Jinming Zhang, Masahiro Ono, Hideo Saji, Hongmei Jia, Boli Liu

European Journal of Medicinal Chemistry 2012 Volume 57() pp:51-58

Publication Date(Web):November 2012

DOI:10.1016/j.ejmech.2012.08.031

In continuation of our study on the 2-phenylquinoxaline scaffold as potential β-amyloid imaging probes, two [18F]fluoro-pegylated 2-phenylquinoxaline derivatives, 2-(4-(2-[18F]fluoroethoxy)phenyl)-N-methylquinoxalin-6-amine ([18F]4a) and 2-(4-(2-(2-(2-[18F]fluoroethoxy)ethoxy)ethoxy)phenyl)-N-methylquinoxalin-6-amine ([18F]4b) were prepared. Both of them displayed high binding affinity to Aβ1-42 aggregates (Ki = 10.0 ± 1.4 nM for 4a, Ki = 5.3 ± 3.2 nM for 4b). The specific and high binding of [18F]4a and [18F]4b to Aβ plaques was confirmed by in vitro autoradiography on brain sections of AD human and transgenic mice. In biodistribution in normal mice, [18F]4a displayed high initial brain uptake (8.17% ID/g at 2 min) and rapid washout from the brain. These preliminary results suggest [18F]4a may be a potential PET imaging agent for Aβ plaques in the living human brain.Graphical abstractHighlights► Two novel 18F-labeled 2-phenylquinoxaline derivatives were synthesized. ► Both of them displayed high affinity to Aβ1-42 aggregates. ► They showed excellent plaque labeling on brain sections of AD human and Tg mice. ► [18F]4a showed high initial uptake (8.17% ID/g) and rapid washout from the brain.

Synthesis and biological evaluation of novel technetium-99m labeled phenylbenzoxazole derivatives as potential imaging probes for β-amyloid plaques in brain

Co-reporter:Xuedan Wang, Mengchao Cui, Pingrong Yu, Zijing Li, Yanping Yang, Hongmei Jia, Boli Liu

Bioorganic & Medicinal Chemistry Letters 2012 Volume 22(Issue 13) pp:4327-4331

Publication Date(Web):1 July 2012

DOI:10.1016/j.bmcl.2012.05.010

Two uncharged 99mTc-labeled phenylbenzoxazole derivatives were biologically evaluated as potential imaging probes for β-amyloid plaques. The 99mTc and corresponding rhenium complexes were synthesized by coupling monoamine–monoamide dithiol (MAMA) and bis(aminoethanethiol) (BAT) chelating ligand via a pentyloxy spacer to phenylbenzoxazole. The fluorescent rhenium complexes 6 and 9 selectively stainined the β-amyloid plaques on the sections of transgenic mouse, and showed high affinity for Aβ(1–42) aggregates (Ki = 11.1 nM and 14.3 nM, respectively). Autoradiography in vitro indicated that [99mTc]6 clearly labeled β-amyloid plaques on the sections of transgenic mouse. Biodistribution experiments in normal mice revealed that [99mTc]6 displayed moderate initial brain uptake (0.81% ID/g at 2 min), and quickly washed out from the brain (0.25% ID/g at 60 min). The preliminary results indicate that the properties of [99mTc]6 are promising, although additional refinements are needed to improve the ability to cross the blood–brain barrier.

Novel (E)-5-styryl-2,2′-bithiophene derivatives as ligands for β-amyloid plaques

Co-reporter:Mengchao Cui, Zijing Li, Ruikun Tang, Hongmei Jia, Boli Liu

European Journal of Medicinal Chemistry 2011 Volume 46(Issue 7) pp:2908-2916

Publication Date(Web):July 2011

DOI:10.1016/j.ejmech.2011.04.015

In continuation of our investigation on the bithiophene structure as potential β-amyloid probes, a series of (E)-5-styryl-2,2′-bithiophene (SBTP) derivatives was designed and synthesized. In vitro binding showed that all of them displayed high binding affinities to Aβ1–42 aggregates (Ki = 0.10–41.05 nM). Moreover, two radio-iodinated probes, [125I]-(E)-5-(4-iodostyryl)-2,2′-bithiophene ([125I]8) and [125I]-(E)-5-iodo-5′-(4-methoxystyryl)-2,2′-bithiophene ([125I]31) were prepared. Both of them displayed specific labeling of Aβ plaques in the brain sections of AD model mice with low background. In vivo biodistribution in normal mice indicated that [125I]8 exhibited high initial brain uptake (2.11% ID/g at 2 min) and rapid clearance (0.41% ID/g at 30 min). These preliminary results suggest that SBTP derivatives may be served as novel β-amyloid imaging probes.Highlights► (E)-5-styryl-2,2′-bithiophene derivatives showed high affinity to Aβ aggregates. ► High tolerance for steric bulk at para position of the phenyl ring was found. ► 125I labeled probes showed excellent plaque labeling in the brain of AD model mice. ► One of the tracers showed high uptake and fast washout from the normal mice brain.

99mTc- and Re-labeled 6-dialkylamino-2-naphthylethylidene derivatives as imaging probes for β-amyloid plaques

Co-reporter:Mengchao Cui, Ruikun Tang, Zijing Li, Huiying Ren, Boli Liu

Bioorganic & Medicinal Chemistry Letters 2011 Volume 21(Issue 3) pp:1064-1068

Publication Date(Web):1 February 2011

DOI:10.1016/j.bmcl.2010.11.096

Based on the conjugate strategy, two neutral 99mTc labeled 2-(1-(6-(dialkylamino)naphthalen-2-yl)ethylidene)malononitrile (DDNP) and 1-(6-(dialkylamino)naphthalen-2-yl)ethanone (ENE) derivatives, and their corresponding rhenium complexes were synthesized. In vitro fluorescent staining indicated that the corresponding rhenium derivatives selectively stained the β-amyloid (Aβ) plaques in the brain sections of AD model mice with low background. Compared with FDDNP and FENE, the affinities of the corresponding rhenium derivatives to Aβ aggregates decreased about 10–14-fold. In vivo biodistribution experiments in normal mice showed that 99mTc-MAMA-ENE displayed medium initial brain uptake (0.65 %ID/g at 2 min) with a reasonable washout from the brain (0.19 %ID/g at 2 h) while 99mTc-MAMA-DDNP showed a low brain uptake (0.28 %ID/g at 2 min). Further optimize these 99mTc-labeled tracers in order to improve their binding affinities to Aβ plaques and diffusion through the blood brain barrier may generate useful imaging agents for SPECT.

Novel imaging agents for β-amyloid plaque based on the N-benzoylindole core

Co-reporter:Yang Yang, Xin-Hong Duan, Jun-Yuan Deng, Bing Jin, Hong-Mei Jia, Bo-Li Liu

Bioorganic & Medicinal Chemistry Letters 2011 Volume 21(Issue 18) pp:5594-5597

Publication Date(Web):15 September 2011

DOI:10.1016/j.bmcl.2011.06.077

We report the synthesis and evaluation of a series of N-benzoylindole derivatives as novel potential imaging agents for β-amyloid plaques. In vitro binding studies using Aβ1–40 aggregates versus [125I]TZDM showed that all these derivatives demonstrated high binding affinities (Ki values ranged from 8.4 to 121.6 nM). Moreover, two radioiodinated compounds [125I]7 and [125I]14 were prepared. Autoradiography for [125I]14 displayed intense and specific labeling of Aβ plaques in the brain sections of AD model mice (C57, APP/PS1) with low background. In vivo biodistribution in normal mice exhibited sufficient initial brain uptake for imaging (2.19% and 2.00% ID/g at 2 min postinjection for [125I]7 and [125I]14, respectively). Although additional modifications are necessary to improve brain uptake and clearance from the brain, the N-benzoylindole may be served as a backbone structure to develop novel β-amyloid imaging probes.

Synthesis and evaluation of novel benzothiazole derivatives based on the bithiophene structure as potential radiotracers for β-amyloid plaques in Alzheimer’s disease

Co-reporter:Meng-Chao Cui, Zi-Jing Li, Rui-Kun Tang, Bo-Li Liu

Bioorganic & Medicinal Chemistry 2010 Volume 18(Issue 7) pp:2777-2784

Publication Date(Web):1 April 2010

DOI:10.1016/j.bmc.2010.02.002

In this study, six novel benzothiazole derivatives based on the bithiophene structure were developed as potential β-amyloid probes. In vitro binding studies using Aβ aggregates showed that all of them demonstrated high binding affinities with Ki values ranged from 0.11 to 4.64 nM. In vitro fluorescent staining results showed that these compounds can intensely stained Aβ plaques within brain sections of APP/PS1 transgenic mice, animal model for AD. Two radioiodinated compounds [125I]-2-(5′-iodo-2,2′-bithiophen-5-yl)-6-methoxybenzo[d]thiazole [125I]10 and [125I]-2-(2,2′-bithiophen-5-yl)-6-iodobenzo[d]thiazole [125I]13 were successfully prepared through an iododestannylation reaction. Furthermore, in vitro autoradiography of the AD model mice brain sections showed that both [125I]10 and [125I]13 labeled the Aβ plaques specifically with low background. In vivo biodistribution studies in normal mice indicated that [125I]13 exhibited high brain uptake (3.42% ID/g at 2 min) and rapid clearance from the brain (0.53% ID/g at 60 min), while [125I]10 showed lower brain uptake (0.87% ID/g at 2 min). In conclusion, these preliminary results of this study suggest that the novel radioiodinated benzothiazole derivative [125I]13 may be a candidate as an in vivo imaging agent for detecting β-amyloid plaques in the brain of AD patients.

Novel anilinophthalimide derivatives as potential probes for β-amyloid plaque in the brain

Co-reporter:Xin-Hong Duan, Jin-Ping Qiao, Yang Yang, Meng-Chao Cui, Jiang-Ning Zhou, Bo-Li Liu

Bioorganic & Medicinal Chemistry 2010 Volume 18(Issue 3) pp:1337-1343

Publication Date(Web):1 February 2010

DOI:10.1016/j.bmc.2009.12.023

A group of novel 4,5-dianilinophthalimide derivatives has been synthesized in this study for potential use as β-amyloid (Aβ) plaque probes. Staining of hippocampus tissue sections from Alzheimer’s disease (AD) brain with the representative compound 9 indicated selective labeling of it to Aβ plaques. The binding affinity of radioiodinated [125I]9 for AD brain homogenates was 0.21 nM (Kd), and of other derivatives ranged from 0.9 to 19.7 nM, except for N-methyl-4,5-dianilinophthalimide (Ki > 1000 nM). [125I]9 possessed the optimal lipophilicity with Log P value of 2.16, and its in vivo biodistribution in normal mice exhibited excellent initial brain uptake (5.16% ID/g at 2 min after injection) and a fast washout rate (0.56% ID/g at 60 min). The encouraging results suggest that this novel derivative of [123I]9 may have potential as an in vivo SPECT probe for detecting amyloid plaques in the brain.A novel anilinophthalimide derivative of [125I]MAPH is a promising candidate probe for SPECT imaging in the brain.

Fluorine-18 labeled galactosylated chitosan for asialoglycoprotein-receptor-mediated hepatocyte imaging

Co-reporter:Wenjiang Yang, Tiantian Mou, Wenyan Guo, Huihui Jing, Cheng Peng, Xianzhong Zhang, Yunchuan Ma, Boli Liu

Bioorganic & Medicinal Chemistry Letters 2010 Volume 20(Issue 16) pp:4840-4844

Publication Date(Web):15 August 2010

DOI:10.1016/j.bmcl.2010.06.106

Galactosylated chitosan (GC) was prepared by reacting lactobionic acid with water-soluble chitosan. GC was labeled with fluorine-18 by conjugation with N-succinimidyl-4-18F-fluorobenzoate ([18F]SFB) under a slightly basic condition. After rapid purification with HiTrap desalting column, [18F]FB-GC was obtained with high radiochemical purity (>97%) determined by radio-HPLC. The total reaction time for [18F]FB-GC was about 150 min. Typical decay-corrected radiochemical yield was about 4–8%. Ex vivo biodistribution in normal mice showed that [18F]FB-GC had moderate activity accumulation in liver with very good retention (11.13 ± 1.63, 10.97 ± 1.90 and 10.77 ± 0.95% ID/g at 10, 60, 120 min after injection, respectively). The other tissues except kidney showed relative low radioactivity accumulation. The high liver/background ratio affords promising biological properties to get clear images. The specific binding of this radiotracer to the ASGP receptor was confirmed by blocking experiment in mice. Compared with the non-blocking group the hepatic uptake of [18F]FB-GC significantly declined in all selected time points. The better liver retention properties of [18F]FB-GC than that of albumin based imaging agents may improve imaging quality and simplify pharmacokinetic model of liver function in the future application with PET imaging.Chitosan based novel ASGP imaging agent [18F]FB-GC was synthesized and evaluated in mice.

Synthesis and biological evaluation of 99mTc, Re-monoamine-monoamide conjugated to 2-(4-aminophenyl)benzothiazole as potential probes for β-amyloid plaques in the brain

Co-reporter:Xiangji Chen, Pingrong Yu, Lianfeng Zhang, Boli Liu

Bioorganic & Medicinal Chemistry Letters 2008 Volume 18(Issue 4) pp:1442-1445

Publication Date(Web):15 February 2008

DOI:10.1016/j.bmcl.2007.12.071

The benzothiazole aniline (BTA) conjugated with monoamine-monoamide (MAMA) was synthesized and then labeled with 99mTc. Its corresponding rhenium analogue was synthesized, and the fluorescent staining was performed in brain sections of both Tg mouse and Alzheimer’s disease (AD) patient. The fluorescent rhenium complex Re-MAMA-BTA selectively bound to the amyloid aggregates in the brain sections of both APP Tg mouse and AD patient. The analogous 99mTc-MAMA-BTA complex could enter the normal mouse brain with high initial uptake. These results are encouraging for further exploration of their derivatives as imaging agents for Aβ plaques in the brain.The synthesis and biological evaluation of 99mTc, Re-MAMA-BTA were reported here.

Synthesis and in vitro evaluation of new diphenyl ether derivatives as serotonin transporter ligands

Co-reporter:YunHang Guo;XiangJi Chen;HongMei Jia

Science China Chemistry 2008 Volume 51( Issue 5) pp:457-463

Publication Date(Web):2008 May

DOI:10.1007/s11426-008-0007-6

For the development of new ligands as potential imaging agents for the serotonin transporter (SERT), a series of diphenyl ether derivatives have been synthesized, characterized, and evaluated for their in vitro binding affinities to the SERT. Among the above compounds, 2-(2-((dimethylamino)methyl)-4-fluorophenoxy)-5-bromobenzenamine (15) and 2-(2-((dimethylamino)methyl)-4-fluorophenoxy)-5-iodobenzene amine (16) show high binding affinities for the SERT with Ki values of 0.28 and 0.20 nmol·L−1, respectively. They can be further labeled with carbon-11, fluorine-18, iodine-123 or bromine-76, and evaluated as useful imaging agents for the SERT. Moreover, the study of the structure-activity relationship (SAR) provides some useful information for the future design of new ligands.

Aβ-binding molecules: Possible application as imaging probes and as anti-aggregation agents

Co-reporter:XinHong Duan;BoLi Liu

Science China Chemistry 2008 Volume 51( Issue 9) pp:801-807

Publication Date(Web):2008 September

DOI:10.1007/s11426-008-0075-7

As amyloid β (Aβ) is at the centre of pathogenesis of Alzheimer’s disease (AD), Aβ aggregate-specific probes for in vivo studies of Aβ are potentially important for the early diagnosis and the assessment of new treatment strategies in the AD brain by noninvasive imaging. Several series of compounds derived from Congo red (CR) and Thioflavin T (ThT) have been evaluated as potential probes for the Aβ imaging. They include a diversity of core structures contributing to their affinities to Aβ. Small-molecule inhibitors were known to inhibit the formation of Aβ oligomers and fibrils. This inhibition has to be performed in such a way that these inhibitors bind to Aβ in the binding channel where Aβ-binding probes should sit. Therefore, several of them were used as novel core structures to develop Aβ probes, with their derivatives exhibiting good Aβ affinities. This approach will facilitate the design of a variety of candidates for Aβ probe molecules and anti-aggregation-therapeutic drugs. Moreover, the finding of Aβ probes with diverse core structures recognized by binding sites on Aβs will likely provide a promising perspective for the design of 99mTc-labeled probe-derived molecules.

Preparation and biodistribution of novel 99mTc(CO)3-CNR complexes for myocardial imaging

Co-reporter:Guiyang Hao;Jianying Zang;Boli Liu

Journal of Labelled Compounds and Radiopharmaceuticals 2007 Volume 50(Issue 1) pp:13-18

Publication Date(Web):22 JAN 2007

DOI:10.1002/jlcr.1151

We evaluated lipophilicity and biodistribution of a series of ^99mTc(CO)₃-ether isonitrile complexes to determine whether different lipophilicity and structure of isonitrile ligands would improve the imaging properties of the radiopharmaceutical for the heart. Novel ^99mTc(CO)₃-MIBI analogs were prepared and analyzed by radio-HPLC, and their lipophilicity was determined. These new complexes could be bi- or tri-substituted in specified pH conditions like ^99mTc(CO)₃-MIBI. These new complexes exhibited low liver, lungs and blood uptake compared with [^99mTc(CO)₃(MIBI)₃]⁺ though their heart uptake was not so high. Among these complexes, [^99mTc(CO)₃(EPI)₂(OH₂)]⁺ showed higher target to non-target ratios at 5 and 30 min post-injection than that of [^99mTc(CO)₃(MIBI)₃]⁺. Copyright © 2007 John Wiley & Sons, Ltd.

Synthesis, separation and biodistribution of 99mTc-CO-MIBI complex

Co-reporter:Lin Zhu;Jian Ying Zang;Gui Yang Hao;Bo Li Liu;Yu Zhi Guo

Journal of Labelled Compounds and Radiopharmaceuticals 2004 Volume 47(Issue 8) pp:513-521

Publication Date(Web):10 JUN 2004

DOI:10.1002/jlcr.839

^99mTc-CO-MIBI was prepared by a two-step procedure involving the convenient preparation of the [^99mTc(CO)₃(OH₂)₃]⁺ precursor and followed by the substitution of the water molecules by the MIBI (2-methoxyisobutylisonitrile) ligands. In a second step, the reaction solution was adjusted to different pH values, and then the product, ^99mTc-CO-MIBI, was confirmed to be a mixture of two complexes: complex A and complex B, whose labeling yields could be over 90%. The ratio of complex B to the sum of A and B could increase gradually from 0 to 1 when pH was shifted from 3.0 to 9.0. These changes were monitored by thin layer chromatography (TLC) and high performance liquid chromatography (HPLC). The two complexes were stable within 8 h at room temperature in vitro. The partition coefficient of the two complexes indicated that there was distinct difference between them. Biodistribution in mice demonstrated that complex B showed better myocardial imaging properties than that of complex A. The heart/liver ratios of complex A, the mixture, and complex B were 1.57, 1.93, and 2.33, respectively, for 30 min post-injection. The discovery of chemical and biological properties of ^99mTc-CO-MIBI would certainly promote the research on a new promising myocardial perfusion-imaging agent. Copyright © 2004 John Wiley & Sons, Ltd.

Synthesis and biological evaluation of one novel technetium-99m-labeled nitroquipazine derivative as an imaging agent for serotonin transporter

Co-reporter:Yunhang Guo, Xiangji Chen, Hongmei Jia, Xinmin Ji, Boli Liu

Applied Radiation and Isotopes (December 2008) Volume 66(Issue 12) pp:1804-1809

Publication Date(Web):December 2008

DOI:10.1016/j.apradiso.2008.06.009