同: ガドリニウム

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the 7th letter of the Roman alphabet (同)g

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/12/16 18:57:01」(JST)

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Gadopentetic acid is one of the trade names for a gadolinium-based MRI contrast agent, usually administered as a salt of a complex of gadolinium with DTPA (diethylenetriaminepentacetate) with the chemical formula A₂[Gd(DTPA)(H₂O)]; when cation A is the protonated form of the amino sugar meglumine the salt goes under the name "Gadopentetate dimeglumine". It was described in 1981 and introduced as the first MRI contrast agent in 1987. It is used to assist imaging of blood vessels and of inflamed or diseased tissue where the blood vessels become "leaky". It is often used when viewing intracranial lesions with abnormal vascularity or abnormalities in the blood–brain barrier. It is usually injected intravenously. Gd-DTPA is classed as an acyclic, ionic gadolinium contrast medium. Its paramagnetic property reduces the T1 relaxation time (and to some extent the T2 and T2* relaxation times) in NMR, which is the source of its clinical utility.

A bottle of Magnevist contrast agent.

Marketed as Magnevist by Bayer Schering Pharma, it was the first intravenous contrast agent to become available for clinical use, and is in widespread use around the world. Similar contrast agents are Dotarem (gadoterate) manufactured by Guerbet, MultiHance (gadobenate dimeglumine) and ProHance (gadoteridol) manufactured by Bracco, Omniscan (gadodiamide) manufactured by GE Healthcare, and OptiMARK (gadoversetamide) manufactured by Mallinckrodt.

Gadolinium based agents may cause a toxic reaction known as nephrogenic systemic fibrosis (NSF) in patients with severe kidney problems.^[1]^[2]

Compared to other gadolinium-based MRI contrast agents, Gadopentetate dimeglumine (Gd-DTPA2-) chelates allow delayed Gadolinium-enhanced Magnetic Resonance of Cartilage (dGEMRIC). The unique charge characteristic of this complex allows researchers to inversely measure spin-lattice relaxation times as they are related to the concentration of proteoglycan aggregates and charged glycosaminoglycan side chains in articular cartilage.^[3]^[4]

Chemical structure and mode of action

In the complex of Gd³⁺ and DTPA^5- the gadolinium ion is 9-coordinate, surrounded by the 3 nitrogen atoms and 5 oxygen atoms from the carboxylate groups. The ninth coordination site is occupied by a water molecule.^[5] This water molecule is labile and exchanges rapidly with water molecules in the immediate vicinity of the gadolinium complex. The gadolinium ion has 7 unpaired electrons with parallel spins and is strongly paramagnetic with an ⁸S electronic ground state. The relaxation time of the water molecules is affected by their intermittent binding to the paramagnetic centre. This alters their MRI properties and enables contrast enhancement to be achieved.^[6]

References

^ Murphy KJ, Brunberg JA, Cohan RH (1996). "Adverse reactions to gadolinium contrast media: a review of 36 cases". American Journal of Roentgenology 167 (4): 847–849. doi:10.2214/ajr.167.4.8819369. PMID 8819369.
^ H.S. Thomsen, S.K. Morcos and P. Dawson (November 2006). "Is there a causal relation between the administration of gadolinium-based contrast media and the development of nephrogenic systemic fibrosis (NSF)?". Clinical Radiology 61 (11): 905–906. doi:10.1016/j.crad.2006.09.003. PMID 17018301.
^ Bashir A, Gray ML, Boutin RD, Burstein D. Glycosaminoglycan in articular cartilage: in vivo assessment with delayed Gd(DTPA)(2-)-enhanced MR imaging. Radiology. Nov 1997;205(2) 551–558.
^ Bashir A, Gray ML, Hartke J, Burstein D. Nondestructive imaging of human cartilage glycosaminoglycan concentration by MRI. Magn Reson Med. May 1999;41(5) 857–865.
^ A. Dean Sherry, Peter Caravan, Robert E. Lenkinski "Primer on Gadolinium Chemistry" J. Magnetic Resonance 2009, volume 30, p1240–1248. doi:10.1002/jmri.21966
^ Caravan, Peter; Ellison, Jeffrey J.; McMurry, Thomas J.; Lauffer, Randall B. (1999). "Gadolinium(III) Chelates as MRI Contrast Agents: Structure, Dynamics, and Applications". Chem. Revs. 99 (9): 2293–2342. doi:10.1021/cr980440x. PMID 11749483.

External links

Bayer Healthcare Pharmaceuticals page on Magnevist (for US)
Bayer Schering Pharma global Magnevist Website
"Gadopentetate Dimeglumine". Magnetic Resonance—Technology Information Portal. Retrieved 2006-03-27.

UpToDate Contents

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English Journal

One-step synthesis of water-dispersible ultra-small Fe3O4 nanoparticles as contrast agents for T1 and T2 magnetic resonance imaging.

Wang G1, Zhang X, Skallberg A, Liu Y, Hu Z, Mei X, Uvdal K.Author information 1Department of Chemistry, College of Pharmacy, Liaoning Medical University, Jinzhou, 121001, China.AbstractUniform, highly water-dispersible and ultra-small Fe3O4 nanoparticles were synthesized via a modified one-step coprecipitation approach. The prepared Fe3O4 nanoparticles not only show good magnetic properties, long-term stability in a biological environment, but also exhibit good biocompatibility in cell viability and hemolysis assay. Due to the ultra-small sized and highly water-dispersibility, they exhibit excellent relaxivity properties, the 1.7 nm sized Fe3O4 nanoparticles reveal a low r2/r1 ratio of 2.03 (r1 = 8.20 mM(-1) s(-1), r2 = 16.67 mM(-1) s(-1)); and the 2.2 nm sized Fe3O4 nanoparticles also appear to have a low r2/r1 ratio of 4.65 (r1 = 6.15 mM(-1) s(-1), r2 = 28.62 mM(-1) s(-1)). This demonstrates that the proposed ultra-small Fe3O4 nanoparticles have great potential as a new type of T1 magnetic resonance imaging contrast agents. Especially, the 2.2 nm sized Fe3O4 nanoparticles, have a competitive r1 value and r2 value compared to commercial contrasting agents such as Gd-DTPA (r1 = 4.8 mM(-1) s (-1)), and SHU-555C (r2 = 69 mM(-1) s(-1)). In vitro and in vivo imaging experiments, show that the 2.2 nm sized Fe3O4 nanoparticles exhibit great contrast enhancement, long-term circulation, and low toxicity, which enable these ultra-small sized Fe3O4 nanoparticles to be promising as T1 and T2 dual contrast agents in clinical settings.
Nanoscale.Nanoscale.2014 Mar 7;6(5):2953-63. doi: 10.1039/c3nr05550g. Epub 2014 Jan 31.
Uniform, highly water-dispersible and ultra-small Fe3O4 nanoparticles were synthesized via a modified one-step coprecipitation approach. The prepared Fe3O4 nanoparticles not only show good magnetic properties, long-term stability in a biological environment, but also exhibit good biocompatibility in
PMID 24480995

Evaluation of gadolinium-EOB-DTPA uptake after portal vein embolization: value of an increased flip angle.

Geisel D1, Lüdemann L, Wagner C, Stelter L, Grieser C, Malinowski M, Stockmann M, Seehofer D, Hamm B, Gebauer B, Denecke T.Author information 1Department of Diagnostic and Interventional Radiology, Charité, Campus Virchow-Klinikum, Berlin, Germany.AbstractBACKGROUND: The optimal sequence for Gd-EOB-DTPA uptake measurement in the liver with the purpose of liver function measurement is still not defined.
Acta radiologica (Stockholm, Sweden : 1987).Acta Radiol.2014 Mar 1;55(2):149-54. doi: 10.1177/0284185113495833. Epub 2013 Aug 1.
BACKGROUND: The optimal sequence for Gd-EOB-DTPA uptake measurement in the liver with the purpose of liver function measurement is still not defined.PURPOSE: To prospectively evaluate the effect of an increased flip angle (FA) of a T1-weighted fat-saturated 3D sequence for the measurement of hepatoc
PMID 23908244

In vitro Gd-DTPA relaxometry studies in oxygenated venous human blood and aqueous solution at 3 and 7 T.

Kalavagunta C1, Michaeli S, Metzger GJ.Author information 1Center of Magnetic Resonance Research, University of Minnesota, Minneapolis, MN, 55455, USA.AbstractIn vitro T1 and T2 (*) relaxivities (r1 and r2 (*) ) of Gd-DTPA (GaD) in oxygenated human venous blood (OVB) and aqueous solution (AS) at 3 and 7 T were calculated. GaD concentrations ([GaD]) in OVB and AS were prepared in the range 0-5 mM. All measurements were acquired at 37 ± 2 °C. At both 3 and 7 T, a linear relationship was observed between [GaD] and R1 in both AS and OVB. At 7 T, r1 in AS decreased by 7.5% (p = 0.045) while there was a negligible change in OVB. With respect to R2 (*) , a linear relationship with [GaD] was only observed in AS, while a more complex relationship was observed in OVB; quadratic below and linear above 2 mM at both field strengths. There was a significant increase of over 4-fold in r2 (*) with GaD in OVB at 7 T (for [GaD] above 2 mM, p <<0.01) as compared with 3 T. Furthermore, in comparison to r1 , r2 (*) in AS was less than 2-fold higher at both field strengths while in OVB it was ~20-fold and ~90-fold higher at 3 and 7 T, respectively. This observation emphasizes the importance of r2 (*) knowledge at high magnetic fields, ≥3 T. The comparison between r1 and r2 (*) presented in this work is crucial in the design and optimization of high-field MRI studies making use of paramagnetic contrast agents. This is especially true in multiple compartment systems such as blood, where r2 (*) dramatically increases while r1 remains relatively constant with increasing magnetic field strength. Copyright © 2014 John Wiley & Sons, Ltd.
Contrast media & molecular imaging.Contrast Media Mol Imaging.2014 Mar;9(2):169-76. doi: 10.1002/cmmi.1568.
In vitro T1 and T2 (*) relaxivities (r1 and r2 (*) ) of Gd-DTPA (GaD) in oxygenated human venous blood (OVB) and aqueous solution (AS) at 3 and 7 T were calculated. GaD concentrations ([GaD]) in OVB and AS were prepared in the range 0-5 mM. All measurements were acquired at 37 ± 2 °C. At
PMID 24523062

Japanese Journal

Preparation of polymer-based multimodal imaging agent to visualize the process of bone regeneration.

Liu Jian,Jo Jun-Ichiro,Kawai Yuko,Aoki Ichio,Tanaka Chuzo,Yamamoto Masaya,Tabata Yasuhiko
Journal of controlled release 157(3), 398-405, 2012-02-10
… In addition, the PA-pullulan-F/M conjugates showed an MR ability similar to Gd-DTPA (gadopentetate dimeglumine) of a MR imaging agent clinically used. …
NAID 120003988213

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★リンクテーブル★

リンク元	「ジエチレントリアミン五酢酸」「ガドリニウム」
関連記事	「DT」「G」「DTPA」「Gd」

「ジエチレントリアミン五酢酸」

Gadopentetic acid
Clinical data
AHFS/Drugs.com	Consumer Drug Information
Legal status	?
Pharmacokinetic data
Half-life	Distribution half life 12 minutes, elimination half 100 minutes
Identifiers
CAS number	86050-77-3
ATC code	V08CA01
PubChem	CID 55466
DrugBank	DB00789
ChemSpider	50087
UNII	RH248G8V27
KEGG	D01707
ChEBI	CHEBI:31797
ChEMBL	CHEMBL1200431
Chemical data
Formula	C14H18GdN3O10
	SMILES [Gd+3].[O-]C(=O)CN(CCN(CC(=O)O)CC([O-])=O)CCN(CC([O-])=O)CC(=O)O.O[C@H]([C@@H](O)CNC)[C@H](O)[C@H](O)CO.O[C@@H](CNC)[C@@H](O)[C@H](O)[C@H](O)CO;
	InChI InChI=1S/C14H23N3O10.2C7H17NO5.Gd/c18-10(19)5-15(1-3-16(6-11(20)21)7-12(22)23)2-4-17(8-13(24)25)9-14(26)27;21-8-2-4(10)6(12)7(13)5(11)3-9;/h1-9H2,(H,18,19)(H,20,21)(H,22,23)(H,24,25)(H,26,27);24-13H,2-3H2,1H3;/q;;;+3/p-3/t;2*4-,5+,6+,7+;/m.00./s1 ; Key:LGMLJQFQKXPRGA-VPVMAENOSA-K ;
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