Synthesis of a novel amphiphilic GdPCTA-[12] derivative as a potential micellar MRI contrast agent

Ferroud, Clotilde; Borderies, Hélène; Lasri, Elizabeth; Guy, Alain; Port, Marc

doi:10.1016/j.tetlet.2008.07.160

Cited by 20 publications

(15 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The longitudinal relaxivityo fG d(HD-OBETA) at 298 Ka nd 0.47 Tis3 4.2 mm À1 s À1 .T his value is higher than that found for other micellar aggregates of bis-hydrated (q = 2) Gd III chelates such as Gd(AAZTAC 17 )( 3b), measured under identical experimental conditions (r 1 = 30.0 mm À1 s À1 ). [20] It is worth notingt hat only af ew examples of amphiphilic q = 2G d III chelates capable of self-aggregation in micelles or intercalation into the membrane of liposomesa re known.T ot he best of our knowledge,i na ddition to the above cited Gd(AAZTAC 17 ), just two Gd III complexes based on PCTAa nd PyMTAd erivatives bearing aC 12 chain (5b and 6b)w ith r 1 value at 298 Ko f29.2 (20 MHz) [21] and 30.7 mm À1 s À1 (6.95 MHz), [22] respectively,h ave been reported.…”

Section: Hn Mr Relaxometricc Haracterizationmentioning

confidence: 90%

“…The data for Gd(PCTA-C 12 )w ere fitted without the use of the Lipari-Szabo approach andt hus are not directly comparable. [21] Interestingly,t he relaxivity values at 310 Kf or Gd(HD-OBETA) are almosts uperimposable to those at 298 Kf or both micelles in the diluteds olution and in the further aggregated form (see Figures S2-S5 in the Supporting Information).…”

Section: Hn Mr Relaxometricc Haracterizationmentioning

confidence: 92%

See 1 more Smart Citation

Synthesis of an Amphiphilic Bis‐Aqua Gd(OBETA) Complex for the Preparation of High‐Relaxivity Supramolecular Magnetic Resonance Imaging Probes

et al. 2015

View full text Add to dashboard Cite

Prompted by the favourable relaxometric, thermodynamic and kinetic properties of the bis‐hydrated Gd(OBETA) (OBETA=2,2′‐oxybis(ethylamine)‐N,N,N′,N′‐tetraacetic acid) complex, a novel derivative tailored with an n‐hexadecyl chain was synthesised. The amphiphilic gadolinium complex was designed and prepared with the aim of obtaining high relaxivity supramolecular aggregates by self‐assembly in micelles and liposomes. Thus, lipidic nanoparticles were prepared and characterised by dynamic light scattering and 1H NMR relaxometry. Relaxivity values of up to 48.3 mm−1 s−1 (20 MHz and 298 K) were registered in liposomal aggregates. The binding to human serum albumin (HSA), evaluated both in terms of affinity and relaxometric properties of the supramolecular adduct, yielded exceptionally high relaxivity values (71.4 mm−1 s−1 at 30 MHz and 298 K).

show abstract

Section: Hn Mr Relaxometricc Haracterizationmentioning

confidence: 90%

Section: Hn Mr Relaxometricc Haracterizationmentioning

confidence: 92%

Synthesis of an Amphiphilic Bis‐Aqua Gd(OBETA) Complex for the Preparation of High‐Relaxivity Supramolecular Magnetic Resonance Imaging Probes

et al. 2015

View full text Add to dashboard Cite

show abstract

“…These compounds are azapyridinomacrocycles complexing metal cations such as Gd(III). They must cross the biological barriers and vectorize the therapeutic target [9].…”

Section: Microwaves Assisted Solvent-free Amidationmentioning

confidence: 99%

New activation methods used in green chemistry for the synthesis of high added value molecules

Veitía

Ferroud

2014

Int J Energy Environ Eng

Self Cite

View full text Add to dashboard Cite

In the chemical and pharmaceutical industry, molecular organic chemistry is undergoing a green revolution in order to avoid waste by developing a cleaner and safer chemistry. This change is subject to the new European regulation REACH. One of the major goals of organic synthesis is to design molecules with high added value by developing synthetic methods highly selective, economical and environmentally friendly. To satisfy the societal expectation new activation methods must be developed in order to shorten the synthesis, to respect the principle of atom economy and to substitute pollutants or toxic organic solvents. In this context, our group focuses its research on the synthesis of biologically active molecules, developing new environmentally friendly synthetic strategies and more energy-efficient alternatives such as microwaves, ultrasound, photochemistry or biotransformation. We present here how various activation methods used for the preparation of several high-value compounds can dramatically enhance yields and selectivity. First, we describe microwave-assisted syntheses of precursors of [ 11 C] PIB, a tracer used in PET imaging and amides intermediates of natural products. We describe also the selective reduction of nitro compounds using ultrasound activation and a facile pathway to obtain b 3 -chiral aminoacids by biotransformation using purified nitrilases. Finally the results concerning the alkylation of a-aldehydes, using visible light and dyes as catalysts without transition metal are discussed. Some general considerations concerning the activation methods and their impact on the environment and the energy saving are given.

show abstract

“…Using substituted pyridines leads to the amphiphilic or bifunctional ligands bearing functional groups on the aromatic ring [342,[346][347][348][349].…”

Section: H 3 Pcta and Related Ligandsmentioning

confidence: 99%

Synthesis and Characterization of Ligands and their Gadolinium(III) Complexes

Kotek¹,

Kubíček²,

Hermann³

et al. 2013

The Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging

View full text Add to dashboard Cite

Synthesis of a novel amphiphilic GdPCTA-[12] derivative as a potential micellar MRI contrast agent

Cited by 20 publications

References 28 publications

Synthesis of an Amphiphilic Bis‐Aqua Gd(OBETA) Complex for the Preparation of High‐Relaxivity Supramolecular Magnetic Resonance Imaging Probes

Synthesis of an Amphiphilic Bis‐Aqua Gd(OBETA) Complex for the Preparation of High‐Relaxivity Supramolecular Magnetic Resonance Imaging Probes

New activation methods used in green chemistry for the synthesis of high added value molecules

Synthesis and Characterization of Ligands and their Gadolinium(III) Complexes

Contact Info

Product

Resources

About