Gd-complexes of macrocyclic DTPA conjugates of 1,1′-bis(amino)ferrocenes as high relaxivity MRI blood-pool contrast agents (BPCAs)

Kim, Hee Kyung; Park, Ji Ae; Kim, Kyeong Min; Sk, Nasiruzzaman; Kang, Duk-Sik; Lee, Jongmin; Chang, Yongmin; Kim, Tae‐Jeong

doi:10.1039/c0cc03145c

Cited by 19 publications

(12 citation statements)

References 31 publications

(7 reference statements)

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“…7 An interesting recent report has shown that 1,1¢-bis(amino)ferrocenes are also useful as starting compounds for gadolinium(III)-containing macrocyclic DPTA systems employed as MRI blood-pool contrast agents. 8 Among aminoferrocenes, mono and bisfunctionalized baminoethylferrocenes Fe{(h 5 -C 5 H 4 (CH 2 ) 2 NH 2 )(h 5 -C 5 H 5 )} (1) and Fe{h 5 -C 5 H 4 (CH 2 ) 2 NH 2 } 2 (2) (Chart 1) are particularly interesting compounds since they are able to undergo condensation reactions typical of the primary amino functional group. Pioneering studies in this field were carried out by Gonsalves and Rausch, who have used 1,1¢-bis(b-aminoethyl)ferrocene (2) as starting monomer for the preparation of remarkable examples of ferrocene-containing polyamides and polyureas (see example in Chart 1) via interfacial condensation polymerizations.…”

Section: Introductionmentioning

confidence: 99%

Heterometallic platinum(ii) compounds with β-aminoethylferrocenes: synthesis, electrochemical behaviour and anticancer activity

et al. 2012

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A new family of heterometallic compounds 3-6 containing ferrocenyl and platinum(II) centers has been synthesized by reaction of 1-β-aminoethylferrocene (1) and 1,1'-bis(β-aminoethyl)ferrocene (2) with Pt(II) precursors. Using K(2)[PtCl(4)] as the Pt(II) source, the cis-square-planar neutral compounds [Fe{η(5)-C(5)H(4)(CH(2))(2)NH(2)}(2)PtCl(2)] (3) and [{Fe(η(5)-C(5)H(4)(CH(2))(2)NH(2))(η(5)-C(5)H(5))}(2)PtCl(2)] (5) were obtained. Reaction of cis-[PtCl(2)(dmso)(2)] with 1 and 2 resulted in the displacement of dmso and chloride ligands from the platinum coordination sphere, affording the cationic and neutral compounds [Fe{η(5)-C(5)H(4)(CH(2))(2)NH(2)}(2)Pt(dmso)Cl]Cl (4) and [Fe(η(5)-C(5)H(4)(CH(2))(2)NH(2))(η(5)-C(5)H(5))Pt(dmso)Cl(2)] (6). Compounds 3-6 were thoroughly characterized using multinuclear ((1)H, (13)C, (195)Pt) NMR, IR spectroscopy, ESI mass spectrometry and elemental analysis. Single-crystal X-ray analysis of heterometallic 6 confirmed the cis geometry of the molecule and revealed that the platinum atom is held in a perfect square-planar geometry. The electrochemical behaviour of the heterometallic compounds 3-6, which has been examined by cyclic (CV) and square wave (SWV) voltammetries in dichloromethane and dmso solution, is characterized by the reversible one-electron oxidation of the ferrocene moieties. The results of the biological activity studies revealed that the organometallic complex 5 is active against all cell lines with GI(50) values in the range 1.7-2.3 μM. When compared to the standard anticancer drug cisplatin, heterotrimetallic 5, possessing two aminoethylferrocenyl units coordinated to the Pt(II) center, showed a greater activity profile in the colon cancer cell line. Cell cycle studies revealed that the new mixed compound exhibits a mechanism of action different to cisplatin.

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Section: Introductionmentioning

confidence: 99%

Heterometallic platinum(ii) compounds with β-aminoethylferrocenes: synthesis, electrochemical behaviour and anticancer activity

et al. 2012

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“…7 An interesting recent report has shown that 1,1 0 -bis(amino)ferrocenes are also useful as starting compounds for gadolinium(III)-containing macrocyclic DPTA systems employed as MRI blood-pool contrast agents. 8 Among aminoferrocenes, b-aminoethylferrocene Fe{(Z 5 -C 5 H 4 (CH 2 ) 2 NH 2 )(Z 5 -C 5 H 5 )} (1) is a particularly interesting compound which undergoes condensation reactions typical of the primary amino functional group. Accordingly, 1 is an excellent precursor for the synthesis of ferrocenecontaining polymers and dendrimers.…”

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confidence: 99%

Pt(ii)-activated coupling of aminoethylferrocene with benzonitrile. A facile access route to a new redox-active bis(ferrocenyl-amidine) anion sensor

et al. 2011

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“…FcDA was synthesized according to previously reported procedures . The full synthetic details, including NMR spectra (Figures S1 and S2), are provided in the Supporting Information.…”

Section: Methodsmentioning

confidence: 99%

Stress Relaxation in Epoxy Thermosets via a Ferrocene-Based Amine Curing Agent

et al. 2017

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Physical stress relaxation in rubbery, thermoset polymers is limited by cross-links, which impede segmental motion and restrict relaxation to network defects, such as chain ends. In parallel, the cure shrinkage associated with thermoset polymerizations leads to the development of internal residual stress that cannot be effectively relaxed. Recent strategies have reduced or eliminated such cure stress in thermoset polymers largely by exploiting chemical relaxation processes, wherein temporary cross-links or otherwise transient bonds are incorporated into the polymer network. Here, we explore an alternative approach, wherein physical relaxation is enhanced by the incorporation of organometallic sandwich moieties into the backbone of the polymer network. A standard epoxy resin is cured with a diamine derivative of ferrocene and compared to conventional diamine curing agents. The ferrocene-based thermoset is clearly distinguished from the conventional materials by reduced cure stress with increasing cure temperature as well as unique stress relaxation behavior above its glass transition in the fully cured state. The relaxation experiments exhibit features characteristic of a physical relaxation process. Furthermore, the cure stress is observed to vanish precipitously upon deliberate introduction of network defects through an increasing imbalance of epoxy and amine functional groups. We postulate that these beneficial properties arise from fluxional motion of the cyclopentadienyl ligands on the polymer backbone.

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Gd-complexes of macrocyclic DTPA conjugates of 1,1′-bis(amino)ferrocenes as high relaxivity MRI blood-pool contrast agents (BPCAs)

Cited by 19 publications

References 31 publications

Heterometallic platinum(ii) compounds with β-aminoethylferrocenes: synthesis, electrochemical behaviour and anticancer activity

Heterometallic platinum(ii) compounds with β-aminoethylferrocenes: synthesis, electrochemical behaviour and anticancer activity

Pt(ii)-activated coupling of aminoethylferrocene with benzonitrile. A facile access route to a new redox-active bis(ferrocenyl-amidine) anion sensor

Stress Relaxation in Epoxy Thermosets via a Ferrocene-Based Amine Curing Agent

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