A water-stable gadolinium(III) complex derived from a new pentadentate "expanded porphyrin" ligand

Sessler, Jonathan L.; Murai, Toshiaki; Hemmi, Gregory

doi:10.1021/ic00316a030

Cited by 36 publications

(18 citation statements)

References 9 publications

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“…0'4,1 ']heptucosa-1,3,S, 7,9,11(2 7), 12,14,16,18,20,22(25),23-tridecaene ( I ) . The relevant macrocyclic ligand and texaphyrin (15) metal complex were prepared using standard methods (13,(16)(17)(18)(19)(20), which are described briefly below. The macrocyclic ligand, 2, was then oxidatively metallated using lutetium(II1) acetate hydrate (9.75 g, 0.0230 mol) and triethylamine (22 mL) in air-saturated methanol (1500 mL) at reflux (13).…”

Section: Lutetium(ll1) Complex Of 4s-diethyl-1023-dimethy1-924-bismentioning

confidence: 99%

Lutetium Texaphyrin (PCI‐0123): A Near‐Infrared, Water‐Soluble Photosensitizer

Young

Woodburn

Wright

et al. 1996

Photochem & Photobiology

197

171

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Lutetium texaphyrin, PCI-0123, is a pure, water-soluble photosensitizer with a large broad absorption band centered at 732 nm. The compound was tested for photodynamic therapy (PDT) effectiveness in a murine mammary cancer model. The texaphyrin macrocycle as illustrated by magnetic resonance imaging and 14C-radiolabeled texaphyrin studies was shown to be tumor selective; a tumor-to-muscle ratio of 10.55 was seen after 5 h. Lutetium texaphyrin, at a drug dose of 20 mumol/kg with irradiation 5 h postinjection at 150 J/cm2 and 150 mW/cm2, had significant efficacy (P < 0.0001) in treating neoplasms of moderate size (40 +/- 14 mm3) and also had significant efficacy (P < 0.0001) in treating larger neoplasms (147 +/- 68 mm3). The PDT efficacy was correlated with the time interval between PCI-0123 administration and light exposure. A 100% cure rate was achieved when photoirradiation took place 3 h postinjection compared to 50% for 5 h using 10 mumol/kg and 150 J/cm2 at 150 mW/cm2. The PDT efficacy was attributable to the selective uptake/retention of the texaphyrin photosensitizer in addition to the depth of light penetration achievable at the 732 nm laser irradiation.

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Section: Lutetium(ll1) Complex Of 4s-diethyl-1023-dimethy1-924-bismentioning

confidence: 99%

Lutetium Texaphyrin (PCI‐0123): A Near‐Infrared, Water‐Soluble Photosensitizer

Young

Woodburn

Wright

et al. 1996

Photochem & Photobiology

197

171

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“…[4] Rapid progress has been further inspired by recent discoveries of diverse applications of expanded porphyrins as anion carriers, [5] photodynamic therapy (PDT) sensitizers [6] and magnetic resonance imaging (MRI) contrast agents. [7] Core-modified expanded porphyrins can be prepared from the acid-catalyzed condensation of 16-oxotripyrrane, 16-thiatripyrrane, or 16-selenatripyrrane. [8] In addition, 2,5-bis(arylhydroxymethyl)heterocyclopentadienes have been used as building blocks for the preparation of core-modified porphyrins.…”

Section: Introductionmentioning

confidence: 99%

Cu-Mediated Syntheses of N-Fused and Ring-Modified Trithiahexaphyrins

Hung

Jong

et al. 2002

Chem. Eur. J.

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“…150 A comprehensive study on a series of lanthanides embedded into expanded porphyrins has been performed: lanthanide salts and proton sponge (N,N 00 ,N 00 ,N 00 0 -tetramethyl-1,8-diaminonaphthalene) were reacted with texaphyrin in a chloroform/methanol mixed solvent at room temperature. 151 Pure complexes were difficult to obtain in reasonable yields by direct chromatography on either silica gel or lipophilic Sephadex. A better optimized method made use of oxygenated methanol as the solvent into which a mixture of Ln(NO 3 ) 3 Á xH 2 O and triethylamine was heated.…”

Section: Complexation With Expanded Porphyrins (Texaphyrins)mentioning

confidence: 99%