331. The synthesis of derivatives of corrole (pentadehydrocorrin)

Johnson, A. W.; Price, R.H.

doi:10.1039/jr9600001649

Cited by 44 publications

(37 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The first 2,2Ј-bidipyrrins were obtained by Johnson et al as the respective palladium(II) complexes by a coupling reaction of α,ω-dibromodipyrrins, using 3% palladium oxide on strontium carbonate as the reagent. [1] Only little later did the first free-base ligands as well as some nickel(II) and copper(II) chelates become accessible through a simple demetalation/remetalation protocol. [2,3] The tendency of the employed metal ions Ni II , Pd II , and Cu II to bind to dianionic tetrapyrrole ligands in a square-planar fashion, and the UV/Vis-spectroscopic features observed led to the assignment of these compounds to the metalloporphyrin-like structure 1.…”

Section: Introductionmentioning

confidence: 99%

Molecular and Electronic Structure of (2,2′-Bidipyrrinato)nickel(II) Complexes

Bröring

Brandt

Lex

et al. 2001

Eur. J. Inorg. Chem.

View full text Add to dashboard Cite

Nickel complexes of eight differently substituted 2,2′‐bidipyrrins have been prepared and fully characterized. The X‐ray analyses of three of these complexes revealed helical chiral molecules. Despite the tetrahedral deviation from the square‐planar coordination geometry at the metal centres, all compounds were found to be diamagnetic in nature. For (3,3′,4,4′,8,8′,9,9′‐octaethyl‐10,10′‐dimethyl‐6,6′‐diphenyl2,2′‐bidipyrrinato)nickel, a separation into the enantiomers by chiral MPLC could be achieved, and the first CD spectra of enantiomerically pure tetrapyrrole helicates are reported. An electrochemical study of the new complexes allowed a first insight into the electronic structure of (2,2′‐bidipyrrinato)nickel(II), disclosing a rather high energy HOMO and metal−ligand interaction similar to that observed in metalloporphyrins.

show abstract

Section: Introductionmentioning

confidence: 99%

Molecular and Electronic Structure of (2,2′-Bidipyrrinato)nickel(II) Complexes

Bröring

Brandt

Lex

et al. 2001

Eur. J. Inorg. Chem.

View full text Add to dashboard Cite

show abstract

“…Corroles have received a great deal of attention in recent years (10)(11)(12)(13), owing to dramatic advances in methods for their preparation (14)(15)(16)(17)(18)(19)(20)(21)(22)(23)(24)(25)(26)(27)(28)(29)(30)(31). Of interest here is a gallium(III) complex, 1 [Ga(tpfc)] (32)(33)(34)(35), where tpfc represents the trianion of 5,10,15-tris(pentafluorophenyl)corrole [H 3 (tpfc)].…”

mentioning

confidence: 99%

Cellular uptake and anticancer activity of carboxylated gallium corroles

Pribisko

Palmer²,

Grubbs

et al. 2016

Proc. Natl. Acad. Sci. U.S.A.

View full text Add to dashboard Cite

We report derivatives of gallium(III) tris(pentafluorophenyl)corrole, 1 [Ga(tpfc)], with either sulfonic (2) or carboxylic acids (3, 4) as macrocyclic ring substituents: the aminocaproate derivative, 3 [Ga(ACtpfc)], demonstrated high cytotoxic activity against all NCI60 cell lines derived from nine tumor types and confirmed very high toxicity against melanoma cells, specifically the LOX IMVI and SK-MEL-28 cell lines. The toxicities of 1, 2, 3, and 4 [Ga(3-ctpfc)] toward prostate (DU-145), melanoma (SK-MEL-28), breast (MDA-MB-231), and ovarian (OVCAR-3) cancer cells revealed a dependence on the ring substituent: IC 50 values ranged from 4.8 to >200 μM; and they correlated with the rates of uptake, extent of intracellular accumulation, and lipophilicity. Carboxylated corroles 3 and 4, which exhibited about 10-fold lower IC 50 values (<20 μM) relative to previous analogs against all four cancer cell lines, displayed high efficacy (E max = 0). Confocal fluorescence imaging revealed facile uptake of functionalized gallium corroles by all human cancer cells that followed the order: 4 >> 3 > 2 >> 1 (intracellular accumulation of gallium corroles was fastest in melanoma cells). We conclude that carboxylated gallium corroles are promising chemotherapeutics with the advantage that they also can be used for tumor imaging.

show abstract

“…This is well demonstrated by the changes in corrole chemistry discussed in The Porphyrin Handbook in 2000 1,2 as compared to the much more extensive chemistry discussed in the 2010 edition of the Handbook of Porphyrin Science. 3,4 The original preparation [5][6][7][8][9] and structural characterization 10 of corrole in the 1960s and 1970s was inspired at least in part by the structural similarity of corrole to the naturally occurring corrin ring in vitamin B12. Subsequent study was hampered by synthetic inaccessibility of corroles until 1999, when two new routes to the preparation of free base corrole were published by Paolesse 11 and Gross.…”

Section: Introductionmentioning

confidence: 99%