Specific Delivery of Corroles to Cells via Noncovalent Conjugates with Viral Proteins

Agadjanian, Hasmik; Weaver, Jeremy J.; Mahammed, Atif; Rentsendorj, Altan; Bass, Sam; Kim, Jihee; Dmochowski, Ivan J.; Margalit, Ruth; Gray, Harry B.; Gross, Zeev; Medina-Kauwe, Lali K.

doi:10.1007/s11095-005-9225-1

Cited by 104 publications

(134 citation statements)

References 30 publications

(37 reference statements)

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“…Because NiSOD exists in nature, we were tempted to synthesize the Ni analogue of MnTE-2-PyP 5þ , but to our disappointment and despite favorable electrostatics and electron-deficiency of porphyrin ligand, the log k cat for NiTE-2-PyP 4þ is only 5.43; it is more than two orders of magnitude less active than MnTE-2-PyP 5þ . Its k cat is around the rate constant for O 2 ·À self-dismutation (5Â10 5 M=s, pH 7.0). Contrary to the porphyrin ligand, the ligand field around Ni in NiSOD enzyme allows it to cycle easily between þ 2 and þ 3 oxidation state with O 2 ·À .…”

Section: O Co and Ni Porphyrinsmentioning

confidence: 99%

“…The significant tumor growth suppression and tumorimaging properties of the fluorescent, negatively charged gallium sulfonated corrole noncovalently associated with breast cancer-targeted cell-penetration protein (HerOBK10), which accumulates in HER2 þ tumors, was recently reported; the complex retains integrity in human serum and accumulates in tumor (4,5,43). Nude mice bearing HER2 þ received daily IV injections of 0.008 mg=kg of HerGa complex for 7 days, starting at the time tumors reach 250-300 mm 3 volume; tumor size was measured until 25 days of growth.…”

Section: Corrolesmentioning

confidence: 99%

See 1 more Smart Citation

Superoxide Dismutase Mimics: Chemistry, Pharmacology, and Therapeutic Potential

Batinić‐Haberle

Rebouças

Spasojević

2010

Antioxidants & Redox Signaling

467

689

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Oxidative stress has become widely viewed as an underlying condition in a number of diseases, such as ischemia-reperfusion disorders, central nervous system disorders, cardiovascular conditions, cancer, and diabetes. Thus, natural and synthetic antioxidants have been actively sought. Superoxide dismutase is a first line of defense against oxidative stress under physiological and pathological conditions. Therefore, the development of therapeutics aimed at mimicking superoxide dismutase was a natural maneuver. Metalloporphyrins, as well as Mn cyclic polyamines, Mn salen derivatives and nitroxides were all originally developed as SOD mimics. The same thermodynamic and electrostatic properties that make them potent SOD mimics may allow them to reduce other reactive species such as peroxynitrite, peroxynitrite-derived CO 3 _ À , peroxyl radical, and less efficiently H 2 O 2 . By doing so SOD mimics can decrease both primary and secondary oxidative events, the latter arising from the inhibition of cellular transcriptional activity. To better judge the therapeutic potential and the advantage of one over the other type of compound, comparative studies of different classes of drugs in the same cellular and=or animal models are needed. We here provide a comprehensive overview of the chemical properties and some in vivo effects observed with various classes of compounds with a special emphasis on porphyrin-based compounds. Antioxid. Redox Signal. 13, 877-918.

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Section: O Co and Ni Porphyrinsmentioning

confidence: 99%

Section: Corrolesmentioning

confidence: 99%

Superoxide Dismutase Mimics: Chemistry, Pharmacology, and Therapeutic Potential

Batinić‐Haberle

Rebouças

Spasojević

2010

Antioxidants & Redox Signaling

467

689

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“…1 For decades, in order to reduce mortality, efforts have focused on new approaches for breast tumor treatment (especially chemotherapy) and its early detection. 2 We recently introduced optical imaging in vivo for chemotherapy assessment, 3 and reported that a tumor-targeted gallium corrole (HerGa), comprising sulfonated gallium corrole (S2Ga) complexed with the recombinant tumor-targeting cell penetrating protein, HerPBK10, is highly effective for killing HER2+ breast cancer cells in vitro 4 as well as for tumor detection and treatment in an animal model of HER2+ breast cancer. 5 In those studies, we used fluorescence intensity imaging to validate the tumor-targeting capability of HerGa in vivo and ex vivo.…”

Section: Introductionmentioning

confidence: 99%

Ratiometric spectral imaging for fast tumor detection and chemotherapy monitoring in vivo

et al. 2011

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Abstract. We report a novel in vivo spectral imaging approach to cancer detection and chemotherapy assessment. We describe and characterize a ratiometric spectral imaging and analysis method and evaluate its performance for tumor detection and delineation by quantitatively monitoring the specific accumulation of targeted gallium corrole (HerGa) into HER2-positive (HER2+) breast tumors. HerGa temporal accumulation in nude mice bearing HER2+ breast tumors was monitored comparatively by a. this new ratiometric imaging and analysis method; b. established (reflectance and fluorescence) spectral imaging; c. more commonly used fluorescence intensity imaging. We also tested the feasibility of HerGa imaging in vivo using the ratiometric spectral imaging method for tumor detection and delineation. Our results show that the new method not only provides better quantitative information than typical spectral imaging, but also better specificity than standard fluorescence intensity imaging, thus allowing enhanced in vivo outlining of tumors and dynamic, quantitative monitoring of targeted chemotherapy agent accumulation into them. C 2011 Society of Photo-Optical Instrumentation Engineers (SPIE).

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“…The macrocyclic ring of this complex can be selectively modified to afford molecules that exhibit a wide range of physical and chemical properties (1). Previous work focused on a sulfonic acid derivative of Ga(tpfc), 2 [Ga(2,17-S 2 tpfc)]; notably, 2 possessed potent antitumor activity both in vitro (using human cancer cells) and in vivo (using murine model animals), making it a powerful reagent for both imaging and therapeutic targeting of cancer cells (39,40). Additional studies on the mechanism of cytotoxicity demonstrated that numerous cancer cell lines rapidly take up 2 in vitro and induce cell cycle arrest at late M phase (41,42).…”

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.

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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.

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Specific Delivery of Corroles to Cells via Noncovalent Conjugates with Viral Proteins

Cited by 104 publications

References 30 publications

Superoxide Dismutase Mimics: Chemistry, Pharmacology, and Therapeutic Potential

Superoxide Dismutase Mimics: Chemistry, Pharmacology, and Therapeutic Potential

Ratiometric spectral imaging for fast tumor detection and chemotherapy monitoring in vivo

Cellular uptake and anticancer activity of carboxylated gallium corroles

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