Genomes and Genes
Summary: Porphyrins which are combined with a metal ion. The metal is bound equally to all four nitrogen atoms of the pyrrole rings. They possess characteristic absorption spectra which can be utilized for identification or quantitative estimation of porphyrins and porphyrin-bound compounds.
- Mroz P, Bhaumik J, Dogutan D, Aly Z, Kamal Z, Khalid L, et al. Imidazole metalloporphyrins as photosensitizers for photodynamic therapy: role of molecular charge, central metal and hydroxyl radical production. Cancer Lett. 2009;282:63-76 pubmed publisherThe in vitro photodynamic therapy activity of four imidazole-substituted metalloporphyrins has been studied using human (HeLa) and mouse (CT26) cancer cell lines: an anionic Zn porphyrin and a homologous series of three cationic Zn, Pd ..
- Haeubl M, Reith L, Gruber B, Karner U, Muller N, Knör G, et al. DNA interactions and photocatalytic strand cleavage by artificial nucleases based on water-soluble gold(III) porphyrins. J Biol Inorg Chem. 2009;14:1037-52 pubmed publisher..The potential of the novel water-soluble cationic metallointercalator complex [Au(III)(TMPy3Pyr1P)]Cl4 to serve as a catalytic photonuclease for the cleavage of DNA has been demonstrated. ..
- Zahedi Avval F, Berndt C, Pramanik A, Holmgren A. Mechanism of inhibition of ribonucleotide reductase with motexafin gadolinium (MGd). Biochem Biophys Res Commun. 2009;379:775-9 pubmed publisher..These data can elucidate an important effect of MGd on the cancer cells with overproduction of RNR and its efficacy as an anticancer agent and not only as a general radiosensitizer. ..
- Jackson I, Chen L, Batinic Haberle I, Vujaskovic Z. Superoxide dismutase mimetic reduces hypoxia-induced O2*-, TGF-beta, and VEGF production by macrophages. Free Radic Res. 2007;41:8-14 pubmed
- Castello P, Drechsel D, Day B, Patel M. Inhibition of mitochondrial hydrogen peroxide production by lipophilic metalloporphyrins. J Pharmacol Exp Ther. 2008;324:970-6 pubmed..b>Metalloporphyrins are a class of catalytic antioxidants that are capable of detoxifying a wide range of reactive oxygen ..
- Drel V, Pacher P, Vareniuk I, Pavlov I, Ilnytska O, Lyzogubov V, et al. Evaluation of the peroxynitrite decomposition catalyst Fe(III) tetra-mesitylporphyrin octasulfonate on peripheral neuropathy in a mouse model of type 1 diabetes. Int J Mol Med. 2007;20:783-92 pubmed..The findings provide rationale for development of potent peroxynitrite decomposition catalysts for the treatment of diabetic neuropathy. ..
- Duplain H, Sartori C, Dessen P, Jayet P, Schwab M, Bloch J, et al. Stimulation of peroxynitrite catalysis improves insulin sensitivity in high fat diet-fed mice. J Physiol. 2008;586:4011-6 pubmed publisher..Stimulation of peroxynitrite catalysis attenuates HFD-induced insulin resistance in mice by restoring insulin signalling and insulin-stimulated glucose uptake in skeletal muscle tissue...
- Juhasz B, Varga B, Czompa A, Bak I, Lekli I, Gesztelyi R, et al. Postischemic cardiac recovery in heme oxygenase-1 transgenic ischemic/reperfused mouse myocardium. J Cell Mol Med. 2011;15:1973-82 pubmed publisher..Immunohistochemical staining of HO-1 was intensified in HO-1 Tg compared to the NTg myocardium. Thus, the HO-1 Tg mouse model suggests a valuable therapeutic approach in the treatment of ischemic myocardium. ..
- Yu W, Li Z, Wang T, Liu M. Aggregation and supramolecular chirality of achiral amphiphilic metalloporphyrins. J Colloid Interface Sci. 2008;326:460-4 pubmed publisher..All the metalloporphyrins showed good spreading behavior on water surface and can be transferred onto solid substrates...
- Liang L, Huang J, Fulton R, Day B, Patel M. An orally active catalytic metalloporphyrin protects against 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine neurotoxicity in vivo. J Neurosci. 2007;27:4326-33 pubmed..This is the first demonstration of neuroprotection by an orally active catalytic antioxidant in the MPTP mouse model and suggests its potential clinical utility for the treatment of chronic neurodegenerative diseases such as PD. ..
- Spasojevic I, Chen Y, Noel T, Yu Y, Cole M, Zhang L, et al. Mn porphyrin-based superoxide dismutase (SOD) mimic, MnIIITE-2-PyP5+, targets mouse heart mitochondria. Free Radic Biol Med. 2007;42:1193-200 pubmed
- Scheingraber S, Messner S, Matt S, Abel K, Goger S, Kötner K, et al. Metalloporphyrins, used for HO-1 inhibition, themselves affect hepatic microcirculation, liver function, and hepatocellular integrity. Microcirculation. 2009;16:355-63 pubmed publisherb>Metalloporphyrins (MPs) are broadly used in the studies of the role of the heme oxygenase (HO)-1 system in different stress models. However, possible side effects of the MP administration itself have to be further investigated...
- Lum C, Liu X, Sun R, Li X, Peng Y, He M, et al. Gold(III) porphyrin 1a inhibited nasopharyngeal carcinoma metastasis in vivo and inhibited cell migration and invasion in vitro. Cancer Lett. 2010;294:159-66 pubmed publisher..Consistently, in in vitro studies, gold-1a inhibited migration and invasion of C666-1 human NPC cells. The data strongly support the use of gold(III) compounds to treat cancer metastasis. ..
- Takulapalli B, Laws G, Liddell P, Andréasson J, Erno Z, Gust D, et al. Electrical detection of amine ligation to a metalloporphyrin via a hybrid SOI-MOSFET. J Am Chem Soc. 2008;130:2226-33 pubmed publisher..A transistor response to a few hundred attomoles of bound pyridine can be readily detected. This extreme sensitivity, coupled with the ability to reset the device using light, suggests that such systems might be useful as sensors. ..
- Seo W, Ju S, Song H, Goh A, Jun J, Kang Y, et al. Celastrol suppresses IFN-gamma-induced ICAM-1 expression and subsequent monocyte adhesiveness via the induction of heme oxygenase-1 in the HaCaT cells. Biochem Biophys Res Commun. 2010;398:140-5 pubmed publisher..These results suggest that celastrol may exert anti-inflammatory responses by suppressing IFN-gamma-induced expression of ICAM-1 and subsequent monocyte adhesion via expression of HO-1 in the keratinocytes. ..
- Rajagopal A, Rao A, Amigo J, Tian M, Upadhyay S, Hall C, et al. Haem homeostasis is regulated by the conserved and concerted functions of HRG-1 proteins. Nature. 2008;453:1127-31 pubmed publisherHaems are metalloporphyrins that serve as prosthetic groups for various biological processes including respiration, gas sensing, xenobiotic detoxification, cell differentiation, circadian clock control, metabolic reprogramming and ..
- Lahaye D, Muthukumaran K, Hung C, Gryko D, Reboucas J, Spasojevic I, et al. Design and synthesis of manganese porphyrins with tailored lipophilicity: investigation of redox properties and superoxide dismutase activity. Bioorg Med Chem. 2007;15:7066-86 pubmed..The influence of the substituents on the Mn(III)/Mn(II) reduction potentials has been characterized, and the superoxide dismutase activity of the compounds has been examined. ..
- Mehta M, Shapiro W, Phan S, Gervais R, Carrie C, Chabot P, et al. Motexafin gadolinium combined with prompt whole brain radiotherapy prolongs time to neurologic progression in non-small-cell lung cancer patients with brain metastases: results of a phase III trial. Int J Radiat Oncol Biol Phys. 2009;73:1069-76 pubmed publisher..MGd significantly prolonged the interval to neurologic progression in non-small-cell lung cancer patients with brain metastases receiving prompt WBRT. The toxicity was acceptable. ..
- Hocking R, DeBeer George S, Gross Z, Walker F, Hodgson K, Hedman B, et al. Fe L- and K-edge XAS of low-spin ferric corrole: bonding and reactivity relative to low-spin ferric porphyrin. Inorg Chem. 2009;48:1678-88 pubmed publisher..These differences decrease the bonding interactions with axial ligands and contribute to the increased axial ligand lability and reactivity of ferric corroles relative to ferric porphyrins. ..
- Spasojevic I, Chen Y, Noel T, Fan P, Zhang L, Reboucas J, et al. Pharmacokinetics of the potent redox-modulating manganese porphyrin, MnTE-2-PyP(5+), in plasma and major organs of B6C3F1 mice. Free Radic Biol Med. 2008;45:943-9 pubmed publisher..The calculated pharmacokinetic parameters will be used to design optimal dosing regimens in future preclinical studies utilizing this and similar compounds. ..
- Walter A, Etienne Selloum N, Sarr M, Kane M, Beretz A, Schini Kerth V. Angiotensin II induces the vascular expression of VEGF and MMP-2 in vivo: preventive effect of red wine polyphenols. J Vasc Res. 2008;45:386-94 pubmed publisher..Thus, prevention of VEGF and MMP-2 expression might be involved in the protective effect of red wine on coronary heart diseases. ..
- Genovese T, Cuzzocrea S. Role of free radicals and poly(ADP-ribose)polymerase-1 in the development of spinal cord injury: new potential therapeutic targets. Curr Med Chem. 2008;15:477-87 pubmed..g. peroxynitrite decomposition catalysts, selective superoxide dismutase mimetics (SODm), PARP-1 and PARG inhibitors. ..
- Gauter Fleckenstein B, Fleckenstein K, Owzar K, Jiang C, Batinic Haberle I, Vujaskovic Z. Comparison of two Mn porphyrin-based mimics of superoxide dismutase in pulmonary radioprotection. Free Radic Biol Med. 2008;44:982-9 pubmed..However, MnTE-2-PyP5+ at 6 mg/kg proved to be more effective in reducing expression of key molecular factors known to play an important role in radiation-induced lung injury...
- Levrand S, Pacher P, Pesse B, Rolli J, Feihl F, Waeber B, et al. Homocysteine induces cell death in H9C2 cardiomyocytes through the generation of peroxynitrite. Biochem Biophys Res Commun. 2007;359:445-50 pubmed..These results provide the first demonstration that HCY kills cardiomyocytes through the generation of peroxynitrite and can activate key signaling cascades in the myocardium. ..
- Gauter Fleckenstein B, Fleckenstein K, Owzar K, Jiang C, Reboucas J, Batinic Haberle I, et al. Early and late administration of MnTE-2-PyP5+ in mitigation and treatment of radiation-induced lung damage. Free Radic Biol Med. 2010;48:1034-43 pubmed publisher..The radioprotective effects are presumably mediated through its ability both to suppress oxidative stress and to decrease activation of key transcription factors and proangiogenic and profibrogenic cytokines. ..
- Nakagaki S, Wypych F. Nanofibrous and nanotubular supports for the immobilization of metalloporphyrins as oxidation catalysts. J Colloid Interface Sci. 2007;315:142-57 pubmed..and synthetic, are important alternative matrices for the immobilization of metallocomplexes, especially metalloporphyrins, as oxidation catalysts...
- Abdelsaid M, Pillai B, Matragoon S, Prakash R, Al Shabrawey M, El Remessy A. Early intervention of tyrosine nitration prevents vaso-obliteration and neovascularization in ischemic retinopathy. J Pharmacol Exp Ther. 2010;332:125-34 pubmed publisher..Early inhibition of tyrosine nitration with use of epicatechin or NAC can represent safe and effective vascular-protective agents in ischemic retinopathy...
- Klassen S, Rabkin S. The metalloporphyrin FeTPPS but not by cyclosporin A antagonizes the interaction of peroxynitrate and hydrogen peroxide on cardiomyocyte cell death. Naunyn Schmiedebergs Arch Pharmacol. 2009;379:149-61 pubmed publisher..The ability of FeTPPS to reduce reactive nitrogen-induced cell death, and protein nitration suggests that FeTPPS is a useful agent to maintain cell viability and is better than cyclosporin in this situation...
- Man D, Słota R, Mele G, Li J. Fluidity of liposome membranes doped with metalloporphyrins: an ESR study. Z Naturforsch C. 2008;63:440-4 pubmed..25 and 50 h, most probably due to hydration of the hydrophilic part of the membrane. ..
- Genovese T, Mazzon E, Esposito E, Muià C, Di Paola R, Bramanti P, et al. Beneficial effects of FeTSPP, a peroxynitrite decomposition catalyst, in a mouse model of spinal cord injury. Free Radic Biol Med. 2007;43:763-80 pubmed
- Rabbani Z, Batinic Haberle I, Anscher M, Huang J, Day B, Alexander E, et al. Long-term administration of a small molecular weight catalytic metalloporphyrin antioxidant, AEOL 10150, protects lungs from radiation-induced injury. Int J Radiat Oncol Biol Phys. 2007;67:573-80 pubmed..AEOL 10150 has its primary impact on the cascade of events after irradiation, and adding the drug before irradiation and its short-term administration have no significant additional benefits. ..
- Gridley D, Makinde A, Luo X, Rizvi A, Crapo J, Dewhirst M, et al. Radiation and a metalloporphyrin radioprotectant in a mouse prostate tumor model. Anticancer Res. 2007;27:3101-9 pubmed..Possible mechanisms include reduction of radiation-induced HIF-1alpha and an altered cytokine profile. ..
- Brushett C, Qiu B, Atalar E, Yang X. High-resolution MRI of deep-seated atherosclerotic arteries using motexafin gadolinium. J Magn Reson Imaging. 2008;27:246-50 pubmed..This study provides initial evidence that MGd may enhance MR vessel wall imaging for the characterization of plaque in deep-seated arteries. ..
- Magda D, Miller R. Motexafin gadolinium: a novel redox active drug for cancer therapy. Semin Cancer Biol. 2006;16:466-76 pubmed..The molecular target for MGd appears to be thioredoxin reductase which, when inhibited, results in cellular redox stress, cytotoxicity and an increase in tumor responsiveness to a variety of treatments. ..
- Sklavos M, Bertera S, Tse H, Bottino R, He J, Beilke J, et al. Redox modulation protects islets from transplant-related injury. Diabetes. 2010;59:1731-8 pubmed publisher..These results suggest that the addition of a redox modulation strategy would be a beneficial clinical approach for islet preservation in syngeneic, allogeneic, and xenogeneic transplantation. ..
- Mao X, Crapo J, Mekonnen T, Lindsey N, Martinez P, Gridley D, et al. Radioprotective effect of a metalloporphyrin compound in rat eye model. Curr Eye Res. 2009;34:62-72 pubmed publisher..These results demonstrated that MnTE-2-PyP protected both photoreceptors and retinal capillaries from radiation damage, suggesting that this metalloporphyrin antioxidant is effective in regulating the damage induced by proton radiation. ..
- Sibley S, Sosinsky K, Gulian L, Gibbs E, Pasternack R. Probing the mechanism of insulin aggregation with added metalloporphyrins. Biochemistry. 2008;47:2858-65 pubmed publisher..the correlation between observed kinetics and amyloid structure for various concentration ranges of added metalloporphyrins. Observed structures include fibrils as well as circular, ring-like structures formed as a result of the ..
- Makinde A, Luo Owen X, Rizvi A, Crapo J, Pearlstein R, Slater J, et al. Effect of a metalloporphyrin antioxidant (MnTE-2-PyP) on the response of a mouse prostate cancer model to radiation. Anticancer Res. 2009;29:107-18 pubmed..The drug-induced enhancement of certain immune parameters suggests that MnTE-2-PyP may be beneficial not only as a normal tissue radioprotectant, but also as a facilitator of antitumor immunity. ..
- Milaeva E, Gerasimova O, Jingwei Z, Shpakovsky D, Syrbu S, Semeykin A, et al. Synthesis and antioxidative activity of metalloporphyrins bearing 2,6-di-tert-butylphenol pendants. J Inorg Biochem. 2008;102:1348-58 pubmed publisherThe novel metalloporphyrins (M=HH, Fe, Mn, Co, Cu, Zn) bearing 2,6-di-tert-butylphenol pendants as antioxidant substituents, and a long chain hydrocarbon palmitoyl group have been synthesized...
- Makarska M, Pratviel G. Long-range charge transport through double-stranded DNA mediated by manganese or iron porphyrins. J Biol Inorg Chem. 2008;13:973-9 pubmed publisher..Long-range charge transport is likely to be a universal mechanism for any two-electron oxidant acting by electron abstraction provided that the second electron abstraction is slower than hole transfer. ..
- Reboucas J, Spasojevic I, Batinic Haberle I. Pure manganese(III) 5,10,15,20-tetrakis(4-benzoic acid)porphyrin (MnTBAP) is not a superoxide dismutase mimic in aqueous systems: a case of structure-activity relationship as a watchdog mechanism in experimental therapeutics and biology. J Biol Inorg Chem. 2008;13:289-302 pubmed
- ..The main examples that are emphasized regarding the above respect are catalysis, imaging, and aspects relevant to drug development. ..
- Hachmeister J, Valluru L, Bao F, Liu D. Mn (III) tetrakis (4-benzoic acid) porphyrin administered into the intrathecal space reduces oxidative damage and neuron death after spinal cord injury: a comparison with methylprednisolone. J Neurotrauma. 2006;23:1766-78 pubmed
- McCarthy J, Weissleder R. Model systems for fluorescence and singlet oxygen quenching by metalloporphyrins. ChemMedChem. 2007;2:360-5 pubmed..developed a model system to systematically investigate the excited-state quenching ability of a number of metalloporphyrins. Central metal ions that prefer four-coordinate, square planar orientations (Ag(II), Cu(II), Ni(II), Pd(II), ..
- Evans J, Xu F, Sirisawad M, Miller R, Naumovski L, de Montellano P. Motexafin gadolinium-induced cell death correlates with heme oxygenase-1 expression and inhibition of P450 reductase-dependent activities. Mol Pharmacol. 2007;71:193-200 pubmed..Inhibition of HO1 by MGd may contribute to its anticancer activity, whereas its in vitro inhibition of a broad spectrum of P450 enzymes indicates that a potential exists for drug-drug interactions. ..
- Taketani S, Ishigaki M, Mizutani A, Uebayashi M, Numata M, Ohgari Y, et al. Heme synthase (ferrochelatase) catalyzes the removal of iron from heme and demetalation of metalloporphyrins. Biochemistry. 2007;46:15054-61 pubmed..Metal ions such as zinc and cobalt were also removed from the corresponding metalloporphyrins. The addition of zinc ions led to the formation of zinc protoporphyrin...
- Stevenson D, Wong R. Metalloporphyrins in the management of neonatal hyperbilirubinemia. Semin Fetal Neonatal Med. 2010;15:164-8 pubmed publisher..Preventing the production of excess bilirubin may be a more logical approach. Synthetic heme analogs, metalloporphyrins, are competitive inhibitors of heme oxygenase, the rate-limiting enzyme in bilirubin production, and their ..
- Shubina T, Marbach H, Flechtner K, Kretschmann A, Jux N, Buchner F, et al. Principle and mechanism of direct porphyrin metalation: joint experimental and theoretical investigation. J Am Chem Soc. 2007;129:9476-83 pubmed..For metalation with Zn, we calculated a barrier of the first hydrogen transfer step of 32.6 kcal mol(-1), in good agreement with the overall experimental activation energy of 31 kcal mol(-1). ..
- Wong R, Vreman H, Schulz S, Kalish F, Pierce N, Stevenson D. In vitro inhibition of heme oxygenase isoenzymes by metalloporphyrins. J Perinatol. 2011;31 Suppl 1:S35-41 pubmed publisher..b>Metalloporphyrins (Mps) are heme derivatives that competitively inhibit HO and thereby suppress hyperbilirubinemia...
- Wu T, Khoo N, Zhou F, Day B, Parks D. Decreased hepatic ischemia-reperfusion injury by manganese-porphyrin complexes. Free Radic Res. 2007;41:127-34 pubmedReactive oxygen and nitrogen species have been implicated in ischemia-reperfusion (I/R) injury. Metalloporphyrins (MP) are stable catalytic antioxidants that can scavenge superoxide, hydrogen peroxide, peroxynitrite and lipid peroxyl ..
- Sharma S, Gupta S. Neuroprotective effect of MnTMPyP, a superoxide dismutase/catalase mimetic in global cerebral ischemia is mediated through reduction of oxidative stress and DNA fragmentation. Eur J Pharmacol. 2007;561:72-9 pubmed..This study demonstrates that the neuroprotective effect of MnTMPyP in global ischemia is mediated through reduction in oxidative stress and DNA fragmentation. ..
- Ling X, Liu D. Temporal and spatial profiles of cell loss after spinal cord injury: Reduction by a metalloporphyrin. J Neurosci Res. 2007;85:2175-85 pubmed..Our profiles provide a database for pharmacological intervention, and our results on MnTBAP treatment support an important role for antioxidant therapy in spinal cord injury. ..
- Kupai K, Csonka C, Fekete V, Odendaal L, van Rooyen J, Marais D, et al. Cholesterol diet-induced hyperlipidemia impairs the cardioprotective effect of postconditioning: role of peroxynitrite. Am J Physiol Heart Circ Physiol. 2009;297:H1729-35 pubmed publisher..Furthermore, hyperlipidemia blocks the cardioprotective effect of postconditioning at least in part via deterioration of the postconditioning-induced early increase in peroxynitrite formation...