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Article: Single-Cell Profiling Reveals Immune-Based Mechanisms Underlying Tumor Radiosensitization by a Novel Mn Porphyrin Clinical Candidate, MnTnBuOE-2-PyP

Noh, Sun Up / Lim, Jinyeong / Shin, Sung-Won / Kim, Yeeun / Park, Woong-Yang / Batinic-Haberle, Ines / Choi, Changhoon / Park, Won

Antioxidants (Basel, Switzerland)

2024 Volume 13, Issue 4

Abstract: Manganese porphyrins reportedly exhibit synergic effects when combined with irradiation. However, an in-depth understanding of intratumoral heterogeneity and immune pathways, as affected by Mn porphyrins, remains limited. Here, we explored the mechanisms ...

Abstract	Manganese porphyrins reportedly exhibit synergic effects when combined with irradiation. However, an in-depth understanding of intratumoral heterogeneity and immune pathways, as affected by Mn porphyrins, remains limited. Here, we explored the mechanisms underlying immunomodulation of a clinical candidate, MnTnBuOE-2-PyP
Language	English
Publishing date	2024-04-17
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	2704216-9
ISSN	2076-3921
ISSN	2076-3921
DOI	10.3390/antiox13040477
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Article: Antibacterial Activity of Synthetic Cationic Iron Porphyrins.

Tovmasyan, Artak / Batinic-Haberle, Ines / Benov, Ludmil

Antioxidants (Basel, Switzerland)

2020 Volume 9, Issue 10

Abstract: Widespread antibiotic resistance demands new strategies for fighting infections. Porphyrin-based compounds were long ago introduced as photosensitizers for photodynamic therapy, but light-independent antimicrobial activity of such compounds has not been ... ...

Abstract	Widespread antibiotic resistance demands new strategies for fighting infections. Porphyrin-based compounds were long ago introduced as photosensitizers for photodynamic therapy, but light-independent antimicrobial activity of such compounds has not been systematically explored. The results of this study demonstrate that synthetic cationic amphiphilic iron
Language	English
Publishing date	2020-10-10
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	2704216-9
ISSN	2076-3921
ISSN	2076-3921
DOI	10.3390/antiox9100972
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Article ; Online: Ascorbate-dependent and ascorbate-independent Mn porphyrin cytotoxicity: anticancer activity of Mn porphyrin-based SOD mimics through ascorbate-dependent and -independent routes.

Hasan, Bader / Tovmasyan, Artak / Batinic-Haberle, Ines / Benov, Ludmil

Redox report : communications in free radical research

2021 Volume 26, Issue 1, Page(s) 85–93

Abstract: Objective: The aim of this study was to investigate how modifications at the periphery of the porphyrin ring affect the anticancer activity of Mn porphyrins (MnPs)-based SOD mimics.: Methods: Six compounds: MnTE-2-PyP with a short ethyl chain on the ... ...

Abstract	Objective: The aim of this study was to investigate how modifications at the periphery of the porphyrin ring affect the anticancer activity of Mn porphyrins (MnPs)-based SOD mimics. Methods: Six compounds: MnTE-2-PyP with a short ethyl chain on the pyridyl ring; MnTnHexOE-2-PyP and MnTnOct-2-PyP with linear 8-atom alkyl chains, but the former with an oxygen atom within the alkyl chain; MnTE-2-PyPhP and MnTPhE-2-PyP with pyridyl and phenyl substituents, were investigated. Cytotoxicity was studied using pII and MDA-MB-231 cancer cell lines. Viability was assessed by the MTT (3-[4,5-dimethylthiazol-2-yl)]-2,5-diphenyltetrazolium bromide) assay and cell proliferation was determined by the sulforhodamine B assay. Results: Cellular uptake was increased with the increase of the lipophilicity of the compounds, whereas reduction potential ( Conclusion: Two different processes account for MnPs cytotoxicity. MnPs with appropriate
MeSH term(s)	Antioxidants ; Ascorbic Acid/pharmacology ; Metalloporphyrins/metabolism ; Metalloporphyrins/pharmacology ; Oxidation-Reduction ; Porphyrins/pharmacology ; Superoxide Dismutase/metabolism
Chemical Substances	Antioxidants ; Metalloporphyrins ; Porphyrins ; Superoxide Dismutase (EC 1.15.1.1) ; Ascorbic Acid (PQ6CK8PD0R)
Language	English
Publishing date	2021-04-26
Publishing country	England
Document type	Journal Article
ZDB-ID	1305290-1
ISSN	1743-2928 ; 1351-0002
ISSN (online)	1743-2928
ISSN	1351-0002
DOI	10.1080/13510002.2021.1917214
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Zs.A 4584: Show issues

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Article ; Online: Effect of the nature of the chelated metal on the photodynamic activity of metalloporphyrins.

Abbas, Ghadeer / Alibrahim, Fatemah / Kankouni, Rawan / Al-Belushi, Sara / Al-Mutairi, Dalal A / Tovmasyan, Artak / Batinic-Haberle, Ines / Benov, Ludmil

Free radical research

2023 Volume 57, Issue 6-12, Page(s) 487–499

Abstract: Coordination of metal ions by the tetrapyrrolic macrocyclic ring of porphyrin-based photosensitizers (PSs) affects their photophysical properties and consequently, their photodynamic activity. Diamagnetic metals increase the singlet oxygen quantum yield ... ...

Abstract	Coordination of metal ions by the tetrapyrrolic macrocyclic ring of porphyrin-based photosensitizers (PSs) affects their photophysical properties and consequently, their photodynamic activity. Diamagnetic metals increase the singlet oxygen quantum yield while paramagnetic metals have the opposite effect. Since singlet oxygen is considered the main cell-damaging species in photodynamic therapy (PDT), the nature of the chelated cation would directly affect PDT efficacy. This expectation, however, is not always supported by experimental results and numerous exceptions have been reported. Understanding the effect of the chelated metal is hindered because different chelators were used. The aim of this work was to investigate the effect of the nature of chelated cation on the photophysical and photodynamic properties of metalloporphyrins, using the same tetrapyrrole core as a chelator of Ag(II), Cu(II), Fe(III), In(III), Mn(III), or Zn(II). Results demonstrated that with the exception of Ag(II), all paramagnetic metalloporphyrins were inefficient as generators of singlet oxygen and did not act as PSs. In contrast, the coordination of diamagnetic ions produced highly efficient PSs. The unexpected photodynamic activity of the Ag(II)-containing porphyrin was attributed to reduction of the chelated Ag(II) to Ag(I) or to demetallation of the complex, caused by cellular reductants and/or by exposure to light. Our results indicate that in biological systems, where PSs localize to various organelles and are subjected to the action of enzymes, reactive metabolites, and reducing or oxidizing agents, their physicochemical and photosensitizing properties change. Consequently, the photophysical properties alone cannot predict the anticancer efficacy of a PS.
MeSH term(s)	Metalloporphyrins/pharmacology ; Metalloporphyrins/chemistry ; Photochemotherapy/methods ; Singlet Oxygen ; Ferric Compounds ; Photosensitizing Agents/pharmacology ; Photosensitizing Agents/chemistry ; Porphyrins/pharmacology ; Porphyrins/chemistry ; Cations
Chemical Substances	Metalloporphyrins ; Singlet Oxygen (17778-80-2) ; Ferric Compounds ; Photosensitizing Agents ; Porphyrins ; Cations
Language	English
Publishing date	2023-12-26
Publishing country	England
Document type	Journal Article
ZDB-ID	1194130-3
ISSN	1029-2470 ; 1071-5762
ISSN (online)	1029-2470
ISSN	1071-5762
DOI	10.1080/10715762.2023.2288997
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Zs.A 2236: Show issues

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Article ; Online: Thiol regulation by Mn porphyrins, commonly known as SOD mimics.

Batinic-Haberle, Ines / Tome, Margaret E

Redox biology

2019 Volume 25, Page(s) 101139

Abstract: Superoxide dismutases play an important role in human health and disease. Three decades of effort have gone into synthesizing SOD mimics for clinical use. The result is the Mn porphyrins which have SOD-like activity. Several clinical trials are underway ... ...

Abstract	Superoxide dismutases play an important role in human health and disease. Three decades of effort have gone into synthesizing SOD mimics for clinical use. The result is the Mn porphyrins which have SOD-like activity. Several clinical trials are underway to test the efficacy of these compounds in patients, particularly as radioprotectors of normal tissue during cancer treatment. However, aqueous chemistry data indicate that the Mn porphyrins react equally well with multiple redox active species in cells including H
MeSH term(s)	Animals ; Humans ; Manganese/pharmacology ; Oxidation-Reduction ; Porphyrins/pharmacology ; Sulfhydryl Compounds/metabolism ; Superoxide Dismutase/metabolism ; Thermodynamics
Chemical Substances	Porphyrins ; Sulfhydryl Compounds ; Manganese (42Z2K6ZL8P) ; Superoxide Dismutase (EC 1.15.1.1)
Language	English
Publishing date	2019-02-13
Publishing country	Netherlands
Document type	Journal Article ; Research Support, Non-U.S. Gov't ; Review
ZDB-ID	2701011-9
ISSN	2213-2317 ; 2213-2317
ISSN (online)	2213-2317
ISSN	2213-2317
DOI	10.1016/j.redox.2019.101139
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Article ; Online: Mn porphyrins as a novel treatment targeting sickle cell NOXs to reverse and prevent acute vaso-occlusion in vivo.

Thamilarasan, Madhan / Estupinan, Rodolfo / Batinic-Haberle, Ines / Zennadi, Rahima

Blood advances

2020 Volume 4, Issue 11, Page(s) 2372–2386

Abstract: In sickle cell disease (SCD), adhesion of sickle red blood cells (SSRBCs) and activated leukocytes in inflamed venules affects blood rheology, causing vaso-occlusive manifestations and vital reduction in microvascular blood flow. Recently, we found that ... ...

Abstract	In sickle cell disease (SCD), adhesion of sickle red blood cells (SSRBCs) and activated leukocytes in inflamed venules affects blood rheology, causing vaso-occlusive manifestations and vital reduction in microvascular blood flow. Recently, we found that NADPH oxidases (NOXs) create a vicious feedback loop within SSRBCs. This positive feedback loop mediates SSRBC adhesion to the endothelium. We show for the first time the therapeutic effectiveness of the redox-active manganese (Mn) porphyrins MnTnBuOE-2-PyP5+ (MnBuOE; BMX-001) and MnTE-2-PyP5+ (MnE; BMX-010, AEOL10113) to treat established vaso-occlusion in a humanized sickle mouse model of an acute vaso-occlusive crisis using intravital microscopy. These Mn porphyrins can suppress SSRBC NOX activity. Subcutaneous administration of only 1 dose of MnBuOE or MnE at 0.1 to 2 mg/kg after the inflammatory trigger of vaso-occlusion, or simultaneously, reversed and reduced leukocyte and SSRBC adhesion, diminished leukocyte rolling, restored blood flow, and increased survival rate. Furthermore, MnBuOE and MnE administered to sickle mice subcutaneously at 0.1 to 1 mg/kg for 28 days (except on weekends) did not exacerbate anemia, which seemed to be due to downregulation of both SSRBC reactive oxygen species production and exposure of the eryptotic marker phosphatidylserine. In addition, Mn porphyrins ameliorated leukocytosis, venous blood gases, endothelial activation, and organ oxidative damage. Our data suggest that Mn porphyrins, likely by repressing NOX-mediated adhesive function of SSRBCs and activated leukocytes, could represent a novel, safe therapeutic intervention to treat or prevent the establishment of acute pain crises. These NOX-targeted antioxidants merit further assessment in SCD clinical trials.
MeSH term(s)	Anemia, Sickle Cell/drug therapy ; Animals ; Cell Adhesion ; Erythrocytes, Abnormal ; Mice ; NADPH Oxidases ; Porphyrins/therapeutic use
Chemical Substances	Porphyrins ; NADPH Oxidases (EC 1.6.3.-)
Language	English
Publishing date	2020-06-01
Publishing country	United States
Document type	Journal Article ; Research Support, N.I.H., Extramural
ZDB-ID	2915908-8
ISSN	2473-9537 ; 2473-9529
ISSN (online)	2473-9537
ISSN	2473-9529
DOI	10.1182/bloodadvances.2020001642
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Zs.A 7153: Show issues

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Article ; Online: Ortho Isomeric Mn(III) N-Alkyl- and Alkoxyalkylpyridylporphyrins-Enhancers of Hyaluronan Degradation Induced by Ascorbate and Cupric Ions.

Valachová, Katarína / Rapta, Peter / Moura, Nuno M M / Batinic-Haberle, Ines / Šoltés, Ladislav

International journal of molecular sciences

2021 Volume 22, Issue 16

Abstract: High levels of hyaluronic acid (HA) in tumors correlate with poor outcomes with several types of cancers due to HA-driven support of adhesion, migration and proliferation of cells. In this study we explored how to enhance the degradation of HA into low- ... ...

Abstract	High levels of hyaluronic acid (HA) in tumors correlate with poor outcomes with several types of cancers due to HA-driven support of adhesion, migration and proliferation of cells. In this study we explored how to enhance the degradation of HA into low-molecular fragments, which cannot prevent the immune system to fight tumor proliferation and metastases. The physiological solution of HA was exposed to oxidative degradation by ascorbate and cupric ions in the presence of either one of three
MeSH term(s)	Ascorbic Acid/chemistry ; Copper/chemistry ; Hyaluronic Acid/chemistry ; Magnesium/chemistry ; Metalloporphyrins/chemistry ; Oxidation-Reduction ; Superoxide Dismutase/metabolism
Chemical Substances	Metalloporphyrins ; manganese (III) meso-tetrakis(N-ethylpyridinium-2-yl)porphyrin ; Copper (789U1901C5) ; Hyaluronic Acid (9004-61-9) ; Superoxide Dismutase (EC 1.15.1.1) ; Magnesium (I38ZP9992A) ; Ascorbic Acid (PQ6CK8PD0R)
Language	English
Publishing date	2021-08-10
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	2019364-6
ISSN	1422-0067 ; 1422-0067 ; 1661-6596
ISSN (online)	1422-0067
ISSN	1422-0067 ; 1661-6596
DOI	10.3390/ijms22168608
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Article ; Online: Mn Porphyrin-Based Redox-Active Drugs: Differential Effects as Cancer Therapeutics and Protectors of Normal Tissue Against Oxidative Injury.

Batinic-Haberle, Ines / Tovmasyan, Artak / Spasojevic, Ivan

Antioxidants & redox signaling

2018 Volume 29, Issue 16, Page(s) 1691–1724

Abstract: Significance: After approximatelty three decades of research, two Mn(III) porphyrins (MnPs), MnTE-2-PyP: Critical issues: Differential effects of MnPs on normal versus tumor cells/tissues, which support their translation into clinic, arise from ... ...

Abstract	Significance: After approximatelty three decades of research, two Mn(III) porphyrins (MnPs), MnTE-2-PyP Critical issues: Differential effects of MnPs on normal versus tumor cells/tissues, which support their translation into clinic, arise from differences in their accumulation and redox environment of such tissues. This in turn results in different yields of MnP-driven modifications of proteins. Thus far, direct evidence for such modification of NF-κB, mitogen-activated protein kinases (MAPK), phosphatases, Nrf2, and endogenous antioxidative defenses was provided in tumor, while indirect evidence shows the modification of NF-κB and Nrf2 translational activities by MnPs in normal tissue. Future directions: Studies that simultaneously explore differential effects in same animal are lacking, while they are essential for understanding of extremely intricate interactions of metal-based drugs with complex cellular networks of normal and cancer cells/tissues.
MeSH term(s)	Animals ; Antineoplastic Agents/chemistry ; Antineoplastic Agents/metabolism ; Antineoplastic Agents/pharmacology ; Humans ; Manganese/chemistry ; Manganese/metabolism ; Manganese/pharmacology ; Metal-Organic Frameworks/chemistry ; Metal-Organic Frameworks/metabolism ; Metal-Organic Frameworks/pharmacology ; Neoplasms/drug therapy ; Neoplasms/pathology ; Oxidation-Reduction ; Oxidative Stress/drug effects ; Porphyrins/chemistry ; Porphyrins/metabolism ; Porphyrins/pharmacology ; Protective Agents/chemistry ; Protective Agents/metabolism ; Protective Agents/pharmacology
Chemical Substances	Antineoplastic Agents ; Metal-Organic Frameworks ; Porphyrins ; Protective Agents ; Manganese (42Z2K6ZL8P)
Language	English
Publishing date	2018-08-28
Publishing country	United States
Document type	Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't ; Review
ZDB-ID	1483836-9
ISSN	1557-7716 ; 1523-0864
ISSN (online)	1557-7716
ISSN	1523-0864
DOI	10.1089/ars.2017.7453
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Zs.A 5488: Show issues

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Article ; Online: A Redox-active Mn Porphyrin, MnTnBuOE-2-PyP

Chaiswing, Luksana / Yarana, Chontida / St Clair, William / Tovmasyan, Artak / Batinic-Haberle, Ines / Spasojevic, Ivan / St Clair, Daret

Oxidative medicine and cellular longevity

2022 Volume 2022, Page(s) 9664636

Abstract: We have employed a redox-active MnP (MnTnBuOE-2- ... ...

Abstract	We have employed a redox-active MnP (MnTnBuOE-2-PyP
MeSH term(s)	Antioxidants ; Carboplatin/pharmacology ; Carboplatin/therapeutic use ; Cell Line ; Female ; Humans ; Hydrogen Peroxide ; Metalloporphyrins/therapeutic use ; Ovarian Neoplasms/drug therapy ; Oxidation-Reduction ; Porphyrins ; Superoxide Dismutase
Chemical Substances	Antioxidants ; Metalloporphyrins ; Mn(III) meso-tetrakis(N-n-butoxyethylpyridinium-2-yl)porphyrin ; Porphyrins ; Hydrogen Peroxide (BBX060AN9V) ; Carboplatin (BG3F62OND5) ; Superoxide Dismutase (EC 1.15.1.1)
Language	English
Publishing date	2022-05-09
Publishing country	United States
Document type	Journal Article
ZDB-ID	2455981-7
ISSN	1942-0994 ; 1942-0994
ISSN (online)	1942-0994
ISSN	1942-0994
DOI	10.1155/2022/9664636
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Article ; Online: UVB-induced inactivation of manganese-containing superoxide dismutase promotes mitophagy via ROS-mediated mTORC2 pathway activation.

Dhar, Sanjit K / Batinic-Haberle, Ines / St Clair, Daret K

The Journal of biological chemistry

2019 Volume 294, Issue 17, Page(s) 6831–6842

Abstract: Mitochondria are major sites of energy metabolism that influence numerous cellular events, including immunity and cancer development. Previously, we reported that the mitochondrion-specific antioxidant enzyme, manganese-containing superoxide dismutase ( ... ...

Abstract	Mitochondria are major sites of energy metabolism that influence numerous cellular events, including immunity and cancer development. Previously, we reported that the mitochondrion-specific antioxidant enzyme, manganese-containing superoxide dismutase (MnSOD), has dual roles in early- and late-carcinogenesis stages. However, how defective MnSOD impacts the chain of events that lead to cell transformation in pathologically normal epidermal cells that have been exposed to carcinogens is unknown. Here, we show that UVB radiation causes nitration and inactivation of MnSOD leading to mitochondrial injury and mitophagy. In keratinocytes, exposure to UVB radiation decreased mitochondrial oxidative phosphorylation, increased glycolysis and the expression of autophagy-related genes, and enhanced AKT Ser/Thr kinase (AKT) phosphorylation and cell growth. Interestingly, UVB initiated a prosurvival mitophagy response by mitochondria-mediated reactive oxygen species (ROS) signaling via the mammalian target of the mTOR complex 2 (mTORC2) pathway. Knockdown of rictor but not raptor abrogated UVB-induced mitophagy responses. Furthermore, fractionation and proximity-ligation assays reveal that ROS-mediated mTOC2 activation in mitochondria is necessary for UVB-induced mitophagy. Importantly, pretreatment with the MnSOD mimic MnTnBuOE-2-PyP
MeSH term(s)	Animals ; Autophagy/physiology ; Cell Line ; Mechanistic Target of Rapamycin Complex 2/metabolism ; Mice ; Mitochondria/drug effects ; Mitochondria/enzymology ; Mitochondria/metabolism ; Mitophagy/radiation effects ; Nitrates/metabolism ; Oxidation-Reduction ; Rapamycin-Insensitive Companion of mTOR Protein/physiology ; Reactive Oxygen Species/metabolism ; Regulatory-Associated Protein of mTOR/physiology ; Superoxide Dismutase/antagonists & inhibitors ; Ultraviolet Rays
Chemical Substances	Nitrates ; Rapamycin-Insensitive Companion of mTOR Protein ; Reactive Oxygen Species ; Regulatory-Associated Protein of mTOR ; Rptor protein, mouse ; rictor protein, mouse ; Superoxide Dismutase (EC 1.15.1.1) ; Mechanistic Target of Rapamycin Complex 2 (EC 2.7.11.1)
Language	English
Publishing date	2019-03-11
Publishing country	United States
Document type	Journal Article ; Research Support, N.I.H., Extramural
ZDB-ID	2997-x
ISSN	1083-351X ; 0021-9258
ISSN (online)	1083-351X
ISSN	0021-9258
DOI	10.1074/jbc.RA118.006595
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