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Antioxidants (Basel)
2023 Feb 05;122:. doi: 10.3390/antiox12020386.
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Shallow- and Deep-Water Ophiura Species Produce a Panel of Chlorin Compounds with Potent Photodynamic Anticancer Activities.
Klimenko A
,
Huber R
,
Marcourt L
,
Tabakaev D
,
Koval A
,
Dautov SS
,
Dautova TN
,
Wolfender JL
,
Thew R
,
Khotimchenko Y
,
Queiroz EF
,
Katanaev VL
.
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A Pacific brittle star Ophiura sarsii has previously been shown to produce a chlorin (3S,4S)-14-Ethyl-9-(hydroxymethyl)-4,8,13,18-tetramethyl-20-oxo-3-phorbinepropanoic acid (ETPA) (1) with potent phototoxic activities, making it applicable to photodynamic therapy. Using extensive LC-MS metabolite profiling, molecular network analysis, and targeted isolation with de novo NMR structure elucidation, we herein identify five additional chlorin compounds from O. sarsii and its deep-sea relative O. ooplax: 10S-Hydroxypheophorbide a (2), Pheophorbide a (3), Pyropheophorbide a (4), (3S,4S,21R)-14-Ethyl-9-(hydroxymethyl)-21-(methoxycarbonyl)-4,8,13,18-tetramethyl-20-oxo-3-phorbinepropanoic acid (5), and (3S,4S,21R)-14-Ethyl-21-hydroxy-9-(hydroxymethyl)-4,8,13,18-tetramethyl-20-oxo-3-phorbinepropanoic acid (6). Chlorins 5 and 6 have not been previously reported in natural sources. Interestingly, low amounts of chlorins 1-4 and 6 could also be identified in a distant species, the basket star Gorgonocephalus cf. eucnemis, demonstrating that chlorins are produced by a wide spectrum of marine invertebrates of the class Ophiuroidea. Following the purification of these major Ophiura chlorin metabolites, we discovered the significant singlet oxygen quantum yield upon their photoinduction and the resulting phototoxicity against triple-negative breast cancer BT-20 cells. These studies identify an arsenal of brittle star chlorins as natural photosensitizers with potential photodynamic therapy applications.
Agius,
Photodynamic action of bonellin, an integumentary chlorin of Bonellia viridis, Rolando (Echiura, Bonelliidae).
1979, Pubmed
Agius,
Photodynamic action of bonellin, an integumentary chlorin of Bonellia viridis, Rolando (Echiura, Bonelliidae).
1979,
Pubmed
Aroso,
Photodynamic disinfection and its role in controlling infectious diseases.
2021,
Pubmed
Atanasov,
Natural products in drug discovery: advances and opportunities.
2021,
Pubmed
Bandaranayake,
The nature and role of pigments of marine invertebrates.
2006,
Pubmed
Chansakaow,
Isolation of pyropheophorbide a from the leaves of Atalantia monophylla (ROXB.) CORR. (Rutaceae) as a possible antiviral active principle against herpes simplex virus type 2.
1996,
Pubmed
Chen,
The seafood Musculus senhousei shows anti-influenza A virus activity by targeting virion envelope lipids.
2020,
Pubmed
Cheng,
Cytotoxic pheophorbide-related compounds from Clerodendrum calamitosum and C. cyrtophyllum.
2001,
Pubmed
Dührkop,
SIRIUS 4: a rapid tool for turning tandem mass spectra into metabolite structure information.
2019,
Pubmed
Eichwurzel,
Photophysical studies of the pheophorbide a dimer.
2000,
Pubmed
Gomes,
Marine Invertebrate Metabolites with Anticancer Activities: Solutions to the "Supply Problem".
2016,
Pubmed
Guillarme,
Method transfer for fast liquid chromatography in pharmaceutical analysis: application to short columns packed with small particle. Part II: gradient experiments.
2008,
Pubmed
Hamblin,
Photodynamic Therapy for Cancer: What's Past is Prologue.
2020,
Pubmed
Jacobi,
A new synthesis of chlorins.
2001,
Pubmed
Katanaev,
The Anticancer Drug Discovery Potential of Marine Invertebrates from Russian Pacific.
2019,
Pubmed
Katanaev,
Mining Natural Compounds to Target WNT Signaling: Land and Sea Tales.
2021,
Pubmed
Kennedy,
Porphyrins in invertebrates.
1975,
Pubmed
Khotimchenko,
Marine Natural Products from the Russian Pacific as Sources of Drugs for Neurodegenerative Diseases.
2022,
Pubmed
Kim,
NPClassifier: A Deep Neural Network-Based Structural Classification Tool for Natural Products.
2021,
Pubmed
Klimenko,
A Cytotoxic Porphyrin from North Pacific Brittle Star Ophiura sarsii.
2020,
Pubmed
,
Echinobase
Klimenko,
Chlorin Endogenous to the North Pacific Brittle Star Ophiura sarsii for Photodynamic Therapy Applications in Breast Cancer and Glioblastoma Models.
2022,
Pubmed
,
Echinobase
Klimenko,
Shallow- and Deep-Water Ophiura Species Produce a Panel of Chlorin Compounds with Potent Photodynamic Anticancer Activities.
2023,
Pubmed
Li,
Clinical development and potential of photothermal and photodynamic therapies for cancer.
2020,
Pubmed
O'Neal,
Toward a general synthesis of chlorins.
2008,
Pubmed
Ohshima,
Pheophorbide a, a potent endothelin receptor antagonist for both ETA and ETB subtypes.
1994,
Pubmed
Pandey,
Nature: a rich source for developing multifunctional agents. Tumor-imaging and photodynamic therapy.
2006,
Pubmed
Pluskal,
MZmine 2: modular framework for processing, visualizing, and analyzing mass spectrometry-based molecular profile data.
2010,
Pubmed
Queiroz,
Utility of dry load injection for an efficient natural products isolation at the semi-preparative chromatographic scale.
2019,
Pubmed
Queirós,
Photodynamic therapy in dermatology: Beyond current indications.
2020,
Pubmed
Rutz,
Taxonomically Informed Scoring Enhances Confidence in Natural Products Annotation.
2019,
Pubmed
Smoot,
Cytoscape 2.8: new features for data integration and network visualization.
2011,
Pubmed
Stöhr,
Global diversity of brittle stars (Echinodermata: Ophiuroidea).
2012,
Pubmed
,
Echinobase
Tan,
Management of glioblastoma: State of the art and future directions.
2020,
Pubmed
Wang,
Sharing and community curation of mass spectrometry data with Global Natural Products Social Molecular Networking.
2016,
Pubmed
Zhu,
Comparison between porphin, chlorin and bacteriochlorin derivatives for photodynamic therapy: Synthesis, photophysical properties, and biological activity.
2018,
Pubmed
