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Dermacozine N, the First Natural Linear Pentacyclic Oxazinophenazine with UV–Vis Absorption Maxima in the Near Infrared Region, along with Dermacozines O and P Isolated from the Mariana Trench Sediment Strain Dermacoccus abyssi MT 1.1ᵀ
dc.contributor.author | Juhasz, Bertalan | |
dc.contributor.author | Pech-Puch, Dawrin | |
dc.contributor.author | Tabudravu, Jioji | |
dc.contributor.author | Cautain, Bastien | |
dc.contributor.author | Reyes, Fernando | |
dc.contributor.author | Jiménez, Carlos | |
dc.contributor.author | Kyeremeh, Kwaku | |
dc.contributor.author | Jaspars, Marcel | |
dc.date.accessioned | 2021-07-13T09:39:52Z | |
dc.date.available | 2021-07-13T09:39:52Z | |
dc.date.issued | 2021-06-03 | |
dc.identifier.citation | Juhasz, B.; Pech-Puch, D.; Tabudravu, J.N.; Cautain, B.; Reyes, F.; Jiménez, C.; Kyeremeh, K.; Jaspars, M. Dermacozine N, the First Natural Linear Pentacyclic Oxazinophenazine with UV–Vis Absorption Maxima in the Near Infrared Region, along with Dermacozines O and P Isolated from the Mariana Trench Sediment Strain Dermacoccus abyssi MT 1.1ᵀ. Mar. Drugs 2021, 19, 325. https://doi.org/10.3390/md19060325 | es_ES |
dc.identifier.issn | 1660-3397 | |
dc.identifier.uri | http://hdl.handle.net/2183/28189 | |
dc.description.abstract | [Abstract] Three dermacozines, dermacozines N–P (1–3), were isolated from the piezotolerant Actinomycete strain Dermacoccus abyssi MT 1.1ᵀ, which was isolated from a Mariana Trench sediment in 2006. Herein, we report the elucidation of their structures using a combination of 1D/2D NMR, LC-HRESI-MSⁿ, UV–Visible, and IR spectroscopy. Further confirmation of the structures was achieved through the analysis of data from density functional theory (DFT)–UV–Visible spectral calculations and statistical analysis such as two tailed t-test, linear regression-, and multiple linear regression analysis applied to either solely experimental or to experimental and calculated ¹³C-NMR chemical shift data. Dermacozine N (1) bears a novel linear pentacyclic phenoxazine framework that has never been reported as a natural product. Dermacozine O (2) is a constitutional isomer of the known dermacozine F while dermacozine P (3) is 8-benzoyl-6-carbamoylphenazine-1-carboxylic acid. Dermacozine N (1) is unique among phenoxazines due to its near infrared (NIR) absorption maxima, which would make this compound an excellent candidate for research in biosensing chemistry, photodynamic therapy (PDT), opto-electronic applications, and metabolic mapping at the cellular level. Furthermore, dermacozine N (1) possesses weak cytotoxic activity against melanoma (A2058) and hepatocellular carcinoma cells (HepG2) with IC₅₀ values of 51 and 38 μM, respectively. | es_ES |
dc.description.sponsorship | Reino Unido. Engineering and Physical Sciences Research Council; EP/R030065/1 | es_ES |
dc.language.iso | eng | es_ES |
dc.publisher | MDPI | es_ES |
dc.relation.uri | https://doi.org/10.3390/md19060325 | es_ES |
dc.rights | Atribución 4.0 Internacional (CC BY 4.0) | es_ES |
dc.rights.uri | https://creativecommons.org/licenses/by/4.0/ | * |
dc.subject | Deep sea natural products | es_ES |
dc.subject | Mariana Trench | es_ES |
dc.subject | Dermacoccus abyssi MT 1.1ᵀ | es_ES |
dc.subject | ¹³C-NMR chemical shift linear and multiple regression | es_ES |
dc.subject | (DFT)-UV-Vis spectral calculation | es_ES |
dc.subject | Phenoxazine | es_ES |
dc.subject | Dermacozine | es_ES |
dc.subject | Absorption maxima in the near infrared region | es_ES |
dc.title | Dermacozine N, the First Natural Linear Pentacyclic Oxazinophenazine with UV–Vis Absorption Maxima in the Near Infrared Region, along with Dermacozines O and P Isolated from the Mariana Trench Sediment Strain Dermacoccus abyssi MT 1.1ᵀ | es_ES |
dc.type | info:eu-repo/semantics/article | es_ES |
dc.rights.access | info:eu-repo/semantics/openAccess | es_ES |
UDC.journalTitle | Marine Drugs | es_ES |
UDC.volume | 19 | es_ES |
UDC.issue | 6 | es_ES |
UDC.startPage | 325 | es_ES |
dc.identifier.doi | 10.3390/md19060325 |
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