Synthesis and Characterization of Novel Fluoro‐glycosylated Porphyrins that can be Utilized as Theranostic Agents

Arja, Katriann; Elgland, Mathias; Appelqvist, Hanna; Konradsson, Peter; Lindgren, Mikael; Nilsson, K. Peter R.

doi:10.1002/open.201800020

Cited by 15 publications

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“…Nilsson and co-workers selected the strategy shown in Scheme 19 to prepare the tri-glucosylated-porphyrin conjugate P65 and analogues (the click step was extended also to galactose and N-acetyl glucosamine azides) to be used as theranostic agents [47,48]. For that, the asymmetric porphyrin precursor P62 was treated successively with chlorosulfonic acid, propargylamine in the presence of N,N-diisopropylethylamine (DIPEA) and Zn(II) acetate in order to gain porphyrin P63 at a total yield of 40%.…”

Section: Carbohydrate-porphyrin Conjugatesmentioning

confidence: 99%

Azides and Porphyrinoids: Synthetic Approaches and Applications. Part 1—Azides, Porphyrins and Corroles

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Azides and porphyrinoids (such as porphyrin and corrole macrocycles) can give rise to new derivatives with significant biological properties and as new materials’ components. Significant synthetic approaches have been studied. A wide range of products (e.g., microporous organic networks, rotaxane and dendritic motifs, dendrimers as liquid crystals, as blood substitutes for transfusions and many others) can now be available and used for several medicinal and industrial purposes.

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Section: Carbohydrate-porphyrin Conjugatesmentioning

confidence: 99%

Azides and Porphyrinoids: Synthetic Approaches and Applications. Part 1—Azides, Porphyrins and Corroles

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“…Schematic drawing showing A) the molecular design of fluoroglycosyated porphyrins and B) the desirable properties of a porphyrin based multimodal theranostic agent. Adapted fromArja et al ChemistryOpen 2018;7;495-503, with permission 148. group at C-2 with the radioactive fluorine-18 instead of fluorine-19, a potential PET tracer is obtained with the possibility for diagnosis on the organ to the full-body scale.…”

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“…General conditions and reagents: i) HSO3Cl, r.t.; ii) propargylamine, DIPEA, DCM, r.t.; iii) Zn(OAc)2*2H2O, DCM, MeOH, r.t., 40 % over 3 steps; iv) LiCl, DMF, MW, 160 °C, 77 %. Adapted from Arja et al ChemistryOpen 2018;7;495-503, with permission 148. …”

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“…Chemical structures of fluoroglycosylated porphyrin 52, 53 and 54, as well as reference compound 56 lacking FDG and 57 that is void of any carbohydrates. Adapted from Arja et al ChemistryOpen 2018;7;495-503, with permission 148. …”

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confidence: 99%

“…Significant differences were determined by ANOVA and p ≤ 0.05 are indicated with asterisks in the figure. Adapted from Arja et al ChemistryOpen 2018;7;495-503, with permission 148.…”

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Multimodal Porphyrin-Based Conjugates: Synthesis and characterization for applications as amyloid ligands, photodynamic therapy agents and chiroptical materials

Arja¹

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Organic compounds that interact both with certain biological targets and display specific photophysical properties can be utilized as molecular tools to visualize and possibly affect disease related processes taking place in living organisms. In this regard, porphyrins are a class of naturally occurring molecules that possess intriguingly interesting photophysical properties where they can act as luminescent probes by emitting detectable light, as well as photosensitizers in the light mediated therapy denoted photodynamic therapy. In this thesis, the porphyrin structure has been synthetically combined with other types of molecules to achieve compounds with desirable multimodal characteristics. During my doctoral studies at Chemistry department at Linköping university, several people have contributed to the scientific work that I carried out, helped me with the everyday matters or supported me in general. I would like to thank all these fantastic people and especially acknowledge some of them: Professor Peter Nilsson, my supervisor, for all the guidance and support through the years. You are an expert on helping me see the possibilities in seemingly tiny things that would eventually lead to fascinating research projects. Professor Peter Konradsson, my co-supervisor, for the help in navigating in the world of organic chemistry and for the all the philosophical discussions about the rest of the world. All the past and present members of the Nilsson group: Therése for always being the wise and calm ideal of a researcher; Hamid with his never-disturbed and inspiring enthusiasm in synthetic chemistry; the chatty and positive Bisse for all her advice on chemistry and life, and for all the enjoyable coffee breaks and lunches; Elisabet for being one of the few downright good people left in this world and surely one of the persons with the highest number of different interests; Hanna for the fruitful collaborations and pleasant company; Karin, Rozalyn, Leffe, Jeff, Andreas, Timmy and Mikaela for all the help and for all the memorable moments at works. Mathias Elgland, another downright good person with a plethora of positive qualities ranging from being an excellent chemist to a worthy friend. I am deeply grateful for all the scientific collaborations and the friendship along the side. Thank you for your most enjoyable company over my many years at Linköping university! Linda Lantz, my roomie and a dear colleague and a friend, for cheering my days with interesting scientific and even more interesting non-scientific talk. You inspire with you strong and independent angles of life philosophy. Marcus Bäck, for being a truly understanding and reliable friend and a helpful colleague, and for backing me up with "Det gör du rätt i". Jakob Wallgren for m/baking my days with all these splendid pastries and with your pleasant company! People in Organic chemistry corridor: Xiongyu Wu, a true sensei in chemistry; Yun, Tobias, Roger.

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Structural, Photophysical, and Photobiological Studies on BODIPY‐Anthracene Dyads

et al. 2020

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We report the structural, photophysical, and photobiological properties of a promising BODIPY‐anthracene dyad (BAD) that was previously shown to induce a therapeutic effect against MDA‐MB‐468 cells. The BODIPY was synthesized and its crystal structure was elucidated. We further investigate the potential of this molecule as a versatile photosensitizer for photodynamic therapy against AY27 and F98 cancer cell models. Both necrosis and apoptosis were found to play a role in cell death and G1 phase arrestation was observed following PDT. From time‐resolved spectroscopic analysis of absorbance and luminescence, it was found that the singlet oxygen quantum yield of the most promising BODIPY‐anthracene dyad is high (>70 %) and originates from a triplet state. Interestingly, despite the efficient PDT effect, long‐lived triplet states or singlet oxygen formation were not observed when water (or D2O) was used as the solvent but were readily observed in solvents such as MeOH and EtOH.

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Synthesis and Characterization of Novel Fluoro‐glycosylated Porphyrins that can be Utilized as Theranostic Agents

Cited by 15 publications

References 40 publications

Azides and Porphyrinoids: Synthetic Approaches and Applications. Part 1—Azides, Porphyrins and Corroles

Azides and Porphyrinoids: Synthetic Approaches and Applications. Part 1—Azides, Porphyrins and Corroles

Multimodal Porphyrin-Based Conjugates: Synthesis and characterization for applications as amyloid ligands, photodynamic therapy agents and chiroptical materials

Structural, Photophysical, and Photobiological Studies on BODIPY‐Anthracene Dyads

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