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Synthesis and characterization of novel 5-monocarbohydrate-10,20-bis-aryl-porphyrins

Flávio Figueira

QOPNA&LAQV-Requinte and Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal

CICECO — Aveiro Institute of Materials and Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal

E-mail Address: ffigueira@ua.pt

Corresponding authors.

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Leandro M. O. Lourenço

QOPNA&LAQV-Requinte and Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal

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Maria G. P. M. S. Neves

QOPNA&LAQV-Requinte and Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal

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José A. S. Cavaleiro

QOPNA&LAQV-Requinte and Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal

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, and

João P. C. Tomé

QOPNA&LAQV-Requinte and Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal

CQE and Departamento de Engenharia Química, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais Nº1, 1049-001 Lisboa, Portugal

E-mail Address: jtome@tecnico.ulisboa.pt

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https://doi.org/10.1142/S1088424619501049Cited by:3 (Source: Crossref)

Abstract

The synthesis of derivatives bearing glucose or galactose units linked by an acrylate spacer to one free meso position of a bis-aryl-porphyrin macrocycle was developed and characterized by standard spectroscopic techniques. The new mono-substituted gluco- and galacto-porphyrin derivatives 5–8 present an alternative to the widespread tetra-aryl porphyrin functionalization. Singlet oxygen studies showed a comparable singlet oxygen production with TPP. Furthermore, the less bulky architectures here synthesized present an opportunity to enhance the PDT and PDI capabilities of glycoporphyrins with a simple synthetic modification at one of the meso positions.

Dedicated to Professor Atsuhiro Osuka on the occasion of his 65th birthday.

Keywords:

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References

1. Josefsen LB and Boyle RW. Theranostics 2012; 2: 916–966. Crossref, Web of Science, Google Scholar
2. Nicolaou KC and Mitchell HJ. Angew. Chem. Int. Ed. 2001; 40: 1576–1624. Crossref, Web of Science, Google Scholar
3. Seeberger PH and Werz DB. Nature 2007; 446: 1046–1051. Crossref, Web of Science, Google Scholar
4. Appelhans D, Klajnert-Maculewicz B, Janaszewska A, Lazniewska J and Voit B. Chem. Soc. Rev. 2015; 44: 3968–3996. Crossref, Web of Science, Google Scholar
5. Kang B, Opatz T, Landfester K and Wurm FR. Chem. Soc. Rev. 2015; 44: 8301–8325. Crossref, Web of Science, Google Scholar
6. Marradi M, Chiodo F, Garcia I and Penades S. Chem. Soc. Rev. 2013; 42: 4728–4745. Crossref, Web of Science, Google Scholar
7. Figueira F, Rodrigues JMM, Farinha AAS, Cavaleiro JAS and Tomé JPC. J. Porphyrins Phthalocyanines 2016; 20: 950–965. Link, Web of Science, Google Scholar
8. Figueira F, Cavaleiro JAS and Tomé JPC. J. Porphyrins Phthalocyanines 2011; 15: 517–533. Link, Web of Science, Google Scholar
9. Figueira F, Pereira PMR, Cavaleiro JAS and Tomé JPC. Curr. Org. Synth. 2014; 11: 110–126. Crossref, Web of Science, Google Scholar
10. Figueira F, Farinha ASF, Muteto PV, Poleto MD, Verli H, Gomes MTSR, Tome AC, Cavaleiro JAS and Tome JPC. Chem. Commun. 2016; 52: 2181–2184. Crossref, Web of Science, Google Scholar
11. Rodrigues JMM, Farinha ASF, Muteto PV, Woranovicz-Barreira SM, Almeida Paz FA, Neves MGPMS, Cavaleiro JAS, Tomé AC, Gomes MTSR, Sessler JL and Tomé JPC. Chem. Commun. 2014; 50: 1359–1361. Crossref, Web of Science, Google Scholar
12. Rodrigues JMM, Farinha AAS, Tomé AC, Cavaleiro JAS and Tomé JPC. Sens. Actuators, B 2016; 224: 81–87. Crossref, Web of Science, Google Scholar
13. Castro KADF, Rodrigues JMM, Mendes RF, Neves MdGPMS, Simões MMQ, Cavaleiro JAS, Almeida Paz FA, Tomé JPC and Nakagaki S. J. Catal. 2016; 344: 303–312. Crossref, Web of Science, Google Scholar
14. Pereira PMR, Silva S, Bispo M, Zuzarte M, Gomes C, Girão H, Cavaleiro JAS, Ribeiro CAF, Tomé JPC and Fernandes R. Bioconjugate Chem. 2016; 27: 2762–2769. Crossref, Web of Science, Google Scholar
15. Castro KADF, Figueira F, Mendes RF, Almeida Paz FA, Neves MdGPMS, Cavaleiro JAS, Nakagaki S, Tomé JPC and Simões MMQ. Polyhedron 2019; 158: 478–484. Crossref, Web of Science, Google Scholar
16. Pereira CF, Liu Y, Howarth A, Figueira F, Rocha J, Hupp JT, Farha OK, Tomé JPC and Almeida Paz FA. ACS Appl. Nano Mater. 2019; 2: 465–469. Crossref, Web of Science, Google Scholar
17. Pereira CF, Figueira F, Mendes RF, Rocha J, Hupp JT, Farha OK, Simões MMQ, Tomé JPC and Paz FAA. Inorg. Chem. 2018; 57: 3855–3864. Crossref, Web of Science, Google Scholar
18. Castro KADF, Figueira F, Mendes RF, Cavaleiro JAS, Neves MdGPMS, Simões MMQ, AlmeidaPaz FA, Tomé JPC and Nakagaki S. ChemCatChem 2017; 9: 2939–2945. Crossref, Web of Science, Google Scholar
19. Vieira C, Gomes ATPC, Mesquita MQ, Moura NMM, Neves MGPMS, Faustino MAF and Almeida A. Front. Microbiol. 2018; 9: 2665–2665. Crossref, Web of Science, Google Scholar
20. Alves E, Faustino MAF, Neves MGPMS, Cunha Â, Nadais H and Almeida A. J. Photochem. Photobiol. C 2015; 22: 34–57. Crossref, Web of Science, Google Scholar
21. Fernández L, Lin Z, Schneider RJ, Esteves VI, Cunha Â and Tomé JPC. ChemPhotoChem 2018; 2: 596–605. Crossref, Web of Science, Google Scholar
22. Alves E, Rodrigues JMM, Faustino MAF, Neves MGPMS, Cavaleiro JAS, Lin Z, Cunha Â, Nadais MH, Tomé JPC and Almeida A. Dyes Pigm. 2014; 110: 80–88. Crossref, Web of Science, Google Scholar
23. Cavaleiro JAS, Tome JPC and Faustino MAF. Synthesis of Glycoporphyrins, Springer Berlin: Heidelberg, 2007. Crossref, Google Scholar
24. Ethirajan M, Chen Y, Joshi P and Pandey RK. Chem. Soc. Rev. 2011; 40: 340–362. Crossref, Web of Science, Google Scholar
25. Pisarek S, Maximova K and Gryko D. Tetrahedron 2014; 70: 6685–6715. Crossref, Web of Science, Google Scholar
26. Singh S, Aggarwal A, Bhupathiraju NVSDK, Arianna G, Tiwari K and Drain CM. Chem. Rev. 2015; 115: 10261–10306. Crossref, Web of Science, Google Scholar
27. Silva S, Pereira PMR, Silva P, Paz FAA, Faustino MAF, Cavaleiro JAS and Tomé JPC. Chem. Commun. 2012; 48: 3608–3610. Crossref, Web of Science, Google Scholar
28. Samaroo D, Vinodu M, Chen X and Drain CM. J. Comb. Chem. 2007; 9: 998–1011. Crossref, Web of Science, Google Scholar
29. Vedachalam S, Choi BH, Pasunooti KK, Ching KM, Lee K, Yoon HS and Liu XW. Med. Chem. Commun. 2011; 2: 371–377. Crossref, Web of Science, Google Scholar
30. Wyrębek P, Osuch-Kwiatkowska A, Pakulski Z, Jarosz S and Ostrowski S. J. Porphyrins Phthalocyanines 2013; 17: 384–391. Link, Web of Science, Google Scholar
31. Serra A, Pineiro M, Santos CI, Rocha Gonsalves AMD, Abrantes M, Laranjo M and Botelho MF. Photochem. Photobiol. 2010; 86: 206–212. Crossref, Web of Science, Google Scholar
32. Silva JN, Silva AMG, Tome JP, Ribeiro AO, Domingues MRM, Cavaleiro JAS, Silva AMS, Graca M, Neves M, Tome AC, Serra OA, Bosca F, Filipe P, Santuse R and Morliere P. Photochem. Photobiol. Sci. 2008; 7: 834–843. Crossref, Web of Science, Google Scholar
33. Gariboldi MB, Ravizza R, Baranyai P, Caruso E, Banfi S, Meschini S and Monti E. Bioorg. Med. Chem. 2009; 17: 2009–2016. Crossref, Web of Science, Google Scholar
34. Banfi S, Caruso E, Buccafurni L, Murano R, Monti E, Gariboldi M, Papa E and Gramatica P. J. Med. Chem. 2006; 49: 3293–3304. Crossref, Web of Science, Google Scholar
35. Yorimitsu H and Osuka A. Asian J. Org. Chem. 2013; 2: 356–373. Crossref, Web of Science, Google Scholar
36. Aksenova AA, Sebyakin YL and Mironov AF. Russ. J. Bioorg. Chem. 2003; 29: 201–219. Crossref, Web of Science, Google Scholar
37. Tomé JPC. University of Aveiro: PhD Thesis, 2001. Google Scholar
38. Tomé JPC, Neves MGPMS, Tomé AC and Cavaleiro J. In International Conference on Porphyrins and Phthalocyanines (ICPP-1): Dijon, France, 2000. Google Scholar
39. Armarego WLF and Chai CLL. In Purification of Laboratory Chemicals (Seventh Edition), Butterworth–Heinemann: Boston, 2013. Google Scholar
40. DiMagno SG, Lin VSY and Therien MJ. J. Org. Chem. 1993; 58: 5983–5993. Crossref, Web of Science, Google Scholar
41. Littler BJ, Miller MA, Hung CH, Wagner RW, O’Shea DF, Boyle PD and Lindsey JS. J. Org. Chem. 1999; 64: 1391–1396. Crossref, Web of Science, Google Scholar
42. Littler BJ, Miller MA, Hung CH, Wagner RW, O’Shea DF, Boyle PD and Lindsey JS. J. Org. Chem. 1999; 64: 1391–1396. Crossref, Web of Science, Google Scholar
43. Bruckner C, Posakony JJ, Johnson CK, Boyle RW, James BR and Dolphin D. J. Porphyrins Phthalocyanines 1998; 2: 455–465. Link, Web of Science, Google Scholar
44. Nistri D, Dei D, Chiti G, Cocchi A, Fantetti L and Roncucci G. J. Porphyrins Phthalocyanines 2005; 9: 290–297. Link, Web of Science, Google Scholar
45. Pomin VH. In Glycosylation, 1st ed., Petrescu DS. (Ed.) In Tech, 2012. Google Scholar