Synthesis and Characterization of Tetrakis(allyloxy) Substituted Zn(II), Pt(II) and Pd(II) Phthalocyaninates

I. D. Burtsev,^a Ya. B. Platonova,^a,b A. N. Volov,^a and L. G. Tomilova^a,b@

^aDepartment of Chemistry, Lomonosov Moscow State University, 119991 Moscow, Russian Federation

^bInstitute of Physiologically Active Compounds, Russian Academy of Sciences, 142432 Chernogolovka, Russian Federation

^@Corresponding author E-mail: tom@org.chem.msu.ru

DOI: 10.6060/mhc200286t

Macroheterocycles 2020 13(2) 126-129

2(3)-Tetrakis(allyloxy) substituted phthalocyanine complexes of Zn(II), Pt(II) and Pd(II) have been obtained from a phthalocyanine ligand in high yields (up to 90 %). Both thermal and microwave irradiation techniques were successfully applied for complexes of Pd(II). Platinum and palladium complexes were synthesized for the first time and the new method for the synthesis of zinc complex was proposed. The obtained compounds were characterized by a combination of MALDI/TOF mass spectrometry, UV–Vis, and ¹⁹⁵Pt NMR spectroscopies. Photochemical properties of platinum(II) phthalocyanine were investigated. It was shown that this complex maintained high production of singlet oxygen and potentially can be used in photodynamic therapy.

References:

Click here to expand or collapse this section

1. Dolmans D.E.J.G.J., Fukumura D., Jain R.K. Nat. Rev. Cancer 2003, 3, 380-387.
https://doi.org/10.1038/nrc1071

2. Yu L., Wang Q., Yeung K.-W., Fong W.-P., Lo P.-C. Chem. Asian J. 2018, 13, 3509-3517.
https://doi.org/10.1002/asia.201800852

3. Zhang J., Jiang C., Longo J.P.F., Azevedo R.B., Zhang H., Muehlmann L.A. Acta Pharm. Sin. B 2018, 8(2), 137-146.
https://doi.org/10.1016/j.apsb.2017.09.003

4. Che Y., Yang W., Tang G., Dumoulin F., Zhao J., Liu L., İşci Ü. J. Mater. Chem. A 2018, 6, 5785-5793.
https://doi.org/10.1039/C8TC00513C

5. Doherty R.E., Sazanovich I.V., McKenzie L.K., Stasheuski A.S., Baggaley E., Bottomley S. et al. Sci. Rep. 2016, 6, 22668.
https://doi.org/10.1038/srep22668

6. Zhao J., Wu W., Sun J., Guo S. Chem. Soc. Rev. 2013, 42(12), 5323-5351.
https://doi.org/10.1039/c3cs35531d

7. Aggarwal A., Singh S., Zhang Y., Anthes M., Samaroo D., Gao R., Drain C.M. Tetrahedron Lett. 2011, 52, 5456-5459.
https://doi.org/10.1016/j.tetlet.2011.08.028

8. Moriwaki S., Misawa J., Yoshinari Y., Yamada I., Takigawa M., Tokura Y. Photodermatol. Photoimmunol. Photomed. 2001, 17(5), 241-243.
https://doi.org/10.1034/j.1600-0781.2001.170507.x

9. Allison R.R., Sibata C.H. Photodiagnosis Photodyn. Ther. 2010, 7(2), 61-75.
https://doi.org/10.1016/j.pdpdt.2010.02.001

10. Steiner M., Hartmann I., Perrino E., Casi G., Samatanga B., Jelezarov I. et al. Chem Sci. 2013, 4, 297-302.
https://doi.org/10.1039/C2SC21107F

11. Peng Z.-H., Sima M., Salama M.E., Kopeckova P., Kopecek J. J. Drug Target 2013, 21(10), 968-980.
https://doi.org/10.3109/1061186X.2013.833207

12. Park C.-K., Kim Y.H., Hwangbo S., Cho H. Int. J. Nanomedicine 2017, 12, 8185-8196.
https://doi.org/10.2147/IJN.S148332

13. Heukers R., Van Bergen en Henegouwen P., Oliveira S. Nanomed. Nanotechnol. 2014, 10(7), 1441-1451.
https://doi.org/10.1016/j.nano.2013.12.007

14. Zheng X. Pandey R.K.P. Anti-Cancer Agents Med. Chem. 2008, 8, 241-268.
https://doi.org/10.2174/187152008783961897

15. Gorlach B., Hellriegel C., Steinbrecher S., Yuksel H., Albert K., Plies E., Hanack M. J. Mater. Chem. 2001, 11, 3317-3325.
https://doi.org/10.1039/b104554g

16. Nas A., Kantekin H., Durmuş M., Gümrükçüoğlu N. J Lumin. 2014, 154, 15-21.
https://doi.org/10.1016/j.jlumin.2014.03.058

17. Zhang F.L., Huang Q., Zheng K., Li J., Liu J.Y., Xue J.P. Chem. Commun. 2013, 49(83), 9570-9572.
https://doi.org/10.1039/c3cc45487h

18. Khan T.K., Bröring M., Mathura S., Ravikanth M. Coord. Chem. Rev. 2013, 257(15-16), 2348-2387.
https://doi.org/10.1016/j.ccr.2013.04.007

19. Still B.M., Anil Kumar P.G., Aldrich-Wright J.R., Price W.S. Chem. Soc. Rev. 2007, 36, 665-686.
https://doi.org/10.1039/B606190G

20. Wang Y.-C., Chen M.-Y., Wu H.-Y., Chen J.-H., Wang S.-S., Tung J.-Y. Polyhedron 2014, 67, 73-80.
https://doi.org/10.1016/j.poly.2013.08.046

21. Krasnovskii A.A. Photochem. Photobiol. 1979, 29(1), 29-36.
https://doi.org/10.1111/j.1751-1097.1979.tb09255.x

References of Supporting Information

22. Krasnovsky A.A. Jr, Kozlov A.S., Roumbal Ya.V. Photochem. Photobiol. 2012, 11, 988-997.
https://doi.org/10.1039/c2pp05350k

23. Wilkinson F., Helman W.P., Ross A.B. J. Phys. Chem. Ref. Data 1993, 22, 113-262.
https://doi.org/10.1063/1.555934

24. Young R.H., Brewer D., Keller R.A. J. Am. Chem. Soc. 1973, 95, 375-379.
https://doi.org/10.1021/ja00783a012

Attachment	Size
mhc200286t.pdf	700.98 KB
mhc200286t_supp.pdf	7.94 MB

Журнал "Макрогетероциклы"

Navigation

Languages

News

Search

Synthesis and Characterization of Tetrakis(allyloxy) Substituted Zn(II), Pt(II) and Pd(II) Phthalocyaninates

References: