Synthesis of Water-Soluble Non-Aggregated Porphyrin-β-Cyclodextrin Tetraconjugate

A. Lyubimtsev,^a@ E. Kudrik,^a D. Tyurin,^a N. Zheglova,^a and S. Syrbu^b

Dedicated to Academician Aslan Yu. Tsivadze on the ocassion of his 75th Birthday

^aResearch Institute of Macroheterocycles, Ivanovo State University of Chemistry and Technology, 153000 Ivanovo, Russia

^bG.A. Krestov Institute of Solution Chemistry of Russian Academy of Sciences, 153045 Ivanovo, Russia

^@Corresponding author E-mail: alexlyubimtsev@mail.ru

DOI: 10.6060/mhc161183l

Macroheterocycles 2017 10(4-5) 510-513

The novel porphyrin–β-cyclodextrin (Por-β-CD) conjugate 3 was synthesized and investigated. Addition of four β-CD units to the porphyrin macrocycle leads to formation of non-aggregated water-soluble covalently linked conjugate, which does not demonstrate any self-assembled species even at high concentrations. New conjugate 3 forms inclusion complexes with ruthenium, simulating antitumor drug NAMI-A. The formation of stable inclusion complex was detected by UV-Vis spectroscopy..

References:

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1. Moylan C., Scanlan E., Senge M. Curr. Med. Chem. 2015, 22, 2238–2348.
https://doi.org/10.2174/0929867322666150429113104

2. Mercorillo G., Puglisi R., Spina E., Vitalini D. J. Porphyrins Phthalocyanines 2016, 20, 700–707.
https://doi.org/10.1142/S1088424616500644

3. Zhao J., Zhang H-Y., Sun H-L., Liu Y. Chem. Eur. J. 2015, 21, 4457–4464.
https://doi.org/10.1002/chem.201405943

4. Mineo P. Org. Biomol. Chem. 2014, 12, 3663–3670.
https://doi.org/10.1039/c4ob00393d

5. Shi W-J., Menting R., Ermilov E., Lo P-C., Röder B., Ng D.K.P. Chem. Commun. 2013, 49, 5277–5279.
https://doi.org/10.1039/c3cc00095h

6. Aggelidou C., Theodossiou T.A., Yannakopoulou K. Photochem. Photobiol. 2013, 89, 1011–1019.
https://doi.org/10.1111/php.12127

7. Oliveri V., Puglisi A., Vecchio G. Dalton Trans. 2011, 40, 2913–2919.
https://doi.org/10.1039/c0dt01480j

8. Fathalla M., Li S-C., Diebold U., Alb A., Jayawickramarajah J. Chem. Commun. 2009, 4209–4211.
https://doi.org/10.1039/b908050c

9. Hosokawa K., Miura Yu., Kiba T., Kakuchi T., Sato S. Chem. Lett. 2008, 37(1), 60–61.
https://doi.org/10.1246/cl.2008.60

10. Liu Yu, Ke C-F., Zhang H-Yi., Cui J., Ding F. J. Am. Chem. Soc. 2008, 130, 600–605.
https://doi.org/10.1021/ja075981v

11. Puglisi A., Purrello R., Rizzarelli E., Sortino S., Vecchio G. New J. Chem. 2007, 31, 1499–1506.
https://doi.org/10.1039/b703680a

12. Kralova J., Synytsya A., Pouckova P., Koc M., Dvorak M., Kral V. Photochem. Photobiol. 2006, 82, 432–438.
https://doi.org/10.1562/2005-05-06-RA-516

13. Singh S., Aggarwal A., Bhupathiraju N.V.S., Arianna G., Tiwari K., Drain C.M. Chem. Rev. 2015, 115, 10261−10306.
https://doi.org/10.1021/acs.chemrev.5b00244

14. Ackroyd R., Kelly C., Brown N., Reed M. Photochem. Photobiol. 2001, 74, 656–669.
https://doi.org/10.1562/0031-8655(2001)074<0656:THOPAP>2.0.CO;2

15. Dougherty T.J., Gomer C.J., Henderson B.W., Jori G., Kessel D., Korbelik M., Moan J., Peng Q. J. Natl. Cancer Inst. 1998, 90, 889–905.
https://doi.org/10.1093/jnci/90.12.889

16. Sternberg E.T., Dolphin D., Brückner C. Tetrahedron 1998, 54, 4151–4202.
https://doi.org/10.1016/S0040-4020(98)00015-5

17. Crini G. Chem. Rev. 2014, 114, 10940–10975.
https://doi.org/10.1021/cr500081p

18. Simões S., Rey-Rico A., Concheiroc A., Alvarez-Lorenzo C. Chem. Commun. 2015, 51, 6275–6289.
https://doi.org/10.1039/C4CC10388B

19. Kejík Z., Bříza T., Králová J., Poučková P., Král A., Martásek P., Král V. Bioorg. Med. Chem. Lett. 2011, 21, 5514–5520.
https://doi.org/10.1016/j.bmcl.2011.06.101

20. Králová J., Kejík Z., Bříza T., Poučková P., Král A., Martásek P., Král V. J. Med. Chem. 2010, 53, 128–138.
https://doi.org/10.1021/jm9007278

21. Li J., Loh X. Advanced Drug Delivery Reviews 2008, 60, 1000–1017.
https://doi.org/10.1016/j.addr.2008.02.011

22. Nishiyabu R., Kano K. Eur. J. Org. Chem. 2004, 4985–4988.
https://doi.org/10.1002/ejoc.200400309

23. Kano K., Nishiyabu R., Yamazaki T., Yamazaki I. J. Am. Chem. Soc. 2003, 125, 10625–10634.
https://doi.org/10.1021/ja035055q

24. Lang K., Král V., Kapusta P., Kubát P., Vašek P. Tetrahedron Lett. 2002, 43, 4919–4922.
https://doi.org/10.1016/S0040-4039(02)00954-1

25. Breslow R., Yang J., Yan J. Tetrahedron 2002, 58, 653–659.
https://doi.org/10.1016/S0040-4020(01)01098-5

26. Breslow R., Yan J., Belvedere S. Tetrahedron Lett. 2002, 43, 363–365.
https://doi.org/10.1016/S0040-4039(01)02142-6

27. French R., Holzer P., Leuenberger M., Nold M., Woggon W-D. J. Inorg. Biochem. 2002, 88, 295–304.
https://doi.org/10.1016/S0162-0134(01)00363-4

28. French R., Holzer P., Leuenberger M., Woggon W-D. Angew. Chem. Int. Ed. 2000, 39(7), 1267–1269.
https://doi.org/10.1002/(SICI)1521-3773(20000403)39:7<1267::AID-ANIE1267>3.0.CO;2-7

29. Carofiglio T., Fornasier R., Lucchini V., Tonellato U. J. Org. Chem. 2000, 65, 9013–9021.
https://doi.org/10.1021/jo0010678

30. Chen W-H., Yan J-M., Tagashira Yu., Yamaguchi M., Fujita K. Tetrahedron Lett. 1999, 40, 891–894.
https://doi.org/10.1016/S0040-4039(98)02475-7

31. Breslow R., Zhang X., Xu R., Maletic M., Merger R. J. Am. Chem. Soc. 1996, 118, 11678–11679.
https://doi.org/10.1021/ja962295f

32. Kuroda Ya., Hiroshige T., Sera T., Ogoshi H. Carbohydr. Res. 1989, 192, 347–350.
https://doi.org/10.1016/0008-6215(89)85193-6

33. Nango M., Higuchi M., Gondo H., Hara M. J. Chem. Soc., Chem. Commun. 1989, 1550–1553.
https://doi.org/10.1039/C39890001550

34. Gonzales M., Weedon A. Can. J. Chem. 1985, 63, 602–608.
https://doi.org/10.1139/v85-099

35. Alessio E., Balducci G., Calligaris M., Costa G., Attia W., Mestroni G. Inorg. Chem. 1991, 30, 609–618.
https://doi.org/10.1021/ic00004a005

36. Page S. Educ. Chem. 2012, 1, 26–29.
https://doi.org/10.5923/j.chemistry.20110102.05

37. Ivanova Yu.B., Razgonyaev O.V., Semeikin A.S., Mamardashvili N.Zh. Russ. J. Phys. Chem. A. 2016, 90, 994–999.

https://doi.org/10.1134/S0036024416050174

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Synthesis of Water-Soluble Non-Aggregated Porphyrin-β-Cyclodextrin Tetraconjugate

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