The Interaction of Deuteroporphyrin IX and its Dimethyl Ester with Oligoethylene Glycols

T. K. Rocheva,^@D. V. Belykh

Institute of Chemistry, Komi Scientific Center, Ural Division, Russian Academy of Sciences, 167000 Syktyvkar, Russia

^@Corresponding author E-mail: tatyanrocheva@yandex.ru

The esterification of carboxyl groups of deuteroporphyrin IX and transesterification of ester groups of dimethyl ester of deuteroporphyrin IX with di-, tetra-, hexaethylene glycols were studied. It is shown, that depending on the oligoethylene glycol and the reaction conditions used, both derivatives with two polyester moieties in the molecule (one for each propionate substituent) and derivatives with one polyester moiety linking the propionate substituents of porphyrin can be obtained.

References:

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1. Porphyrins: Structure, Properties and Synthesis (Enikolopyan N.S., Ed.) Moscow: Nauka,1985. 334 p. (in Russ.). [Порфирины: структура, свойства, синтез (Ениколопян Н.С., ред.) М.: Наука, 1985. 334 c.]

2. Kepczynski M., Pandian R.P., Smith K.M., Ehrenberg B. J. Photochem. Photobiol. 2002, 76(2), 127-134.
https://doi.org/10.1562/0031-8655(2002)076<0127:DLBCOP>2.0.CO;2

3. Uchoa A.F., Oliveira C.S., Baptista M.S. J. Porphyrins Phthalocyanines 2010, 14, 832-845.
https://doi.org/10.1142/S108842461000263X

4. Fakhar-e-Alam M., Kishwar S., Khan Y., Siddique M., Atif M., Nur O., Willander M. Laser Phys. 2011, 21(11), 1978-1988.
https://doi.org/10.1134/S1054660X1119011X

5. Kishwar S., Asif M.H., Nur O., Willander M., Larsson P.-O. Nanoscale Res. Lett. 2010, 5, 1669-1674.
https://doi.org/10.1007/s11671-010-9693-z

6. Yee K.K.L., Soo K.C., Bay B.H., Olivo M. Photochem. Photobiol. 2002, 76(6), 678-682.
https://doi.org/10.1562/0031-8655(2002)076<0678:ACOPIA>2.0.CO;2

7. Pandey R.K., Smith K. M., Dougherty T.J. J. Med. Chem. 1990, 33, 2032-2038.
https://doi.org/10.1021/jm00169a038

8. Kustov A.V., Kruchin S.O., Smirnova N.L., Berezin D.B. Macroheterocycles 2016, 9, 373-377.
https://doi.org/10.6060/mhc160647k

9. Brunner H., Schellerer K.-M., Treittinger B. Inorg. Chim. Acta 1997, 264 (1-2), 67-79.
https://doi.org/10.1016/S0020-1693(97)05593-X

10. Brunner H., Arndt M.R., Treittinger B. Inorg. Chim. Acta 2004, 357, 1649-1669.
https://doi.org/10.1016/S0020-1693(03)00479-1

11. Brunner H., Obermeier H., Szeimies R.-M. Chem. Ber. 1995, 128, 173-181.
https://doi.org/10.1002/cber.19951280215

12. Imai K., Aimoto T., Sato M., Kimura R. Chem. Pharm. Bull. 1990, 38, 258-260.
https://doi.org/10.1248/cpb.38.258

13. Cahyana A.H., Shuto Y., Kinoshita Y. Biosci. Biotechnol. Biochem. 1993, 57, 680-681.
https://doi.org/10.1271/bbb.57.680

14. Tsolekile N., Nelana S., Oluwafemi O.S. Moleculs 2019, 24, 2669.
https://doi.org/10.3390/molecules24142669

15. Cahyana A.H., Shuto Y., Kinoshita Y. Biosci. Biotech. Biochern. 1992, 56, 1533-1535.
https://doi.org/10.1271/bbb.56.1533

16. Hu B., Zhou W., Ma D., Liu Z. Catal. Commun. 2008, 10, 83-85.
https://doi.org/10.1016/j.catcom.2008.07.044

17. Fu L., Simakova A., Park S., Wang Yi, Fantin M., Matyjaszewski K. Molecules 2019, 24, 3969.
https://doi.org/10.3390/molecules24213969

18. Sun C., Hu B., Liu Z. Heteroat. Chem. 2012, 23(3), 295-303.
https://doi.org/10.1002/hc.21017

19. Sun C.G., Hu B.C., Zhou W.Y., Xu S.C., Deng Q.Z., Liu Z.L. Chin. Chem. Lett. 2011, 18, 527-530.
https://doi.org/10.1016/j.cclet.2010.12.011

20. Hu B., Sun C., Deng Q., Liu Z. J. Incl. Phenom. Macrocycl. Chem. 2013, 76, 345-352.
https://doi.org/10.1007/s10847-012-0205-x

21. Kumadaki I., Ando A., Omote M. J. Fluorine Chem. 2001, 109, 67-81.
https://doi.org/10.1016/S0022-1139(01)00381-5

22. Yap B.C.-M., Simpkins G.L., Collyer C.A., Hunter N., Crossley M.J. Org. Biomol. Chem. 2009, 7, 2855-2863.
https://doi.org/10.1039/b904340c

23. Luciano M., Brückner C. Molecules 2017, 22, 980.
https://doi.org/10.3390/molecules22060980

24. Hitomi Y., Ekawa T., Kodera M. Chem. Lett. 2014, 43, 732-734.
https://doi.org/10.1246/cl.140029

25. Ohashi N., Nomura A., Kodera M., Hitomi Y. Chem. Lett. 2017, 46, 1754-1756.
https://doi.org/10.1246/cl.170821

26. Belykh D.V., Startseva O.M., Patov S.A. Macroheterocycles 2014, 7, 401-413.
https://doi.org/10.6060/mhc140500b

27. Lashin V., Koso T. V., Stranius K., Muuronen M., Heikkinen S., Kavakka J., Tkachenko N.V., Helaja J. RSC Adv. 2013, 3, 11485-11488.
https://doi.org/10.1039/c3ra41741g

28. Gunter M.J., Johnston M.R., Skelton B.W., White A.H. J. Chem. Soc. Perkin Trans. 1994, 1, 1009-1018.
https://doi.org/10.1039/P19940001009

29. Sun C., Hu B., Zhao D., Liu Z. Dyes Pigm. 2013, 96, 130-137.
https://doi.org/10.1016/j.dyepig.2012.07.008

30. Blagodarov S.V., Zheltukhina G.A., Urban A. S., Shishkina E. E., Nebolsin V. E. Mendeleev Commun. 2019, 29, 209-211.
https://doi.org/10.1016/j.mencom.2019.03.032

31. Koifman O.I., Ageeva T.A., Beletskaya I.P., Averin A.D., Yakushev A.A., Tomilova L.G., Dubinina T.V. et al. Macroheterocycles 2020, 13, 311-467.
https://doi.org/10.6060/mhc200814k

32. Belykh D.V., Zainullina E.N., Startseva O.M. Macroheterocycles 2020, 13, 260-268.
https://doi.org/10.6060/mhc200607b

33. Hu B., Zhou W., Tang Y., Huang C., Liu Z. Ultrasonics Sonochemistry 2010, 17, 288-291.
https://doi.org/10.1016/j.ultsonch.2009.09.008

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The Interaction of Deuteroporphyrin IX and its Dimethyl Ester with Oligoethylene Glycols

References: