Solid State Physicochemical Study of Chlorophyll a Derivatives and Their Glycol Conjugates

Dmitry B. Berezin,^a@ Dmitry V. Belykh,^b Olga M. Startseva,^b Nikolay G. Manin,^c Mikhail A. Krest’yaninov,^c and Andrey V. Kustov^c

^aIvanovo State University of Chemistry and Technology, Institute of Macroheterocyclic Compounds, 153000 Ivanovo, Russia

^bInstitute of Chemistry of Komi Scientific Center of Ural Division of Russian Academy of Sciences, 167982 Syktyvkar, Russia

^cKrestov Institute of Solution Chemistry of Russian Academy of Sciences, 153045 Ivanovo, Russia

^@Corresponding author E-mail: berezin@isuct.ru

DOI: 10.6060/mhc160963c

Macroheterocycles 2017 10(1) 72-76

This study focuses on solid state physico-chemical properties of recently synthesized potential sensitizers for photodynamic therapy developed on a chlorophyll a platform. Pheophorbide a and chlorin e₆ derivatives as well as two their glycol conjugates have been synthesized and identified via UV-Vis, NMR and mass spectra. The behavior of photosensitizers (PSs) in a solid state has been studied. They were found to be stable in inert atmosphere at least up to 520 K, the thermal stability decreases from phlorin to chlorin molecules and, especially, after their glycol substitution. The thermodestruction of macroheterocycles takes place after their melting. Both glycol conjugates form intramolecular H-bonds in two different conformations, what is confirmed by phase transitions on DSC curves and quantum-chemical analysis data.

References:

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1. Bonnett R. Chemical Aspects of Photodynamic Therapy. London: VHC Publ., 2000. 285 p.

2. Mironov A.F. Modern State of Photosensitizers Chemistry on the Basis of Porphyrins and Relative Compounds. In: Advances in Porphyrin Chemistry, Vol. 4 (Golubchikov O.A., Ed.). St-Petersburg: St-Petersburg State University Edition, 2004. pp. 271–292 (in Russ.)

3. Brandis A.S., Salomon Y.; Schetz, A. Chlorophyll Sensitizers in Photodynamic Therapy; In Chlorophylls and Bacteriochlorophylls: Biochemistry, Biophysics, Functions and Application; Grimm, B.; Porra, R.J.; Rüdiger, W.; Scheer, H., Eds., Springer: Berlin, Germany, 2006, p. 461-483.
https://doi.org/10.1007/1-4020-4516-6_32

4. In: Handbook of Porphyrin Science, Vol. 3, Phototherapy, Radioimmunotherapy and Imaging (Kadish K.M., Smith K.M., Guilard R., Eds.) New York: World Sc. Publ. Ltd., 2010, 448 p.

5. Huang L., Dai T., Hamblin M.R. Antimicrobial Photodynamic Inactivation and Photodynamic Therapy for Infections. In: Methods in Molecular Biology. Vol. 635. Photodynamic Therapy. Methods and Protocols (Gomer C.J., Ed.). New York: Springer, 2010, pp. 155–173.

6. Celli J.P., Spring B.Q., Rizvi I., Evans C.L., Samkoe K.S., Verma S., Pogue B.W., Hasan T. Chem. Rev. 2010, 110, 2795-2838.
https://doi.org/10.1021/cr900300p

7. Agostinis P., Berg K., Cengel K.A., Foster T.H., Girotti A.W., Gollnick S.O., Hahn S.T., Hamblin M.R., Juzeniene A., Kessel, D., et al. Photodynamic Therapy of Cancer: an Update. CA Cancer J. Clin. 2011, 61, 250-281.
https://doi.org/10.3322/caac.20114

8. Vakrat-Haglili Y., Weiner L., Brumfeld V., Brandis A., Salomon Y., Mcllroy B., Wilson B.C., Pawlak A., Rozanowska M., Sarna T., Scherz J. Am. Chem. Soc. 2005, 127, 17, 6487-6497.
https://doi.org/10.1021/ja046210j

9. Kustov A.V., Belykh D.V., Startseva O.M., Kruchin S.O., Venediktov E.A., Berezin D.B. Pharm. Anal. Acta 2016, 7, 5, 1000480.
http://dx.doi.org/10.4172/2153-2435.1000480

10. Krasnovskiy A.A., Jr. Singlet Oxygen and Mechanism of Photodynamic Action of Porphyrins. In: Advances in Porphyrin Chemistry, Vol. 3 (Golubchikov O.A., Ed.). St-Petersburg: St-Petersburg State University Edition, 2001, 191–216 (in Russ.)

11. Vermathen M., Marzorati M., Bigler P. J. Phys. Chem. B 2013, 117, 6990-7001.
https://doi.org/10.1021/jp403331n

12. Karimov D.R., Makarov V.V., Kruchin S.O., Berezin D.B., Smirnova N.L., Berezin M.B., Zheltova E.N., Strel'nikov A.I., Kustov A.V. Khimija Rastitel'nogo Syr'ja 2014, 17, 189-196 (in Russ.)

13. Koifman O.I., Ponomarev G.V. A Method for Obtaining of Methylpheophorbide a. Pus. Patent. N 2012107000/15. Published 20.08.2013 № 23 (in Russ.).

14. Startseva O.M., Belykh D.V., Shegera V.M., Tulaeva L.A. Butlerov Commun. 2014, 38, 43-48.

15. Frisch M.J., Trucks G.W., Schlegel H.B., et al., GAUSSIAN'09, Revision D.01, Gaussian, Inc., Wallingford CT, 2009.

16. Ditchfield R., Hehre W.J., Pople J.A. J. Chem. Phys. 1971, 54, 2, 724-728.
https://doi.org/10.1063/1.1674902

17. Weinhold F. J. Mol. Struct.: THEOCHEM 1997, 398-399, 181-197.
https://doi.org/10.1016/S0166-1280(96)04936-6

18. Glendening E.D., Reed A.E., Weinhold F. NBO 3.0 Program Manual (Univ. Wisconsin, Madison, 1998).
http://nbo.chem.wisc.edu/nboman.pdf

19. Alabugin I.V., Manoharan M., Peabody S., Weinhold F. J. Am. Chem. Soc. 2003, 125, 19, 5973-5987.
https://doi.org/10.1021/ja034656e

20. Berezin D.B., Krest'yaninov M.A. J. Struct. Chem. 2014, 55, 5, 822-830.
https://doi.org/10.1134/S0022476614050047

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Solid State Physicochemical Study of Chlorophyll a Derivatives and Their Glycol Conjugates

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