Solubility and Thermodynamics of Dissolution of 13,17-Di-N-(2-aminoethyl)amide of Deuteroporphyrin-IX in Aqueous HCl and Tetraoxalate Buffer at 288-328 K

Andrey V. Kustov,^a,b@ Sergey O. Kruchin,^a Nataliya L. Smirnova,^aand Dmitriy B. Berezin^c

^aG.A. Krestov Institute of Solution Chemistry, Russian Academy of Sciences, 153045 Ivanovo, Russian Federation

^bIvanovo State Medical Academy, 153012 Ivanovo, Russian Federation

^cResearch Institute of Macroheretocyclic Compounds, Ivanovo State University of Chemistry and Technology, 153000 Ivanovo, Russian Federation

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

DOI: 10.6060/mhc160647k

Macroheterocycles 2016 9(4) 373-377

This paper describes the thermodynamic study of aqueous solutions of 13,17-di-N-(2-aminoethyl)amide of deuteroporphyrin-IX (DDA) which is considered as a potential red natural dye and a perspective substrate for creating new water-soluble sensitizers for photodynamic therapy (PDT). Solubility of the macrocycle in highly aqueous solutions of hydrochloric acid and standard tetraoxalate buffer has been determined in the temperature range from T=288 K to T=328 K. Solubility values are found to decrease with the temperature in both cases due to the weakening of porphyrin basicity at elevated temperatures. Free energies, enthalpies and entropies of solution have been computed from solubility data via the Clark and Glue equation. Enthalpies and entropies of solution are negative and constant for both cases in the temperature range studied. The negative enthalpic term favors DDA dissolution, but large and negative entropies of solution induce the overall unfavorable free energy change.

References:

Click here to expand or collapse this section

1. Bonnett R. Chemical Aspects of Photodynamic Therapy. Amsterdam: Gordon and Reach Science Publishers, 2000.

2. Agostinis P., Berg K., Cengel K.A., Foster T.H., Girotti A.W. et al. CA Cancer J. Clin. 2011, 61, 250-281.
http://dx.doi.org/10.3322/caac.20114

3. Chou J.-H., Kosal M.E., Nalwa H.S., Rakow N.A., Suslick K.S. Applications of Porphyrins and Metalloporphyrins to Materials Chemistry. New York: Academic Press, 2000.

4. Mamardashvili G.M., Berezin B.D. Thermodynamics of Porphyrin Dissolution. In: Advances in Porphyrin Chemistry, Vol. 3 (Golubchikov O.A., Ed.). St.-Petersburg: NII Khimii SPbGU, 2001. p. 130-149 (in Russ.)

5. Ghani F., Kristen J., Riegler H. J. Chem. Eng. Data 2012, 57, 439−449.
http://dx.doi.org/10.1021/je2010215

6. Chunlin L., Wang Q., Shen B., Xiong Zh., Chen C. J. Chem. Eng. Data 2015, 60, 925–931.
http://dx.doi.org/10.1021/je501002a

7. Berezin D.B., Karimov D.R., Venediktov E.A., Kustov A.V., Makarov V.V., Romanenko Yu.V. Macroheterocycles 2015, 8, 384-388.
http://dx.doi.org/10.6060/mhc151088b

8. Kustov A.V., Smirnova N.L., Berezin D.B., Berezin M.B. J. Chem. Thermodyn. 2015, 83, 104-109.
http://dx.doi.org/10.1016/j.jct.2014.12.013

9. Kustov A.V., Smirnova N.L., Berezin D.B., Berezin M.B. J. Chem. Thermodyn. 2015, 89, 123-126.
http://dx.doi.org/10.1016/j.jct.2015.05.016

10. Kustov A.V., Smirnova N.L. J. Chem. Eng. Data 2010, 55, 3055-3058.
http://dx.doi.org/10.1021/je9010689

11. Berezin D.B. Macrocyclic Effect and Structural Chemistry of Porphyrins. Moscow: Krasand, 2010. 421 p. (in Russ.).

12. Clarke E.C.W., Glew D.N. Trans. Faraday Soc. 1966, 62, 539-547.
http://dx.doi.org/10.1039/tf9666200539

Attachment	Size
mhc160647k.pdf	657.83 KB

Журнал "Макрогетероциклы"

Navigation

Languages

News

Search

Solubility and Thermodynamics of Dissolution of 13,17-Di-N-(2-aminoethyl)amide of Deuteroporphyrin-IX in Aqueous HCl and Tetraoxalate Buffer at 288-328 K

References: