On the possibility of theoretical prediction of benzanthrone dye lipophilicity
Keywords:
benzanthrone dyes, lipophilicity, correlation coefficient
Abstract
The present study was aimed at comparing the prediction power of several computational methods in
evaluating the lipophilicity (logP) of a series of newly synthesized benzanthrone derivatives, tentatively
divided into three groups: 1) aminobenzanthrones, 2) amidinobenzanthrones, and 3) bromine-containing
amidinobenzanthrones. Experimental partition coefficients (log p K ) were derived from fluorescence
titration experiments. Analysis of the correlation coefficients between the experimental and theoretically
predicted lipophilicity values showed that generally log p K rather poorly correlates with logP of the
examined compounds. The best agreement between calculated and experimental lipophilicities was
observed for KOWWIN (group1), XLOGP3 (group2) and ALOGPs (group 3) methods, pointing to the
importance of different structure- and property-based factors in determining the dye lipophilicity. It is
concluded that computed logP, with careful choice of calculation method, can be effectively used for
prediction of membrane partition properties of benzanthrones, in combination with other molecular and
quantum-chemical descriptors.
Downloads
Download data is not yet available.
References
1. Refat M. S. Spectroscopic and physicochemical studies of charge-transfer complexes of some benzanthrone derivatives “luminophore dyes” with iodine as acceptor / M. S. Refat, S. M. Aqeel, I. Grabchev // Canad. J. Analyt. Sci. Spectr. − 2004. − V. 49. − P. 258–265.
2. On the synthesis and properties of some copolymers of some benzanthrone dye derivatives with methylmethacrylate / T. Konstantinova, Hr. Konstantinov, T. Kaneva, A. Spirieva // Polym. Degrad. Stab. − 1998. − V. 62. − P. 323–326.
3. Carlini F. New daylight fluorescent pigments / F. Carlini, C. Paffoni, G. Boffa // Dye. Pigment. − 1982. − V. 3. − P. 59–69.
4. Grabchev I. Functional properties of azomethine substituted benzanthrone dyes for use in nematic liquid crystals / I. Grabchev, V. Bojinov, I. Moneva // J. Mol. Str. − 1998. − V. 471. − P. 19–25.
5. DNA binding studies of a solvatochromic fluorescence probe 3-methoxybenzanthrone / X. Yang, W.-H. Liu, W.-J. Jin [et al.] // Spectrochim. Acta A. − 1999. − V. 55. − P. 2719–2727.
6. New fluorescent probes for detection and characterization of amyloid fibrils / G. P. Gorbenko, V. M. Trusova, E. Kirilova [et al.] // Chem. Phys. Lett. – 2010. – V. 495. − P. 275–279.
7. Novel benzanthrone aminoderivatives for membrane studies / V. Trusova, E. Kirilova, I. Kalnina [et al.] // J. Fluoresc. − 2012. − V. 22. − P. 953–959.
8. Immune state of patients with different pathologies monitored by fluorescent probe 3-aminobenzanthrone derivative / I. Kalnina, R. Bruvere, T. Zvagule [et al.] // Proc. Latv. Acad. Sci. − 2006. − V. 60. − P. 113–120.
9. Fluorescent probe ABM for screening gastrointestinal patient’s immune state / I. Kalnina, L. Klimkane, E. Kirilova [et al.] // J. Fluoresc. − 2007. − V. 17. − P. 619–625.
10. Comparative effect of benzanthrone and 3-bromobenzanthrone on hepatic xenobiotic metabolism and anti-oxidative defense system in guinea pigs / R. P. Singh, R. Khanna, J. l. Kaw [et al.] // Mol. Toxicol. − 2003. − V. 77. − P. 94–99.
11. Singh G. B. Recent studies on the toxicity of benzanthrone / G. B. Singh, S. K. Khanna, M. Das // J. Sci. Ind. US Res. − 1990. − V. 49. − P. 288–296.
12. Leach A. R. An introduction to chemoinformatics / A. R. Leach, V. J. Gillet // Springer. 2007.
13. Gonta S. Fluorescent substituted amidines of benzanthrone: synthesis, spectroscopy and quantum chemical calculations / S. Gonta, M. Utinans, G. Kirilov [et al.] // Spectrochim. Acta A. − 2013. − V. 101. − P. 325–334.
14. Mui B. Extrusion technique to generate liposomes of defined size / B. Mui, L. Chow, M. J. Hope // Meth. Enzymol. − 2003. − V. 367. − P. 3–14.
15. Simple method of calculating octanol/water partition coefficient / I. Moriguchi, S. Hirono, Q. Liu [et al.] // Chem. Pharm. Bull. − 1992. − V. 40. − P. 127–130.
16. Atomic physicochemical parameters for three dimensional structure directed quantitative structure-activity relationships. 4. Additional parameters for hydrophobic and dispersive interactions and their application for an automated superposition of certain naturally occurring nucleoside antibiotics / V. N. Viswanadhan, A. K. Ghose, G. R. Revankar, R. K. Robins // J. Chem. Inf. Comput. Sci. − 1989. − V. 29. − P. 163–172.
17. Tetko I. V. Computing chemistry on the web / I. V. Tetko // Drug Discov. Today. − 2005. − V. 10. − P. 1497–1500.
18. Tetko I. Application of associative neural networks for prediction of lipophilicity in ALOGPS 2.1 program / I. Tetko, V. Tanchuk // J. Chem. Inf. Comput. Sci. − 2002. − V. 42. − P. 1136–1145.
19. Santos N. Quantifying molecular partition into model systems of biomembranes: an emphasis on optical spectroscopic methods / N. Santos, M. Prieto, M. Castanho // Biochim. Biophys. Acta. − 2003. − V. 1612. − P. 123–135.
20. Ivkov V. Dynamic structure of lipid bilayer / V. Ivkov, G. Berestovsky // Nauka, Moscow. 1981.
21. Spectroscopic study of benzanthrone 3-N-derivatives as new hydrophobic fluorescent probes for biomolecules / E. Kirilova, I. Kalnina, G. Kirilov, I. Meirovics // J. Fluoresc. − 2008. − V. 18. − P. 645–648.
22. Mannhold R. Calculation procedures for molecular lipophilicity: a comparative study / R. Mannhold, K. Dross // Quant. Struct.-Act. Relat. − 1996. − V. 15. − P. 403–409.
23. Determination of lipophilicity for antitumor acridinone derivatives supported by gradient high-performance liquid chromatography method / M. Koba, M. Belca, T. Ciesielski, T. Baczec // Cent. Eur. J. Chem. − 2012. − V. 10. − P. 216–223.
24. Lipophilicity in molecular modeling / B. Testa, P. Carrupt, P. Gaillard [et al.] // Pharm. Research. − 1996. − V. 13. − P. 335–343.
2. On the synthesis and properties of some copolymers of some benzanthrone dye derivatives with methylmethacrylate / T. Konstantinova, Hr. Konstantinov, T. Kaneva, A. Spirieva // Polym. Degrad. Stab. − 1998. − V. 62. − P. 323–326.
3. Carlini F. New daylight fluorescent pigments / F. Carlini, C. Paffoni, G. Boffa // Dye. Pigment. − 1982. − V. 3. − P. 59–69.
4. Grabchev I. Functional properties of azomethine substituted benzanthrone dyes for use in nematic liquid crystals / I. Grabchev, V. Bojinov, I. Moneva // J. Mol. Str. − 1998. − V. 471. − P. 19–25.
5. DNA binding studies of a solvatochromic fluorescence probe 3-methoxybenzanthrone / X. Yang, W.-H. Liu, W.-J. Jin [et al.] // Spectrochim. Acta A. − 1999. − V. 55. − P. 2719–2727.
6. New fluorescent probes for detection and characterization of amyloid fibrils / G. P. Gorbenko, V. M. Trusova, E. Kirilova [et al.] // Chem. Phys. Lett. – 2010. – V. 495. − P. 275–279.
7. Novel benzanthrone aminoderivatives for membrane studies / V. Trusova, E. Kirilova, I. Kalnina [et al.] // J. Fluoresc. − 2012. − V. 22. − P. 953–959.
8. Immune state of patients with different pathologies monitored by fluorescent probe 3-aminobenzanthrone derivative / I. Kalnina, R. Bruvere, T. Zvagule [et al.] // Proc. Latv. Acad. Sci. − 2006. − V. 60. − P. 113–120.
9. Fluorescent probe ABM for screening gastrointestinal patient’s immune state / I. Kalnina, L. Klimkane, E. Kirilova [et al.] // J. Fluoresc. − 2007. − V. 17. − P. 619–625.
10. Comparative effect of benzanthrone and 3-bromobenzanthrone on hepatic xenobiotic metabolism and anti-oxidative defense system in guinea pigs / R. P. Singh, R. Khanna, J. l. Kaw [et al.] // Mol. Toxicol. − 2003. − V. 77. − P. 94–99.
11. Singh G. B. Recent studies on the toxicity of benzanthrone / G. B. Singh, S. K. Khanna, M. Das // J. Sci. Ind. US Res. − 1990. − V. 49. − P. 288–296.
12. Leach A. R. An introduction to chemoinformatics / A. R. Leach, V. J. Gillet // Springer. 2007.
13. Gonta S. Fluorescent substituted amidines of benzanthrone: synthesis, spectroscopy and quantum chemical calculations / S. Gonta, M. Utinans, G. Kirilov [et al.] // Spectrochim. Acta A. − 2013. − V. 101. − P. 325–334.
14. Mui B. Extrusion technique to generate liposomes of defined size / B. Mui, L. Chow, M. J. Hope // Meth. Enzymol. − 2003. − V. 367. − P. 3–14.
15. Simple method of calculating octanol/water partition coefficient / I. Moriguchi, S. Hirono, Q. Liu [et al.] // Chem. Pharm. Bull. − 1992. − V. 40. − P. 127–130.
16. Atomic physicochemical parameters for three dimensional structure directed quantitative structure-activity relationships. 4. Additional parameters for hydrophobic and dispersive interactions and their application for an automated superposition of certain naturally occurring nucleoside antibiotics / V. N. Viswanadhan, A. K. Ghose, G. R. Revankar, R. K. Robins // J. Chem. Inf. Comput. Sci. − 1989. − V. 29. − P. 163–172.
17. Tetko I. V. Computing chemistry on the web / I. V. Tetko // Drug Discov. Today. − 2005. − V. 10. − P. 1497–1500.
18. Tetko I. Application of associative neural networks for prediction of lipophilicity in ALOGPS 2.1 program / I. Tetko, V. Tanchuk // J. Chem. Inf. Comput. Sci. − 2002. − V. 42. − P. 1136–1145.
19. Santos N. Quantifying molecular partition into model systems of biomembranes: an emphasis on optical spectroscopic methods / N. Santos, M. Prieto, M. Castanho // Biochim. Biophys. Acta. − 2003. − V. 1612. − P. 123–135.
20. Ivkov V. Dynamic structure of lipid bilayer / V. Ivkov, G. Berestovsky // Nauka, Moscow. 1981.
21. Spectroscopic study of benzanthrone 3-N-derivatives as new hydrophobic fluorescent probes for biomolecules / E. Kirilova, I. Kalnina, G. Kirilov, I. Meirovics // J. Fluoresc. − 2008. − V. 18. − P. 645–648.
22. Mannhold R. Calculation procedures for molecular lipophilicity: a comparative study / R. Mannhold, K. Dross // Quant. Struct.-Act. Relat. − 1996. − V. 15. − P. 403–409.
23. Determination of lipophilicity for antitumor acridinone derivatives supported by gradient high-performance liquid chromatography method / M. Koba, M. Belca, T. Ciesielski, T. Baczec // Cent. Eur. J. Chem. − 2012. − V. 10. − P. 216–223.
24. Lipophilicity in molecular modeling / B. Testa, P. Carrupt, P. Gaillard [et al.] // Pharm. Research. − 1996. − V. 13. − P. 335–343.
Cited
How to Cite
Zhytniakivska, O. A., Girych, M. S., Gorbenko, G. P., Kirilova, E. M., Kirilov, G. K., & Kinnunen, P. (1). On the possibility of theoretical prediction of benzanthrone dye lipophilicity. Biophysical Bulletin, 2(30). Retrieved from https://periodicals.karazin.ua/biophysvisnyk/article/view/1594
Section
Molecular biophysics
Authors who publish with this journal agree to the following terms:
- Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
- Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.
- Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (See The Effect of Open Access).
