A COMPARATIVE STUDY OF ANTIOXIDANT PROPERTIES OF 2-[SUBSTITUTED ARYLIDEAMINO]-1, 3, 4-THIADIAZINO [6, 5B] INDOLES AND THEIR INCLUSION COMPLEXES WITH Β-CYCLODEXTRIN
Abstract
Inclusion complexes of 2-[Arylidenamino]-1, 3, 4-thiadiazino [6, 5b] indoles have been prepared with β-Cyclodextrin for increasing solubility in polar medium. The formation of inclusion complexes has been confirmed from the study of changes in physical and spectral properties of the compounds. The determination of thermodynamic stability constant and other thermodynamic properties indicates that the inclusion complexes are comparatively stable and their formation is thermodynamically allowed. Finally, the compounds and their inclusion complexes are screened for antioxidant activities and it is found that the inclusion complex formation increases the antioxidant activities significantly.
Keywords:
Substituted indole, β Cyclodextrin, Inclusion complex, Thermodynamic stability, Antioxidant activityDOI
https://doi.org/10.25004/IJPSDR.2012.040304References
1. Vandemiale G, Grattaglino I, Altomare E. An update on the role of free radicals and antioxidant defence in human disease. International Journal of Clinical Laboratory Research 1999; 29: 49-55.
2. Valko M, Rhodes CJ, Moncol J, Izakovic M, Mazur M. Free radicals, metals and antioxidant stress induced cancer. Chemical Biology Interactive 2006; 160: 1-40.
3. Chen G, Wang Y, Hao X, Mu S, Sun Q. Simple Isatin derivatives as free radical scavengers: Synthesis, biological evaluation and structure-activity relationship. Chemistry Central Journal 2011; 5: 1-5.
4. Bankson DD, Kestin M, Rifal N. Role of free radicals in cancer and atherosclerosis. Clinical Lab. Med. 1993; 13: 463-480.
5. Prakash A, Rigelhof F, Miller E. Antioxidant Activity. Cereals Foods World 2000; 45(2): 59-63.
6. Miller HE, Rigelhof F, Marquart L, Prakash A, Kanter M. Antioxidant content of whole grain breakfast cereals, fruits and vegetables. Journal of American Coll. Nutr. 2000; 19(3): 312S-319S.
7. Patil R, Biradar JS. Synthesis and pharmacological evaluation of substituted- 2-triazolo (3, 4-b) (1, 3, 4)-thiadiazoles. Indian Journal of pharmaceutical Science 2001; 63(4): 299-305.
8. Holla BS, Udupa KV. Synthesis and antibacterial activity of nitrofurfuraldehyde as-triazino [5, 6-b] indol-3-ylhydrazones. Journal of Indian Chemical Society 1988; 65(7): 524-525.
9. Panwar H, Verma RS, Srivastava V, Kumar A. Synthesis of some substituted azetidinonyl and thiazolidinonyl-1, 3, 4-thiadiazino[6, 5-b] indoles as prospective antimicrobial agents. Indian Journal of Chemistry 2006; 45B: 2099-2104.
10. Shobha SR, Agaiah B , Sarangpani M. Antioxidant and DNA binding study of 3, 3’-(5, 5’-Methylene)Bis(3-Mercapto-4H-1, 2, 4-Triazol-5, 4-Diyl)Bis(Azan-1-yl-1-ylidene)Diindoline-2-ones. Int. J. Pharm. Technol. 2011; 2: 366-374.
11. Pose-Vilarnovo B, Predomo-Lopez I, Echezarreta-Lopez M. Improvement of water solubility of sulfamethizole through its complexation with β- and hydroxypropyl-β-cyclodextrin: Characterization of the interaction in solution and in solid state. Journal of Pharmaceutical Science 2001; 13(3) : 325-331
12. Belikov VG, Komapantseva EV. Khimiko Farmatsevticheskii Zhurnal. 1990; 24(7): 19.
13. Yano H, Hiramaya F, Arima H. Preparation of prednisolone-appended α-, β- and γ-cyclodextrins: Substitution at secondary hydroxyl groups and <I>in vitro</I> hydrolysis behavior. Journal of. Pharmaceutical. Science 2001; 90(4): 493-503.
14. Panda S, Tripathy JK. Studies on inclusion complexes of substituted indole derivatives with activating and deactivating group. J. Chem. Pharm Res. 2010; 2: 722-732.
15. Panda S, Tripathy JK. Thermodynamic, spectral and antimicrobial properties of inclusion complex of 2-[Benzylidenamino]-1,3,4-thiadiazino[6,5b] indole and 2-[Furfurlidenamino]-1,3,4-thiadiazino[6,5b] indole –a comparative study. Research Journal of Pharmaceutical Technology 2011; 4: 1693-1698.
16. Tripathy JK, Panda S. Thermodynamic and spectral studies of inclusion complexes of substituted indole derivatives with β-cyclodextrin. Asian J. Chem. 2011; 23: 1631-1635.
17. Higuchi T, Connors K. Phase-solubility techniques. Adv. Anal. Chem. Instrum. 1965; 4: 117-212.
18. Panda S, Nayak S S. Inclusion complexes of Acridone and Its Semicarbazone Derivative with β-cyclodextrin-A Thermodynamic, Spectral and Antibacterial Study. Journal of Research in Chemistry 2009; 2(4): 539-543.
19. Tagashira M, Ohtake Y. A new antioxidative 1, 3-benzodioxide from Melissa officinals. Planta Medicinal Journal 1998; 64: 555-558.
20. Mukna AP, Nagarsenkar MS. American Association of Pharmaceutical Science. Pharmaceutical Science Technology 2001; 5(1): 19.
21. Bensi HA, Hilderband JH. A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. Journal of American Chemical Society 1999; 71: 2703-2707.
22. Szetli J. Molecular entrapment and release properties of drugs by cyclodextrins. Controlled Drug Bio-availability. Vol. 3, Willey Interscience publications, New York, 1985, pp: 365.
23. Mohammed KG, Moji CA. Elucidation of solution state complexation in wet granulated Oven Dried Ibuprofen and β-cyclodextrin: FTIR and 1H NMR Studies. Pharmaceutical Development and Technology 2001; 6: 315-324.
24. Nayak S, Panda S, Panda P, Padhy MS. Studies on acridone derivatives with and without inclusion complex formation with β-cyclodextrin. Bulgarian Chemical communication 2010, 42(2): 147-152.
25. Tommasini S, Raneri D, Ficarra R, Calabro ML, Stancanelli R. Improvement in solubility and dissolution rate of flavonoids by complexation with β-cyclodextrin. Journal of pharmaceutical and biomedical Analysis 2004; 35: 379-387.
26. Rajewski RA, Stella VJ. Pharmaceutical applications of cyclodextrins in vivo drug delivery. Journal of Pharmaceutical. Science 1996; 85: 1142-1169.
27. Loukas YL, Vraka V, Gregordias G. Novel non-acidic formulations of haloperidol complexed with β-cyclodextrin derivatives. Journal of Pharmaceutical and Biomedical Analysis 1997; 16: 263-268.
28. Stalin T, Vasantharani P, Shanti B, Sekhar A, Rajendiran N. Inclusion Complexes of trihydroxybenzene with α- and β-cyclodextrin. Indian Journal of Chemistry Sec A 2006; 45: 1113-1120.
29. Astakhova AV, Demina NB. Astakhova AV, Demina NB. Modern drug technologies: Synthesis, characterization and use of inclusion complexes between drugs and cyclodextrins (A Review). Journal of Pharmaceutical Chemistry 2004, 38(2): 105-108.
2. Valko M, Rhodes CJ, Moncol J, Izakovic M, Mazur M. Free radicals, metals and antioxidant stress induced cancer. Chemical Biology Interactive 2006; 160: 1-40.
3. Chen G, Wang Y, Hao X, Mu S, Sun Q. Simple Isatin derivatives as free radical scavengers: Synthesis, biological evaluation and structure-activity relationship. Chemistry Central Journal 2011; 5: 1-5.
4. Bankson DD, Kestin M, Rifal N. Role of free radicals in cancer and atherosclerosis. Clinical Lab. Med. 1993; 13: 463-480.
5. Prakash A, Rigelhof F, Miller E. Antioxidant Activity. Cereals Foods World 2000; 45(2): 59-63.
6. Miller HE, Rigelhof F, Marquart L, Prakash A, Kanter M. Antioxidant content of whole grain breakfast cereals, fruits and vegetables. Journal of American Coll. Nutr. 2000; 19(3): 312S-319S.
7. Patil R, Biradar JS. Synthesis and pharmacological evaluation of substituted- 2-triazolo (3, 4-b) (1, 3, 4)-thiadiazoles. Indian Journal of pharmaceutical Science 2001; 63(4): 299-305.
8. Holla BS, Udupa KV. Synthesis and antibacterial activity of nitrofurfuraldehyde as-triazino [5, 6-b] indol-3-ylhydrazones. Journal of Indian Chemical Society 1988; 65(7): 524-525.
9. Panwar H, Verma RS, Srivastava V, Kumar A. Synthesis of some substituted azetidinonyl and thiazolidinonyl-1, 3, 4-thiadiazino[6, 5-b] indoles as prospective antimicrobial agents. Indian Journal of Chemistry 2006; 45B: 2099-2104.
10. Shobha SR, Agaiah B , Sarangpani M. Antioxidant and DNA binding study of 3, 3’-(5, 5’-Methylene)Bis(3-Mercapto-4H-1, 2, 4-Triazol-5, 4-Diyl)Bis(Azan-1-yl-1-ylidene)Diindoline-2-ones. Int. J. Pharm. Technol. 2011; 2: 366-374.
11. Pose-Vilarnovo B, Predomo-Lopez I, Echezarreta-Lopez M. Improvement of water solubility of sulfamethizole through its complexation with β- and hydroxypropyl-β-cyclodextrin: Characterization of the interaction in solution and in solid state. Journal of Pharmaceutical Science 2001; 13(3) : 325-331
12. Belikov VG, Komapantseva EV. Khimiko Farmatsevticheskii Zhurnal. 1990; 24(7): 19.
13. Yano H, Hiramaya F, Arima H. Preparation of prednisolone-appended α-, β- and γ-cyclodextrins: Substitution at secondary hydroxyl groups and <I>in vitro</I> hydrolysis behavior. Journal of. Pharmaceutical. Science 2001; 90(4): 493-503.
14. Panda S, Tripathy JK. Studies on inclusion complexes of substituted indole derivatives with activating and deactivating group. J. Chem. Pharm Res. 2010; 2: 722-732.
15. Panda S, Tripathy JK. Thermodynamic, spectral and antimicrobial properties of inclusion complex of 2-[Benzylidenamino]-1,3,4-thiadiazino[6,5b] indole and 2-[Furfurlidenamino]-1,3,4-thiadiazino[6,5b] indole –a comparative study. Research Journal of Pharmaceutical Technology 2011; 4: 1693-1698.
16. Tripathy JK, Panda S. Thermodynamic and spectral studies of inclusion complexes of substituted indole derivatives with β-cyclodextrin. Asian J. Chem. 2011; 23: 1631-1635.
17. Higuchi T, Connors K. Phase-solubility techniques. Adv. Anal. Chem. Instrum. 1965; 4: 117-212.
18. Panda S, Nayak S S. Inclusion complexes of Acridone and Its Semicarbazone Derivative with β-cyclodextrin-A Thermodynamic, Spectral and Antibacterial Study. Journal of Research in Chemistry 2009; 2(4): 539-543.
19. Tagashira M, Ohtake Y. A new antioxidative 1, 3-benzodioxide from Melissa officinals. Planta Medicinal Journal 1998; 64: 555-558.
20. Mukna AP, Nagarsenkar MS. American Association of Pharmaceutical Science. Pharmaceutical Science Technology 2001; 5(1): 19.
21. Bensi HA, Hilderband JH. A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. Journal of American Chemical Society 1999; 71: 2703-2707.
22. Szetli J. Molecular entrapment and release properties of drugs by cyclodextrins. Controlled Drug Bio-availability. Vol. 3, Willey Interscience publications, New York, 1985, pp: 365.
23. Mohammed KG, Moji CA. Elucidation of solution state complexation in wet granulated Oven Dried Ibuprofen and β-cyclodextrin: FTIR and 1H NMR Studies. Pharmaceutical Development and Technology 2001; 6: 315-324.
24. Nayak S, Panda S, Panda P, Padhy MS. Studies on acridone derivatives with and without inclusion complex formation with β-cyclodextrin. Bulgarian Chemical communication 2010, 42(2): 147-152.
25. Tommasini S, Raneri D, Ficarra R, Calabro ML, Stancanelli R. Improvement in solubility and dissolution rate of flavonoids by complexation with β-cyclodextrin. Journal of pharmaceutical and biomedical Analysis 2004; 35: 379-387.
26. Rajewski RA, Stella VJ. Pharmaceutical applications of cyclodextrins in vivo drug delivery. Journal of Pharmaceutical. Science 1996; 85: 1142-1169.
27. Loukas YL, Vraka V, Gregordias G. Novel non-acidic formulations of haloperidol complexed with β-cyclodextrin derivatives. Journal of Pharmaceutical and Biomedical Analysis 1997; 16: 263-268.
28. Stalin T, Vasantharani P, Shanti B, Sekhar A, Rajendiran N. Inclusion Complexes of trihydroxybenzene with α- and β-cyclodextrin. Indian Journal of Chemistry Sec A 2006; 45: 1113-1120.
29. Astakhova AV, Demina NB. Astakhova AV, Demina NB. Modern drug technologies: Synthesis, characterization and use of inclusion complexes between drugs and cyclodextrins (A Review). Journal of Pharmaceutical Chemistry 2004, 38(2): 105-108.
Published
01-07-2012
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“A COMPARATIVE STUDY OF ANTIOXIDANT PROPERTIES OF 2-[SUBSTITUTED ARYLIDEAMINO]-1, 3, 4-THIADIAZINO [6, 5B] INDOLES AND THEIR INCLUSION COMPLEXES WITH Β-CYCLODEXTRIN”. International Journal of Pharmaceutical Sciences and Drug Research, vol. 4, no. 3, July 2012, pp. 191-4, https://doi.org/10.25004/IJPSDR.2012.040304.
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How to Cite
“A COMPARATIVE STUDY OF ANTIOXIDANT PROPERTIES OF 2-[SUBSTITUTED ARYLIDEAMINO]-1, 3, 4-THIADIAZINO [6, 5B] INDOLES AND THEIR INCLUSION COMPLEXES WITH Β-CYCLODEXTRIN”. International Journal of Pharmaceutical Sciences and Drug Research, vol. 4, no. 3, July 2012, pp. 191-4, https://doi.org/10.25004/IJPSDR.2012.040304.
