Carvone Schiff base of isoniazid as a novel antitumor agent: Nanoemulsion development and pharmacokinetic evaluation

Journal of Molecular Liquids

Volumn 203, Issue , 2015, Pages 111-119

  Bhat, Mashooq A ^a   Iqbal, Muzaffar ^a   Al Dhfyan, Abdullah ^b   Shakeel, Faiyaz ^c  

^a KING SAUD UNIVERSITY   (Saudi Arabia)

^b KING FAISAL SPECIALIST HOSPITAL AND RESEARCH CENTER   (Saudi Arabia)

^c KING SAUD UNIVERSITY   (Saudi Arabia)

Author keywords

Cytotoxicity; Droplet size; Isoniazid schiff base; Nanoemulsion; Pharmacokinetic

Indexed keywords

CYTOTOXICITY; DISEASES; DROPS; DRUG PRODUCTS; FUNCTIONAL GROUPS; HYDRAZINE; MONOTERPENES; REFRACTIVE INDEX; TITRATION; VISCOSITY;

ANTICANCER POTENTIALS; DROPLET SIZES; HUMAN COLON CANCER CELLS; NANOEMULSION; PHARMACOKINETIC EVALUATION; PHARMACOKINETIC STUDIES; POLYDISPERSITY INDICES; SCHIFF-BASE;

PHARMACOKINETICS;

EID: 84920742534     PISSN: 01677322     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molliq.2014.12.037     Document Type: Article

References (38)

1. H.S.N. Kumar, T. Parumasivam, F. Jumaat, P. Ibrahim, M.Z. Asmawi, and A. Sadikun Synthesis and evaluation of isonicotinoyl hydrazone derivatives as antimycobacterial and anticancer agents Med. Chem. Res. 23 2014 269 279
2. O.H. Sjo, M. Berg, M. Merok, M. Kolberg, A. Svindland, R.A. Lothe, and A. Nesbakken Peritoneal carcinomatosis of colon cancer origin: highest incidence in women and in patients with right-sided tumors J. Surg. Oncol. 104 2011 792 797
3. P. Yin, Y. Wang, Y. Qiu, L. Hou, X. Liu, J. Qin, Y. Duan, P. Liu, M. Qiu, and Q. Li Bufalin-loaded mPEG-PLGA-PLL-cRGD nanoparticles: preparation, cellular uptake, distribution and anticancer activity Int. J. Nanomedicine 7 2012 3961 3969
4. D.M. Parkin, F. Bray, J. Ferlay, and P. Pisani Global cancer statistics, 2002 CA Cancer J. Clin. 55 2005 74 108
5. Z. Rahman, K. Kohli, R.K. Khar, M. Ali, N.A. Charoo, and A.A. Shamsher Characterization of 5-fluorouracil microspheres for colonic delivery AAPS PharmSciTech 7 2006 E47
6. M.A. Bhat, and M.A. Al-Omar Synthesis, characterization and in vitro anti-Mycobacterium tuberculosis activity of terpene Schiff bases Med. Chem. Res. 22 2013 4522 4528
7. N. Demirbas, S.A. Karaoglu, A. Demirbas, and K. Sancak Synthesis and antimicrobial activities of some new 1-(5-phenylamino-[1,3,4] thiadiazol-2-yl) methyl-5-oxo-[1,2,4] triazole and 1-(4-phenyl-5-thioxo-[1,2,4] triazol-3-yl) methyl-5-oxo-[1,2,4] triazolederivatives Eur. J. Med. Chem. 39 2004 793 804
8. P. Vicini, M. Incerti, I.A. Doytchinova, P. La Colla, B. Busonera, and R. Loddo Synthesis and anti proliferative activity of benzo[d]isothiazole hydrazones Eur. J. Med. Chem. 41 2006 624 632
9. K. Sztanke, T. Tuzimski, J. Rzymowska, K. Pasternak, and A.M. Kandefer-Szersze Synthesis, determination of the lipophilicity, anticancer and antimicrobial properties of some fused 1,2,4-triazole derivatives Eur. J. Med. Chem. 43 2008 404 419
10. T.J. de Faria, M. Roman, N.M. de Souza, R.D. Vecchi, J.V. de Assis, A.L.G. dos Santos, I.H. Bechtold, N. Winter, M.J. Soares, L.P. Silva, M.V. De Almeida, and A. Bafica An isoniazid analogue promotes Mycobacterium tuberculosis-nanoparticle interactions and enhances bacterial killing by macrophages Antimicrob. Agents Chemother. 56 2012 2259 2267
11. F.A.R. Rodrigues, A.C.E. Oleveira, B.C. Cavalcanti, C. Pessoa, A.C. Pinheiro, and M.N.V. De Souza Biological evaluation of isoniazid derivatives as an anticancer class Sci. Pharm. 82 2014 21 28
12. H. Kumar, D. Malhotra, R. Sharma, E. Sausville, and M. Malhotra Synthesis, characterization and evaluation of isoniazid analogues as potent anticancer agents Pharmacologyonline 3 2011 337 343
13. F.K. Alanazi, N. Haq, A.A. Radwan, I.A. Alsarra, and F. Shakeel Formulation and evaluation of cholesterol-rich nanoemulsion (LDE) for drug delivery potential of cholesteryl-maleoyl-5-fluorouracil Pharm. Dev. Technol. 20 2015 266 270
14. F.K. Alanazi, N. Haq, A.A. Radwan, I.A. Alsarra, and F. Shakeel Cholesterol-rich nanoemulsions (LDE) for drug targeting of cholesteryl-succinyl-5-fluorouracil conjugate Curr. Nanosci. 10 2014 287 291
15. F. Shakeel, N. Haq, A. Al-Dhfyan, F.K. Alanazi, and I.A. Alsarra Chemoprevention of skin cancer using low HLB surfactant nanoemulsion of 5-fluorouracil: a preliminary study Drug Deliv. 2013 10.3109/10717544.2013.868557
16. J.A. Moura, C.J. Valduga, E.R. Tavares, I.F. Kretzer, D.A. Maria, and R.C. Maranhão Novel formulation of a methotrexate derivative with a lipid nanoemulsion Int. J. Nanomedicine 6 2011 2285 2295
17. C.H. Azevedo, J.P. Carvalho, C.J. Valduga, and R.C. Maranhão Plasma kinetics and uptake by the tumor of a cholesterol-rich microemulsion (LDE) associated to etoposide oleate in patients with ovarian carcinoma Gynecol. Oncol. 97 2005 178 182
18. D.G. Rodrigues, D.A. Maria, D.C. Fernandes, C.J. Valduga, R.D. Couto, O.C.M. Ibanez, and R.C. Maranhao Improvement of paclitaxel therapeutic index by derivatization and association to a cholesterol-rich microemulsion: in vitro and in vivo studies Cancer Chemother. Pharmacol. 55 2005 565 576
19. M.L. Dias, J.P. Carvalho, D.G. Rodrigues, S.R. Graziani, and R.C. Maranhão Pharmacokinetics and tumor uptake of a derivatized form of paclitaxel associated to a cholesterol-rich nanoemulsion (LDE) in patients with gynecologic cancers Cancer Chemother. Pharmacol. 59 2007 105 111
20. R. Pandey, A. Zahoor, S. Sharma, and G.K. Khuller Nanoparticle encapsulated antitubercular drugs as a potential oral drug delivery system against murine tuberculosis Tuberculosis 83 2003 373 378
21. A. Sharma, R. Pandey, S. Sharma, and G.K. Khuller Chemotherapeutic efficacy of poly(dl-lactide-co-glycolide) nanoparticle encapsulated antitubercular drugs at subtherapeutic dose against experimental tuberculosis Int. J. Antimicrob. Agents 24 2004 599 604
22. P. Blasi, A. Schoubben, S. Giovagnoli, C. Rossi, and M. Ricci Fighting tuberculosis: old drugs, new formulations Expert Opin. Drug Deliv. 6 2009 977 993
23. A. Sosnik, A.M. Carcaboso, and R.J. Glisoni New old challenges in tuberculosis: potentially effective nanotechnologies in drug delivery Adv. Drug Deliv. Rev. 62 2010 547 559
24. R. Pandey, and Z. Ahmad Nanomedicine and experimental tuberculosis: facts, flaws, and future Nanomedicine 7 2011 259 272
25. A. Dorhoi, S.T. Reece, and S.H. Kaufmann For better or for worse: the immune response against Mycobacterium tuberculosis balances pathology and protection Immunol. Rev. 240 2011 235 251
26. S. Shafiq, F. Shakeel, S. Talegaonkar, F.J. Ahmad, R.K. Khar, and M. Ali Development and bioavailability assessment of ramipril nanoemulsion formulation Eur. J. Pharm. Biopharm. 66 2007 227 243
27. F. Shakeel, S. Shafiq, N. Haq, F.K. Alanazi, and I.A. Alsarra Nanoemulsions as potential vehicles for transdermal and dermal delivery of hydrophobic compounds: an overview Expert Opin. Drug Deliv. 9 2012 953 974
28. F. Shakeel, N. Haq, M. Elbadry, F.K. Alanazi, and I.A. Alsarra Ultra fine super selfnanoemulsifying drug delivery system (SNEDDS) enhanced solubility and dissolution of indomethacin J. Mol. Liq. 180 2013 89 94
29. F. Shakeel, N. Haq, F.K. Alanazi, and I.A. Alsarra Impact of various nonionic surfactants on self-nanoemulsification efficiency of two grades of Capryol (Capryol-90 and Capryol-PGMC) J. Mol. Liq. 182 2013 57 63
30. H. Yu, and Q. Huang Improving the oral bioavailability of curcumin using novel organogel-based nanoemulsions J. Agric. Food Chem. 60 2012 5373 5379
31. P. Costa, and J.M.S. Lobo Modeling and comparison of dissolution profiles Eur. J. Pharm. Sci. 15 2001 123 133
32. S. Dash, P.N. Murthy, L. Nath, and P. Chowdhury Kinetic modeling on drug release from controlled drug delivery systems Acta Pol. Pharm. 67 2010 217 223
33. M. Iqbal, M.A. Bhat, and F. Shakeel Development and validation of UHPLC-MS/MS assay for rapid determination of a carvone Schiff base of isoniazid (CSB-INH) in rat plasma: application to pharmacokinetic study Biomed. Chromatogr. 2014 10.1002/bmc.3368
34. M.K. Anwer, S. Jamil, E.O. Ibnouf, and F. Shakeel Enhanced antibacterial effects of clove essential oil by nanoemulsion J. Oleo Sci. 63 2014 347 354
35. O. Nuchuchua, U. Sakulku, N. Uawongyart, S. Puttipipatkhachorm, A. Soottitantawat, and N. Ruktanonchai In vitro characterization and mosquito (Aedes aegypti) repellent activity of essential-oils-loaded nanoemulsions AAPS PharmSciTech 10 2009 1234 1242
36. M. El-Badry, N. Haq, G. Fetih, and F. Shakeel Solubility and dissolution enhancement of tadalafil using self-nanoemulsifying drug delivery system J. Oleo Sci. 63 2014 567 576
37. A. Kajal, S. Bala, S. Kamboj, N. Sharma, and V. Saini Schiff base: a versatile pharmacophore J. Catal. 2013 2013 (E893512)
38. A.J. Guo, X.S. Xu, Y.H. Hu, M.Z. Wang, and X. Tan Effects of ternary complexes of copper with salicylaldihyde-amino acid Schiff base coordination compounds on the proliferation of BGC823 cells Chin. J. Cancer 29 2010 277 282