Grafting of sulfamethoxazole on acrylic acid−vinyl methyl ketone copolymer using the schiff base reaction−application as a drug delivery system

References

• Larsson, M.; Gustafsson, S.; Olsson, E.; Larsson, A. Effect of Calcium Neutralization on Elastic and Swelling Properties of Crosslinked Poly (acrylic acid)-Correlation to in Homogeneities and Phase Behaviour. e-Polymers 2009, 9, 1683–1696.
   Google Scholar
• Calixto, G.; Yoshii, A. C.; Rocha e Silva, H.; Stringhetti Ferreira Cury, B.; Chorilli, M. Polyacrylic Acid Polymers Hydrogels Intended to Topical Drug Delivery: Preparation and Characterization. Pharm. Dev. Technol. 2015, 20, 490–496.
   PubMed Web of Science ®Google Scholar
• De, T. K.; Hoffman, A. S. An Ophthalmic Formulation of a Beta-Adrenoceptor Antagonist, Levobetaxolol, using Poly (Acrylic Acid) Nanoparticles as Carrier: Loading and Release Studies. J. Bioact. Compat. Polym. 2001, 16, 20–31.
   Web of Science ®Google Scholar
• De, T. K.; Hoffman, A. S. A Reverse Microemulsion Polymerization Method for Preparation of Bioadhesive Polyacrylic Acid Nanoparticles for Mucosal Drug Delivery: Loading and Release of Timolol Maleate. Artif. Cells Blood Substit. Immobil. Biotechn. 2001, 29, 31–46.
   PubMed Web of Science ®Google Scholar
• Molnar, R. M.; Bodnar, M.; Hartmann, J. F.; Borbely, J. Preparation and Characterization of Poly (acrylic acid)-Based Nanoparticles. Colloid Polym. Sci. 2009, 287, 739–744.
   Web of Science ®Google Scholar
• Müller, C.; Leithner, K.; Hauptstein, S.; Hintzen, F.; Salvenmoser, W.; Bernkop-Schnürch, A.. Preparation and Characterization of Mucus-Penetrating Papain/Poly (Acrylic Acid) Nanoparticles for Oral Drug Delivery Applications. J. Nanopart. Res. 2013, 15, 1353.
   Web of Science ®Google Scholar
• Larsson, M.; Bergstrand, A.; Mesiah, L.; Van Vooren, C.; Larsson, A. Nanocomposites of Polyacrylic Acid Nanogels and Biodegradable Polyhydroxybutyrate for Bone Regeneration and Drug Delivery. J. Nanomat. 2014, 2014, 1–9.
   Web of Science ®Google Scholar
• Guo, Y.; Sun, J.; Bai, S.; Wu, X. pH-Sensitive Performance of Dextran-Poly(Acrylic Acid) Copolymer and Its Application in Controlled in vitro Release of Ibuprofen. Int. J. Polym. Mater. Polym. Biomater. 2017, 66, 900–906.
   Web of Science ®Google Scholar
• Shabira, F.; Eruma, A.; Tulaina, U. R.; Hussainb, M. A.; Ahmadc, M.; Akhtera, F. Preparation and Characterization of pH Sensitive Crosslinked Linseed Polysaccharides-Co-Acrylic Acid/Methacrylic Acid Hydrogels for Controlled Delivery of Ketoprofen. Des. Monom. Polym. 2017, 20, 485–495.
   PubMed Web of Science ®Google Scholar
• Hussain, Z.; Yousif, E.; Ahmed, A.; Altaie, A. Synthesis and Characterization of Schiff’s Bases of Sulfamethoxazole. Org. Medic. Chem. Lett. 2014, 4, 1–4.
   PubMedGoogle Scholar
• Ross, N. C.; Levine, R. The Chemistry of Methyl Vinyl Ketone. II. Reactions with Esters, β-Keto Esters, Malonic Ester, Amines, Tar Bases, and Inorganic Salts. J. Org. Chem. 1964, 29, 2346–2350.
   Web of Science ®Google Scholar
• Prasad, A.; Trinagaraju, K.; Rao, B. G.; Usha, Y.; Reddy, P. S.; Rao, P. V. Synthesis, Characterization and Biological Activity of Schiff Bases of Acetylacetone. Int. J. Innovat. Res. Dev. 2013, 2, 38–43.
   Google Scholar
• Choi, Y. K.; Chjo, K. H.; Park, S. M.; Doddapaneni, N. Oxygen Reduction at Co(II) 2‐Disalophen Modified Carbon Electrodes. J. Electrochem. Soc. 1995, 142, 4107–4112.
   Web of Science ®Google Scholar
• Prakash, A.; Ahmad, S. Physico-Chemical and Antimicrobial Studies on Ni(II), Cu(II) and Ti(III) Schiff Base Complexes Derived from 2-Furfuraldehyde. Orient. J. Chem. 2009, 25, 391–395.
   Google Scholar
• Drew, W. L.; Barry, A.; O’Toole, R.; Sherris, J. C. Reliability of the Kirby-Bauer Disc Diffusion Method for Detecting Methicillin-Resistant Strains of Staphylococcus Aureus. Appl. Microbiol. 1972, 24, 240–247.
   PubMedGoogle Scholar
• Yutaka Shimodoi1, N. M. The Reaction of Poly Methyl Vinyl Ketone. (Part, I). The Reaction of Poly Methyl Vinyl Ketone with Amines. J. Soc. Chem. Ind., Japan. 1962, 65, 591–594.
   Google Scholar
• Ogawa, T.; Cedeño, R.; Herrera, T. E.; Almaraz, B.; Inoue, M. Electric Conductivities of Poly (Vinyl Ketone) S Reacted with Phosphoryl Chloride. In Raymond B. Seymour (ed) Conductive Polymers; Springer: Boston, MA, 1981; Vol. 15, p 85–94.
   Google Scholar
• Reine, A. H.; Arthur, J. C.; George, M. Graft Copolymers of Cellulose and Vinylic Ketones. I. Preparation of Poly (Methyl Vinyl Ketone)–Cotton Cellulose Copolymers. J. Appl. Polym. Sci. 1972, 16, 1893–1899.
   Web of Science ®Google Scholar
• Pasynkiewicz, S.; Diem, T.; Korol, A. Copolymerization of Methyl Vinyl Ketone with Vinyl Compounds or Dienes in the Presence of Alkyl‐Aluminium Chloride or Aluminium Bromide. Macromol. Chem. Phys. 1970, 137, 61–66.
   Google Scholar
• Tsuruta, T.; Fujio, R. Copolymerization of Methyl Vinyl Ketone with Alkylene Oxide. Macromol. Chem. Phys. 1963, 64, 219–223.
   Google Scholar
• Koral, J. N. (Inventor). Alkyl vinyl ketone-acetaldehyde copolymers. Google Patents (assignee) [US3293215A], 1966.
   Google Scholar
• Masuda, S.; Minagawa, K.; Tanaka, M.; Asahi, Y. editors. Copolymerization of Methyl Vinyl Ketone with Styrene in the Presence of Cobalt (II) Nitrate. Macromol. Symp. 1991, 47, 329–336.
   Google Scholar
• Foltzer, M. A.; Reese, R. E. Trimethoprim-Sulfamethoxazole and Other Sulfonamides. Med. Clin. North Am. 1987, 71, 1177–1194.
   PubMed Web of Science ®Google Scholar
• Mofenson, L. M.; Oleske, J.; Serchuck, L.; Van Dyke, R.; Wilfert, C. Treating Opportunistic Infections Among HIV-Exposed and Infected Children Recommendations from CDC; No. RR-14; The National Institutes of Health, and The Infectious Diseases Society of America. Recommendations and Reports December 3, 2004 / Vol. 53. Available at http://www.ncbi.nlm.nih.gov/pubmed/15577752.
   Google Scholar
• Bhat, I. K.; Mishra, S. K.; James, J. P.; Shastry, C. S. Antimicrobial Studies of Synthesized Azetidinone Derivatives from Sulfamethoxazole Moiety. J. Chem. Pharm. Res. 2011, 3, 114–118.
   Google Scholar
• Cairns, D. Essentials of Pharmaceutical Chemistry, 4th ed.; London, UK: Pharmaceutical Press, 2012.
   Google Scholar
• Semlali, A.; Jacques, E.; Rouabhia, M.; Milot, J.; Laviolette, M.; Chakir, J. Regulation of Epithelial Cell Proliferation by Bronchial Fibroblasts Obtained from Mild Asthmatic Subjects. Allergy 2010, 65, 1438–1445.
   PubMed Web of Science ®Google Scholar
• Semlali, A.; Chakir, J.; Goulet, J. P.; Chmielewski, W.; Rouabhia, M. Whole Cigarette Smoke Promotes Human Gingival Epithelial Cell Apoptosis and Inhibits Cell Repair Processes. J. Periodont. Res. 2011, 46, 533–541.
   PubMed Web of Science ®Google Scholar
• Petty, R. D.; Sutherland, L. A.; Hunter, E. M.; Cree, I. A. Comparison of MTT and ATP‐Based Assays for the Measurement of Viable Cell Number. J. Biolumin. Chemilumin. 1995, 10, 29–34.
   PubMedGoogle Scholar
• Al-Odayni, A.-B. M.; Aouak, T.; Alghamdi, A. A.; Saeed, W. S.; Ouladsmane, M.; Karama, U.; Alothman, Z. A. Ibuprofen Grafted on Poly (2-Hydroxyethylmethacrylate): Synthesis, Mass Transfer and in Vitro Drug Release Investigations. Int. J. Polym. Mater. Polym. Biomater. 2018, 67, 36–49. DOI:10.1080/00914037.2017.1297940.
   Web of Science ®Google Scholar
• Khripach, V.; Ivanova, G. Alkylation of Enolates by 3-Methyl-4-Chloro-4, 5, 6, 7-Tetrahydrobenz [1, 2-d] Isoxazole. Chem. Heterocycl. Compound 1990, 26, 1150–1154.
   Google Scholar
• Kesimli, B.; Topacli, A. Infrared Studies on Co and Cd Complexes of Sulfamethoxazole. Spectrochim. Acta Part A: Mol. Biomol. Spectr. 2001, 57, 1031–1036.
   Web of Science ®Google Scholar
• Gao, H.; Harmon, J. P. An Empirical Correlation between Glass Transition Temperatures and Structural Parameters for Polymers with Linear and Branched Alkyl Substituents. J. Appl. Polym. Sci. 1997, 64, 507–517.
   Web of Science ®Google Scholar
• Tong, J.; Xu, X.; Liu, S.; Che, T.; Li, Y.; Hu, Z.; Meng, Y. Prediction of Glass Transition Temperature of Polyacrylate using a Quantitative Structure Property Relationship Model. Polym. Sci. Series A 2013, 55, 487–492.
   Web of Science ®Google Scholar
• Knipe, J. M.; Peppas, N. A. Multi-Responsive Hydrogels for Drug Delivery and Tissue Engineering Applications. Regen. Biomater. 2014, 1, 57–65.
   PubMedGoogle Scholar
• Thomson, I.; Erizal, S.; YeyetCahyati, S.; Sundani Nurono, S.; Auzal, Halim. Int. J. Pharmacol. 2008, 4, 140–144.
   Google Scholar
• Gürbüz, M. U.; Ertürk, A. S.; Tülü, M. Synthesis of Surface-Modified TREN-Cored PAMAM Dendrimers and their Effects on the Solubility of Sulfamethoxazole (SMZ) as an Analog Antibiotic Drug. Pharmaceut. Dev. Technol. 2017, 22, 678–689.
   PubMed Web of Science ®Google Scholar
• Fioritto, A. F.; Bhattachar, S. N.; Wesley, J. A. Solubility Measurement of Polymorphic Compounds via the pH-metric Titration Technique. Int. J. Pharmaceut. 2007, 330, 105–113.
   PubMed Web of Science ®Google Scholar
• Kitao, K.; Kubo, K.; Morishita, T.; Yata, N.; Kamada, A. Studies on Absorption of Drugs. VII. Absorption of Isomeric N1-Heterocyclic Sulfonamides from the Rat Small Intestines and Relations between Physicochemical Property and Absorption of Unionized Sulfonamides. Chem. Pharmaceut. Bull. 1973, 21, 2417–2426.
   PubMed Web of Science ®Google Scholar
• Yalkowsky, S. H.; He, Y.; Jain, P. Handbook of Aqueous Solubility Data; Boca Raton, London, New York: CRC press, 2016.
   Google Scholar
• Wan, L. S.; Heng, P. W.; Wong, L. F. Relationship between Swelling and Drug Release in a Hydrophilic Matrix. Drug Dev. Ind. Pharm. 1993, 19, 1201–1210.
   Web of Science ®Google Scholar
• Comyn, J. Introduction to Polymer Permeability and the Mathematics of Diffusion. Polymer Permeability; Springer, London, UK. 1985; pp 1–10.
   Google Scholar
• Masaro, L.; Zhu, X. Physical Models of Diffusion for Polymer Solutions, Gels and Solids. Prog. Polym. Sci. 1999, 24, 731–775.
   Web of Science ®Google Scholar
• Reinhard, C. S.; Radomsky, M. L.; Saltzman, W. M.; Hilton, J.; Brem, H. Polymeric Controlled Release of Dexamethasone in Normal Rat Brain. J. Controll. Rel. 1991, 16, 331–339.
   Web of Science ®Google Scholar
• Cypes, S. H.; Saltzman, W. M.; Giannelis, E. P. Organosilicate-Polymer Drug Delivery Systems: Controlled Release and Enhanced Mechanical Properties. J. Controll. Rel. 2003, 90, 163–169.
   PubMed Web of Science ®Google Scholar
• Frank, A.; Rath, S. K.; Venkatraman, S. S. Controlled Release from Bioerodible Polymers: Effect of Drug Type and Polymer Composition. J. Controlled. Rel. 2005, 102, 333–344.
   PubMed Web of Science ®Google Scholar
• Lee, Y. Y.; Erdogan, A.; Rao, S. S. How to Assess Regional and Whole Gut Transit Time with Wireless Motility Capsule. J. Neurogastroenterol. Motil. 2014, 20, 265–270.
   PubMed Web of Science ®Google Scholar
• Belzer, C.; De Vos, W. M.; Microbes Inside—from Diversity to Function: The Case of Akkermansia. ISME J. 2012, 6, 1449–1458.
   PubMed Web of Science ®Google Scholar