Concomitant drugs-loaded microcapsules of roxithromycin and theophylline with pH-sensitive controlled-releasing properties

References

• Tang, W.; Zhou, J.; Miao, L.; Shi, G. Clinical Features in Patients of Cough Variant Asthma with Normal and High Level of Exhaled Fractional Nitric Oxide. Clin. Respir. J. 2018, 12, 595–600. DOI: 10.1111/crj.12568.
   PubMed Web of Science ®Google Scholar
• Hara, J.; Fujimura, M.; Ohkura, N.; Sakai, T.; Yamamura, K.; Abo, M.; Koba, H.; Watanabe, S.; Yoneda, T.; Nishikawa, S. The Measurement of Cough Response to Bronchoconstriction Induced by Methacholine Inhalation in Healthy Subjects: An Examination Using the Astograph Method. Exp. Lung Res. 2017, 43, 1–9.
   PubMed Web of Science ®Google Scholar
• Pender, E. S.; Pollack, C. V. Cough-Variant Asthma in Children and Adults: Case Reports and Review. J. Emerg. Med. 1990, 8, 727–731. DOI: 10.1016/0736-4679(90)90287-6.
   PubMedGoogle Scholar
• Delaforge, M.; Sartori, E.; Mansuy, D. In Vivo and in Vitro Effects of a New Macrolide Antibiotic Roxithromycin on Rat Liver Cytochrome P-450: Comparison with Troleandomycin and Erythromycin. Chem-Biol. Interact 1988, 68, 179–188. DOI: 10.1016/0009-2797(88)90015-4.
   PubMed Web of Science ®Google Scholar
• Lohmann, S. M.; Miech, R. P.; Butcher, F. R. Effects of Isoproterenol, Theophylline and Carbachol on Cyclic Nucleotide Levels and Relaxation of Bovine Tracheal Smooth Muscle. Biochim. Biophys. Acta. 1977, 499, 238–250. DOI: 10.1016/0304-4165(77)90006-X.
   PubMedGoogle Scholar
• Saintsalvi, B.; Tremblay, D.; Surjus, A.; Lefebvre, M. A. A Study of the Interaction of Roxithromycin with Theophylline and Carbarmazepine. J. Antimicrob. Chemother. 1987, 20, 121–129. DOI: 10.1093/jac/20.suppl_B.121.
   PubMed Web of Science ®Google Scholar
• Shirahata, K.; Fujimoto, K.; Arioka, H.; Shouda, R.; Kudo, K.; Ikeda, S.-I. Prevalence and Clinical Features of Cough Variant Asthma in a General Internal Medicine Outpatient Clinic in Japan. Respirology 2005, 10, 354–358. DOI: 10.1111/j.1440-1843.2005.00709.x.
   PubMed Web of Science ®Google Scholar
• Rang, L. C.; Murray, H. E.; Wells, G. A.; Macgougan, C. K. Can Peripheral Venous Blood Gases Replace Arterial Blood Gases in Emergency Department Patients? Can. J. Emerg. Med. Care 2002, 4, 7–15. DOI: 10.1017/S1481803500006011.
   Google Scholar
• Wilson, J. D.; Sutherland, D. C.; Thomas, A. C. Has the Change to Beta-Agonists Combined with Oral Theophylline Increased Cases of Fatal Asthma? Lancet 1981, 317, 1235–1237. DOI: 10.1016/S0140-6736(81)92403-X.
   Google Scholar
• Lal, D.; Manocha, S.; Ray, A.; Vijayan, V. K.; Kumar, R. Comparative Study of the Efficacy and Safety of Theophylline and Doxofylline in Patients with Bronchial Asthma and Chronic Obstructive Pulmonary Disease. J. Basic. Clin. Physiol. Pharmacol. 2015, 26, 443–451.
   PubMedGoogle Scholar
• Shoji, T.; Yoshida, S.; Sakamoto, H.; Hasegawa, H.; Nakagawa, H.; Amayasu, H. Anti-Inflammatory Effect of Roxithromycin in Patients with Aspirin-Intolerant Asthma. Clin. Exp. Allergy 1999, 29, 950–956. DOI: 10.1046/j.1365-2222.1999.00551.x.
   PubMed Web of Science ®Google Scholar
• Damodharan, N.; Mothilal, M.; Thejomayananthan, P. Formulation and Evaluation of bi-Layered Floating Tablets of Theophylline. Pharmacia Lettre 2009, 1, 227–233.
   Google Scholar
• Tonon, R. V.; Grosso, C. R. F.; Hubinger, M. D. Influence of Emulsion Composition and Inlet Air Temperature on the Microencapsulation of Flaxseed Oil by Spray Drying. Food Res. Int 2011, 44, 282–289. DOI: 10.1016/j.foodres.2010.10.018.
   Web of Science ®Google Scholar
• Wang, Y.; Wang, X.; Li, L.; Gu, Z.; Yu, X. Controlled Drug Release from a Novel Drug Carrier of Calcium Polyphosphate/Chitosan/Aldehyde Alginate Scaffolds Containing Chitosan Microspheres. Rsc Adv. 2014, 4, 24810–24815. DOI: 10.1039/c4ra03566f.
   Web of Science ®Google Scholar
• Mandal, T. K.; Bostanian, L. A.; Graves, R. A.; Chapman, S. R.; Womack, I. Development of Biodegradable Microcapsules as Carrier for Oral Controlled Delivery of Amifostine. Drug Dev. Ind. Pharm. 2002, 28, 339–344. DOI: 10.1081/DDC-120002849.
   PubMed Web of Science ®Google Scholar
• Gaitzsch, J.; Huang, X.; Voit, B. Engineering Functional Polymer Capsules toward Smart Nanoreactors. Chem. Rev. 2016, 116, 1053–1093. DOI: 10.1021/acs.chemrev.5b00241.
   PubMed Web of Science ®Google Scholar
• And, A. J. K.; Caruso, F. Stepwise Self-Assembled Poly(Amidoamine) Dendrimer and Poly(Styrenesulfonate) Microcapsules as Sustained Delivery Vehicles. Biomacromolecules 2002, 3, 1154–1162. DOI: 10.1021/bm025562k.
   PubMed Web of Science ®Google Scholar
• Li, W.; Zhang, L. Y.; Ge, X. H.; Xu, B. Y.; Zhang, W. X.; Qu, L. L.; Choi, C.; Xu, J. H.; Zhang, A.; Lee, H.; Weitz, D. Microfluidic Fabrication of Microparticles for Biomedical Applications. Chem. Soc. Rev. 2018, 47, 5646. DOI: 10.1039/C7CS00263G.
   PubMed Web of Science ®Google Scholar
• Sivakumar, S.; Bansal, V.; Cortez, C.; Chong, S.; Zelikin, A.; Caruso, F. Degradable, Surfactant-Free, Monodisperse Polymer-Encapsulated Emulsions as Anticancer Drug Carriers. Adv. Mater. 2009, 21, 1820–1824. DOI: 10.1002/adma.200802475.
   Web of Science ®Google Scholar
• Chern, Y. T.; Chen, L. W. Interfacial Polyfunctional Condensation: Effect of the Reaction Conditions. J. Appl. Polym. Sci. 1991, 42, 2543–2550. DOI: 10.1002/app.1991.070420920.
   Web of Science ®Google Scholar
• Vaslin-Reimann, S.; Lafuma, F.; Audebert, R. Reversible Flocculation of Silica Suspensions by Water-Soluble Polymers. Colloid & Polymer Sci. 1990, 268, 476–483. DOI: 10.1007/BF01411007.
   Web of Science ®Google Scholar
• Mou, C. L.; Wang, W.; Li, Z. L.; Ju, X. J.; Xie, R.; Deng, N. N.; Wei, J.; Liu, Z.; Chu, L. Y. Trojan-Horse-like Stimuli-Responsive Microcapsules. Adv Sci (Weinh) 2018, 5, 1700960.DOI: 10.1002/advs.201700960.
   PubMedGoogle Scholar
• Chen, L. J.; Chen, C. N.; Lin, S. Y. Preparation method of microdispersed tablet formulation of spray-dried sodium diclofenac enteric-coated microcapsules. U.S. Patent 5202159 A, 1993.
   Google Scholar
• Gharsallaoui, A.; Roudaut, G.; Chambin, O.; Voilley, A.; Saurel, R. Applications of Spray-Drying in Microencapsulation of Food Ingredients: An Overview. Food Res. Int. 2007, 40, 1107–1121. DOI: 10.1016/j.foodres.2007.07.004.
   Web of Science ®Google Scholar
• Kadota, K.; Nishimura, T.; Hotta, D.; Tozuka, Y. Preparation of Composite Particles of Hydrophilic or Hydrophobic Drugs with Highly Branched Cyclic Dextrin via Spray Drying for Dry Powder Inhalers. Powder Technol. 2015, 283, 16–23. DOI: 10.1016/j.powtec.2015.05.014.
   Web of Science ®Google Scholar
• Choudhary, P. D.; Pawar, H. A. Recently Investigated Natural Gums and Mucilages as Pharmaceutical Excipients: An Overview. J. Pharm. 2014, 2014, 1–9. DOI: 10.1155/2014/204849.
   Google Scholar
• Nimmannit, U.; Suwanpatra, N. Microencapsulation of Drugs by the Coacervation Technique Using Ethylcellulose and Acrylate-Methacrylate Copolymer as Wall Materials. J. Microencapsul. 1996, 13, 643–649. DOI: 10.3109/02652049609026048.
   PubMed Web of Science ®Google Scholar
• Lee, J. S.; Feijen, J. Polymersomes for Drug Delivery: design, Formation and characterization. J. Control Release. 2012, 161, 473–483. DOI: 10.1016/j.jconrel.2011.10.005.
   PubMed Web of Science ®Google Scholar
• Jiang, W.; Zhou, Y.; Yan, D. Hyperbranched Polymer Vesicles: From Self-Assembly, Characterization, Mechanisms, and Properties to Applications. Chem. Soc. Rev. 2015, 44, 3874–3889. DOI: 10.1039/C4CS00274A.
   PubMed Web of Science ®Google Scholar
• Liu, B.; Zhou, H.; Zhou, S.; Zhang, H.; Feng, A.; Jian, C.; Hu, J.; Gao, W.; Yuan, J. Synthesis and Self-Assembly of CO2-Temperature Dual Stimuli-Responsive Triblock Copolymers. Macromolecules 2014, 47, 2938–2946. DOI: 10.1021/ma5001404.
   Web of Science ®Google Scholar
• Oliveira, H.; Pérez-Andrés, E.; Thevenot, J.; Sandre, O.; Berra, E.; Lecommandoux, S. Magnetic Field Triggered Drug Release from Polymersomes for Cancer Therapeutics. J. Control Release 2013, 169, 165–170. DOI: 10.1016/j.jconrel.2013.01.013.
   PubMed Web of Science ®Google Scholar
• Kim, H.; Kang, Y. J.; Jeong, E. S.; Kang, S.; Kim, K. T. Glucose-Responsive Disassembly of Polymersomes of Sequence-Specific Boroxole-Containing Block Copolymers under Physiologically Relevant Conditions. Acs Macro Lett. 2012, 1, 1194–1198. DOI: 10.1021/mz3004192.
   Web of Science ®Google Scholar
• Lale, S. V.; Kumar, A.; Prasad, S.; Bharti, A. C.; Koul, V. Folic Acid and Trastuzumab Functionalized Redox Responsive Polymersomes for Intracellular Doxorubicin Delivery in Breast Cancer. Biomacromolecules 2015, 16, 1736–1752. DOI: 10.1021/acs.biomac.5b00244.
   PubMed Web of Science ®Google Scholar
• Lin, W.; Hu, Q.; Jiang, K.; Yang, Y.; Yang, Y.; Cui, Y.; Qian, G. A Porphyrin-Based Metal–Organic Framework as a pH-Responsive Drug Carrier. J. Solid State Chem. 2016, 237, 307–312. DOI: 10.1016/j.jssc.2016.02.040.
   Web of Science ®Google Scholar
• Wu, X. L.; Kim, J. H.; Koo, H.; Bae, S. M.; Shin, H.; Kim, M. S.; Lee, B.-H.; Park, R.-W.; Kim, I.-S.; Choi, K.; et al. Tumor-Targeting Peptide Conjugated pH-Responsive Micelles as a Potential Drug Carrier for Cancer Therapy. Bioconjug. Chem. 2010, 21, 208–213. DOI: 10.1021/bc9005283.
   PubMed Web of Science ®Google Scholar
• Jiang, Z.; Xia, D.; Li, Y.; Li, J.; Li, Q.; Chen, M.; Huang, Y.; Besenbacher, F.; Dong, M. Facilitating the Mechanical Properties of a High-Performance pH-Sensitive Membrane by Cross-Linking Graphene Oxide and Polyacrylic Acid. Nanotechnology 2013, 24, 335704–335709. DOI: 10.1088/0957-4484/24/33/335704.
   PubMed Web of Science ®Google Scholar
• Robertson, J. D.; Yealland, G.; Avila-Olias, M.; Chierico, L.; Bandmann, O.; Renshaw, S. A.; Battaglia, G. pH-Sensitive Tubular Polymersomes: Formation and Applications in Cellular Delivery. Acs Nano 2014, 8, 4650–4661. DOI: 10.1021/nn5004088.
   PubMed Web of Science ®Google Scholar
• Chen, Z.; Xu, L.; Liang, Y.; Zhao, M. pH-Sensitive Water-Soluble Nanospheric Imprinted Hydrogels Prepared as Horseradish Peroxidase Mimetic Enzymes. Adv. Mater. 2009, 22, 1488–1492. DOI: 10.1002/adma.200903122.
   Web of Science ®Google Scholar
• Dong, Z.; Wang, Q.; Du, Y. Alginate/Gelatin Blend Films and Their Properties for Drug Controlled Release. J. Membr. Sci. 2006, 280, 37–44. DOI: 10.1016/j.memsci.2006.01.002.
   Web of Science ®Google Scholar
• Zhou, Y.; Yin, X.; Chen, J.; Feng, D.; Zhu, L. Encapsulation Efficiency and Release of Citral Using Methylcellulose as Emulsifier and Interior Wall Material in Composite Polysaccharide Microcapsules. Adv. Polym. Technol. 2018, 37, 1–11.
   Web of Science ®Google Scholar
• Bakand, S.; Hayes, A.; Winder, C. An Integrated in Vitro Approach for Toxicity Testing of Airborne Contaminants. J. Toxicol. Environ. Health, Part A 2007, 70, 1604–1612. DOI: 10.1080/15287390701434604.
   PubMed Web of Science ®Google Scholar
• Gruenheid, S.; Moual, H. L. Resistance to Antimicrobial Peptides in Gram-Negative Bacteria. Fems Microbiol. Lett. 2012, 330, 81–89. DOI: 10.1111/j.1574-6968.2012.02528.x.
   PubMed Web of Science ®Google Scholar
• Egan, L. J.; Sandborn, W. J.; Mays, D. C.; Tremaine, W. J.; Lipsky, J. J. Dialysis of the Rectum for Sampling Drug Concentrations in the Luminal Extracellular Fluid of the Gut: Technique and Precision. Aliment. Pharmacol. Ther. 1998, 12, 679–684. DOI: 10.1046/j.1365-2036.1998.00352.x.
   PubMed Web of Science ®Google Scholar
• Haque, M. A.; Chen, J.; Aldred, P.; Adhikari, B. Drying and Denaturation Characteristics of Whey Protein Isolate in the Presence of Lactose and Trehalose. Food Chem. 2015, 177, 8–16. DOI: 10.1016/j.foodchem.2014.12.064.
   PubMed Web of Science ®Google Scholar
• Danafar, H.; Rostamizadeh, K.; Hamidi, M. Polylactide/Poly(Ethylene Glycol)/Polylactide Triblock Copolymer Micelles as Carrier for Delivery of Hydrophilic and Hydrophobic Drugs: A Comparison Study. J. Pharm. Invest. 2017, 48, 1–11.
   Google Scholar
• Li, G.; Song, S.; Zhang, T.; Qi, M.; Liu, J. pH-Sensitive Polyelectrolyte Complex Micelles Assembled from CS-g-PNIPAM and ALG-g-P(NIPAM-co-NVP) for Drug Delivery. Int. J. Biol. Macromol. 2013, 62, 203–210. DOI: 10.1016/j.ijbiomac.2013.08.041.
   PubMed Web of Science ®Google Scholar
• Villa, N. M.; Gonçalves, M. C.; Nogueira, A. C.; Herculano, L. S.; Medina, A. N.; Bazotte, R. B.; Bruschi, M. L. Formulation Characterization, Of Ethylcellulose Microparticles Containing. l-Alanyl- l-Glutamine Peptide. Drug Dev. Ind. Pharm. 2014, 40, 1308–1317. DOI: 10.3109/03639045.2013.817417.
   PubMed Web of Science ®Google Scholar
• Bao, W.; Zhou, J.; Luo, J.; Wu, D. PLGA Microspheres with High Drug Loading and High Encapsulation Efficiency Prepared by a Novel Solvent Evaporation Technique. J. Microencapsul. 2006, 23, 471–479. DOI: 10.1080/02652040600687613.
   PubMed Web of Science ®Google Scholar
• Rogers, T. L.; Wallick, D. Reviewing the Use of Ethylcellulose, Methylcellulose and Hypromellose in Microencapsulation. Part 1: Materials Used to Formulate Microcapsules. Drug Dev. Ind. Pharm. 2012, 38, 129–157. DOI: 10.3109/03639045.2011.590990.
   PubMed Web of Science ®Google Scholar
• Zugasti, M. E.; Zornoza, A.; Goñi, M. M.; Isasi, J. R.; Vélaz, I.; Martín, C.; Sánchez, M.; Martínez-Ohárriz, M. C. Influence of Soluble and Insoluble Cyclodextrin Polymers on Drug Release from Hydroxypropyl Methylcellulose Tablets. Drug Dev. Ind. Pharm. 2009, 35, 1264–1270. DOI: 10.1080/03639040902882306.
   PubMed Web of Science ®Google Scholar
• Roy, H.; Brahma, C. K.; Nandi, S.; Parida, K. R. Formulation and Design of Sustained Release Matrix Tablets of Metformin Hydrochloride: Influence of Hypromellose and Polyacrylate Polymers. Int. J. App. Basic Med. Res. 2013, 3, 55–63. DOI: 10.4103/2229-516X.112242.
   PubMedGoogle Scholar
• Khanal, B. K. S.; Bhandari, B.; Prakash, S.; Liu, D.; Zhou, P.; Bansal, N. Modifying Textural and Microstructural Properties of Low Fat Cheddar Cheese Using Sodium Alginate. Food Hydrocolloids 2018, 83, 97–108. DOI: 10.1016/j.foodhyd.2018.03.015.
   Web of Science ®Google Scholar
• Li, X.; Wang, L.; Wang, B. Optimization of Encapsulation Efficiency and Average Particle Size of Hohenbuehelia Serotina Polysaccharides Nanoemulsions Using Response Surface Methodology. Food Chem. 2017, 229, 479–486. DOI: 10.1016/j.foodchem.2017.02.051.
   PubMed Web of Science ®Google Scholar
• Chen, H.; Clarkson, B. H.; Sun, K.; Mansfield, J. F. Self-Assembly of Synthetic Hydroxyapatite Nanorods into an Enamel Prism-like Structure. J. Colloid Interface Sci. 2005, 288, 97–103. DOI: 10.1016/j.jcis.2005.02.064.
   PubMed Web of Science ®Google Scholar
• Thomas, R. J. Particle Size and Pathogenicity in the Respiratory Tract. Virulence 2013, 4, 847–858. DOI: 10.4161/viru.27172.
   PubMed Web of Science ®Google Scholar
• Xie, Y.; Wang, A.; Lu, Q.; Hui, M. The Effects of Rheological Properties of Wall Materials on Morphology and Particle Size Distribution of Microcapsule. Czech J. Food Sci. 2010, 28, 433–439. DOI: 10.17221/49/2009-CJFS.
   Web of Science ®Google Scholar
• Katsoufidou, K.; Yiantsios, S. G.; Karabelas, A. J. An Experimental Study of UF Membrane Fouling by Humic Acid and Sodium Alginate Solutions: The Effect of Backwashing on Flux Recovery. Desalination 2008, 220, 214–227. DOI: 10.1016/j.desal.2007.02.038.
   Web of Science ®Google Scholar
• Giri, I. C.; Sharma, A. K.; Bhanja, S. B.; Ellaiah, P.; Murthy, K. V. R.; Das, D. Preparation and in-Vitro Evaluation of Mucoadhesive Microcapsules of Acyclovir. Int. J. Pharm. Sci. Rev. Res. 2010, 5, 18–24.
   Google Scholar
• Johnson, I. M.; Prakash, H.; Prathiba, J.; Raghunathan, R.; Malathi, R. Spectral Analysis of Naturally Occurring Methylxanthines (Theophylline, Theobromine and Caffeine) Binding with DNA. PLoS One 2012, 7, 1–11.
   Web of Science ®Google Scholar
• Indian herbal Pharmacopoeia. Indian Herbal Pharmacopoeia, Revised New Edition. Indian Drug Manufacturers Association, Mumbai, India, 2002.
   Google Scholar
• Hashino, M.; Katagiri, T.; Kubota, N.; Ohmukai, Y.; Maruyama, T.; Matsuyama, H. Effect of Membrane Surface Morphology on Membrane Fouling with Sodium Alginate. J. Membr. Sci. 2011, 366, 258–265. DOI: 10.1016/j.memsci.2010.10.014.
   Web of Science ®Google Scholar
• Xu, F.; Qiu, S.; Liang, J.; Wu, R.; Sun, L.; Li, F. Low Temperature Heat Capacity and Thermal Analysis of Caffeine, Theophylline and Aminophylline. Acta Phys-Chim. Sin. 2010, 26, 2096–2102.
   Web of Science ®Google Scholar
• Li, W. Studies on the Thermal Kinetics of Thermal Decomposition and Stability of Macrolide Drugs. Chin. J. Pharm. Anal. 2010, 30, 1544–1547.
   Google Scholar
• Filho, G. R.; de Assunção, R. M. N.; Vieira, J. G.; Meireles, C. d S.; Cerqueira, D. A.; da Silva Barud, H.; Ribeiro, S. J. L.; Messaddeq, Y. Characterization of Methylcellulose Produced from Sugar Cane Bagasse Cellulose: Crystallinity and Thermal Properties. Polym. Degrad. Stab. 2007, 92, 205–210. DOI: 10.1016/j.polymdegradstab.2006.11.008.
   Web of Science ®Google Scholar
• Said, A. A.; Hassan, R. M. Thermal Decomposition of Some Divalent Metal Alginate Gel Compounds. Polym. Degrad. Stab. 1993, 39, 393–397. DOI: 10.1016/0141-3910(93)90015-B.
   Web of Science ®Google Scholar
• Guilherme, M. R.; Moura, M. R.; Radovanovic, E.; Geuskens, G.; Rubira, A. F.; Muniz, E. C. Novel Thermo-Responsive Membranes Composed of Interpenetrated Polymer Networks of Alginate-Ca2+, and Poly(N-Isopropylacrylamide). Polymer 2005, 46, 2668–2674. DOI: 10.1016/j.polymer.2005.01.082.
   Web of Science ®Google Scholar
• Jing, L.; Zhao, X. Preparation of Compound Vitamin Microcapsules Using Cross-Linked Gelatin as Wall Material. Chin. Pharm. J. 2013, 48, 888–893.
   Google Scholar
• Yang, X.; Wang, Y.; Huang, X.; Ma, Y.; Huang, Y.; Yang, R.; Duan, H.; Chen, Y. Multi-Functionalized Graphene Oxide Based Anticancer Drug-Carrier with Dual-Targeting Function and pH-Sensitivity. J. Mater. Chem. 2011, 21, 3448–3454. DOI: 10.1039/C0JM02494E.
   Web of Science ®Google Scholar
• Yamasaki, O.; Akiyama, H.; Toi, Y.; Arata, J. A Combination of Roxithromycin and Imipenem as an Antimicrobial Strategy against Biofilms Formed by Staphylococcus aureus. J. Antimicrob. Chemother. 2001, 48, 573–577. DOI: 10.1093/jac/48.4.573.
   PubMed Web of Science ®Google Scholar
• Zheng, S.; Xiao, Z.; Pan, Y.; Han, M.; Dong, Q. Continuous Release of Interleukin 12 from Microencapsulated Engineered Cells for Colon Cancer Therapy. WJG. 2003, 9, 951–955. DOI: 10.3748/wjg.v9.i5.951.
   PubMed Web of Science ®Google Scholar