Injectable Supramolecular Hydrogel from Insulin-Loaded Triblock PCL-PEG-PCL Copolymer and γ-Cyclodextrin with Sustained-Release Property

AAPS PharmSciTech

Volumn 16, Issue 1, 2014, Pages 140-149

  Khodaverdi, Elham ^a,b   Heidari, Zinat ^a,b   Tabassi, Sayyed A Sajadi ^a,b   Tafaghodi, Mohsen ^a   Alibolandi, Mona ^b   Tekie, Farnaz Sadat Mirzazadeh ^c   Khameneh, Bahman ^b   Hadizadeh, Farzin ^b  

^a MASHHAD UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^b MASHHAD UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^c TEHRAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

Author keywords

insulin; PCL PEG PCL; supramolecular hydrogel; triblock copolymer; CD

Indexed keywords

8 ANILINO 1 NAPHTHALENESULFONIC ACID; COPOLYMER; GAMMA CYCLODEXTRIN; INSULIN; MACROGOL; POLYCAPROLACTONE; DELAYED RELEASE FORMULATION; GAMMA CYCLODEXTRIN DERIVATIVE; GAMMA-CYCLODEXTRIN; HYDROGEL; MACROGOL DERIVATIVE; MACROMOLECULE; POLY(EPSILON-CAPROLACTONE)-B-POLY(ETHYLENEGLYCOL)-B-POLY(EPSILON-CAPROLACTONE); POLYESTER;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL STRUCTURE; CIRCULAR DICHROISM; COMPLEX FORMATION; DIFFERENTIAL SCANNING CALORIMETRY; DRUG STABILITY; ENCAPSULATION; GEL PERMEATION CHROMATOGRAPHY; GELATION; HYDROGEL; HYDROPHOBICITY; IN VITRO STUDY; INSULIN RELEASE; MICROWAVE IRRADIATION; POLYMERIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING; SCANNING ELECTRON MICROSCOPY; SUSTAINED DRUG RELEASE; SYNTHESIS; X RAY POWDER DIFFRACTION; ADMINISTRATION AND DOSAGE; CHEMISTRY; DELAYED RELEASE FORMULATION; DIFFUSION; DRUG FORMULATION; INJECTION; MACROMOLECULE; PROCEDURES;

DELAYED-ACTION PREPARATIONS; DIFFUSION; DRUG COMPOUNDING; DRUG STABILITY; GAMMA-CYCLODEXTRINS; HYDROGELS; INJECTIONS; INSULIN; MACROMOLECULAR SUBSTANCES; POLYESTERS; POLYETHYLENE GLYCOLS;

EID: 84922068622     PISSN: None     EISSN: 15309932     Source Type: Journal    
DOI: 10.1208/s12249-014-0198-4     Document Type: Article

References (43)

1. Li J. Self-assembled supramolecular hydrogels based on polymer–cyclodextrin inclusion complexes for drug delivery. NPG Asia Mater. 2010;2(3):112–8.
2. Bromberg LE, Ron ES. Temperature-responsive gels and thermogelling polymer matrices for protein and peptide delivery. Adv Drug Deliv Rev. 1998;31(3):197–221.
3. Bender ML, Komiyama M. Cyclodextrin chemistry. Berlin: Springer; 1978.
4. Harada A, Li J, Kamachi M. Double-stranded inclusion complexes of cyclodextrin threaded on poly (ethylene glycol). Nature. 1994;370(6485):126–8.
5. Li J, Harada A, Kamachi M. Sol–gel transition during inclusion complex formation between α-cyclodextrin and high molecular weight poly (ethylene glycol) s in aqueous solution. Polym J. 1994;26(9):1019–26.
6. Li J, Ni X, Leong KW. Injectable drug-delivery systems based on supramolecular hydrogels formed by poly (ethylene oxide) s and α-cyclodextrin. J Biomed Mater Res A. 2003;65(2):196–202.
7. Harada A, Li J, Kamachi M. The molecular necklace: a rotaxane containing many threaded α-cyclodextrins. Nature. 1992;356(6367):325–7.
8. Li J, Li X, Toh KC, Ni X, Zhou Z, Leong KW. Inclusion complexation and formation of polypseudorotaxanes between poly [(ethylene oxide)-r an-(propylene oxide)] and cyclodextrins. Macromolecules. 2001;34(26):8829–31.
9. Huh KM, Cho YW, Chung H, Kwon IC, Jeong SY, Ooya T, et al. Supramolecular hydrogel formation based on inclusion complexation between poly (ethylene glycol)-modified chitosan and α-cyclodextrin. Macromol Biosci. 2004;4(2):92–9.
10. Higashi T, Hirayama F, Misumi S, Arima H, Uekama K. Design and evaluation of polypseudorotaxanes of pegylated insulin with cyclodextrins as sustained release system. Biomaterials. 2008;29(28):3866–71.
11. Ma D, Zhang H-B, Chen D-H, Zhang L-M. Novel supramolecular gelation route to in situ entrapment and sustained delivery of plasmid DNA. J Colloid Interface Sci. 2011;364(2):566–73.
12. Prabaharan M, Mano J. Chitosan derivatives bearing cyclodextrin cavitiesas novel adsorbent matrices. Carbohydr Polym. 2006;63(2):153–66.
13. Ganta S, Devalapally H, Shahiwala A, Amiji M. A review of stimuli-responsive nanocarriers for drug and gene delivery. J Control Release. 2008;126(3):187–204.
14. Li J, Li X, Ni X, Wang X, Li H, Leong KW. Self-assembled supramolecular hydrogels formed by biodegradable PEO–PHB–PEO triblock copolymers and α-cyclodextrin for controlled drug delivery. Biomaterials. 2006;27(22):4132–40.
15. Vyas A, Saraf S, Saraf S. Cyclodextrin based novel drug delivery systems. J Incl Phenom Macrocycl Chem. 2008;62(1–2):23–42.
16. Yu J, Fan H, Huang J, Chen J. Fabrication and evaluation of reduction-sensitive supramolecular hydrogel based on cyclodextrin/polymer inclusion for injectable drug-carrier application. Soft Matter. 2011;7(16):7386–94.
17. Harries M, Smith I. The development and clinical use of trastuzumab (Herceptin). Endocr-Relat Cancer. 2002;9(2):75–85.
18. Kerbel R, Folkman J. Clinical translation of angiogenesis inhibitors. Nat Rev Cancer. 2002;2(10):727–39.
19. Marshall H. Anti-CD20 antibody therapy is highly effective in the treatment of follicular lymphoma. Trends Immunol. 2001;22(4):183–4.
20. McCarthy AA. New approaches to diabetes disease control, insulin delivery, and monitoring. Chem Biol. 2004;11(12):1597–8.
21. Banting F, Best CH, Collip JB, Campbell WR, Fletcher AA. Pancreatic extracts in the treatment of diabetes mellitus. Can Med Assoc J. 1922;12(3):141.
22. Onuki Y, Morishita M, Takayama K. Formulation optimization of water-in-oil-water multiple emulsion for intestinal insulin delivery. J Control Release. 2004;97(1):91–9.
23. Takenaga M, Yamaguchi Y, Kitagawa A, Ogawa Y, Kawai S, Mizushima Y, et al. Optimum formulation for sustained-release insulin. Int J Pharm. 2004;271(1):85–94.
24. Takenaga M, Yamaguchi Y, Kitagawa A, Ogawa Y, Mizushima Y, Igarashi R. A novel sustained-release formulation of insulin with dramatic reduction in initial rapid release. J Control Release. 2002;79(1):81–91.
25. Hoare T, Pelton R. Charge-switching, amphoteric glucose-responsive microgels with physiological swelling activity. Biomacromolecules. 2008;9(2):733–40.
26. Lin C-C, Metters AT. Hydrogels in controlled release formulations: network design and mathematical modeling. Adv Drug Deliv Rev. 2006;58(12):1379–408.
27. van Dijk‐Wolthuis W, Van Steenbergen M, Underberg W, Hennink W. Degradation kinetics of methacrylated dextrans in aqueous solution. J Pharm Sci. 1997;86(4):413–7.
28. Irie T, Uekama K. Pharmaceutical applications of cyclodextrins. III. Toxicological issues and safety evaluation. J Pharm Sci. 1997;86(2):147–62.
29. Khodaverdi A, Akbari A, Tekie FSM, Mohajeri SA, Zohuri G, Hadizadeh F. Sustained delivery of amphotericin B and vancomycin hydrochloride by an injectable thermogelling tri-block copolymer. PDA J Pharm Sci Technol. 2013. doi:10.5731/pdajpst.2013.00908.
30. Jeong B, Choi Y, Bae Y, Zentner G, Kim S. New biodegradable polymers for injectable drug delivery systems. J Control Release. 1999;62(1):109–14.
31. Abu Hashim II, Higashi T, Anno T, Motoyama K, Abd-ElGawad A-EH, El-Shabouri MH, et al. Potential use of γ-cyclodextrin polypseudorotaxane hydrogels as an injectable sustained release system for insulin. Int J Pharm. 2010;392(1):83–91.
32. Khodaverdi E, Rajabi O, Farhadi F, Jalali A, Mirzazadeh TF. Preparation and investigation of poly (N-isopropylacrylamide-acrylamide) membranes in temperature responsive drug delivery. Iran J Basic Med Sci. 2010;13(3):102–10.
33. Bradford MM. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem. 1976;72(1):248–54.
34. Li X, Li J. Supramolecular hydrogels based on inclusion complexation between poly (ethylene oxide)‐b‐poly (ε‐caprolactone) diblock copolymer and α-cyclodextrin and their controlled release property. J Biomed Mater Res A. 2008;86(4):1055–61.
35. Masaro L, Zhu X. Physical models of diffusion for polymer solutions, gels and solids. Prog Polym Sci. 1999;24(5):731–75.
36. Möckel JE, Lippold BC. Zero-order drug release from hydrocolloid matrices. Pharm Res. 1993;10(7):1066–70.
37. Sarkar P, Bharill S, Gryczynski I, Gryczynski Z, Nair MP, Lacko AG. Binding of 8-anilino-1-naphthalenesulfonate to lecithin: cholesterol acyltransferase studied by fluorescence techniques. J Photochem Photobiol B Biol. 2008;92(1):19–23.
38. Hoogenboom R, Schubert US. Microwave-assisted polymer synthesis: recent developments in a rapidly expanding field of research. Macromol Rapid Commun. 2007;28(4):368–86.
39. Sosnik A, Gotelli G, Abraham GA. Microwave-assisted polymer synthesis (MAPS) as a tool in biomaterials science: how new and how powerful. Prog Polym Sci. 2011;36(8):1050–78.
40. Zhao S-P, Zhang L-M, Ma D. Supramolecular hydrogels induced rapidly by inclusion complexation of poly(epsilon-caprolactone)-poly(ethylene glycol)-poly(epsilon-caprolactone) block copolymers with alpha-cyclodextrin in aqueous solutions. J Phys Chem B. 2006;110(25):12225–9.
41. Ni X, Cheng A, Li J. Supramolecular hydrogels based on self-assembly between PEO-PPO-PEO triblock copolymers and α-cyclodextrin. J Biomed Mater Res A. 2009;88(4):1031–6.
42. Kopecek J. Hydrogels: from soft contact lenses and implants to self-assembled nanomaterials. J Polym Sci A Polym Chem. 2009;47(22):5929–46.
43. Khodaverdi E, Tekie FSM, Mohajeri SA, Ganji F, Zohuri G, Hadizadeh F. Preparation and investigation of sustained drug delivery systems using an injectable, thermosensitive, in situ forming hydrogel composed of PLGA–PEG–PLGA. AAPS PharmSciTech. 2012;13(2):590–600.