Nano-network with dual temperature and pH responsiveness based on copolymers of 2-hydroxyethyl methacrylate with 3,9-divinyl-2,4,8,10- tetraoxaspiro[5.5]-undecane

Journal of Nanoparticle Research

Volumn 13, Issue 12, 2011, Pages 6953-6962

  Chiriac, Aurica P ^a   Nita, Loredana E ^a   Nistor, Manuela T ^a  

^a PETRU PONI INSTITUTE OF MACROMOLECULAR CHEMISTRY   (Romania)

Author keywords

3,9 Divinyl 2,4,8,10 tetraoxaspiro 5.5 undecane; Emulsion polymerization; Hydroxyethyl methacrylate; Nano network; Nanoscale sensor; Temperature and pH sensitivity

Indexed keywords

2-HYDROXYETHYL METHACRYLATE; 3,9-DIVINYL-2,4,8,10-TETRAOXASPIRO [5.5]-UNDECANE; CO-MONOMER; COMONOMERS; FTIR; HYDRODYNAMIC RADIUS; HYDROXYETHYL METHACRYLATE; NANONETWORK; NANOSCALE SENSORS; PARTICLE HYDRODYNAMICS; PARTICLES SIZES; POLYMERIC PARTICLES; SODIUM LAURYL SULFATES;

BUTADIENE; EMULSION POLYMERIZATION; HYDRODYNAMICS; THERMOANALYSIS; ZETA POTENTIAL;

COPOLYMERS;

2 HYDROXYETHYLMETHACRYLIC ACID; 3,9 DIVINYL 2,4,8,10 TETRAOXASPIRO[5.5]UNDECANE; ALKANE DERIVATIVE; COPOLYMER; DODECYL SULFATE SODIUM; METHACRYLIC ACID DERIVATIVE; MONOMER; NANOPARTICLE; POLYVINYL ALCOHOL; UNCLASSIFIED DRUG; VALERIC ACID DERIVATIVE;

ARTICLE; COLLOID; CONDUCTANCE; CROSS LINKING; EMULSION; HYDRODYNAMICS; INFRARED SPECTROSCOPY; PARTICLE SIZE; PH; POLYMERIZATION; PRIORITY JOURNAL; SCANNING ELECTRON MICROSCOPY; SYNTHESIS; TEMPERATURE; THERMOGRAVIMETRY; X RAY DIFFRACTION; ZETA POTENTIAL;

EID: 84856882047     PISSN: 13880764     EISSN: 1572896X     Source Type: Journal    
DOI: 10.1007/s11051-011-0605-7     Document Type: Article

References (54)

1. Akihiko K, Teruo O (2002) Intelligent thermoresponsive polymeric stationary phases for aqueous chromatography of biological compounds. Prog Polym Sci 27:1165-1193
2. Ali AMI, Tauer K, Sedlak M (2005) Comparing emulsion polymerization of methacrylate-monomers with different hydrophilicity. Polymer 46:1017-1023
3. Bae Y, Jang W, Nishiyama N, Fukushima S, Kataoka K (2005) Multi-functional polymeric micelles with folate-mediated cancer cell targeting and pH-triggered drug releasing properties for active intracellular drug delivery. Mol Bio-syst 1:242-250 (Pubitemid 41442434)
4. Bailey WJ, Iwama H, Tsushima R (1976) Synthesis of elastomers by cationic polymerization with expansion in volume. J Polym Sci Symp 56:117-127 (Pubitemid 8551240)
5. Bajpai AK, Shukla SK, Bhanu S, Kankane S (2008) Responsive polymers in controlled drug delivery. Prog Polym Sci 33: 1088-1118
6. Borisov OV, Zhulina EB (2005) Reentrant morphological transitions in copolymer micelles with pH-sensitive corona. Langmuir 21:3229-3231 (Pubitemid 40538329)
7. Bose RK, Lau KKS (2009) Initiated CVD of poly (2-hydroxy-ethyl methacrylate) hydrogels: synthesis, characterization and in vitro biocompatibility. Chem Vap Deposit 15: 150-155
8. Brahim S, Narinesingh D, Elie AG (2001) Anal Chim Acta 448: 27-36
9. Capps DB (1959) US Pat 2, 889, 290, 2 June 1959
10. Chiriac AP, Nita LE, Nistor M (2011) Copolymerization of 2-hydroxyethyl methacrylate with a comonomer with spi-roacetal moiety. J Pol Sci A Pol Chem 49:1543-1551
11. Chu HH, Fu DC (1998) Preparation of poly (hydroxyethyl methacrylate) and poly (hydroxypropyl methacrylate) lattices. Macromol Rapid Commun 19:107-110
12. Chu HH, Lin CS (2003) The effect of initiators on the emulsion polymerization of 2-hydroxyethyl methacrylate. J Polym Res 10:283-287
13. Cramer CJ, Truhlar DG, French AD (1997) Exo-anomeric effects on energies and geometries of different conformations of glucose and related systems in the gas phase and aqueous solution. Carbohydr Res 298:1-14 (Pubitemid 27083686)
14. Ebara M, Yamato M, Hirose M, Aoyagi T, Kikuchi A, Sakai K (2003) Copolymerization of 2-carboxyisopropylacryla mide with N-isopropylacrylamide accelerates cell detachment from grafted surfaces of reducing temperature. Bio-macromolecules 4:344-349 (Pubitemid 36527105)
15. Fang L, Urban MW (2010) Recent advances and challenges in designing stimuli-responsive polymers. Prog Polym Sci 35: 3-23
16. Favre S, Vogel P, Gerber-Lemaire S (2008) Recent synthetic approaches toward non-anomeric spiroketals in natural products. Molecules 13:2570-2600
17. 2OH (m = 1-4): the role of the CH···O intermolecular interactions. J Phys Chem 99:8066-8070
18. Hachułka K, Lekkab M, Okrajnic J, Ambroziakc W, Wandelta B (2010) Polymeric sensing system molecularly imprinted towards enhanced adhesion of Saccharomyces cerevisiae. Biosens Bioelectron 26:50-54
19. Horak D, Lednicky F, Rehak V, Svec F (1993) Porous poly (HEMA) beads prepared by suspension polymerization in aqueous medium. J Appl Polym Sci 49:2041-2050
20. Juaristi E (1979) The attractive and repulsive gauche effect. J Chem Educ 56:438-441
21. Juaristi E, Antunez S (1992) Conformational analysis of 5-substituted 1, 3-dioxanes. 6. Study of the attractive gauche effect in O-C-C-O. Tetrahedron 48:5941-5950
22. Kamei S, Okubo M, Matsuda T, Matsumoto T (1986) Adsorption of trypsin onto styrene-2-hydroxyethyl methacrylate copolymer microspheres and its enzymatic activity. Coll Polym Sci 264:743-747 (Pubitemid 17463036)
23. Klaikherd A, Nagamani C, Thayumanavan S (2009) Multi-stimuli sensitive amphiphilic block copolymer assemblies. J Am Chem Soc 131:4830-4838
24. Kobayashi M, Aoki S, Sakai H, Kawazoe K, Kihara N, Sasaki T, Kitagawa I (1993) Altohyrtin A, a potent anti-tumor macrolide from the Okinawan marine sponge Hyrtios altum. Tetrahedron Lett 34:2795-2798
25. Kok FN, Bozoglu F, Hasirci V (2002) Construction of an acet-ylcholin-esterase/choline oxidase biosensor for aldicarb determination. Biosens Bioelectron 17:531-539 (Pubitemid 34327406)
26. Kulkarni BA, Roth GP, Lobkovsky E, Porco JA (2002) Combinatorial synthesis of natural product-like molecules using a first-generation spiroketal scaffold. J Comb Chem 4: 56-72
27. Landfester K, Willert M, Antonietti M (2000) Macromolecules 33:2370-2376
28. Langer R, Peppas NA (2003) Advances in biomaterials, drug delivery and bionanotechnology. AIChE J 49:2990-3006 (Pubitemid 38009884)
29. Martin G, Jain RK (1994) Noninvasive measurement of interstitial pH profiles in normal and neoplastic tissue using fluorescence ratio imaging microscopy. Cancer Res 54: 5670-5674 (Pubitemid 24346265)
30. Medina-Castillo AL, Fernandez-Sanchez JF, Segura-Carretero A, Fernandez-Gutierrez A (2009) A semi-empirical model to simplify the synthesis of homogeneous and transparent cross-linked polymers and their application in the preparation of optical sensing films. Biosens Bioelectron 25: 442-449
31. Mitsuhashi S, Shima H, Kawamura T, Kikuchi K, Oikawa M, Ichihara A, Oikawa H (1999) The spiroketals containing a benzyloxymethyl moiety at C8 position showed the most potent apoptosis-inducing activity. Bioorg Med Chem Lett 9:2007-2012 (Pubitemid 29336391)
32. Moorea T, Adhikaria R, Gunatillakea P (2005) Chemosynthesis of bioresorbable poly (g-butyrolactone) by ring-opening polymerisation: a review. Biomaterials 26:3771-3782
33. Motornov M, Roiter Y, Tokarev I, Minko S (2010) Stimuli-responsive nanoparticles, nanogels and capsules for integrated multifunctional intelligent systems. Prog Polym Sci 35:174-211
34. Nita LE, Chiriac AP, Nistor MT (2011) Upon the emulsion polymerization of 2-hydroxyethyl methacrylate with 3, 9-divinyl-2, 4, 8, 10-tetraoxaspiro[5.5]- undecane. Coll Surf A 381:111-117
35. Norcross RD, Paterson I (1995) Total synthesis of bioactive marine macrolides. Chem Rev 95:2041-2114
36. O'Hagan D (1991) The polyketide metabolites. Ellis Horwood Ed, Chichester
37. O'Hagan D (1995) Biosynthesis of fatty acid and polyketide metabolites. Nat Prod Rep 12:1-32
38. Okubo M, Yamamoto Y, Kamei S (1989) XPS analysis (ESCA) of the surface composition of poly (styrene/2-hydroxyethyl methacrylate) microspheres produced by emulsifier-free emulsion polymerization. Coll Polym Sci 267:861-865 (Pubitemid 20621117)
39. Paterson I, Gottschling D, Menche D (2005) Towards the combinatorial synthesis of spongistatin fragment libraries by using asymmetric aldol reactions on solid support. Chem Commun 28:3568-3570 (Pubitemid 43338626)
40. Pettit GR, Chicacz ZA, Gao F, Herald CL, Boyd MR, Schmidt JM, Hooper JNA (1993) Antineoplastic agents. 257. Isolation and structure of spongistatin. J Org Chem 58: 1302-1304 (Pubitemid 23138825)
41. Plavec J, Thibaudeau C, Chattopadhyaya J (1996) How do the energetics of the stereoelectronic gauche and anomeric effects modulate the conformation of nucleosides and nucleotides. Pure Appl Chem 68:2137-2144 (Pubitemid 126465455)
42. Rapoport N (2007) Physical stimuli-responsive polymeric micelles for anti-cancer drug delivery. Prog Polym Sci 32: 962-990 (Pubitemid 47198285)
43. Robinson KL, Khan MA, Banez MVD, Wang XS, Armes SP (2001) Controlled polymerization of 2-hydroxyethyl methacrylate by atrp at ambient temperature. Macromole-cules 34:3155-3158 (Pubitemid 34216934)
44. Salamone JC (1996) Polymeric materials, vol 10. Encyclopedia, CRC Press, pp 7854-7858
45. Sasanuma Y, Sugita K (2006) The attractive gauche effect in ethylene oxides. Polym J (Tokyo, Japan) 38:983-988 (Pubitemid 44719788)
46. Schmoljohann D, Oswald J, Jorgensen B, Nitschke M, Beyerlein D, Werner C (2003) Thermo-responsive PNIPAAm-g-PEG films for controlled cell detachment. Biomacromol-ecules 4:1733-1739 (Pubitemid 37455587)
47. Schoonbrood HAS, Aerdts AM, German AL, Vandervelden GPM (1995) Determination of the intra-and intermolecu-lar microstructure of bulk and emulsion copolymers of styrene and 2-hydroxyethyl methacrylate by means of proton nmr and gradient polymer elution chromatography. Macromolecules 28:518-525
48. Shan-Yang L, Yih-Dih C (2000) Simultaneous formation and detection of the reaction product of solid-state aspartame sweetener by FT-IR/DSC microscopic system. Food Addit Contam 17:821-827
49. Tauer K, Kroschwitz JI (2003) Heterophase polymerization, encyclopedia of polymer science and technology. Wiley-Interscience, New York
50. Trapp ML, Watts JK, Weinberg N, Pinto BM (2006) Component analysis of the X-C-Y anomeric effect (X=O, S; Y=F, OMe, NHMe) by DFT molecular orbital calculations and natural bond orbital analysis. Can J Chem 84:692-701 (Pubitemid 44047320)
51. Trump RP, Bartlett PA (2003) Amino acid-derived heterocycles as combinatorial library targets: spirocyclic ketal lactones. J Comb Chem 5:285-291 (Pubitemid 37140575)
52. Vila A, Mosquera RA (2007) Atoms in molecules interpretation of the anomeric effect in the O-CO unit. J Comput Chem 28:1516-1530 (Pubitemid 46853790)
53. Zalar FV (1972) A new spiroacetal polymer. Macromolecules 5:539-541
54. Zefirov NS, Samoshin VV, Subbotin OA, Baranenkov VI, Wolfe S (1978) The gauche effect on the nature of the interactions between electronegative substituents in trans-1, 2-disubstituted cyclohexanes. Tetrahedron 34:2953-2959