Abstract
The thermal and thermooxidative behavior of sodium salt of hyaluronic acid (HA) and its n-hexyl, n-decyl, n-tetradecyl and n-hexadecyl ether derivatives having an equal degree of substitution have been studied by means of differential scanning calorimetry (DSC) and thermogravimetry (TG). Derivatives were prepared by a substitution of H atom at the OH bound to the sixth C of N-acetyl-D-glucosamin of HA unit by n-hexyl, n-decyl, n-tetradecyl and n-hexadecyl chains. Both thermal and thermooxidative degradation of HA and derivatives resulted in multistep process. The main interest of this work was focused on processes occurring in the course of the first decomposition step. Experimental DSC data showed lower stability of derivatives and, remarkably lower heat evolution in comparison with original HA. On the other hand, TG measurement recorded lower mass loss for derivates which indicated appearance of new types of crosslinking reactions. Oxidative stability was evaluated by means of DSC that provided the induction period and the protection factor determination. Derivates showed remarkably lower stability in comparison with original HA; comparing each other, the highest oxidation stability showed n-decyl and n-tetradecyl derivates.
Similar content being viewed by others
References
K Meyer JW Palmer (1934) J. Biol. Chem. 107 629 Occurrence Handle1:CAS:528:DyaA2MXhs12kug%3D%3D
V. C. Hascall, in Biology of Carbohydrates, V.Ginsburg and P. Robbins (Eds), 1981, p. 1.
L Roden (1980) Biochemistry of Glycoproteins and Proteoglycans Plenum New York 267
NE Larsen EA Balazs (1991) Adv. Drug Delivery Rev. 7 279 Occurrence Handle10.1016/0169-409X(91)90007-Y Occurrence Handle1:CAS:528:DyaK3MXmvVKqu7g%3D
RE Fraser TC Laurent UBG Laurent (1997) J. Intern. Med. 27 242
L Lapčík Jr. J Schurz (1991) Colloid Polym. Sci. 269 633
L. Lapčík Jr., in Symposium of biomedical engineering and biotechnology, Prague 1994, p. 10.
L Lapčík Jr. L Lapčík S De Smedt J Demeester P Chabreček (1998) Chem. Review 98 2663
GD Prestwich KP Vercruysse (1998) Crit. Rev. Ther. Drug Carrier Syst. 15 513
EA Balazs JL Denlinger (1989) Ciba Found Symp. 143 265 Occurrence Handle1:STN:280:By%2BD3s3gs10%3D
RN Rosier RJ O'Keefe (2000) Instr. Course Lect. 49 495 Occurrence Handle1:STN:280:DC%2BD3cvhtlKqtA%3D%3D
D Campoccia P Doherty M Radice P Brun G Abatangelo DF Williams (1998) Biomaterials 19 2101 Occurrence Handle10.1016/S0142-9612(98)00042-8 Occurrence Handle1:CAS:528:DyaK1MXktVKh
KP Vercruysse DM Marecak JF Marecek GD Prestwich (1997) Bioconjug. Chem. 8 686 Occurrence Handle10.1021/bc9701095 Occurrence Handle1:CAS:528:DyaK2sXlslGmsLk%3D
P Bulpitt D Aeschlimann (1999) J. Biomed. Mater. Res. 47 152 Occurrence Handle10.1002/(SICI)1097-4636(199911)47:2<152::AID-JBM5>3.0.CO;2-I Occurrence Handle1:CAS:528:DyaK1MXmtVant7w%3D
Y Luo KR Kirker GD Prestwich (2000) J. Control Release 69 169 Occurrence Handle10.1016/S0168-3659(00)00300-X Occurrence Handle1:CAS:528:DC%2BD3cXmvFOrs7w%3D
XZ Shu Y Liu Y Luo MC Roberts GD Prestwich (2002) Biomacromolecules 3 1304 Occurrence Handle10.1021/bm025603c Occurrence Handle1:CAS:528:DC%2BD38XntlaitrY%3D
YD Park N Tirelli JA Hubbell (2003) Biomaterials 24 893 Occurrence Handle1:CAS:528:DC%2BD38Xps1Onu78%3D
A Ramamurthi I Vesely (2002) J. Biomed. Mater. Res. 60 195 Occurrence Handle10.1002/jbm.10061
K Tomihata Y Ikada (1997) Biomaterials 18 189 Occurrence Handle1:CAS:528:DyaK2sXhtVansL0%3D
JR Glass KT Dickerson K Stecker JW Polarek (1996) Biomaterials 17 1101 Occurrence Handle10.1016/0142-9612(96)85911-4 Occurrence Handle1:CAS:528:DyaK28Xjtl2rs74%3D
A Ramamurthi I Vesely (2003) J. Biomed. Mater. Res. 66A 317 Occurrence Handle10.1002/jbm.a.10588 Occurrence Handle1:CAS:528:DC%2BD3sXmtlyqsrc%3D
K. Benešová, Structure and properties of hyaluronic acid and its derivatization. Diploma Thesis, BUT FCH Brno 1998, in Czech.
P. Kmínková, Synthesis and physical-chemical characterization of alkyl (C6) derivates of hyaluronic acids, Diploma Thesis, BUT FCH Brno 1998, in Czech.
L. Lapčík and M. Veselý, Chemistry Workshop 95, Prague, 1995, p 121.
MA Villetti JS Crespo MS Soldi ATN Pires R Borsali V Soldi (2002) J. Therm. Anal. Cal. 67 295 Occurrence Handle10.1023/A:1013902510952 Occurrence Handle1:CAS:528:DC%2BD38Xit1Cmsr4%3D
P Šimon A Kučma (1999) J. Therm. Anal. Cal. 56 1107
J March (1985) Advanced Organic Chemistry. Reactions, Mechanisms and Structure John Wiley New York
RA Johnstone ME Rose (1979) Tetrahedron 35 2169 Occurrence Handle10.1016/0040-4020(79)87035-0 Occurrence Handle1:CAS:528:DyaL3cXksVKitrg%3D
P Šimon M Veverka J Okuliar (2004) J. Int. Pharm. 270 21
JE Sealey G Samaranayake JG Todd WG Glasser (1996) J. Polym. Sci. Part B, Polym. Phys. 34 1613 Occurrence Handle10.1002/(SICI)1099-0488(19960715)34:9<1613::AID-POLB10>3.0.CO;2-A Occurrence Handle1:CAS:528:DyaK28XjslKgtrw%3D
Y Tokita K Oshima A Okamoto (1997) Polym. Degrad. Stab. 55 159 Occurrence Handle1:CAS:528:DyaK2sXht1ehtL4%3D
F Heatley JE Scott (1988) Biochem. J. 254 489 Occurrence Handle1:CAS:528:DyaL1cXlsVCqsL4%3D
JE Scott C Cummings A Brass Y Chen (1991) Biochem. J. 274 699 Occurrence Handle1:CAS:528:DyaK3MXhvVSktrk%3D
P Jandura B Riedl BV Kokta (2000) Polym. Degrad. Stab. 70 387 Occurrence Handle1:CAS:528:DC%2BD3cXosV2mtb8%3D
BW Hopkins GS Tschumper (2004) J. Phys. Chem. Part A 108 2941 Occurrence Handle1:CAS:528:DC%2BD2cXhtVyltL4%3D
RP Schwarzenbach PM Gschwend DM Imboden (1993) Environmental Organic Chemistry Wiley New York
P Buurman B van Lagen A Piccolo (2002) Org. Geochem. 33 367 Occurrence Handle10.1016/S0146-6380(01)00167-X Occurrence Handle1:CAS:528:DC%2BD38XhtlCqu7c%3D
J Kučerík J Kovář M Pekař (2004) J. Therm. Anal. Cal. 76 55
P Šimon (2004) J. Therm. Anal. Cal. 76 123
Z Cibulková P Šimon P Lehocký J Balko (2005) Polym. Degrad. Stab. 87 479
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Benešová, K., Pekař, M., Lapčík, L. et al. Stability evaluation of n-alkyl hyaluronic acid derivates by DSC and TG measurement . J Therm Anal Calorim 83, 341–348 (2006). https://doi.org/10.1007/s10973-005-6870-x
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10973-005-6870-x