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Volumn 98, Issue 2, 2013, Pages 1288-1296

Alginate esters via chemoselective carboxyl group modification

Author keywords

Alginate; Chemoselective; Derivatization; Drug delivery; DS; Enhancement; Esters; Modification; Naringenin; Solubility

Indexed keywords

CHEMOSELECTIVE; DERIVATIZATIONS; DS; MODIFICATION; NARINGENIN;

EID: 84884698634     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2013.08.014     Document Type: Article
Times cited : (55)

References (39)
  • 1
    • 0034658316 scopus 로고    scopus 로고
    • Hydrophobically associating alginate derivatives: Surface tension properties of their mixed aqueous solutions with oppositely charged surfactants
    • DOI 10.1006/jcis.2000.6788
    • V.G. Babak, E.A. Skotnikova, I.G. Lukina, S. Pelletier, P. Hubert, and E. Dellacherie Hydrophobically associating alginate derivatives: Surface tension properties of their mixed aqueous solutions with oppositely charged surfactants Journal of Colloid and Interface Science 225 2000 505 510 (Pubitemid 30313930)
    • (2000) Journal of Colloid and Interface Science , vol.225 , Issue.2 , pp. 505-510
    • Babak, V.G.1    Skotnikova, E.A.2    Lukina, I.G.3    Pelletier, S.4    Hubert, P.5    Dellacherie, E.6
  • 2
    • 0037432066 scopus 로고    scopus 로고
    • Hepatocyte ApoB-containing lipoprotein secretion is decreased by the grapefruit flavonoid, naringenin, via inhibition of MTP-mediated microsomal triglyceride accumulation
    • DOI 10.1021/bi026731o
    • N.M. Borradaile, L.E. de Dreu, P.H. Barrett, C.D. Behrsin, and M.W. Huff Hepatocyte apoB-containing lipoprotein secretion is decreased by the grapefruit flavonoid, naringenin, via inhibition of MTP-mediated microsomal triglyceride accumulation Biochemistry 42 2003 1283 1291 (Pubitemid 36184069)
    • (2003) Biochemistry , vol.42 , Issue.5 , pp. 1283-1291
    • Borradaile, N.M.1    De Dreu, L.E.2    Barrett, P.H.R.3    Behrsin, C.D.4    Huff, M.W.5
  • 3
    • 3142782823 scopus 로고    scopus 로고
    • Biochemical analysis of the processive mechanism for epimerization of alginate by mannuronan C-5 epimerase AlgE4
    • DOI 10.1042/BJ20031265
    • C. Campa, S.v. Holtan, N. Nilsen, T.M. Bjerkan, B.r.T. Stokke, and G. Skjåk-Bræk Biochemical analysis of the processive mechanism for epimerization of alginate by mannuronan C-5 epimerase AlgE4 Biochemical Journal 381 2004 155 164 (Pubitemid 38937048)
    • (2004) Biochemical Journal , vol.381 , Issue.1 , pp. 155-164
    • Campa, C.1    Holtan, S.2    Nilsen, N.3    Bjerkan, T.M.4    Stokke, B.T.5    Skjak-Braek, G.6
  • 4
    • 0025328709 scopus 로고
    • Cloning of Pseudomonas aeruginosa algG, which controls alginate structure
    • C.E. Chitnis, and D.E. Ohman Cloning of Pseudomonas aeruginosa algG, which controls alginate structure Journal of Bacteriology 172 1990 2894 2900 (Pubitemid 20179734)
    • (1990) Journal of Bacteriology , vol.172 , Issue.6 , pp. 2894-2900
    • Chitnis, C.E.1    Ohman, D.E.2
  • 5
    • 67349139611 scopus 로고    scopus 로고
    • Utility of hydroxypropylmethylcellulose acetate succinate (HPMCAS) for initiation and maintenance of drug supersaturation in the GI milieu
    • W. Curatolo, J.A. Nightingale, and S.M. Herbig Utility of hydroxypropylmethylcellulose acetate succinate (HPMCAS) for initiation and maintenance of drug supersaturation in the GI milieu Pharmaceutical Research 26 2009 1419 1431
    • (2009) Pharmaceutical Research , vol.26 , pp. 1419-1431
    • Curatolo, W.1    Nightingale, J.A.2    Herbig, S.M.3
  • 6
    • 0011957339 scopus 로고    scopus 로고
    • Alginates
    • G.O. Phillips, P.A. Williams
    • K.I. Draget Alginates G.O. Phillips, P.A. Williams, Handbook of hydrocolloids 2009 379 395
    • (2009) Handbook of Hydrocolloids , pp. 379-395
    • Draget, K.I.1
  • 7
    • 66149151048 scopus 로고    scopus 로고
    • Naringenin: A potential immunomodulator for inhibiting lung fibrosis and metastasis
    • G. Du, L. Jin, X. Han, Z. Song, H. Zhang, and W. Liang Naringenin: A potential immunomodulator for inhibiting lung fibrosis and metastasis Cancer Research 69 2009 3205 3212
    • (2009) Cancer Research , vol.69 , pp. 3205-3212
    • Du, G.1    Jin, L.2    Han, X.3    Song, Z.4    Zhang, H.5    Liang, W.6
  • 8
    • 80054728029 scopus 로고    scopus 로고
    • Naringenin inhibits the assembly and long-term production of infectious hepatitis C virus particles through a PPAR-mediated mechanism
    • J. Goldwasser, P.Y. Cohen, W. Lin, D. Kitsberg, P. Balaguer, and S.J. Polyak Naringenin inhibits the assembly and long-term production of infectious hepatitis C virus particles through a PPAR-mediated mechanism Journal of Hepatology 55 2011 963 971
    • (2011) Journal of Hepatology , vol.55 , pp. 963-971
    • Goldwasser, J.1    Cohen, P.Y.2    Lin, W.3    Kitsberg, D.4    Balaguer, P.5    Polyak, S.J.6
  • 10
    • 1142303337 scopus 로고    scopus 로고
    • What is the true solubility advantage for amorphous pharmaceuticals?
    • DOI 10.1023/A:1007516718048
    • B. Hancock, and M. Parks What is the true solubility advantage for amorphous pharmaceuticals? Pharmaceutical Research 17 2000 397 404 (Pubitemid 30395293)
    • (2000) Pharmaceutical Research , vol.17 , Issue.4 , pp. 397-404
    • Hancock, B.C.1    Parks, M.2
  • 11
    • 0037088307 scopus 로고    scopus 로고
    • 13C NMR spectroscopy for detailed analyses of the Azotobacter vinelandii mannuronan C-5 epimerase reaction
    • DOI 10.1016/S0304-4165(02)00195-2, PII S0304416502001952
    • M. Hartmann, A.S. Duun, S. Markussen, H. Grasdalen, S. Valla, and G. Skjåk-Bræk Time-resolved 1H and 13C NMR spectroscopy for detailed analyses of the Azotobacter vinelandii mannuronan C-5 epimerase reaction Biochimica et Biophysica Acta 1570 2002 104 112 (Pubitemid 34460693)
    • (2002) Biochimica et Biophysica Acta - General Subjects , vol.1570 , Issue.2 , pp. 104-112
    • Hartmann, M.1    Duun, A.S.2    Markussen, S.3    Grasdalen, H.4    Valla, S.5    Skjak-Braek, G.6
  • 12
    • 0036165561 scopus 로고    scopus 로고
    • Mode of action of recombinant Azotobacter vinelandii mannuronan C-5 epimerases AlgE2 and AlgE4
    • DOI 10.1002/bip.10017
    • M. Hartmann, O.B. Holm, G.A.B. Johansen, G. Skjåk-Bræk, and B.T. Stokke Mode of action of recombinant Azotobacter vinelandii mannuronan C-5 epimerases AlgE2 and AlgE4 Biopolymers 63 2002 77 88 (Pubitemid 34142921)
    • (2002) Biopolymers , vol.63 , Issue.2 , pp. 77-88
    • Hartmann, M.1    Holm, O.B.2    Johansen, G.A.B.3    Skjak-Braek, G.4    Stokke, B.T.5
  • 13
    • 0033617262 scopus 로고    scopus 로고
    • The recombinant Azotobacter vinelandii mannuronan C-5-epimerase AlgE4 epimerizes alginate by a nonrandom attack mechanism
    • H.K. Høidal, H. Ertesvåg, G. Skjåk-Bræk, B.T. Stokke, and S. Valla The recombinant Azotobacter vinelandii mannuronan C-5-epimerase AlgE4 epimerizes alginate by a nonrandom attack mechanism Journal of Biological Chemistry 274 1999 12316 12322
    • (1999) Journal of Biological Chemistry , vol.274 , pp. 12316-12322
    • Høidal, H.K.1    Ertesvåg, H.2    Skjåk-Bræk, G.3    Stokke, B.T.4    Valla, S.5
  • 14
    • 84866407410 scopus 로고    scopus 로고
    • Inhibition of solution crystal growth of ritonavir by cellulose polymers - Factors influencing polymer effectiveness
    • G.A. Ilevbare, H. Liu, K.J. Edgar, and L.S. Taylor Inhibition of solution crystal growth of ritonavir by cellulose polymers - Factors influencing polymer effectiveness CrystEngComm 14 2012 6503 6514
    • (2012) CrystEngComm , vol.14 , pp. 6503-6514
    • Ilevbare, G.A.1    Liu, H.2    Edgar, K.J.3    Taylor, L.S.4
  • 15
    • 84861891898 scopus 로고    scopus 로고
    • Understanding polymer properties important for crystal growth inhibition-impact of chemically diverse polymers on solution crystal growth of ritonavir
    • G.A. Ilevbare, H. Liu, K.J. Edgar, and L.S. Taylor Understanding polymer properties important for crystal growth inhibition-impact of chemically diverse polymers on solution crystal growth of ritonavir Crystal Growth & Design 12 2012 3133 3143
    • (2012) Crystal Growth & Design , vol.12 , pp. 3133-3143
    • Ilevbare, G.A.1    Liu, H.2    Edgar, K.J.3    Taylor, L.S.4
  • 16
    • 77249138794 scopus 로고    scopus 로고
    • Dissolution rate and stability study of flavanone aglycones, naringenin and hesperetin, by drug delivery systems based on polyvinylpyrrolidone (PVP) nanodispersions
    • F.I. Kanaze, E. Kokkalou, I. Niopas, P. Barmpalexis, E. Georgarakis, and D. Bikiaris Dissolution rate and stability study of flavanone aglycones, naringenin and hesperetin, by drug delivery systems based on polyvinylpyrrolidone (PVP) nanodispersions Drug Development and Industrial Pharmacy 36 2010 292 301
    • (2010) Drug Development and Industrial Pharmacy , vol.36 , pp. 292-301
    • Kanaze, F.I.1    Kokkalou, E.2    Niopas, I.3    Barmpalexis, P.4    Georgarakis, E.5    Bikiaris, D.6
  • 17
    • 79953899346 scopus 로고    scopus 로고
    • Synthesis of cellulose adipate derivatives
    • N. Kar, H. Liu, and K.J. Edgar Synthesis of cellulose adipate derivatives Biomacromolecules 12 2011 1106 1115
    • (2011) Biomacromolecules , vol.12 , pp. 1106-1115
    • Kar, N.1    Liu, H.2    Edgar, K.J.3
  • 18
    • 34147176581 scopus 로고    scopus 로고
    • The tablet formulation of lopinavir/ritonavir provides similar bioavailability to the soft-gelatin capsule formulation with less pharmacokinetic variability and diminished food effect
    • DOI 10.1097/QAI.0b013e31803133c5
    • C.E. Klein, Y.L. Chiu, W. Awni, T. Zhu, R.S. Heuser, and T. Doan The tablet formulation of lopinavir/ritonavir provides similar bioavailability to the soft-gelatin capsule formulation with less pharmacokinetic variability and diminished food effect Journal of Acquired Immune Deficiency Syndromes 44 2007 401 410 (Pubitemid 46555374)
    • (2007) Journal of Acquired Immune Deficiency Syndromes , vol.44 , Issue.4 , pp. 401-410
    • Klein, C.E.1    Chiu, Y.-L.2    Awni, W.3    Zhu, T.4    Heuser, R.S.5    Doan, T.6    Breitenbach, J.7    Morris, J.B.8    Brun, S.C.9    Hanna, G.J.10
  • 19
    • 1942452912 scopus 로고    scopus 로고
    • Production of microspheres based on hydrophobically associating alginate derivatives by dispersion/gelation in aqueous sodium chloride solutions
    • M. Leonard, M. Rastello de Boisseson, P. Hubert, and E. Dellacherie Production of microspheres based on hydrophobically associating alginate derivatives by dispersion/gelation in aqueous sodium chloride solutions Journal of Biomedical Materials Research Part A 68A 2004 335 342 (Pubitemid 38524727)
    • (2004) Journal of Biomedical Materials Research - Part A , vol.68 , Issue.2 , pp. 335-342
    • Leonard, M.1    Rastello De Boisseson, M.2    Hubert, P.3    Dellacherie, E.4
  • 20
    • 84881023322 scopus 로고    scopus 로고
    • Enhancement of naringenin solution concentration by solid dispersion in cellulose derivative matrices
    • 10.1007/s10570-013-9970-y
    • B. Li, H. Liu, M. Amin, L. Wegiel, L.S. Taylor, and K.J. Edgar Enhancement of naringenin solution concentration by solid dispersion in cellulose derivative matrices Cellulose 2013 10.1007/s10570-013-9970-y
    • (2013) Cellulose
    • Li, B.1    Liu, H.2    Amin, M.3    Wegiel, L.4    Taylor, L.S.5    Edgar, K.J.6
  • 22
    • 84862247771 scopus 로고    scopus 로고
    • Direct synthesis of cellulose adipate derivatives using adipic anhydride
    • H. Liu, N. Kar, and K.J. Edgar Direct synthesis of cellulose adipate derivatives using adipic anhydride Cellulose 19 2012 1279 1293
    • (2012) Cellulose , vol.19 , pp. 1279-1293
    • Liu, H.1    Kar, N.2    Edgar, K.J.3
  • 23
    • 84863301279 scopus 로고    scopus 로고
    • A win-win solution in oral delivery of lipophilic drugs: Supersaturation via amorphous solid dispersions increases apparent solubility without sacrifice of intestinal membrane permeability
    • J.M. Miller, A. Beig, R.A. Carr, J.K. Spence, and A. Dahan A win-win solution in oral delivery of lipophilic drugs: Supersaturation via amorphous solid dispersions increases apparent solubility without sacrifice of intestinal membrane permeability Molecular Pharmaceutics 9 2012 2009 2016
    • (2012) Molecular Pharmaceutics , vol.9 , pp. 2009-2016
    • Miller, J.M.1    Beig, A.2    Carr, R.A.3    Spence, J.K.4    Dahan, A.5
  • 24
    • 81255158563 scopus 로고    scopus 로고
    • Chemical modification of alginates in organic solvent systems
    • S.N. Pawar, and K.J. Edgar Chemical modification of alginates in organic solvent systems Biomacromolecules 12 2011 4095 4103
    • (2011) Biomacromolecules , vol.12 , pp. 4095-4103
    • Pawar, S.N.1    Edgar, K.J.2
  • 25
    • 84856615725 scopus 로고    scopus 로고
    • Alginate derivatization: A review of chemistry, properties and applications
    • S.N. Pawar, and K.J. Edgar Alginate derivatization: A review of chemistry, properties and applications Biomaterials 33 2012 3279 3305
    • (2012) Biomaterials , vol.33 , pp. 3279-3305
    • Pawar, S.N.1    Edgar, K.J.2
  • 26
    • 0034563689 scopus 로고    scopus 로고
    • Amphiphilic derivatives of sodium alginate and hyaluronate: Synthesis and physico-chemical properties of aqueous dilute solutions
    • S. Pelletier, P. Hubert, F. Lapicque, E. Payan, and E. Dellacherie Amphiphilic derivatives of sodium alginate and hyaluronate: Synthesis and physico-chemical properties of aqueous dilute solutions Carbohydrate Polymers 43 2000 343 349
    • (2000) Carbohydrate Polymers , vol.43 , pp. 343-349
    • Pelletier, S.1    Hubert, P.2    Lapicque, F.3    Payan, E.4    Dellacherie, E.5
  • 27
    • 33947623163 scopus 로고    scopus 로고
    • Zero-order release formulations using a novel cellulose ester
    • DOI 10.1007/s10570-006-9079-7, Polysaccharides in Drug Delivery
    • J.D. Posey-Dowty, T.L. Watterson, A.K. Wilson, K.J. Edgar, M.C. Shelton, and L.R. Lingerfelt Zero-order release formulations using a novel cellulose ester Cellulose 14 2007 73 83 (Pubitemid 46486882)
    • (2007) Cellulose , vol.14 , Issue.1 , pp. 73-83
    • Posey-Dowty, J.D.1    Watterson, T.L.2    Wilson, A.K.3    Edgar, K.J.4    Shelton, M.C.5    Lingerfelt, L.R.6
  • 29
    • 84904807892 scopus 로고    scopus 로고
    • Enhanced dissolution of poorly soluble drugs from solid dispersions in carboxymethylcellulose acetate butyrate matrices
    • American Chemical Society Washington, DC
    • M.C. Shelton, J.D. Posey-Dowty, L. Lingerfelt, S.K. Kirk, S. Klein, and K.J. Edgar Enhanced dissolution of poorly soluble drugs from solid dispersions in carboxymethylcellulose acetate butyrate matrices Polysaccharide materials: Performance by design Vol. 1017 2009 American Chemical Society Washington, DC 93 113
    • (2009) Polysaccharide Materials: Performance by Design , vol.1017 VOL. , pp. 93-113
    • Shelton, M.C.1    Posey-Dowty, J.D.2    Lingerfelt, L.3    Kirk, S.K.4    Klein, S.5    Edgar, K.J.6
  • 30
    • 0013979606 scopus 로고
    • The influence of pH on the rate of hydrolysis of acidic polysaccharides
    • O.H.A. Smidsrød, and B. Larsen The influence of pH on the rate of hydrolysis of acidic polysaccharides Acta Chemica Scandinavica 20 1966 1026 1034
    • (1966) Acta Chemica Scandinavica , vol.20 , pp. 1026-1034
    • Smidsrød, O.H.A.1    Larsen, B.2
  • 31
    • 0000255573 scopus 로고
    • Sulfoxides as nucleophiles
    • S.G. Smith, and S. Winstein Sulfoxides as nucleophiles Tetrahedron 3 3 1958 317 319
    • (1958) Tetrahedron , vol.3 , Issue.3 , pp. 317-319
    • Smith, S.G.1    Winstein, S.2
  • 32
    • 0037509102 scopus 로고
    • The acid hydrolysis of glycosides: I. General conditions and the effect of the nature of the aglycone
    • T.E. Timell The acid hydrolysis of glycosides: I. General conditions and the effect of the nature of the aglycone Canadian Journal of Chemistry 42 1964 1456
    • (1964) Canadian Journal of Chemistry , vol.42 , pp. 1456
    • Timell, T.E.1
  • 35
    • 65249093693 scopus 로고    scopus 로고
    • The structure-activity correlation on the inhibitory effects of flavonoids on cytochrome P450 3A activity
    • M. Tsujimoto, M. Horie, H. Honda, K. Takara, and K. Nishiguchi The structure-activity correlation on the inhibitory effects of flavonoids on cytochrome P450 3A activity Biological and Pharmaceutical Bulletin 32 2009 671 676
    • (2009) Biological and Pharmaceutical Bulletin , vol.32 , pp. 671-676
    • Tsujimoto, M.1    Horie, M.2    Honda, H.3    Takara, K.4    Nishiguchi, K.5
  • 36
    • 0343457689 scopus 로고
    • A new unsaturated uronide isolated from alginase hydrolysate
    • I. Tsujino, and T. Saito A new unsaturated uronide isolated from alginase hydrolysate Nature 192 1961 970 971
    • (1961) Nature , vol.192 , pp. 970-971
    • Tsujino, I.1    Saito, T.2
  • 37
    • 77955242670 scopus 로고    scopus 로고
    • Small scale screening to determine the ability of different polymers to inhibit drug crystallization upon rapid solvent evaporation
    • B. Van Eerdenbrugh, and L.S. Taylor Small scale screening to determine the ability of different polymers to inhibit drug crystallization upon rapid solvent evaporation Molecular Pharmaceutics 7 2010 1328 1337
    • (2010) Molecular Pharmaceutics , vol.7 , pp. 1328-1337
    • Van Eerdenbrugh, B.1    Taylor, L.S.2
  • 39
    • 84863402416 scopus 로고    scopus 로고
    • TBAF and cellulose esters: Unexpected deacylation with unexpected regioselectivity
    • D. Xu, and K.J. Edgar TBAF and cellulose esters: Unexpected deacylation with unexpected regioselectivity Biomacromolecules 13 2012 299 303
    • (2012) Biomacromolecules , vol.13 , pp. 299-303
    • Xu, D.1    Edgar, K.J.2


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