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Volumn 100, Issue 8, 2011, Pages 3307-3315

Analysis of 2,2'-Azobis (2-amidinopropane) dihydrochloride degradation and hydrolysis in aqueous solutions

Author keywords

AAPH; ABAP; Azonitrile; Free radicals; Liquid chromatographymass spectrometry; Oxidation; Polysorbate; Stability; Surfactants

Indexed keywords

2,2' AZOBIS(2 AMIDINOPROPANE); AZO COMPOUND; OXIDIZING AGENT;

EID: 79958838317     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.22578     Document Type: Article
Times cited : (109)

References (30)
  • 1
    • 0005783122 scopus 로고
    • Chemistry of 2,2'-Azobisisobutyramidine hydrochloride in aqueous solution: A water-soluble azo initiator
    • Dougherty T. 1961. Chemistry of 2, 2'-Azobisisobutyramidine hydrochloride in aqueous solution: A water-soluble azo initiator. J Am Chem Soc 83:4849-4853.
    • (1961) J Am Chem Soc , vol.83 , pp. 4849-4853
    • Dougherty, T.1
  • 2
    • 0030857729 scopus 로고    scopus 로고
    • The pH dependence of lipid peroxidation using water-soluble azo initiators
    • Hanlon M, Seybert D. 1997. The pH dependence of lipid peroxidation using water-soluble azo initiators. Free Radic Biol Med 23:712-719.
    • (1997) Free Radic Biol Med , vol.23 , pp. 712-719
    • Hanlon, M.1    Seybert, D.2
  • 3
    • 33745903417 scopus 로고    scopus 로고
    • Evaluation of solution oxygenation requirements for azonitrile-based oxidative forced degradation studies of pharmaceutical compounds
    • Nelson E, Harmon P, Szymanik R, Teresk M, Li L, Seburg R, Reed R. 2006. Evaluation of solution oxygenation requirements for azonitrile-based oxidative forced degradation studies of pharmaceutical compounds. J Pharm Sci 95:1527-1539.
    • (2006) J Pharm Sci , vol.95 , pp. 1527-1539
    • Nelson, E.1    Harmon, P.2    Szymanik, R.3    Teresk, M.4    Li, L.5    Seburg, R.6    Reed, R.7
  • 4
    • 0000192646 scopus 로고
    • Oxidation of lipids. XII. Inhibition of oxidation of soybean phosphatidylcholine and methyl linoleate in aqueous dispersions by uric acid
    • Niki E, Saito M, Yoshikawa Y, Yamamoto Y, Kamiya Y. 1986. Oxidation of lipids. XII. Inhibition of oxidation of soybean phosphatidylcholine and methyl linoleate in aqueous dispersions by uric acid. Bull Chem Soc Jpn 59:471-477.
    • (1986) Bull Chem Soc Jpn , vol.59 , pp. 471-477
    • Niki, E.1    Saito, M.2    Yoshikawa, Y.3    Yamamoto, Y.4    Kamiya, Y.5
  • 5
    • 71649111656 scopus 로고    scopus 로고
    • Methionine, tryptophan, and histidine oxidation in a model protein, PTH: Mechanisms and stabilization
    • Ji J, Zhang B, Cheng W, Wang Y. 2009. Methionine, tryptophan, and histidine oxidation in a model protein, PTH: Mechanisms and stabilization. J Pharm Sci 98:4485-4500.
    • (2009) J Pharm Sci , vol.98 , pp. 4485-4500
    • Ji, J.1    Zhang, B.2    Cheng, W.3    Wang, Y.4
  • 6
    • 33748929319 scopus 로고    scopus 로고
    • A novel peroxy radical based oxidative stressing system for ranking the oxidizability of drug substances
    • Harmon P, Kosuda K, Nelson E, Mowery M, Reed R. 2006. A novel peroxy radical based oxidative stressing system for ranking the oxidizability of drug substances. J Pharm Sci 95:2014-2028.
    • (2006) J Pharm Sci , vol.95 , pp. 2014-2028
    • Harmon, P.1    Kosuda, K.2    Nelson, E.3    Mowery, M.4    Reed, R.5
  • 7
    • 52449090177 scopus 로고    scopus 로고
    • Polysorbates 20 and 80 used in the formulation of protein biotherapeutics: Structure and degradation pathways
    • Kerwin B. 2008. Polysorbates 20 and 80 used in the formulation of protein biotherapeutics: Structure and degradation pathways. J Pharm Sci 97:2924-2935.
    • (2008) J Pharm Sci , vol.97 , pp. 2924-2935
    • Kerwin, B.1
  • 8
    • 0000883211 scopus 로고
    • The mechanism of decomposition of azo compounds. III. Cage effects with positively charged geminate radical pairs
    • Hammond G, Neuman R. 1963. The mechanism of decomposition of azo compounds. III. Cage effects with positively charged geminate radical pairs. J Am Chem Soc 85:1501-1508.
    • (1963) J Am Chem Soc , vol.85 , pp. 1501-1508
    • Hammond, G.1    Neuman, R.2
  • 9
    • 0015650860 scopus 로고
    • Competition between thermal decomposition and hydrolysis of 2,2'-azobis(2-amidinopropane) in aqueous solution
    • Ito K. 1973. Competition between thermal decomposition and hydrolysis of 2, 2'-azobis(2-amidinopropane) in aqueous solution. J Polym Sci 11:1673-1681.
    • (1973) J Polym Sci , vol.11 , pp. 1673-1681
    • Ito, K.1
  • 10
    • 0001239144 scopus 로고    scopus 로고
    • Comparison of 2,2'-azobis(2-amidinopropane) hydrochloride (AAPH) and 2,2'-azobis(2,4-dimethylvaleronitrile) (AMVN) as free radical initiators: A spin-trapping study
    • Krainev A, Bigelow D. 1996. Comparison of 2, 2'-azobis(2-amidinopropane) hydrochloride (AAPH) and 2, 2'-azobis(2, 4-dimethylvaleronitrile) (AMVN) as free radical initiators: A spin-trapping study. J Chem Soc Perkin Trans 2:747-754.
    • (1996) J Chem Soc Perkin Trans , vol.2 , pp. 747-754
    • Krainev, A.1    Bigelow, D.2
  • 11
    • 33748322763 scopus 로고
    • The elucidation of peroxyl radical reactions in aqueous solution with the help of radiation-chemical methods
    • von Sonntag C, Schuchmann H. 1991. The elucidation of peroxyl radical reactions in aqueous solution with the help of radiation-chemical methods. Angew Chem It Ed Engl 30:1229-1253.
    • (1991) Angew Chem It Ed Engl , vol.30 , pp. 1229-1253
    • von Sonntag, C.1    Schuchmann, H.2
  • 12
    • 0347598252 scopus 로고    scopus 로고
    • Mechanistic studies on the decomposition of water soluble azo-radical-initiators
    • Wahl R, Zeng L, Madison S, DePinto R, Shay B. 1998. Mechanistic studies on the decomposition of water soluble azo-radical-initiators. J Chem Soc Perkin Trans 2: 2009-2017.
    • (1998) J Chem Soc Perkin Trans , vol.2 , pp. 2009-2017
    • Wahl, R.1    Zeng, L.2    Madison, S.3    DePinto, R.4    Shay, B.5
  • 13
    • 0001280056 scopus 로고
    • A study of the mechanism of cumene autoxidation. Mechanism of the interaction of t-peroxy radicals
    • Blanchard H. 1959. A study of the mechanism of cumene autoxidation. Mechanism of the interaction of t-peroxy radicals. J Am Chem Soc 81:4548-4552.
    • (1959) J Am Chem Soc , vol.81 , pp. 4548-4552
    • Blanchard, H.1
  • 14
    • 0001896864 scopus 로고
    • Peroxy radicals
    • Ingold K. 1969. Peroxy radicals. Acc Chem Res 2:1-9.
    • (1969) Acc Chem Res , vol.2 , pp. 1-9
    • Ingold, K.1
  • 15
    • 0020789781 scopus 로고
    • Rate constants for the reactions of free radicals with oxygen in solution
    • Maillard B, Ingold K, Scaiano J. 1983. Rate constants for the reactions of free radicals with oxygen in solution. J Am Chem Soc 105:5095-5099.
    • (1983) J Am Chem Soc , vol.105 , pp. 5095-5099
    • Maillard, B.1    Ingold, K.2    Scaiano, J.3
  • 16
    • 37049093065 scopus 로고
    • Thermal isomerisation of methyl linoleate hydroperoxides. Evidence of molecular oxygen as a leaving group in a radical rearrangement
    • Chan H, Levett G, Matthew J. 1978. Thermal isomerisation of methyl linoleate hydroperoxides. Evidence of molecular oxygen as a leaving group in a radical rearrangement. J Chem Soc Chem Commun 647:756-775.
    • (1978) J Chem Soc Chem Commun , vol.647 , pp. 756-775
    • Chan, H.1    Levett, G.2    Matthew, J.3
  • 17
    • 0001523691 scopus 로고
    • Unified mechanism for polyunsaturated fatty acid autoxidation. Competition of peroxy radical hydrogen atom abstraction, β-scission, and cyclization
    • Porter N, Lehman L, Weber B, Smith K. 1981. Unified mechanism for polyunsaturated fatty acid autoxidation. Competition of peroxy radical hydrogen atom abstraction, β-scission, and cyclization. J Am Chem Soc 103:6447-6455.
    • (1981) J Am Chem Soc , vol.103 , pp. 6447-6455
    • Porter, N.1    Lehman, L.2    Weber, B.3    Smith, K.4
  • 18
    • 38949110666 scopus 로고    scopus 로고
    • Initiation of lipid autoxidation by ABAP at pH 4-10 in SDS micelles
    • Musialik M, Kita M, Litwinienko G. 2008. Initiation of lipid autoxidation by ABAP at pH 4-10 in SDS micelles. Org Biomol Chem 6:677-681.
    • (2008) Org Biomol Chem , vol.6 , pp. 677-681
    • Musialik, M.1    Kita, M.2    Litwinienko, G.3
  • 19
    • 0001094345 scopus 로고
    • Kinetic electron paramagnetic resonance study of the reactions of t-butylperoxyl radicals in aqueous solution
    • Bennett J. 1990. Kinetic electron paramagnetic resonance study of the reactions of t-butylperoxyl radicals in aqueous solution. J Chem Soc Faraday Trans 86:3247-3252.
    • (1990) J Chem Soc Faraday Trans , vol.86 , pp. 3247-3252
    • Bennett, J.1
  • 20
    • 37049098094 scopus 로고
    • Electron spin resonance studies. Part 61. The generation and reactions of the t-butoxyl radical in aqueous solution
    • Gilbert B, Marshal P, Norman R, Pineda N, Williams P. 1981. Electron spin resonance studies. Part 61. The generation and reactions of the t-butoxyl radical in aqueous solution. J Chem Soc Perkin Trans 2:1392-1400.
    • (1981) J Chem Soc Perkin Trans , vol.2 , pp. 1392-1400
    • Gilbert, B.1    Marshal, P.2    Norman, R.3    Pineda, N.4    Williams, P.5
  • 22
    • 0002461229 scopus 로고
    • Rate constants for reaction of hydroxyl radicals with tris, tricine, and Hepes buffers
    • Hicks M, Gebicki J. 1986. Rate constants for reaction of hydroxyl radicals with tris, tricine, and Hepes buffers. FEBS Lett 199:92-94.
    • (1986) FEBS Lett , vol.199 , pp. 92-94
    • Hicks, M.1    Gebicki, J.2
  • 23
    • 1242352716 scopus 로고
    • Organic radical-radical reactions. Disproportionation vs. combination
    • Gibian M, Corley R. 1973. Organic radical-radical reactions. Disproportionation vs. combination. Chem Rev 73:441-464.
    • (1973) Chem Rev , vol.73 , pp. 441-464
    • Gibian, M.1    Corley, R.2
  • 25
    • 0035117422 scopus 로고    scopus 로고
    • Contribution of haemoglobin and membrane constituents modification to human erythrocyte damage promoted by peroxyl radicals of different charge and hydrophobicity
    • Celedón G, Rodriguez I, España J, Escobar J, Lissi E. 2001. Contribution of haemoglobin and membrane constituents modification to human erythrocyte damage promoted by peroxyl radicals of different charge and hydrophobicity. Free Radic Res 34:17-31.
    • (2001) Free Radic Res , vol.34 , pp. 17-31
    • Celedón, G.1    Rodriguez, I.2    España, J.3    Escobar, J.4    Lissi, E.5
  • 26
    • 33847089388 scopus 로고
    • Studies on models for tetrahydrofolic acid. 8. Hydrolysis and methoxyaminolysis of amidines
    • Burdick B, Benkovic P, Benkovic S. 1977. Studies on models for tetrahydrofolic acid. 8. Hydrolysis and methoxyaminolysis of amidines. J Am Chem Soc 99:5716-5725.
    • (1977) J Am Chem Soc , vol.99 , pp. 5716-5725
    • Burdick, B.1    Benkovic, P.2    Benkovic, S.3
  • 27
    • 0000409775 scopus 로고
    • Direct observation of a tetrahedral intermediate during amidine hydrolysis
    • Robinson D. 1970. Direct observation of a tetrahedral intermediate during amidine hydrolysis. J Am Chem Soc 92:3138-3146.
    • (1970) J Am Chem Soc , vol.92 , pp. 3138-3146
    • Robinson, D.1
  • 28
    • 33646169402 scopus 로고
    • Mechanism and catalysis of the hydrolysis of a formamidinium compound
    • Robinson D, Jencks W. 1967. Mechanism and catalysis of the hydrolysis of a formamidinium compound. J Am Chem Soc 89:7088-7098.
    • (1967) J Am Chem Soc , vol.89 , pp. 7088-7098
    • Robinson, D.1    Jencks, W.2
  • 29
    • 1542480456 scopus 로고
    • The chemistry of the amidines
    • Shriner R. 1944. The chemistry of the amidines. Chem Rev 35:351-425.
    • (1944) Chem Rev , vol.35 , pp. 351-425
    • Shriner, R.1
  • 30
    • 0003606860 scopus 로고
    • The thermal decomposition of methyl isopropyl di-imide: A homogenous unimolecular reaction. The thermal decomposition of hydrazoic acid and methyl azide
    • Ramsperger H. 1929. The thermal decomposition of methyl isopropyl di-imide: A homogenous unimolecular reaction. The thermal decomposition of hydrazoic acid and methyl azide. J Am Chem Soc 51:2134-2143.
    • (1929) J Am Chem Soc , vol.51 , pp. 2134-2143
    • Ramsperger, H.1


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