The interaction of penicillin with high molecular components of plasma expander such as dextran, 6-hydroxyethylstarch, and polygeline were studied. The formation of penicilloyl polysaccharides and smaller amounts of penicilloyl polygeline during incubation were confirmed by ultrafiltration and gelfiltration.
The ultrafiltration through Collodion-Bags SM 13200 was found to be a rapid and convenient method for the determination of macromolecular penicilloates.
The accelerated degradation by the formation of penicilloyl esters with glucose and lactic acid was also suggested.
SchneiderCHde WeckAL. The reaction of benzylpenicillin with carbohydrates at neutral pH with a note on the immunogenicity of hapten polysaccharide conjugates. Immunochemistry1967; 4: 331–43.
2.
SchneiderCHde WeckALStaubleE. Carboxymethylcellulose additives in penicillins and elicitation of anaphylactic reactions. Experientia1971; 27: 167–8.
3.
MolinariMSchneiderCHde WeckALGrundenEPfeutiCH. Über pseudomonovalente Penicilloyl-Kohlenhydrate. Z Immunitaetsforsch Immunobiol1973; 146 (suppl):225–38.
4.
MorenoCHaleCHewettR. The use of hapten-polysaccharide conjugates for the induction of β-cell tolerance involving IgE responses I. Preparation, characterization and specific tolerogenic activity of penicilloyl substituted levans affecting IgE responses in normal and sensitized mice. Clin Exp Immunol1978; 31: 499–511.
5.
NakagawaTOtzUde WeckALSchneiderCH. Induction of immunological tolerance to the penicilloyl antigenic determinant. III. Suppression of benzylpenicilloyl-specific IgE antibody formation by cleavable penicilloylated dextran. Int Arch Allergy Appl Immunol1980; 64: 210–6.
6.
TuttDESchwartzMA. Specificity in the cyclohepta-amylose-catalysed hydrolysis of penicillins. Chem Commun1970: 113–4.
7.
SimberkoffMSThomasLMcGregorDShenkeinILevineBB. Inactivation of penicillins by carbohydrate solutions at alkaline pH. N Engl J Med1970; 283: 116–9.
8.
HemSLRussoEJBahalSMLeviRS. Kinetic analysis of complex formation between penicillin and sucrose. J Pharm Sci1973; 62: 267–70.
9.
BundgaardHLarsenC. Kinetics and mechanism of reaction of benzylpenicillin and ampicillin with carbohydrates and polyhydric alcohols in aqueous solution. Arch Pharm Chem Sci Ed1978; 6: 184–200.
10.
MizukamiYIchimuraFYamanaT. Effect of β-cyclodextrin on degradation of penicillins and cephalosporins in acidic and weak alkaline solutions. Yakuzaigaku1978; 38: 45–50.
11.
SchneiderCHde WeckAL. Unterscheidung der Penicilloinsäuren von functionellen Derivaten ihrer α-Carboxygruppe mittels Penamaldat-Stabilitatsbestimmung. Helv Chim Acta1966; 49: 1689–94.
12.
SchwartzMADelduceAJ. Kinetic analysis of penicilloic acid and penicilloylamide in combination: Application to products of reaction of penicillin with tromethamine (Tris) and poly-L-lysine. J Pharm Sci1969; 58: 1137–9.
13.
TsujiAYamanaTMiyamotoEKiyaE. Chemical reactions involved in penicillin allergy: Kinetics and mechanism of penicillin aminolysis. J Pharm Pharmacol1975; 27: 580–7.
14.
SchneiderCHde WeckAL. Zur Kenntnis der Benzylpenicilloinsäure. Helv Chim Acta1967; 50: 2011–8.
15.
SchneiderCHde WeckAL. Studies on the direct neutral penicilloylation of functional groups occurring on proteins. Biochim Biophys Acta1968; 168: 27–35.
16.
FinholtPJürgensenGKristiansenH. Catalytic effect of buffers on degradation of penicillin G in aqueous solution. J Pharm Sci1965; 54: 387–93.
17.
KingetRBontinkAMHerbotsH. Problems of dialysis techniques in the study of macromolecular binding of drugs. Int J Pharm1979; 3: 65–72.
18.
KohlerLH. Differentiation of carbohydrates by anthrone reaction rate and color intensity. Anal Chem1952; 24: 1567–79.
19.
ScottTAJrMelvinEH. Determination of dextran with anthrone. Anal Chem1953; 25: 1656–61.
20.
BundgaardHliverK. A new spectrophotometric method for the determination of penicillins. J Pharm Pharmacol1972; 24: 790–4.
21.
StewartGT. Proteinaceous and polymeric residues in β-lactam antibiotics and bacitracin. Antimicrob Agents Chemother1968; 8: 128–35.
22.
BundgaardH. Impurities as a factor in therapeutic equivalence of drugs. Analysis of ampicillin formulation for antigenic polymerization products. Arch Pharm Chem Sci Ed1978; 6: 463–8.
23.
BundgaardHLarsenC. Piperadinedione formation from reaction of ampicillin with carbohydrates and alcohols in aqueous solution. Int J Pharm1979; 3: 1–11.
24.
SmithHMarshallAC. Polymers formed by some β-lactam antibiotics. Nature1971; 232: 45–6.
25.
StanfieldMKButcherBTStewartGT. Spectroscopic analysis of polymers of benzylpenicillin and ampicillin. Anal Biochem1978; 89: 1–13.
26.
YamanaTTsujiAMiyamotoEKiyaE. The reaction of benzylpenicillin with amines containing hydroxy groups. J Pharm Pharmacol1975; 27: 771–4.
27.
BundgaardH. Penicillin allergy. Kinetics of penicilloylation of serum albumins by various penicillins. Acta Pharm Suec1977; 14: 391–402.
28.
StewartGT. Macromolecular residues contributing to the allergenicity of penicillins and cephalosporins. Antimicrob Agents Chemother1967: 543–9.
29.
StewartGT. Allergenic residues in penicillins. Lancet1967; 1: 1177–83.
30.
SmithHDewdneyJMWheelerAW. A comparison of the amounts and the antigenicity of polymeric materials formed in aqueous solution by some β-lactam antibiotics. Immunology1971; 21: 527–33.
31.
DewdneyJMSmithHWheelerAW. The formation of antigenic polymers in aqueous solutions of β-lactam antibiotics. Immunology1971; 21: 517–25.
32.
AhlstedtSKristoffersonASvardPOThorLOrtengrenB. Ampicillin polymers as elicitors of passive cutaneous anaphylaxis. Int Arch Allergy Appl Immunol1976; 26: 10–16.
33.
TakeuchiYNishimuraYYamajiYKimuraY. The basic study on penicillin allergy (1). Immunoresponses to penicillin G polymer in rat. Allergy (Jpn J Allergol)1977; 26: 504–10.
34.
TakeuchiY. The basic study on penicillin allergy (2). Determination of penicillin G polymer in procaine penicillin G suspension. Allergy (Jpn J Allergol)1977; 26: 504–10.
35.
TakeuchiYNishimuraYYamajiYKimuraY. The basic study on penicillin allergy (3). Immunoresponses to procaine penicillin G suspension in rat. Allergy (Jpn J Allergol)1978; 27: 459–64.
36.
TakeuchiYNishimuraYHayashiNKimuraY. On the binding capacity of penicillin G polymers to serum protein (especially on the analysis by continuous flow countercurrent dialysis). Chemotherapy (Tokyo)1980; 28: 9–13.
