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Chemical Compound Review

Pre-pen     2-[5-carboxypentylcarbamoyl- (2...

Synonyms: CHEMBL1201779, AC1L3OEE, AC1Q5KWZ, CID119212, DAP001314, ...
 
 
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Disease relevance of Benzylpenicilloyl

  • When classified according to initial reaction type, most anaphylactic patients (93.3%) were associated with minor determinant reactivity, whereas most urticaria patients (80%) reacted to BPO [1].
  • The delayed type hypersensitivity (DTH) for benzylpenicilloyl (BPO) group was observed in the footpad swelling reaction (FSR) in mice [2].
  • Skin testing with a mixture of benzylpenicilloyl polylysine (major determinant) and a minor determinant mixture detects all patients at risk of major anaphylaxis [3].
 

High impact information on Benzylpenicilloyl

  • OBJECTIVE--To establish (1) the prevalence of positive penicillin skin tests among outpatients with well-defined but variable history of penicillin allergy and (2) the reproducibility, safety, and negative predictive value of skin testing with benzylpenicilloyl polylysine (PPL) and a minor-determinant mixture (MDM) [4].
  • High titered IgE, IgG, and IgM antibody responses to the major antigenic determinant of penicillin, the benzylpenicilloyl hapten, were elicited by the intraperitoneal injection of the hapten coupled to keyhole limpet hemocyanin mixed with the appropriate adjuvant [5].
  • Origin and fate of IgE-bearing lymphocytes. II. Gut-associated lymphoid tissue as sites of first appearance of IgE-bearing B lymphocytes and hapten-specific IgE antibody-forming cells in mice immunized with benzylpenicilloyl-keyhole limpet hemocyanin by various routes: relation to asialo GM1 ganglioside+ cells and IgE/CD23 immune complexes [6].
  • With this method IgE antibody directed against the benzylpenicilloyl determinant of penicillin (BPO) was measured quantitatively in sera from seven penicillin allergic patients [7].
  • Group A consisted of patients with a positive skin test response to benzylpenicilloyl or minor determinant mixture, and group B consisted of those with a selective response to amoxicillin and good tolerance to benzylpenicillin [8].
 

Biological context of Benzylpenicilloyl

 

Anatomical context of Benzylpenicilloyl

 

Associations of Benzylpenicilloyl with other chemical compounds

 

Gene context of Benzylpenicilloyl

  • The ability of interleukin (IL)-6 or interferon-alpha (IFN-alpha) to regulate expression of low-affinity Fc(epsilon) receptor (CD23) and serum levels of CD23 was studied in benzylpenicilloyl-keyhole limpet hemocyanin-sensitized BALB/c mice at the peak of a hapten-specific immunoglobulin E (IgE) antibody-forming cell (AFC) response [18].
  • The ability of cytokines (IL-4, IL-5, IL-6, IFN-alpha, IFN-gamma, TNF-alpha, GmCSF) to regulate peak benzylpenicilloyl (BPO)-specific IgE antibody-forming cell (AFC) responses was investigated [19].
  • Furthermore, the allele was strongly associated with increased serum-specific benzylpenicilloyl (BPO)-, phenoxomethylpenicillanyl (PVA)- or ampicillanyl (APA)-IgE levels in patients with positive specific IgE (P < 0.05) [20].
  • Recently we have shown that active immunization of syngenic animals with anti-ovalbumin antibodies evokes an anti-idiotypic (aId) response, which in consequence leads to suppression of the anti-hapten (benzylpenicilloyl, BPO; dinitrophenyl, DNP) IgE and IgG formation subsequently attempted by immunization with low doses of hapten-OVA conjugates [21].
  • The ability of IL-6 or IFN alpha or antibodies to these cytokines to regulate serum levels of hapten specific immunoglobulins (IgM, IgG1, IgE, IgA) was studied in BPO-KLH (benzylpenicilloyl-keyhole limpet hemocyanin) sensitized BALB/c mice at the peak of a hapten specific IgE antibody forming cell (AFC) response [22].
 

Analytical, diagnostic and therapeutic context of Benzylpenicilloyl

  • The unresponsiveness to BPO of spleen cells from immunosuppressed donors was also maintained in adoptive cell transfer experiments in spite of the additional administration of the immunizing antigen under conditions expected to yield a secondary IgE response [23].
  • Transient bisalbuminemia: separation by isoelectric focusing of human albumin fractions linked to different numbers of benzylpenicilloyl groups [24].
  • The specificity of the IgG and IgM antibodies for the BPO determinant was confirmed by ELISA inhibition with BPO-aminocaproate [25].
  • Immunoaffinity (IA) and reversed-phase (RP) high-performance liquid chromatography were combined for the identification of the specific binding sites of benzylpenicilloyl (BPO) groups on human serum albumin (HSA) [26].

References

  1. Immediate hypersensitivity to penicillins. Studies on Italian subjects. Romano, A., Blanca, M., Mayorga, C., Venuti, A., Gasbarrini, G. Allergy (1997) [Pubmed]
  2. Delayed type hypersensitivity for penicillin in mice. I. Induction and characterization of delayed type hypersensitivity for penicillin in mice. Shiho, O., Nakagawa, Y., Kawaji, H. J. Antibiot. (1981) [Pubmed]
  3. Penicillin anaphylaxis: a review of sensitization, treatment, and prevention. Miles, A.M., Bain, B. Journal of the Association for Academic Minority Physicians : the official publication of the Association for Academic Minority Physicians. (1992) [Pubmed]
  4. Clinical experience with penicillin skin testing in a large inner-city STD clinic. Gadde, J., Spence, M., Wheeler, B., Adkinson, N.F. JAMA (1993) [Pubmed]
  5. Induction if immunological tolerance to the major antigenic determinant of penicillin: a therapeutic approach to penicillin allergy. Chiorazzi, N., Eshhar, Z., Katz, D.H. Proc. Natl. Acad. Sci. U.S.A. (1976) [Pubmed]
  6. Origin and fate of IgE-bearing lymphocytes. II. Gut-associated lymphoid tissue as sites of first appearance of IgE-bearing B lymphocytes and hapten-specific IgE antibody-forming cells in mice immunized with benzylpenicilloyl-keyhole limpet hemocyanin by various routes: relation to asialo GM1 ganglioside+ cells and IgE/CD23 immune complexes. Auci, D.L., Chice, S.M., Heusser, C., Athanassiades, T.J., Durkin, H.G. J. Immunol. (1992) [Pubmed]
  7. Measurement of absolute amounts of antigen-specific human IgE by a radioallergosorbent test (RAST) elution technique. Schellenberg, R.R., Adkinson, N.F. J. Immunol. (1975) [Pubmed]
  8. Natural evolution of skin test sensitivity in patients allergic to beta-lactam antibiotics. Blanca, M., Torres, M.J., García, J.J., Romano, A., Mayorga, C., de Ramon, E., Vega, J.M., Miranda, A., Juarez, C. J. Allergy Clin. Immunol. (1999) [Pubmed]
  9. Identification of lysine residue 199 of human serum albumin as a binding site for benzylpenicilloyl groups. Yvon, M., Wal, J.M. FEBS Lett. (1988) [Pubmed]
  10. Antibodies against the benzylpenicilloyl moiety as a probe for penicillin-binding proteins. Hakenbeck, R., Briese, T., Ellerbrok, H. Eur. J. Biochem. (1986) [Pubmed]
  11. Modulation of NK and K cell activity by trypsin treatment of effector cells. Scheiner, O., Wiedermann, G., Rumpold, H., Steiner, R., Kraft, D., Stemberger, H. Immunobiology (1980) [Pubmed]
  12. Rat mast cell degranulation triggered by murine anti-idiotypic antibodies. Nakagawa, T., Blaser, K., de Weck, A.L. Int. Arch. Allergy Appl. Immunol. (1980) [Pubmed]
  13. Penicillin-induced haemolytic anaemia associated with microangiopathy. McPherson, A.J., Parkin, J.D., Hope, R. Australian and New Zealand journal of medicine. (1976) [Pubmed]
  14. Assessment of histamine release from basophils in whole blood by benzylpenicilloyl poly-L-lysine in penicillin-sensitized patients. Koller, D.Y., Rosenkranz, A.R., Pirker, C., Götz, M., Jarisch, R. Allergy (1992) [Pubmed]
  15. Suppression of the anti-hapten IgE antibody response with hapten-modified spleen cells. Weber, E.A., Blaser, K. Eur. J. Immunol. (1986) [Pubmed]
  16. Drug-protein conjugates--XVII. The effect of storage on the antigenicity and immunogenicity of benzylpenicillin in the rat. Christie, G., Coleman, J.W., Park, B.K. Biochem. Pharmacol. (1988) [Pubmed]
  17. Neuropeptide-mediated regulation of hapten-specific IgE responses in mice. II. Mechanisms of substance P-mediated isotype-specific suppression of BPO-specific IgE antibody-forming cell responses induced in vitro. Carucci, J.A., Herrick, C.A., Durkin, H.G. J. Neuroimmunol. (1994) [Pubmed]
  18. IFN-alpha-mediated suppression of low-affinity FC(epsilon) receptors on Peyer's patch lymphocytes and augmentation of soluble CD23: implications for IgE responses. Miller, H., Bluth, M.H., Chice, S.M., Durkin, H.G., Auci, D.L. J. Leukoc. Biol. (1996) [Pubmed]
  19. Control of IgE responses. III. IL-6 and IFN-alpha are isotype-specific regulators of peak BPO-specific IgE antibody-forming cell responses in mice. Auci, D.L., Kleiner, G.I., Chice, S.M., Dukor, P., Durkin, H.G. Clin. Immunol. Immunopathol. (1993) [Pubmed]
  20. Relationships between specific serum IgE, cytokines and polymorphisms in the IL-4, IL-4Ralpha in patients with penicillins allergy. Qiao, H.L., Yang, J., Zhang, Y.W. Allergy (2005) [Pubmed]
  21. Effect of passively administered isologous anti-idiotypes directed against anti-carrier (ovalbumin) antibodies on the anti-hapten IgE and IgG antibody responses in BALB/c mice. Blaser, K., Nakagawa, T., De Weck, A.L. Immunology (1983) [Pubmed]
  22. IL-6 mediated isotype specific suppression of hapten specific IgE in serum of BPO-KLH sensitized mice: role of IFN alpha in maintainance of hapten specific IgE responses. Auci, D.L., Miller, H., Chice, S.M., Durkin, H.G. Immunol. Invest. (1994) [Pubmed]
  23. Suppression of reaging antibody formation. IV. Suppression of reaginic antibodies to penicillin in the mouse. Lee, W.Y., Sehon, A.H. J. Immunol. (1976) [Pubmed]
  24. Transient bisalbuminemia: separation by isoelectric focusing of human albumin fractions linked to different numbers of benzylpenicilloyl groups. Rocha, J., Bohner, J., Kömpf, J. Electrophoresis (1995) [Pubmed]
  25. Drug-protein conjugates--XII. A study of the disposition, irreversible binding and immunogenicity of penicillin in the rat. Kitteringham, N.R., Christie, G., Coleman, J.W., Yeung, J.H., Park, B.K. Biochem. Pharmacol. (1987) [Pubmed]
  26. Tandem immunoaffinity and reversed-phase high-performance liquid chromatography for the identification of the specific binding sites of a hapten on a proteic carrier. Yvon, M., Wal, J.M. J. Chromatogr. (1991) [Pubmed]
 
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