| InChI=1S/C11H17N2O6P/c1-13(2,3)8-9-18-20(16,17)19-11-6-4-10(5-7-11)12(14)15/h4-7H,8-9H2,1-3H3/p+1 |
| NAIXASFEPQPICN-UHFFFAOYSA-O |
| C[N+](C)(C)CCOP(O)(=O)Oc1ccc(cc1)[N+]([O-])=O |
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epitope
The biological role played by a material entity when bound by a receptor of the adaptive immune system. Specific site on an antigen to which an antibody binds.
hapten
Any substance capable of eliciting an immune response only when attached to a large carrier such as a protein. Examples include dinitrophenols; oligosaccharides; peptides; and heavy metals.
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View more via ChEBI Ontology
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2-{[hydroxy(4-nitrophenoxy)phosphoryl]oxy}-N,N,N-trimethylethanaminium
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4-nitrophenyl 2-(trimethylammonio)ethyl phosphate
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4-nitrophenylphosphorylcholine
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ChEBI
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nitrophenylphosphocholine
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ChEBI
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nitrophenylphosphorylcholine
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ChEBI
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NPCC
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ChEBI
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NPPC
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ChEBI
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O-(4-nitrophenylphosphoryl)choline
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ChEBI
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p-nitrophenyl phosphorylcholine
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ChEBI
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P-NITROPHENYL-PHOSPHOCHOLINE
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PDBeChem
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p-nitrophenylphosphorylcholine
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ChEBI
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phosphocholine 4-nitrophenyl ester
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ChEBI
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10362092
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Beilstein Registry Number
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Beilstein
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10362092
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Reaxys Registry Number
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Reaxys
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Mazzuco RM, Sato MN, Vasconcelos Dde M, Duarte AJ (2007)
Cross-reactivity of anti-phosphorylcholine antibodies to neuromuscular blockers in a murine model of immunization.
International immunopharmacology 7, 1170-1178 [PubMed:17630195]
[show Abstract]
Hypersensitivity reactions to curare-like neuromuscular blocking agents (NMBA) used in anesthesiology are more frequent in females and often occur at the first exposure to these drugs. To evaluate the antibody response to a hapten sharing the same allergenic epitope with NMBA in a murine model of immunization with Nitrophenylphosphorylcholine (NPPC) coupled with Keyhole Limpet Hemocyanin (KLH). BALB/c mice from both sexes were intraperitoneally immunized with NPPC-KLH with alum and boosted twice, on 7 and 14 days. The antibodies were tested for specificity to PC and for cross-reactivity to the haptens, NPPC and PC, as well as to the NMBAs. Mice immunized with NPPC-KLH produced anti-PC antibodies mainly of IgM, IgG1 and IgG3 isotypes, at similar levels in both sexes. Different affinities for the haptens were detectable between isotypes, with anti-PC IgG3 antibody reactivity mostly related to the choline portion of the NPPC hapten. When comparing among sexes, females developed greater IgG2 affinity to the hapten than males. Cross-reactivity to NMBAs was predominant among the anti-PC IgG3 antibodies, mainly in females achieving 75% of inhibition with 16 mM of suxamethonium, while other isotypes achieved up to 30% and was absent for IgE. The investigation of antibody isotypes regarding sensitization to choline-derived structures could contribute to understanding the differential ability of females to produce antibodies that are cross-reactive with NMBAs. | Bay S, Huteau V, Zarantonelli ML, Pires R, Ughetto-Monfrin J, Taha MK, England P, Lafaye P (2004)
Phosphorylcholine-carbohydrate-protein conjugates efficiently induce hapten-specific antibodies which recognize both Streptococcus pneumoniae and Neisseria meningitidis: a potential multitarget vaccine against respiratory infections.
Journal of medicinal chemistry 47, 3916-3919 [PubMed:15267227]
[show Abstract]
Phosphorylcholine (ChoP) is commonly expressed at the surface of pathogens of the respiratory tract, including Streptococcus pneumoniae and Neisseria meningitidis. We designed a synthetic hapten comprising ChoP and part of its native carrier structure in S. pneumoniae, i.e. N-acetyl-D-galactosamine (GalNAc). Protein conjugates of this hapten induced GalNAc-ChoP-specific antibodies which recognized ChoP on both S. pneumoniae and N. meningitidis. GalNAc-ChoP could therefore lead to the rational design of a novel multipurpose vaccine against respiratory infections. | Brown M, Schumacher MA, Wiens GD, Brennan RG, Rittenberg MB (2000)
The structural basis of repertoire shift in an immune response to phosphocholine.
The Journal of experimental medicine 191, 2101-2112 [PubMed:10859335]
[show Abstract]
The immune response to phosphocholine (PC)-protein is characterized by a shift in antibody repertoire as the response progresses. This change in expressed gene combinations is accompanied by a shift in fine specificity toward the carrier, resulting in high affinity to PC-protein. The somatically mutated memory hybridoma, M3C65, possesses high affinity for PC-protein and the phenyl-hapten analogue, p-nitrophenyl phosphocholine (NPPC). Affinity measurements using related PC-phenyl analogues, including peptides of varying lengths, demonstrate that carrier determinants contribute to binding affinity and that somatic mutations alter this recognition. The crystal structure of an M3C65-NPPC complex at 2.35-A resolution allows evaluation of the three light chain mutations that confer high-affinity binding to NPPC. Only one of the mutations involves a contact residue, whereas the other two have indirect effects on the shape of the combining site. Comparison of the M3C65 structure to that of T15, an antibody dominating the primary response, provides clear structural evidence for the role of carrier determinants in promoting repertoire shift. These two antibodies express unrelated variable region heavy and light chain genes and represent a classic example of the effect of repertoire shift on maturation of the immune response. | Heusser CH, Bews JP, Aebersold R, Blaser K (1984)
Anti-phosphorylcholine antibodies with a preferred reactivity for either PC or PC-phenyl represent independent expressions.
Annales d'immunologie 135C, 123-129 [PubMed:6424547]
[show Abstract]
Anti-hapten antibodies to phosphorylcholine(PC)-conjugated proteins can be divided into antibodies reacting preferentially with PC (group I) or with PC-phenyl (group II). We have selected two hybridomas producing group II-type anti-PC antibodies of the IgM and IgE classes, respectively. With one exception, NH2-terminal amino acid sequence analyses of the light chains are identical in their first 21 residues and similar to that of M460, but differ from that of group I-type light chains. These results suggest that PC-phenyl-specific group II antibodies are expressed independently of PC-specific group I antibodies. | Chang SP, Perlmutter RM, Brown M, Heusser CH, Hood L, Rittenberg MB (1984)
Immunologic memory to phosphocholine. IV. Hybridomas representative of Group I (T15-like) and Group II (non-T15-like) antibodies utilize distinct VH genes.
Journal of immunology (Baltimore, Md. : 1950) 132, 1550-1555 [PubMed:6420466]
[show Abstract]
The anti-phosphocholine (PC) memory response elicited in BALB/c mice by phosphocholine-keyhole limpet hemocyanin (PC-KLH) contains two groups of antibodies distinguished by their fine specificity for PC and p-nitrophenylphosphocholine (NPPC). Group I antibodies are inhibited by both PC and NPPC, while Group II antibodies are inhibited appreciably only by NPPC; only Group I antibodies are dominated by the T15 idiotype. Anti-PC hybridomas representative of the memory response to PC-KLH were produced to examine the variable region genes expressed by memory B cells. Two IgM hybridomas were of the Group I type, because they were inhibited by both PC and NPPC and they bound to the pneumococcus R36A. However, only one of these antibodies (PCM-2) expressed a T15 idiotope, while the other (PCM-1) did not express any of three T15 idiotopes. Despite its negative T15 idiotype profile, N-terminal amino acid sequencing of PCM-1 purified heavy chain and Southern blots of the hybridoma DNA indicated that it utilizes the T15 VH and JH1 genes. Three hybridomas, IgG1, IgM, and IgE, typical of Group II antibodies, were examined; these were negative for three T15 idiotopes and displayed measurable avidity only for NPPC in a PC-protein binding inhibition assay. These three hybridoma antibodies, like serum Group II IgG1, did not measurably bind to the bacterium R36A. The heavy chain amino termini of all three of these antibodies were inaccessible for Edman degradation. Southern blots of DNA from the IgG1 hybridoma revealed the T15 VH gene to be in the germ line configuration only and unassociated with any JH segment, indicating that this Group II antibody utilizes a VH gene different from the T15 family. These results signify that, whereas some diversity of the (anti-PC) memory response may be generated by somatic diversification of variable regions important in the primary response, a significant contribution to the overall heterogeneity of memory antibodies originates in the expression of additional variable region genes. |
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