Synthesis of site-specific methotrexate-IgG conjugates View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

1989-08

AUTHORS

J. Kralovec, M. Singh, M. Mammen, A. H. Blair, T. Ghose

ABSTRACT

With a view to increasing drug incorporation without loss of antibody activity, tritium-labeled methotrexate (MTX) was covalently linked to a polyclonal rabbit IgG antibody against bovine serum albumin and a monoclonal mouse IgG antibody against human renal cancer (Dal K20) by a site-specific method based on hydrazone bond formation between MTX hydrazide and the aldehyde groups generated by periodate oxidation of carbohydrate moieties in IgG (which are uncommon in the antigen-binding region). These conjugates were compared with the corresponding non-site-specific MTX-IgG conjugates produced by the N-hydroxysuccinimide active-ester method with regard to synthesis, stability, retention of antibody activity, inhibition of the target enzyme dihydrofolate reductase and antitumor effect. Incorporation levels achieved with the hydrazide method were no greater than with the active-ester method, typically 6-7 mol MTX/mol IgG. Approximately the same dihydrofolate-reductase-inhibitory capacity was observed for MTX bound by either method. Hydrazide conjugates lost bound drug more rapidly than active-ester conjugates on freezing and thawing, on incubation at 37 degrees C and 51 degrees C, and in the presence of serum or rat liver homogenates. Exposure to rat liver homogenates at 37 degrees C, pH 4.6, for 24 h led to the loss of 50%-60% of the bound drug from hydrazide conjugates compared to 20%-30% from the active ester conjugates. Bio-Gel P-2 chromatography of low-molecular-mass fractions, obtained after exposure of each of the conjugates to liver homogenates, revealed the presence of a compound that had the same elution volume and RF on thin-layer chromatography as free MTX. Enzyme-linked immunosorbent assay showed loss of antibody activity of both types of conjugates at 51 degrees C and on freezing and thawing. In a clonogenic assay, the active-ester conjugate of Dal K20 appeared to be equally effective or slightly better as a tumor inhibitor than the corresponding hydrazide conjugate. The hydrazide method may be useful in linking MTX to those monoclonal antibodies that tend to denature when subjected to the active-ester method of linkage. More... »

PAGES

293-302

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/bf00199218

DOI

http://dx.doi.org/10.1007/bf00199218

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1004129795

PUBMED

https://www.ncbi.nlm.nih.gov/pubmed/2787696


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