Synthesis and characterization of water-soluble polyaspartamide-ferrocene conjugates for biomedical applications View Full Text


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Article Info

DATE

1994-06

AUTHORS

Jannie C. Swarts, Eberhard W. Neuse, Gert J. Lamprecht

ABSTRACT

Polymer-ferrocene conjugates are synthesized from the polyamide1, poly-α,β-dl-[N-(3-(morpholin-4-yl)propyl)aspartamide-co-N-(2-aminoethyl)aspartamide, through coupling of amino side groups with the carboxyl function in a number of ferrocenylcarboxylic acids, including ferrocenoic acid, ferrocenylacetic acid, 3-ferrocenylpropanoic acid, 3-ferrocenylbutanoic acid, 4-ferrocenylbutanoic acid, and 4-ferrocenyl-4-hydroxypentanoic acid. The ferrocene complex has been chosen for conjugation by virtue of the cytotoxic properties observed with some of its derivatives. The coupling reactions, mediated by HBTU (O-benzotriazolyl-N,N,N′N′-tetramethyluronium hexafluorophosphate), are brought about inN,N-dimethylformamide solution and lead to degrees of substitution in the range of 25–95%. The resulting conjugates2, fractionated by dialysis in tubing with a 12,000–14,000 molecular mass cutoff and collected in the solid state by freeze-drying, are completely soluble in water after isolation and retain this property in frozen aqueous solutions. Preliminary electrochemical data are reported, indicating a decreasing (i.e., less positive) potential with increasing length of the aliphatic, electron-donating connecting link between the ferrocene and the carboxamide anchoring group. The 4-ferrocenylbutanoyl substituent is associated with the least positive potential of those structures investigated and, hence, should provide conjugates with optimalin vivo stability in the ferricenium state. Selected conjugates will be submitted to screening tests for antineoplastic activity. More... »

PAGES

143-153

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/bf01036539

DOI

http://dx.doi.org/10.1007/bf01036539

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1023905485


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