Active Insolubilized Antibiotics Based on Cellulose and Cellulose Carbonate

Abstract

The coupling of a number of antibiotics to cellulose and cellulose trans-2, 3-carbonate under a series of coupling conditions has been investigated, and it has been shown that by such couplings active insoluble derivatives of antibiotics can be produced. It was found that the antibiotics became firmly bound to cellulose itself, whereas use of cellulose carbonate extended the range of antibacterial activity retained. In the case of cellulose, it was considered that physical adsorption phenomena were operating, whereas a covalent bond was more likely in the case of cellulose carbonate where the antibiotic amino groups could attack the electrophilic cyclic carbonate carbon atoms. The release of antibiotic from the matrix during testing of antibacterial activity was likely due to the action of a cellulase or additionally an esterase in the case of cellulose carbonate. The importance and potential of these new types of chemical derivatives are discussed in terms of new outlets for the commercial use of cellulose.

Active Insolubilized Antibiotics Based on Cellulose-Metal Chelates

“…Although for each of these transition metals, including titanium"', other, more complex ionic species may be present, these are considered to be of less importance in the chelating reactions. Previous work (8) has shown that cellulose itself may tenaciously bind, albeit noncovalently, antibiotics in such a way that in certain instances some of the antibiotic activity is retained. The coupling to cellulose was carried out under these (2) 8), and the cellulose-metal-antibiotic chelates (Table 1) reveals that it is advantageous to use the cellulose-metal-antibiotic chelate derivatives, since wider spectra of activities of the product-immobilized antibiotics are achieved.…”

“…The potentials of active insolubilized derivatives of antibiotics for the production of antimicrobial surfaces and slow-release formulations in medical and industrial fields have already been discussed (8,10). Practically, preliminary work showed that streptomycin and gentamicin can be attached to specialized polymers, poly(N-acryloyl-4-and -5-amino-salicylic acids) (8).…”

“…Practically, preliminary work showed that streptomycin and gentamicin can be attached to specialized polymers, poly(N-acryloyl-4-and -5-amino-salicylic acids) (8). Investigation of the coupling of a number of antibiotics to cellulose trans-2,3-carbonate under a series of coupling conditions, showed that it is possible to produce insoluble derivatives of antibiotics that possess antibacterial activity.…”

“…Whereas cellulose trans-2,3-carbonate has now proved very useful in the field of insolubilization not only for antibiotics (8) but also for enzymes (2,7,11,12), immunoglobulins (4,13), ' British patent application 20617/72. and phytohemagglutinins (N. Ling, J. Bray, and J. F. Kennedy, unpublished data), it cannot be expected to be universally applicable.…”

“…Since ; a portion of the suspension was mixed with an equal volume of double-strength agar (1.6%, wt/vol), and the suspensions were introduced into ditch plates of agar as described previously (8). Antibacterial activity against E. coli, P. aeruginosa, Streptococcus faecalis, and Staphylococcus pyogenes (these organisms, two gram negative and two gram positive, were selected as representative of bacteria) and antifungal activity against A. niger, M. hiemalis, Penicillium chrysogenum, and Saccharomyces cerevisiae (these organisms were selected as representative of fungi) were determined, after inoculation of the plates, as described previously (8). For antibacterial activity, each plate was separately inoculated with cultures of the four organisms in four separate strips perpendicular to the ditch.…”