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(12) Patent Application Publication (10) Pub. No.: US 2006/0116335 A1 Chang Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2006/0116335 A1 Chang Et Al US 2006O116335A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2006/0116335 A1 Chang et al. (43) Pub. Date: Jun. 1, 2006 (54) READY-FOR-COMPLEXATION Publication Classification COMPOSITION (51) Int. Cl. (75) Inventors: William T. H. Chang, Taipei (TW); A6II 3L/724 (2006.01) James H. Y. Chen, Taipei (TW); Wen A6II 3 L/7048 (2006.01) Pin Yeh, Taipei County (TW) (52) U.S. Cl. ................................................. 514/28: 514/58 Correspondence Address: Ladas & Parry (57) ABSTRACT 26 West 61st Street Newew York,York, NY 10O23 (US)US The invention relates to a ready-for-complexation (RFC) (73) Assignee: Lytone Enterprise, Inc. composition, comprising a polyene antimycotic and a cyclo dextrin or the derivatives thereof. Also disclosed is a method (21) Appl. No.: 10/998,257 of using the ready-for-complexation (RFC) composition of the invention to improve the solubility of polyene antimy (22) Filed: Nov. 26, 2004 cotic. US 2006/01 16335 A1 Jun. 1, 2006 READY-FOR-COMPLEXATION COMPOSITION tural products, said composition comprises polyene antimy cotic and a cyclodextrin or the derivatives thereof. FIELD OF THE INVENTION 0008 Another further object of the invention is to pro 0001. The present invention relates to a ready-for-com vide a method of using a ready-for-complexation composi plexation (RFC) composition, comprising a polyene anti tion in culture Substrate against fungal infection, comprising mycotic and a cyclodextrin or the derivatives thereof. providing said composition and applying said composition to a culture Substrate, said composition comprises polyene BACKGROUND OF THE INVENTION antimycotic and a cyclodextrin or the derivatives thereof. 0002 Many polyene antimycotics are known to have antifungal properties useful for treating fungal infections. DETAILED DESCRIPTION OF THE The polyene antimycotics are basically and uniquely char INVENTION acterized by a large lactone ring which includes a chain of 0009. The present invention provides a ready-for-com conjugated double bonds, specifically comprising 4, 5, 6 or plexation (RFC) composition, comprising a polyene anti 7 Such linkages, whereby the compounds are correspond mycotic and a cyclodextrin or the derivatives thereof. ingly known as tetraenes, pentaenes, hexaenes and hep taenes and are collectively called polyenes. EP0434943 0010. According to the invention, the polyene antimy indicates that the polyene antimycotics have a low or almost cotics used in the ready-for-complexation (RFC) composi absent water solubility, which is a common characteristic of tion of the invention are a group of macrocyclic polyketides all the polyenes and causes a strong hindrance to diffusion that interact with membrane sterols and are, therefore, active after application. against fungi but not bacteria. The macrollide rings of polyene antimycotics are larger than those of standard 14- or 0003 Natamycin, an example of polyene antimycotic, is 16-membered nonpolyene macrollides. The latter rings provided to illustrate the solubility defects of the polyene include a chromophore of conjugated double bonds, which antimycotic. Natamycin is a member of the polyene family, are the characteristic polyene structure. According to the and has been used to prevent fungal growth on foods for invention, the polyene antimycotic refers to the polyene more than 30 years. It is common in the surface treatment of macrollides and their derivatives. The polyene macrollide cheese and sausage and can also be used to prevent spoilage derivatives of the invention comprise a main polyene mac of juice and fermented milk by yeast (N. J. Russell and G. rollide backbone derived from any of a variety of polyene W. Gould, Kluewer Academic/Plenum Publishers, New macrollides. Examples of these polyene macrollides include, York, pp. 179-195.) However, due to the amphoteric char but not limited to, natamycin, amphotericin B. aureofacin, acter of the natamycin, it has a low solubility in most candicidin, candidin, levorin, mycoheptin, nystatin, partricin solvents. U.S. Pat. No. 6,156,362 indicates that natamycin is A, partricin B, perimycin, pimaricin, polyfungin, rimocidin relatively insoluble in water, in which its solubility is of the and trichomycin. order 0.005-0.010 weight/weighdditionally; even in solu tion, natamycin is rather unstable. The low solubility of 0011 Natamycin is one preferred embodiment of polyene natamycin also limits its application in food process. An antimycotic of the invention. Natamycin is a commonly enhanced antimycotic activity could be achieved by improv used polyene antimycotic in preventing fungal growth on ing solubility of natamycin, thus making it more available to foods. Natamycin is a creamy white, odorless, tasteless, the food environment. The solubility of natamycin in water especially insoluble crystalline amphoteric powder. The can be increased using alkaline, acidic conditions or organic natamycin Suitable for use in the invention is a known and solvents. However, the dissolved natamycin molecule is commercially available yeast and mold inhibitor that has sensitive to light, oxygen, or extreme pH value. It is well been used to prevent the growth of yeasts and molds in known that dissolved natamycin would rapidly decompose various products. Natamycin also refers to other names Such as pimaricin, antibiotic A 5283, tennecetin, CL 12625, in water. Mycophyt, Myprozine, Natacyn and Pimafucin, all of which 0004. Accordingly, it would be desirable to solve the are collectively referred to as “natamycin' for the purposes problem of poor solubility and solution stability of polyene of the invention. According to the invention, natamycin also antimycotics. includes any compounds having Substantially the same chemical structure as natamycin, e.g., compounds produced SUMMARY OF THE INVENTION by chemical synthesis or biotechnology, provided such com pounds have essentially the same mold and yeast inhibition 0005. An object of the invention is to provide a ready properties. Natamycin, Such as those from Gist-Brocades for-complexation (RFC) composition, comprising a polyene Food Ingredients, Inc. of King of Prussia, Pa. (DELVO antimycotic and a cyclodextrin or the derivatives thereof. CID.RTM) and Cultor Food Science Inc., Roseville, Calif. 0006 Another object of the invention is to provide a (NATAMAX.RTM), is commercially available. method of using the ready-for-complexation (RFC) compo 0012. According to the invention, the cyclodextrins used sition of the invention to improve the solubility of polyene in the ready-for-complexation (RFC) composition of the antimycotics, comprising dissolving the ready-for-complex invention are a group of structurally related Saccharides ation composition in water or buffer solution to form a which are formed by enzymatic cyclization of starch by a cyclodextrin-polyene antimycotic inclusion complex. group of amylases termed glycosyltransferases. The most 0007 Another object of the invention is to provide a common naturally occurring cyclodextrins are C-cyclodex method of using a ready-for-complexation composition for trin, B-cyclodextrin and Y-cyclodextrin consisting of 6, 7 and postharvest treatment, comprising providing said composi 8glucopyranose units, respectively. The most notable feature tion and applying said composition to postharvest agricul of cyclodextrin is their ability to form solid inclusion US 2006/01 16335 A1 Jun. 1, 2006 complexes (host-guest complexes) with a very wide range of For example, the RFC composition of the invention can be Solid, liquid and gaseous compounds by a phenomenon of used for the treatment of postharvest agricultural products molecular complexation. In these complexes, a guest mol and culture substrate. Preferably, the agricultural products ecule is held within the cavity of the cyclodextrin host comprises but not limited to vegetables, fruits and meats. molecule. The term “guest' is used to refer to the compound which is trapped and complexed within the cyclodextrin 0017. The following examples further illustrate the molecule. Cyclodextrins are cyclic oligosaccharides, con present invention, but are not intended to limit the scope of sisting of (C-1,4)-linked C-D-glucopyranose units, with a the present invention. The modifications and Substitutions Somewhat lipophilic central cavity and a hydrophilic outer known to those skilled in the art are still within the scope and Surface. The materials such as natamycin to be complexed spirit of the present invention. are trapped within the cavity of the cyclodextrin molecules and held there through a number of different binding mecha EXAMPLE nisms. According to the invention, appropriate cyclodextrin derivatives can also be used to complex with the natamycin. Example 1 The term “cyclodextrin derivative' refers to modified cyclo dextrin, branched cyclodextrin and their mixtures. Accord ing to the invention, cyclodextrin derivatives include, but Preparation of Ready-for-Complexation (RFC) not limited to, the hydroxypropyl derivatives of C, B and Composition Y-cyclodextrin, Sulfoalkylether cyclodextrins such as Sul fobutylether f3-cyclodextrin, alkylated cyclodextrins such as 0018. The example describes the preparation of RFC the randomly methylated B-cyclodextrin, and various composition of the invention. B-cyclodextrin (B-CD) was branched cyclodextrins such as glucosyl- and maltosyl-3- mixed with the polyene antimycotic powder in a molar ratio cyclodextrin. from 1:1 to 4:1 by hand or mixing devices. The resultant samples were stored at low temperature
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