Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Reexamination Certificate
2001-01-22
2003-02-25
Jones, Dwayne C. (Department: 1614)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
C536S013300, C536S013700, C536S014000, C536S015000, C536S018500, C514S032000, C514S037000, C514S041000, C514S459000, C514S460000
Reexamination Certificate
active
06525182
ABSTRACT:
BACKGROUND
Many natural compounds that bear a guanidine functional group have biological activity that make them useful as pharmaceuticals. Among these compounds are antimicrobials, antifungals, antivirals, neurotoxins, hormones, and agents that act as agonists or antagonists to biological signals. A review of these natural products is presented in Progress in the Chemistry of Organic Natural Products (1995) 66:119 and Berlinck, R. G. S. (1996) Nat. Prod. Reports 13(5):377-409. Much effort has been directed to developing routes for preparing these compounds or their analogues synthetically.
Guanidine-containing bioactive molecules, particularly the analogs or derivatives of the natural products, are now significant targets for drug design and discovery. The guanidine moiety in the bioactive compound frequently occurs in arginine-containing polypeptide chains which may comprise the entire biomolecule or exist as an incorporated moiety. Arginine, together with lysine, another amino acid with a positively charged side chain, plays an important role in biologically active proteins and peptides. Various arginine analogues and derivatives have been synthesized and incorporated into peptides and peptidomimetics to study the structure-activity relationships of arginine-containing molecules. These residues are frequently the critical amino acid residues in peptidomimetics.
Guanidine-containing sugars and sugar-like molecules have a wide range of biologically important uses such as inhibition of inappropriate mitogenic signaling, therapy for bacterial infections, treatment of non-insulin-dependent diabetes, and inhibition of enzymes including thrombin, glycosidases, and nitric oxide synthases.
The development of novel guanidinylated compounds are useful in methods of treating or modulating disease states and other disorders.
SUMMARY OF THE INVENTION
The present invention provides a guanidinoglycoside produced by reacting a compound having the general formula N,N′-diprotected-N″-triflylguanidine (I) with an aminoglycoside under conditions such that the aminoglycoside is guanidinylated thereby producing the guanidinoglycoside.
In one embodiment, the present invention provides a guanidinoglycoside, including, for example, guanidinylated-Boc protected glycosides.
In another embodiment, the present invention provides a guanidinylated tobramycin.
In another embodiment, the invention provides a guanidinylated glucosamine.
In a yet another embodiment, the present invention provides a guanidinylated 2-deoxystreptamine.
The invention further provides a guanidinylated kanamycin A or kanamycin B and guanidinylated paromomycin.
In yet a further embodiment, the present invention provides a guanidinylated neomycin.
The present invention provides a method for identifying a compound that binds to a HIV-1 Rev protein RNA recognition element (RRE). The method includes incubating components comprising a test compound, the RRE, and a labeled Rev protein under conditions sufficient to allow the components to interact; and detecting the labeled Rev protein, wherein the location or emission of the labeled Rev is indicative of a test compound that binds to the RRE.
The present invention also provides a method of treating a subject having or at risk of having a bacterial or viral infection, comprising, contacting the subject with a guanidinoglycoside in an amount sufficient to inhibit or prevent the bacterial or viral infection. The subject may be any animal, including mammals; preferably the mammal is a human.
REFERENCES:
patent: 6072075 (2000-06-01), Goodman et al.
patent: WO 95/29926 (1995-11-01), None
Abstract to Luts, et al., “2-Deoxystreptamine derivatives”, J. Pharm. Sci. 50, pp. 328-330, 1961.*
Abstract to Odo et al., “Guanidination of D-glucosamine”, J. Org. Chem. 23, pp. 1319-1321, 1958.
Baker Tracy
Goodman Murray
Luedtke Nathan
Tor Yitzhak
Gray Cary Ware & Freidenrich LLP
Haile Lisa A.
Jones Dwayne C.
Learn June M.
Regents of the University of California
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