Inhibitors of aminoglycoside 6′- N...

Details Inhibitors of aminoglycoside 6′- N... Inhibitors of aminoglycoside 6′- N...

2006-02-21

2009-12-01

Jiang, Shaojia Anna (Department: 1623)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

C536S016800, C514S062000

Reexamination Certificate

active

07626005

ABSTRACT:
The present invention relates to novel inhibitors of aminoglycoside 6′-N-acetyltransferases, more specifically, AAC(6′)-li and AAC(6′)-ly, as well as compositions and uses thereof. Furthermore, the present invention relates to synthetic methodologies for preparing the inhibitors of aminoglycoside 6′-N-acetyltransferases.

REFERENCES:
Sugimoto, T., Fujii, T., Hatanaka, Y., Yamamura, S., and Ueda, M. Syntheses of novel photoaffinity probes for bioorganic studies on nyctinasty of leguminous plants. (2002) Tetrahedron Letters, v. 43, p. 6529-6532.
Gao, F. et al. (2006) Synthesis and Structure-Activity Relationships of Truncated Bisubstrate Inhibitors of Aminoglycoside 6'-N-Acetyltransferases. Journal of Medicinal Chemistry, vol. 49, p. 5273-5281.
Gao, F., Yan, X., Baettig, O.M., Berghuis, A.M., Auclair, K. (2005) Regio- and Chemoselective 6'-N-Derivatization of Aminoglycosides: Bisubstrate Inhibitors as Probes to Study Aminoglycoside 6-N-Acetyltransferases. Angewandte Chemie International Edition, vol. 44, p. 6859-6862.
The Merck Manual - Second Home Edition, chapter 192, p. 1-5. [retrieved online Sep. 6, 2008].
Agnelli et al., “Dimeric Aminoglycosides as Antibiotics,”Agnew. Chem. Int. Ed., 43:1562-1566, 2004.
Alper et al., “Metal Catalyzed Diazo Transfer for the Synthesis of Azides From Amines,”Tet. Lett., 37:6029-6032, 1996.
Arya et al., “Aminoglycoside—Nucleic Acid Interactions: Remarkable Stabilization of DNA and RNA Triple Helices by Neomycin,”J. Am. Chem. Soc., 123:5385-5395, 2001.
Arya et al., “Aminoglycoside (neomycin) preference is for A-form nucleic acids, not just RNA: results from a competition dialysis study,”J. Am. Chem. Soc., 125:10148-10149, 2003.
Arya et al., “From triplex to B-form duplex stabilization: reversal of target selectivity by aminoglycoside dimers,”Bioorg. Med. Chem. Lett., 14:4643-4646, 2004.
Arya et al., “Neomycin-induced hybrid triplex formation,”J. Am. Chem. Soc., 123:11093-11094, 2001.
Azucena and Mobashery, “Aminoglycoside-modifying enzymes: mechanisms of catalytic processes and inhibition,”Drug Resistance Updates, 4:106-117, 2001.
Boehr et al., “Domain- Domain Interactions in the Aminoglycosides Antibiotic Resistance Enzyme AAC(6′)- APH(2″),”Biochemistry, 43:9846-9855, 2004.
Boto and Coxon, “Nitrogen-15 Nulcear Magnetic Resonance Spectroscopy of Neomycin B and Related Aminoglycosides,”J. Am. Chem. Soc., 105:1021-1028, 1983.
Burk et al., “X-ray structure of the AAC(6′)-Ii antibiotic resistance enzyme at 1.8 A resolution; examination of oligomeric arrangements in GNAT superfamily members,”Prot. Sci., 12:426-437, 2003.
Chou et al., “Regioselective Glycosylation of Neamine Core: A Facile Entry to Kanamycin B Related Analogues,”Org. Lett., 6:585-588, 2004.
Coates et al., “The Future Challenges Facing the Development of New Antimicrobial Drugs,”Nat. Rev., 1:895-910, 2002.
Culebras and Martinez, “Aminoglycoside resistance mediated by the bifunctional enzyme 6′-N-Aminoglycoside Acetyltransferase-2″-O-Aminoglycoside Phosphotransferase,”Front. Biosci., 4:D1-D8, 1999.
Ding et al., “Design and Synthesis of Paromomycin-Related Hetrocycle-Substituted Aminoglycoside Mimetics Based on a Mass Spectrometry RNA-Binding Assay,”Angew. Chem. Int. Ed., 42:3409-3412, 2003.
Ding et al., “Efficient synthesis of neomycin B related aminoglycosides,”Tet. Lett., 41:4049-4052, 2000.
Draker and Wright, “Molecular Mechanism of the Enterococcal Aminoglycoside 6′-N-Acetyltransferase: Role of GNAT-Conserved Residues in the Chemistry of Antibiotic Inactivation,”Biochemistry, 43:446-454, 2004.
Draker et al., “Kinetic Mechanism of the GCN5-Related Chromosomal Aminoglycoside Acetyltransferase AAC(6′)-Ii fromEnterococcus faecium: evidence of Dimer Subunit Cooperativity,”Biochemistry, 42:6565-6574, 2003.
Fourmy et al., “Binding of neomycin-class aminoglycoside antibiotics to the A-site of 16 S rRna,”J. Mol. Biol., 277:347-362, 1998.
Fourmy et al., “Structure of the A Site ofEscherichia coli16S Ribosomal RNA Complexed with and Aminoglycoside Antibiotic,”Science, 274:1367-1375, 1997.
Gallego and Varani, “Targeting RNA with small-molecule drugs: therapeutic promise and chemical challenges,”Acc. Chem. Res., 34:836-843, 2001.
Georgiadis and Constantinou-Kokotou, “Synthesis of Amino Acid Derivatives of Neamine and 2-Deoxystreptamine to be use as Mutasynthons,”J. Carb. Chem., 10:739-748, 1991.
Grapsas et al., “N-(tert-Butoxycarbonyloxy)-5-norbornene-endo-2,3-dicarboximide, a Reagent for the Regioselective Introduction of the tert-Butoxycarbonyl (BOC) Protective Group at Unhindered Amines: Application to Aminoglycoside Chemistry,”J. Org. Chem., 59:1918-1922, 1994.
Greenberg et al., “Design and Synthesis of New Aminoglycosides Containing Neamine as an Optical Core Structure: Correlation of Antibiotic Activity with in Vitro Inhibition of Translation,”J. Am. Chem. Soc., 121:6527-6541, 1999.
Haddad et al., “Design of novel antibiotics that bind to the ribosomal acyltransfer site,”J. Am. Chem. Soc., 124:3229-3237, 2002.
Hanessian and Patil, “Aminoglycoside Antibiotics—A Method for Selective N-Acylation Based on the Temporary Protection of Amino Alcohol Functions as Copper Chelates,”Tet. Lett., 12:1035-1038, 1978.
Hanessian et al., “Design, modeling and synthesis of functionalized paromamine analogs,”Tetrahedron, 57:3255-3265, 2001.
Hanessian et al., “Tobramycin analogues with C-5 aminoalkyl ether chains intended to mimic rings III and IV of paromomycin,”Tetrahedron, 59:983-993, 2003.
Hermann, “Strategies for the Design of Drugs Targeting RNA and RNA-Protein Complexes,”Chem. Int. Ed., 39:1890-1905, 2000.
Hermanson, “The Chemistry of Reactive Groups,”In: Bioconjugate Techniques, Ch. 2., pp. 137-168, Academic Press, Inc, 1995.
Kim and Cole, “Bisubstrate Ketone Analogues as Serotonin N-Acetyltransferase Inhibitors,”J. Med. Chem., 44:2479-2485, 2001.
Li et al., “Role of the acetlytransferase AAC(6′)-Iz modifying enzyme in aminoglycoside resistance inStenotrophomonas maltophilia,”Antimicrob. Chemother., 51:803-811, 2003.
Litovchick et al., “Aminoglycoside- Arginine Conjugates That Bind TAR RNA: Synthesis, Characterization, and Antiviral Activity,”Biochemistry, 39:2838-2852, 2000.
Liu et al., “Deoxystreptamine dimers bind to RNA hairpin loops,”J. Am. Chem. Soc., 126:9196-9197, 2004.
Luedtke et al., “RNA- Ligand Interactions: Affinity and Specificity of Aminoglycoside Dimers and Acridine Conjugates to the HIV-1 Rev Response Element,”Biochemistry, 39:11391-11403, 2003.
Magnet et al., “Aminoglycoside Resistance Resulting from Tight Drug Binding to an Altered Aminoglycoside Acetyltransferase,”Antimicrobial Agents Chemother., 47:1577-1583, 2003.
Magnet et al., “Kinetic and Mutagenic Characterization of the Chromosomally EncodedSalmonella entericaAAC(6′)-Iy Aminoglycoside N-Acetyltransferase,”Biochemistry, 40:3700-3709, 2001.
Marmorstein, “Structure of Histone Acetyltransferases,”J. Mol. Biol., 311:433-444, 2001.
Michael et al., “Enhanced RNA Binding of Dimerized Aminoglycosides,”Bioorg. Med. Chem. Lett., 7:1361-1371, 1999.
Moiseev et al., “alpha-Halo Ketones in C-, N-, O-, and S-Alkylation Reactions,”Russian J. Org. Chem., 39:1685-1701, 2003.
Murray, “The life and times of theEnterococcus,” Clin. Microbiol. Rev., 3:46-65, 1990.
Nunns et al., “Synthesis of neamine libraries for RNA recognition using solution phase chemistry,”Tet. Lett., 40:9341-9345, 1999.
Park et al., “Rapid Combinatorial Synthesis of Aminoglycoside Antibiotic Mimetics: U

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