New macrolide, lincosaminide and streptogramin B antibiotics

Importance of the field: New antibiotics are needed to overcome microbial resistance and to improve on the therapeutic index and clinical effectiveness of existing agents. Area covered in this review: This review covers the journal and patent literature published from about the mid-2000s to 2010 to provide an overview of the large diversity of new chemical entities in the macrolide, lincosaminide and streptogramin B (MLSB) class. What the reader will gain: The review identifies areas of the greatest effort and recent results in pursuing structure–activity relationships among MLSB antibiotics and highlights preclinical and clinical candidates that have arisen from these diverse discovery programs. Take home message: Research on the MLSB class appears promising for the eventual registration and commercialization of several new antibiotics that improve the clinical effectiveness of existing agents and combat antibiotic-resistant pathogens.

[1]  Maxwell M. Reeve,et al.  Synthesis of an Antibacterial Compound Containing a 1,4-Substituted 1H-1,2,3-Triazole: A Scaleable Alternative to the “Click” Reaction , 2010 .

[2]  T. Kaneko,et al.  Novel tethers in ketolide antibiotics. , 2007, Bioorganic & medicinal chemistry letters.

[3]  Bryan M. Li,et al.  Discovery of azetidinyl ketolides for the treatment of susceptible and multidrug resistant community-acquired respiratory tract infections. , 2009, Journal of medicinal chemistry.

[4]  M. Hammerschlag,et al.  Use of cethromycin, a new ketolide, for treatment of community-acquired respiratory infections , 2008 .

[5]  P. Lei,et al.  Synthesis of novel macrolide derivatives with imidazo[4,5-b]pyridinyl sulfur contained alkyl side chains and their antibacterial activity. , 2009, Bioorganic & medicinal chemistry letters.

[6]  Y. Or,et al.  Design, synthesis, and antibacterial activities of novel 3,6-bicyclolide oximes: length optimization and zero carbon linker oximes. , 2008, Bioorganic & medicinal chemistry letters.

[7]  Y. Or,et al.  Synthesis of 3,6-bicyclolides: a novel class of macrolide antibiotics. , 2008, Bioorganic & medicinal chemistry letters.

[8]  T. Arai,et al.  Novel Azalides Derived from Sixteen-Membered Macrolides , 2007, The Journal of Antibiotics.

[9]  E. Bacqué,et al.  Recent Progress in the Field of Antibacterial Pristinamycins , 2005 .

[10]  D. B. Ross.  The FDA and the case of Ketek. , 2007, The New England journal of medicine.

[11]  H. Kirst,et al.  Synthesis and in vitro antimicrobial activity of 3-keto 16-membered macrolides derived from tylosin. , 2002, The Journal of antibiotics.

[12]  P. Mcghee,et al.  In Vitro Activity of CEM-101 against Streptococcus pneumoniae and Streptococcus pyogenes with Defined Macrolide Resistance Mechanisms , 2009, Antimicrobial Agents and Chemotherapy.

[13]  J. Harms,et al.  Ketolides: pharmacological profile and rational positioning in the treatment of respiratory tract infections. , 2008, Expert opinion on pharmacotherapy.

[14]  J. Shimada,et al.  Intrapulmonary Pharmacokinetics of S-013420, a Novel Bicyclolide Antibacterial, in Healthy Japanese Subjects , 2009, Antimicrobial Agents and Chemotherapy.

[15]  L. Kellenberger,et al.  Novel ketolide antibiotics with a fused five-membered lactone ring--synthesis, physicochemical and antimicrobial properties. , 2004, Bioorganic & medicinal chemistry.

[16]  K. Undheim,et al.  Chemoselective synthesis of erythromycin A ketolides substituted in the C10-methyl group. , 2007, Bioorganic & medicinal chemistry.

[17]  Mao-Mao An,et al.  Design, synthesis and antibacterial activity of a novel alkylide: 3-O-(3-aryl-propenyl)clarithromycin derivatives , 2009, The Journal of Antibiotics.

[18]  B. Rubin,et al.  Macrolides as immunomodulatory medications for the therapy of chronic lung diseases. , 2008, Current opinion in pharmacology.

[19]  Hiroshi Ikuta,et al.  In vitro and in vivo antibacterial activities of the tricyclic ketolide TE-802 and its analogs. , 2004, The Journal of antibiotics.

[20]  Shutao Ma,et al.  Synthesis and antibacterial activity of novel 11,12-cyclic carbonate azithromycin 4″-O-carbamate derivatives , 2010, The Journal of Antibiotics.

[21]  Hajime Takashima.  Structural consideration of macrolide antibiotics in relation to the ribosomal interaction and drug design. , 2003, Current topics in medicinal chemistry.

[22]  S. Franzblau,et al.  In Vitro and In Vivo Activities of Macrolide Derivatives against Mycobacterium tuberculosis , 2005, Antimicrobial Agents and Chemotherapy.

[23]  M. Sulc,et al.  Mutasynthesis of Lincomycin Derivatives with Activity against Drug-Resistant Staphylococci , 2009, Antimicrobial Agents and Chemotherapy.

[24]  W. Mcmillen,et al.  Synthesis and Antibacterial Activity of C11, C12‐Cyclic Urea Analogues of Ketolides. , 2008 .

[25]  R. Sawyer,et al.  NXL-103, a combination of flopristin and linopristin, for the potential treatment of bacterial infections including community-acquired pneumonia and MRSA. , 2010, Current opinion in investigational drugs.

[26]  M. Desai,et al.  Synthesis and antibacterial activity of novel C12 ethyl ketolides. , 2006, Bioorganic & medicinal chemistry.

[27]  B. Mordmüller,et al.  In Vitro Activity of Mirincamycin (U24729A) against Plasmodium falciparum Isolates from Gabon , 2009, Antimicrobial Agents and Chemotherapy.

[28]  U. Möllmann,et al.  Preparation and biological evaluation of novel leucomycin analogs derived from nitroso Diels-Alder reactions. , 2010, Organic & biomolecular chemistry.

[29]  S. Lociuro,et al.  A novel ketolide class: Synthesis and antibacterial activity of a lead compound. , 2007, Bioorganic & medicinal chemistry letters.

[30]  Shutao Ma,et al.  Synthesis and antibacterial activity of novel 15-membered macrolide derivatives: 4''-carbamate, 11,12-cyclic carbonate-4''-carbamate and 11,4''-di-O-arylcarbamoyl analogs of azithromycin. , 2009, European journal of medicinal chemistry.

[31]  S. Alihodžić,et al.  Synthesis and biological properties of 4″-O-acyl derivatives of 8a-Aza-8a-homoerythromycin , 2009, The Journal of Antibiotics.

[32]  Y. Yoon,et al.  Combinatorial biosynthesis of 5-O-desosaminyl erythronolide A as a potent precursor of ketolide antibiotics. , 2008, Journal of biotechnology.

[33]  P. Lei,et al.  Synthesis and antibacterial activity of 4''-O-heteroarylcarbamoyl derivatives of macrolide. , 2008, Bioorganic & medicinal chemistry letters.

[34]  A. Bryskier,et al.  Ketolides: novel antibacterial agents designed to overcome resistance to erythromycin A within gram-positive cocci , 2002 .

[35]  K. Ajito,et al.  Novel azalides derived from 16-membered macrolides. Part II: Isolation of the linear 9-formylcarboxylic acid and its sequential macrocyclization with an amino alcohol or an azidoamine. , 2008, Bioorganic & medicinal chemistry.

[36]  E. Giamarellos‐Bourboulis.  Macrolides beyond the conventional antimicrobials: a class of potent immunomodulators. , 2008, International journal of antimicrobial agents.

[37]  Guoqiang Wang,et al.  Synthesis of novel 6,11-O-bridged bicyclic ketolides via a palladium-catalyzed bis-allylation. , 2004, Organic letters.

[38]  Takuji Yoshida,et al.  Novel 16-membered macrolides modified at C-12 and C-13 positions of midecamycin A1 and miokamycin. Part 1: Synthesis and evaluation of 12,13-carbamate and 12-arylalkylamino-13-hydroxy analogues. , 2008, Bioorganic & medicinal chemistry.

[39]  M. Desai,et al.  Synthesis and antibacterial activity of C12 des-methyl ketolides. , 2006, Bioorganic & medicinal chemistry letters.

[40]  许旱峤,et al.  Kirk-Othmer Encyclopedia of Chemical Technology数据库介绍及实例 , 2007 .

[41]  L. Katz,et al.  Precursor-directed biosynthesis of 6-deoxyerythronolide B analogues is improved by removal of the initial catalytic sites of the polyketide synthase , 2006, Journal of Industrial Microbiology & Biotechnology.

[42]  Ronald N. Jones,et al.  CEM-101 Activity against Gram-Positive Organisms , 2010, Antimicrobial Agents and Chemotherapy.

[43]  K. Ajito,et al.  Design and synthesis of novel leucomycin analogues modified at the C-3 position. Part II: 3-O-(3-Aryl-2-propenyl)leucomycin analogues. , 2008, Bioorganic & medicinal chemistry.

[44]  Sarbani Pal.  A Journey Across the Sequential Development of Macrolides and Ketolides Related to Erythromycin , 2006 .

[45]  B. Wimberly.  The use of ribosomal crystal structures in antibiotic drug design. , 2009, Current opinion in investigational drugs.

[46]  M. Desai,et al.  Synthesis and antibacterial activity of novel C12 vinyl ketolides. , 2006, Journal of medicinal chemistry.

[47]  P. Sears,et al.  Synthesis and biological activity of new 5-O-sugar modified ketolide and 2-fluoro-ketolide antibiotics. , 2005, Bioorganic & medicinal chemistry letters.

[48]  K. Undheim,et al.  Preparation of cyclic 2',3'-carbamate derivatives of erythromycin macrolide antibiotics. , 2007, Bioorganic & medicinal chemistry.

[49]  E. Cox,et al.  Ketek--the FDA perspective. , 2007, The New England journal of medicine.

[50]  T. Dougherty,et al.  7.18 – Macrolide Antibiotics , 2007 .

[51]  Daniel N. Wilson,et al.  Distinct Mode of Interaction of a Novel Ketolide Antibiotic That Displays Enhanced Antimicrobial Activity , 2009, Antimicrobial Agents and Chemotherapy.

[52]  G. Amsden.  Anti-inflammatory effects of macrolides--an underappreciated benefit in the treatment of community-acquired respiratory tract infections and chronic inflammatory pulmonary conditions? , 2005, The Journal of antimicrobial chemotherapy.

[53]  P. Lei,et al.  Synthesis and antibacterial activity of derivatives of 6-O-allylic acylides. , 2007, Bioorganic & medicinal chemistry letters.

[54]  M. Page,et al.  Activity of the Novel Macrolide BAL19403 against Ribosomes from Erythromycin-Resistant Propionibacterium acnes , 2007, Antimicrobial Agents and Chemotherapy.

[55]  Y. Or,et al.  Pharmacokinetics of EDP-420 after Multiple Oral Doses in Healthy Adult Volunteers and in a Bioequivalence Study , 2009, Antimicrobial Agents and Chemotherapy.

[56]  R. Reinert.  Clinical efficacy of ketolides in the treatment of respiratory tract infections. , 2004, The Journal of antimicrobial chemotherapy.

[57]  David Rabuka,et al.  An efficient entry to new sugar modified ketolide antibiotics , 2005 .

[58]  V. Lee.  Anti-Gram Positive Agents of Natural Product Origins , 2007 .