Recent developments with macrolide antibiotics

Bibliography

• KIRST HA: Semi-synthetic derivatives of erythromycin. Prog. Med. Chem. (1993) 30:57–88.
   PubMedGoogle Scholar
• •Review of efforts directed towards derivatisation of erythromycin.
   Google Scholar
• KIRST HA: Semi-synthetic derivatives of 16-membered macrolide antibiotics. Prog. Med. Chem. (1994) 31:265–295.
   PubMedGoogle Scholar
• •Review of efforts directed towards derivatisation of many 16-membered macrolides.
   Google Scholar
• OUELLETTE M, KUNDIG C: Microbial multidrug resis-tance. Intern. J. Antimicrob. Agents (1997) 8:179–187.
   PubMedGoogle Scholar
• BRYSKIER A, AGOURIDAS C, CHANTOT JF: New medical targets for macrolides. Exp. Opin. Invest. Drugs (1994) 3 :405–410.
   Google Scholar
• •Brief summary of potential new anti-infective applications for macrolides and new directions for macrolide research.
   Google Scholar
• CHU DTW: Recent developments in 14- and 15-membered macrolides. Exp. Opin. Invest. Drugs (1995) 4:65–94.
   Google Scholar
• BONNEFOY A, GIRARD AM, AGOURIDAS C, CHANTOT JF:Ketolides lack inducibility properties of MLSB resis-tance phenotype. J. Antimicrob. Chemother. (1997) 40:85–90.
   PubMed Web of Science ®Google Scholar
• SCHULIN T, WENNERSTEN CB, MOELLERING RC, ELIO-POULOS GM: In vitro activity of RU 64004, a new ke-tolide antibiotic, against gram-positive bacteria. Antimicrob. Agents Chemother. (1997) 41:1196–1202.
   PubMed Web of Science ®Google Scholar
• AGOURIDAS C, BENEDETTI Y, DENTS A, LE MARTRET 0, CHANTOT JF: Ketolides: a new distinct class of mac-rolide antibacterials. 35th ICAAC. San Francisco, Califor-nia (1995) Abstract F–157.
   Google Scholar
• EDNIE LM, JACOBS MR, APPELBAUM PC: Comparative antianaerobic activities of the ketolides HMR 3647 (RU 66647) and HMR 3004 (RU 64004). Antimicrob. Agents Chemother. (1997) 41:2019–2022.
   PubMed Web of Science ®Google Scholar
• AGOURIDAS C, BONNEFOY A, CHANTOT JF: In vitro an-tibacterial activity of HMR 3647, a novel ketolide highly active against respiratory pathogens. 37th ICAAC. Toronto, Canada (1997) Abstract F–112.
   Google Scholar
• ASAKA T, KASHIMURA M, MISAWA Y et al: A new mac-rolide antibiotic, TE-810; synthesis and biological properties. 35th ICAAC. San Francisco, California (1995) Abstract F–177.
   Google Scholar
• GRIESGRABER G, OR YS, CHU DTW et al.: 3-Keto-11,12-carbazate derivatives of 6-0-methylerythromycin A: synthesis and in vitro activity. J. Antibiot (1996) 49:465–477.
   PubMed Web of Science ®Google Scholar
• ASAKA T, KASHIMURA M, MISAWA Y et al: A new mac-rolide antibiotic, TE-802; synthesis and biological properties. 35th ICAAC. San Francisco, California (1995) Abstract F–176.
   Google Scholar
• PHAN LT, OR YS, SPINA KP et al.: Tricyclic ketolides: mono-substitution on the imine ring. 37th ICAAC. To-ronto, Canada (1997) Abstract F–263.
   Google Scholar
• PHAN LT, OR YS, SPINA KP et al: Tetracyclic ketolides: new antibacterial macrolides. 37th ICAAC. Toronto, Can-ada (1997) Abstract F–264.
   Google Scholar
• ASAKA T, KASHIMURA M, ISHII T et al: New macrolide antibiotics, acylides (3-0-acy1-5-0-desosaminyl-erythronolides). 37th ICAAC. Toronto, Canada (1997) Ab-stract F–262.
   Google Scholar
• ELLIOTT RL, PIREH D, NILIUS AM et al.: Novel 3-deoxy-3-descladinosy1-6-0-methyl erythromycin A analogues. Bioorg. Med. Chem. Lett. (1997) 7:641–646.
   Google Scholar
• GRIESGRABER G, ELLIOTT RL, KRAMER MJ et al: Synthe-sis and in vitro activity of novel 2,3-anhydro-11-hydrazo-6-0-methyl-11,12-carbamate erythromycin derivatives. 37th ICAAC. Toronto, Canada (1997) Abstract F–267.
   Google Scholar
• MORISHITA A, ISHIZAWA K, MUTOH N et al.: Sporeamy-cin A, a new macrolide antibiotic. J. Antibio] (1992) 45:607–612.
   PubMedGoogle Scholar
• KIRST HA: Antibiotics (macrolides). In: Kirk-Othmer En-cyclopedia of Chemical Technology (4th Edition). Howe-Grant M (Ed.), John Wiley & Sons, New York (1992) Volume 3, 169–213.
   Google Scholar
• AJITO K, KURIHARA K, SHIBAHARA S et al.: Cladinose analogues of sixteen-membered macrolide antibiotics. IV. J. Antibiot (1997) 50:150–161.
   PubMedGoogle Scholar
• AJITO K, KURIHARA K, SHIBAHARA S et al.: Cladinose analogues of sixteen-membered macrolide antibiotics. II. J. Antibiot (1997) 50:92–95.
   PubMedGoogle Scholar
• KURIHARA K, AJITO K, SHIBAHARA S et al.: Cladinose analogues of sixteen-membered macrolide antibiotics. I. J. Antibiot (1996) 49:582–592.
   Google Scholar
• KURIHARA K, KIKUCHI N, AJITO K: Cladinose analogues of sixteen-membered macrolide antibiotics. III. J. Anti-biot. (1997) 50:32–44.
   PubMedGoogle Scholar
• AJITO K, SHIMIZU A, SHIBAHARA S eta].: Cladinose ana-logues of sixteen-membered macrolide antibiotics. V. Antibiot (1997) 50:366–369.
   PubMedGoogle Scholar
• NARANDJA A, KELNERIC Z, KOLACNY-BABIC L, SUSKO-VIC B, DJOKIC S: Synthesis and evaluation of polyhy-dro derivatives of tylosin. In: New Macrolides, Azalides, and Streptogramins in Clinical Practice. Neu HC, Young LS, Zinner SH, Acar JF (Eds.), Marcel Dekker, Inc., New York (1995) 196–202.
   Google Scholar
• NARANDJA A, KELNERIC Z, KOLACNY-BABIC L, DJOKIC S:10,11,12,13-Tetrahydro derivatives of tylosin. J. Anti-blot. (1995) 48:248–253.
   PubMedGoogle Scholar
• NARANDJA A, KELNERIC Z, LOPOTAR N: Structure-activity relationship among new dihydro derivatives of 4'-demycarosyl-tylosin. 3rd International Conference on the Macrolides, Azalides and Streptogramins. Lisbon, Portugal (1996) Abstract 14.13
   Google Scholar
• MCFARLAND JW, HECKER SJ, JAYNES BH et al.: Repromi-cin derivatives with potent antibacterial activity against Pasteurella multocida. J. Med. Chem. (1997) 40:1041–1045.
   PubMed Web of Science ®Google Scholar
• •Good example of the use of medicinal chemistry to conduct studies of structure-activity relationships.
   Google Scholar
• MCFARLAND JVV, BERGER CM, FROSHAUER SA et al.: Quantitative structure-activity relationships among macrolide antibacterial agents: in vitro and in vivo po-tency against Pasteurella multocida. J. Med. Chem. (1997) 40:1340–1346.
   PubMedGoogle Scholar
• •Good example of conducting quantitative studies of structure-activity relationships.
   Google Scholar
• STEPHENSON GA, STOWELL JG, TOMA PH et al: Solid-state analysis of polymorphic, isomorphic, and sol-vated forms of dirithromycin. J. Am. Chem. Soc. (1994) 116:5766–5773.
   Google Scholar
• HUANG GW, OKAMOTO R, HIKITA A, PARK Y, OKABE M:Optimization of conditions for conversion of tylosin to a novel antibiotic, acetyl-isovaleryl tylosin (API), by Streptomyces therm otolerans and scale-up to 200-liter pilot-scale fermenter.j Ferm. Bioengin. (1997) 84:77–81.
   Google Scholar
• ARISAWA A, KAWAMURA N, NARITA T et al.: Direct fer-mentative production of acyltylosins by genetically-engineered strains of Streptomyces fradiae. J. Antibiot (1996) 49:349–354.
   PubMed Web of Science ®Google Scholar
• KATZ L, DONADIO S: Polyketide synthesis: prospects for hybrid antibiotics. Ann. Rev. Microbic)]. (1993) 47:875–912.
   PubMed Web of Science ®Google Scholar
• TSOI CJ, KHOSLA C: Combinatorial biosynthesis of 'u-nnatural' natural products: the polyketide example. Chem. Biol. (1995) 2:355–362.
   PubMed Web of Science ®Google Scholar
• KATZ L: Manipulation of modular polyketide syn-thases. Chem. Rev. (1997) 97:2557–2575.
   PubMed Web of Science ®Google Scholar
• ••Recently published overview of changes achieved in thestructure of erythromycin and the biosynthetic and genetic rationale governing those changes.
   Google Scholar
• KHOSLA C: Harnessing the biosynthetic potential of modular polyketide synthases. Chem. Rev. (1997) 97:2577–2590.
   PubMed Web of Science ®Google Scholar
• ••Recent discussion of potential applications resulting fromvarious modifications of polyketide synthase systems found in macrolide-producing organisms.
   Google Scholar
• STAUNTON J, WILKINSON B: Biosynthesis of erythro- mycin and rapamycin. Chem. Rev. (1997) 97:2611–2629.
   PubMed Web of Science ®Google Scholar
• ••Recently published review of structural changes that can beachieved by the rational modification of the biosynthetic systems by which erythromycin and rapamycin are produced.
   Google Scholar
• PILOT MA: Macrolides in roles beyond antibiotic- therapy. Br. J. Surgery (1994) 81:1423–1429.
   PubMedGoogle Scholar
• KIRST HA: Macrolide antibiotics in food-animal health. Exp. Opin. Invest. Drugs (1997) 6:103–117.
   PubMedGoogle Scholar
• •Recent review of uses of macrolides in veterinary practices.
   Google Scholar
• ITOH Z: Motilin and clinical application. Peptides (1997) 18:593–608.
   PubMed Web of Science ®Google Scholar
• TSUZUKI K, SUNAZUKA T, MARUI S et al.: Motilides, mac-rolides with gastrointestinal motor stimulating activ-ity. I. Chem. Pharm. Bull. (1989) 37:2687–2700.
   PubMed Web of Science ®Google Scholar
• FUNABASHI Y, MAESHIBA Y, INATOMI N et al.: Bioactive metabolites of EM574 and EM523, erythromycin de-rivatives having strong gastrointestinal motor stimu-lating activity. J. Antibiot. (1996) 49:794–801.
   PubMedGoogle Scholar
• ISHII M, NAKAMURA T, KASAI F, BABA T, TAKEBE K: Erythromycin derivative improves gastric emptying and insulin requirement in diabetic patients with gas-troparesis. Diabetes Care (1997) 20:1134–1137.
   PubMedGoogle Scholar
• LARTEY PA, NELLANS HN, FAGHIH R et al: Synthesis of 4"-deoxy motilides: identification of a potent and orally active prokinetic drug candidate. J. Med. Chem. (1995) 38:1793–1798.
   PubMedGoogle Scholar
• VERLINDEN M, CRAFT C, OLSON C, MORRISON P, KROODSMA G: Abbott-81229, a new macrolide agent, dose-dependently accelerates solid gastric emptying (GE) in healthy volunteers. Gastroenterology (1997) 112:A846.
   Google Scholar
• KOGA H, SATO T, TSUZUKI K, ONODA H, KUBONIWA H,TAKANASHI H: Potent, acid-stable and orally active macrolide-type motilin receptor agonists, GM-111 and the derivatives. Bioorg Med. Chem. Lett. (1994) 4:1347–1352.
   Google Scholar