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https://www.readbyqxmd.com/read/27319118/the-co-identity-of-lipiarmycin-a3-and-tiacumicin-b
#1
Angelo Bedeschi, Piera Fonte, Giovanni Fronza, Claudio Fuganti, Stefano Serra
The co-identity of the antibiotics lipiarmycin A3 obtained from Actinoplanes deccanensis and tiacumicin B obtained from Dactylosporangium aurantiacum was unambiguously demonstrated through a number of experimental means. Spectroscopic analyses performed on both the antibiotics themselves and on their derivatives showed no difference between the two series of compounds. Moreover, unambiguous confirmation of the postulated identity of the two compounds was achieved by chemical degradation of lipiarmycin A3 and isolation of (3S,4R)-pentane-1,3,4-triol triacetate whose relative configuration was assigned by comparison with the authentic erythro and threo pentane-1,3,4-triol triacetates, obtained by chemical synthesis...
May 2016: Natural Product Communications
https://www.readbyqxmd.com/read/26744587/fidaxomicin-a-novel-agent-for-the-treatment-of-clostridium-difficile-infection
#2
REVIEW
George G Zhanel, Andrew J Walkty, James A Karlowsky
BACKGROUND: Due to the limitations of existing treatment options for Clostridium difficile infection (CDI), new therapies are needed. OBJECTIVE: To review the available data on fidaxomicin regarding chemistry, mechanisms of action and resistance, in vitro activity, pharmacokinetic and pharmacodynamic properties, efficacy and safety in clinical trials, and place in therapy. METHODS: A search of PubMed using the terms "fidaxomicin", "OPT-80", "PAR-101", "OP-1118", "difimicin", "tiacumicin" and "lipiarmycin" was performed...
November 2015: Canadian Journal of Infectious Diseases & Medical Microbiology
https://www.readbyqxmd.com/read/26125969/total-synthesis-of-the-glycosylated-macrolide-antibiotic-fidaxomicin
#3
Elias Kaufmann, Hiromu Hattori, Hideki Miyatake-Ondozabal, Karl Gademann
The first enantioselective total synthesis of fidaxomicin, also known as tiacumicin B or lipiarmycin A3, is reported. This novel glycosylated macrolide antibiotic is used in the clinic for the treatment of Clostridium difficile infections. Key features of the synthesis involve a rapid and high-yielding access to the noviose, rhamnose, and orsellinic acid precursors; the first example of a β-selective noviosylation; an effective Suzuki coupling of highly functionalized substrates; and a ring-closing metathesis reaction of a noviosylated dienoate precursor...
July 17, 2015: Organic Letters
https://www.readbyqxmd.com/read/25510439/total-synthesis-of-the-tiacumicin%C3%A2-b-lipiarmycin-a3-fidaxomicin-aglycone
#4
Florian Glaus, Karl-Heinz Altmann
Tiacumicin B (lipiarmycin A3, fidaxomicin) is an atypical macrolide antibiotic which is used for the treatment of Clostridium difficile infections. Tiacumicin B is also a potent inhibitor of Mycobacterium tuberculosis, but due to its limited oral bioavailability is unsuitable for systemic therapy. To provide a basis for structure-activity studies that might eventually lead to improved variants of tiacumicin B, we have developed an efficient approach to the synthesis of the tiacumicin B aglycone. The synthesis features a high-yielding intramolecular Suzuki cross-coupling reaction to effect macrocyclic ring closure...
February 2, 2015: Angewandte Chemie
https://www.readbyqxmd.com/read/25431322/total-synthesis-of-the-protected-aglycon-of-fidaxomicin-tiacumicin%C3%A2-b-lipiarmycin%C3%A2-a3
#5
Hideki Miyatake-Ondozabal, Elias Kaufmann, Karl Gademann
Fidaxomicin, also known as tiacumicin B or lipiarmycin A3, is a novel macrocyclic antibiotic that is used in hospitals for the treatment of Clostridium difficile infections. This natural product has also been shown to have excellent bactericidal activity against multidrug-resistant Mycobacterium tuberculosis. In spite of its attractive biological activity, no total synthesis has been reported to date. The enantioselective synthesis of the central 18-membered macrolactone is reported herein. The key reactions include ring-closing metathesis between a terminal olefin and a dienoate moiety for macrocyclization, a vinylogous Mukaiyama aldol reaction, and a Stille coupling reaction of sterically demanding substrates...
February 2, 2015: Angewandte Chemie
https://www.readbyqxmd.com/read/25422174/enantioselective-synthesis-of-putative-lipiarmycin-aglycon-related-to-fidaxomicin-tiacumicin%C3%A2-b
#6
William Erb, Jean-Marie Grassot, David Linder, Luc Neuville, Jieping Zhu
An enantioselective synthesis of a putative lipiarmycin aglycon was accomplished and features: 1) Brown's enantioselective alkoxyallylboration and allylation of aldehydes, 2) chain elongation by iterative Horner-Wadsworth-Emmons olefination, 3) Evans' aldol reaction and 4) an ene-diene ring-closing metathesis. A neighboring-group-assisted chemoselective reductive desilylation was uncovered in this study and was instrumental to the realization of the present synthesis.
February 2, 2015: Angewandte Chemie
https://www.readbyqxmd.com/read/25203410/fidaxomicin-a-novel-macrolide-antibiotic-for-clostridium-difficile-infection
#7
REVIEW
Elias B Chahine, Allana J Sucher, Karelee Mantei
OBJECTIVE: To review the chemistry, pharmacology, microbiology, pharmacodynamics, pharmacokinetics, clinical efficacy, tolerability, drug interactions, dosing, and administration of fidaxomicin (FDX). DATA SOURCES: A search of PubMed using the terms "fidaxomicin," "OPT-80," "PAR-101," "OP-1118," "difimicin," "tiacumicin," and "lipiarmycin" was performed. All English-language articles from 1983 to November 2013 were reviewed for relevance. Bibliographies of all articles were reviewed as well as the manufacturer's Web site to further identify relevant information...
September 2014: Consultant Pharmacist: the Journal of the American Society of Consultant Pharmacists
https://www.readbyqxmd.com/read/24689300/the-co-identity-of-lipiarmycin-a3-and-tiacumicin-b
#8
Angelo Bedeschi, Piera Fonte, Giovanni Fronza, Claudio Fuganti, Stefano Serra
The co-identity of the antibiotics lipiarmycin A3 obtained from Actinoplanes deccanensis and tiacumicin B obtained from Dactylosporangium aurantiacum was unambiguously demonstrated through a number of experimental means. Spectroscopic analyses performed on both the antibiotics themselves and on their derivatives showed no difference between the two series of compounds. Moreover, unambiguous confirmation of the postulated identity of the two compounds was achieved by chemical degradation of lipiarmycin A3 and isolation of (3S,4R)-pentane-1,3,4-triol triacetate whose relative configuration was assigned by comparison with the authentic erythro and threo pentane-1,3,4-triol triacetates, obtained by chemical synthesis...
February 2014: Natural Product Communications
https://www.readbyqxmd.com/read/23111588/from-natural-product-to-marketed-drug-the-tiacumicin-odyssey
#9
REVIEW
William Erb, Jieping Zhu
The first members of the tiacumicin family of antibiotics, encompassing more than 40 compounds, were isolated in 1975. Structurally, the core aglycon is an 18-membered macrolactone having two conjugated diene units, one isolated double bond, 5 stereogenic centers and most often, at least one glycosidic linkage. Tiacumicin B, a RNA synthesis inhibitor, is a narrow-spectrum antibiotic against clostridia. For the treatment of Clostridium difficile infection (CDI), it has the same cure rate as vancomycin but with lower relapse rate and was approved by the FDA in May 2011...
January 2013: Natural Product Reports
https://www.readbyqxmd.com/read/22318930/fidaxomicin-for-the-treatment-of-clostridium-difficile-infections
#10
REVIEW
Craig B Whitman, Quinn A Czosnowski
OBJECTIVE: To evaluate the pharmacology, microbiology, safety, and efficacy of fidaxomicin for treatment of Clostridium difficile infections (CDI). DATA SOURCES: Literature was identified through Ovid MEDLINE (1948-December 2011) and International Pharmaceutical Abstracts (1970-December 2011) using the search terms fidaxomicin, OPT-80, PAR-101, OP-118, difimicin, tiacumicin, lipiarmycin, Clostridium difficile, Clostridium difficile infection, Clostridium difficile-associated diarrhea, and cost...
February 2012: Annals of Pharmacotherapy
https://www.readbyqxmd.com/read/22284993/fidaxomicin-the-newest-addition-to-the-armamentarium-against-clostridium-difficile-infections
#11
REVIEW
Jason W Lancaster, S James Matthews
BACKGROUND: Fidaxomicin, a macrolide antibiotic, was the first medication for the management of Clostridium difficile infections (CDI) to be approved by the US Food and Drug Administration in more than 20 years. OBJECTIVE: This article reviews published literature on fidaxomicin for management of CDI, including its chemistry, spectrum of activity, pharmacokinetic properties, pharmacodynamics, therapeutic efficacy, adverse events, dosing, administration, and pharmacoeconomic considerations...
January 2012: Clinical Therapeutics
https://www.readbyqxmd.com/read/21633995/characterization-of-a-sugar-o-methyltransferase-tias5-affords-new-tiacumicin-analogues-with-improved-antibacterial-properties-and-reveals-substrate-promiscuity
#12
Siwen Niu, Tao Hu, Sumei Li, Yi Xiao, Liang Ma, Guangtao Zhang, Haibo Zhang, Xiaohong Yang, Jianhua Ju, Changsheng Zhang
The 18-membered macrocyclic glycoside tiacumicin B, an RNA polymerase inhibitor, is of great therapeutic significance in treating Clostridium difficile infections. The recent characterization of the tiacumicin B biosynthetic gene cluster from Dactylosporangium aurantiacum subsp. hamdenensis NRRL 18085 revealed the functions of two glycosyltransferases, a C-methyltransferase, an acyltransferase, two cytochrome P450s, and a tailoring dihalogenase in tiacumicin biosynthesis. Here we report the genetic confirmation and biochemical characterization of TiaS5 as a sugar-O-methyltransferase, requisite for tiacumicin B biosynthesis...
July 25, 2011: Chembiochem: a European Journal of Chemical Biology
https://www.readbyqxmd.com/read/21186805/characterization-of-tiacumicin-b-biosynthetic-gene-cluster-affording-diversified-tiacumicin-analogues-and-revealing-a-tailoring-dihalogenase
#13
Yi Xiao, Sumei Li, Siwen Niu, Liang Ma, Guangtao Zhang, Haibo Zhang, Gaiyun Zhang, Jianhua Ju, Changsheng Zhang
The RNA polymerase inhibitor tiacumicin B is currently undergoing phase III clinical trial for treatment of Clostridium difficile associated diarrhea with great promise. To understand the biosynthetic logic and to lay a foundation for generating structural analogues via pathway engineering, the tiacumicin B biosynthetic gene cluster was identified and characterized from the producer Dactylosporangium aurantiacum subsp. hamdenensis NRRL 18085. Sequence analysis of a 110,633 bp DNA region revealed the presence of 50 open reading frames (orfs)...
February 2, 2011: Journal of the American Chemical Society
https://www.readbyqxmd.com/read/20931868/-genetic-manipulation-system-for-tiacumicin-producer-dactylosporangium-aurantiacum-nrrl-18085
#14
Yi Xiao, Sumei Li, Liang Ma, Gaiyun Zhang, Jianhua Ju, Changsheng Zhang
OBJECTIVE: To optimize the production of tiacumicin B in Dactylosporangium aurantiacum NRRL 18085, we developed a genetic manipulation system for disrupting genes involved in tiacumicin biosynthesis. METHODS: We developed a method of conjugation to transfer exotic DNA pSET152 into D. aurantiacum NRRL 18085. Using the PCR-targeting system, we disrupted a putative tiacumicin halogenase gene in vitro by "in-frame deletion" in E. coli, and then the resulting cosmid was transferred into D...
August 2010: Wei Sheng Wu Xue Bao, Acta Microbiologica Sinica
https://www.readbyqxmd.com/read/20071495/fidaxomicin-a-macrocyclic-antibiotic-for-the-management-of-clostridium-difficile-infection
#15
REVIEW
Karyn M Sullivan, Linda M Spooner
OBJECTIVE: To evaluate the efficacy and safety of fidaxomicin for the treatment of Clostridium difficile infection. DATA SOURCES: Literature retrieval was accessed through MEDLINE (1966-January 2010) and International Pharmaceutical Abstracts (1970-January 2010) using the terms OPT-80, difimicin, PAR-101, fidaxomicin, tiacumicin, lipiarmycin, and Clostridium difficile. In addition, reference citations from publications identified were reviewed. STUDY SELECTION AND DATA EXTRACTION: All articles published in English that were identified from the data sources were evaluated and pertinent information was included...
February 2010: Annals of Pharmacotherapy
https://www.readbyqxmd.com/read/18363518/opt-80-a-macrocyclic-antimicrobial-agent-for-the-treatment-of-clostridium-difficile-infections-a-review
#16
REVIEW
Michael Gerber, Grit Ackermann
BACKGROUND: Clostridium difficile-associated diarrhoea has become a major problem over the last years. Increasing incidence and more severe clinical cases initiated the search for new treatment options. OBJECTIVE: OPT-80, also known as tiacumicin B, lipiarmycin or PAR-101, is a macrocyclic antimicrobial with little or no systemic absorption after oral administration and narrow activity spectrum against Gram-positive aerobic and anaerobic bacteria. METHODS: Data on OPT-80 available from published studies, presentations at conferences and the manufacturer were collected and reviewed...
April 2008: Expert Opinion on Investigational Drugs
https://www.readbyqxmd.com/read/17955730/treatment-strategies-for-c-difficile-associated-diarrhea
#17
REVIEW
Crenguta Stepan, Christina M Surawicz
Clostridium difficile-associated diarrhea usually occurs as a complication of antibiotic treatment. Recent data shows an increase in incidence rate of CDAD and higher rates of morbidity, colectomy and death. The management of CDAD involves discontinuing the inciting antibiotic agent and treatment with metronidazole or vancomycin. The reduced response rates and higher recurrence rates with metronidazole treatment reported in recent studies raise the question of the effectiveness of metronidazole therapy. After each recurrence, the risks for further relapses grow even bigger (after two recurrences, the risk being greater than 50%) and the management of recurrent CDAD becomes a challenge...
September 2007: Acta Gastroenterologica Latinoamericana
https://www.readbyqxmd.com/read/16289393/natural-products-the-future-scaffolds-for-novel-antibiotics
#18
REVIEW
Mark S Butler, Antony D Buss
Natural products have played a pivotal role in antibiotic drug discovery with most antibacterial drugs being derived from a natural product or natural product lead. However, the rapid onset of resistance to most antibacterial drugs diminishes their effectiveness considerably and necessitates a constant supply of new antibiotics for effective treatment of infections. The natural product templates of actinonin, pleuromutilin, ramoplanin and tiacumicin B, which are compounds undergoing clinical evaluation, represent templates not found in currently marketed antibacterial drugs...
March 30, 2006: Biochemical Pharmacology
https://www.readbyqxmd.com/read/9439690/production-of-brominated-tiacumicin-derivatives
#19
Hochlowski, Jackson, Rasmussen, Buko, Clement, Whittern, McAlpine
Several novel tiacumicin derivatives containing bromine have been produced by the addition of inorganic bromine to the fermentation broth of Dactylosporangium aurantiacum subsp. hamdenesis. Structures were elucidated employing mass spectrometry and NMR spectroscopy. Antibacterial activity of the bromotiacumicins is comparable to that of the parent compounds.
March 1997: Journal of Antibiotics
https://www.readbyqxmd.com/read/9127190/production-of-brominated-tiacumicin-derivatives
#20
J E Hochlowski, M Jackson, R R Rasmussen, A M Buko, J J Clement, D N Whittern, J B McAlpine
Several novel tiacumicin derivatives containing bromine have been produced by the addition of inorganic bromine to the fermentation both of Dactylosporangium aurantiacum subsp, hamdenensis. Structures were elucidated employing mass spectrometry and NMR spectroscopy. Antibacterial activity of the bromotiacumicins is comparable to that of the parent compounds.
March 1997: Journal of Antibiotics
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