Chemistry and biology of the polyene macrolide antibiotics.

Hamilton‐Miller, J. M. T.

doi:10.1128/mmbr.37.3.166-196.1973

Cited by 192 publications

(62 citation statements)

References 96 publications

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“…Macrocycles, particularly macrolactones, are important structural motifs found in a number of biologically active natural products, i.e., macrolides, and approved drugs. [56][57][58] Although a a number of macrolactonization methods are available, the synthesis typically requires using the corresponding seco-acids as substrates and often under highly diluted conditions. 59 Encouraged by the high efficiency and chemoselectivity of this reaction, we explored the synthesis of macrolactones by using reagent 9a (prepared in two steps) with an olefin and an anhydride moiety linked together ( Figures S103 and S104).…”

Section: Resultsmentioning

confidence: 99%

Reagent-Enabled ortho -Alkoxycarbonylation of Aryl Iodides via Palladium/Norbornene Catalysis

Wang

Zhang

Dong

et al. 2016

Chem

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ArticleReagent-Enabled ortho-Alkoxycarbonylation of Aryl Iodides via Palladium/Norbornene Catalysis A distinct method is developed for preparing aryl carboxylic acid derivatives through ortho-alkoxycarbonylation of aryl iodides via palladium/norbornene catalysis, which is enabled by a carefully tuned carbonate anhydride reagent. Using a sterically hindered acyl leaving group realizes selective C-O cleavage, allowing the carboxyl (instead of the acyl) group to be transferred. This method exhibits a board substrate scope and high functional-group compatibility. In addition, this approach provides direct access to macrolactones.

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Section: Resultsmentioning

confidence: 99%

Reagent-Enabled ortho -Alkoxycarbonylation of Aryl Iodides via Palladium/Norbornene Catalysis

Wang

Zhang

Dong

et al. 2016

Chem

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“…Batumin is a linear polyene antibiotic encoded by a large hybrid operon of polyketide synthases and nonribosomal peptide synthetase (PKS-NRPS) comprising of 30 genes [8,9]. Natural PKS-NRPS encoded polyene compounds are versatile in their chemical structures and biological activities [11], which include many potential and clinically approved antibacterial, antiviral, antifungal and anti-cancer drugs [12]. Detailed stereochemical analysis of kalimatacin/batumin antibiotics has recently been published [13].…”

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confidence: 99%

Promising Anticancer Activity of Batumin: A Natural Polyene Antibiotic Produced By Pseudomonas Batumici

et al. 2018

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Cytotoxicity against melanoma and lung carcinoma cells (IC ≈ 5 μg/ml) was detected. Hypercondensed chromatin and apoptotic body formation in batumin-treated cells suggested the induction of apoptosis supported also by an observed increase in the quantity of cells occupying the sub-G1 cell cycle phase. Twofold reduction in the number and volume of lung metastases in Lewis lung carcinoma (3LL)-bearing batumin-treated mice was demonstrated. Highly specific cytotoxicity of batumin against cancer cell lines potentiates further studies.

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“…Nystatin was discovered in the early 1950s as the first polyene antifungal antibiotic (18). It binds to ergosterol, the main sterol in the cell membrane of fungi and Leishmania spp., leading to channel formation, efflux of protons and cations, and concentration-dependent cell death (11,17,19). Although nystatin has potent, broad-spectrum fungicidal activity in vitro, problems with solubilization and systemic toxicity precluded its development as a parenteral therapeutic agent (17).…”

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confidence: 99%

“…It binds to ergosterol, the main sterol in the cell membrane of fungi and Leishmania spp., leading to channel formation, efflux of protons and cations, and concentration-dependent cell death (11,17,19). Although nystatin has potent, broad-spectrum fungicidal activity in vitro, problems with solubilization and systemic toxicity precluded its development as a parenteral therapeutic agent (17). In the late 1980s, however, laboratory investigators at the University of Texas incorporated nystatin into a multilamellar liposome preparation consisting of dimyristoyl phosphatidylcholine (DMPC) and dimyristoyl phosphatidylglycerol (DMPG) in a 7:3 molar ratio (23).…”

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confidence: 99%

Safety and Efficacy of Multilamellar Liposomal Nystatin against Disseminated Candidiasis in Persistently Neutropenic Rabbits

Groll

Petraitis

Petraitienė

et al. 1999

Antimicrob Agents Chemother

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The activity of liposomal nystatin (L-Nys) against subacute disseminated candidiasis was investigated in persistently neutropenic rabbits. Antifungal therapy was administered for 10 days starting 24 h after intravenous inoculation of 103blastoconidia of Candida albicans. Responses to treatment were assessed by the quantitative clearance of the organism from blood and tissues. Treatments consisted of L-Nys at dosages of 2 and 4 mg/kg of body weight/day (L-Nys2 and L-Nys4, respectively) amphotericin B deoxycholate at 1 mg/kg/day (D-AmB), and fluconazole at 10 mg/kg/day (Flu). All treatments were given intravenously once daily. Compared to the results for untreated but infected control animals, treatment with L-Nys2, L-Nys4, D-AmB, and Flu resulted in a significant clearance of the residual burden of C. albicans from the kidney, liver, spleen, lung, and brain (P < 0.0001 by analysis of variance). When the proportion of animals infected at at least one of the five tissue sites studied was evaluated, a dose-dependent response to treatment with L-Nys was found (P < 0.05). Compared to D-AmB-treated rabbits, mean serum creatinine and blood urea nitrogen levels at the end of therapy were significantly lower in animals treated with L-Nys2 (P < 0.001) and L-Nys4 (P < 0.001 and P < 0.01, respectively). L-Nys was less nephrotoxic than conventional amphotericin B and had dose-dependent activity comparable to that of amphotericin B for the early treatment of subacute disseminated candidiasis in persistently neutropenic rabbits.

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Chemistry and biology of the polyene macrolide antibiotics.

Cited by 192 publications

References 96 publications

Reagent-Enabled ortho -Alkoxycarbonylation of Aryl Iodides via Palladium/Norbornene Catalysis

Reagent-Enabled ortho -Alkoxycarbonylation of Aryl Iodides via Palladium/Norbornene Catalysis

Promising Anticancer Activity of Batumin: A Natural Polyene Antibiotic Produced By Pseudomonas Batumici

Safety and Efficacy of Multilamellar Liposomal Nystatin against Disseminated Candidiasis in Persistently Neutropenic Rabbits

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