Simple synthesis of endophenazine G and other phenazines and their evaluation as anti-methicillin-resistant Staphylococcus aureus agents

Udumula, Venkatareddy; Endres, Jennifer L.; Harper, Caleb N.; Jaramillo, Lee; Zhong, Haizhen A.; Bayles, Kenneth W.; Conda‐Sheridan, Martin

doi:10.1016/j.ejmech.2016.09.079

Cited by 20 publications

(15 citation statements)

References 38 publications

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“…A wide variety of membrane electron carriers are synthesized in nature (26)(27)(28)(29). To determine if similar but nonidentical MPh derivatives are synthesized by methanogens, we extracted lipophilic compounds from membranes of genetically tractable M. acetivorans and M. barkeri (Table 1).…”

Section: Resultsmentioning

confidence: 99%

Physiological Evidence for Isopotential Tunneling in the Electron Transport Chain of Methane-Producing Archaea

Duszenko

Buan

2017

Appl Environ Microbiol

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Many, but not all, organisms use quinones to conserve energy in their electron transport chains. Fermentative bacteria and methane-producing archaea (methanogens) do not produce quinones but have devised other ways to generate ATP. Methanophenazine (MPh) is a unique membrane electron carrier found in Methanosarcina species that plays the same role as quinones in the electron transport chain. To extend the analogy between quinones and MPh, we compared the MPh pool sizes between two well-studied Methanosarcina species, Methanosarcina acetivorans C2A and Methanosarcina barkeri Fusaro, to the quinone pool size in the bacterium Escherichia coli. We found the quantity of MPh per cell increases as cultures transition from exponential growth to stationary phase, and absolute quantities of MPh were 3-fold higher in M. acetivorans than in M. barkeri. The concentration of MPh suggests the cell membrane of M. acetivorans, but not of M. barkeri, is electrically quantized as if it were a single conductive metal sheet and near optimal for rate of electron transport. Similarly, stationary (but not exponentially growing) E. coli cells also have electrically quantized membranes on the basis of quinone content. Consistent with our hypothesis, we demonstrated that the exogenous addition of phenazine increases the growth rate of M. barkeri three times that of M. acetivorans. Our work suggests electron flux through MPh is naturally higher in M. acetivorans than in M. barkeri and that hydrogen cycling is less efficient at conserving energy than scalar proton translocation using MPh.IMPORTANCE Can we grow more from less? The ability to optimize and manipulate metabolic efficiency in cells is the difference between commercially viable and nonviable renewable technologies. Much can be learned from methane-producing archaea (methanogens) which evolved a successful metabolic lifestyle under extreme thermodynamic constraints. Methanogens use highly efficient electron transport systems and supramolecular complexes to optimize electron and carbon flow to control biomass synthesis and the production of methane. Worldwide, methanogens are used to generate renewable methane for heat, electricity, and transportation. Our observations suggest Methanosarcina acetivorans, but not Methanosarcina barkeri, has electrically quantized membranes. Escherichia coli, a model facultative anaerobe, has optimal electron transport at the stationary phase but not during exponential growth. This study also suggests the metabolic efficiency of bacteria and archaea can be improved using exogenously supplied lipophilic electron carriers. The enhancement of methanogen electron transport through methanophenazine has the potential to increase renewable methane production at an industrial scale.

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Section: Resultsmentioning

confidence: 99%

Physiological Evidence for Isopotential Tunneling in the Electron Transport Chain of Methane-Producing Archaea

Duszenko

Buan

2017

Appl Environ Microbiol

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“…The synthesis of drug‐like structurally diverse complex molecules with bio‐relevance by energy efficient and environmentally sustainable synthetic strategies have attracted increasing interest in the field of organic synthesis and drug discovery research. In 2017, Udumula and co‐workers [114] first developed an efficient synthetic route of endophenazine and a wide variety of phenazine derivatives ( 169–181 ). Arguably, the most interesting characteristic of the phenazine derivatives was their antibacterial properties.…”

Section: Chemical Synthesismentioning

confidence: 99%

Synthetic strategies of phenazine derivatives: A review

Che

et al. 2022

Journal of Heterocyclic Chem

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Since the growing importance of phenazine derivatives, the efficient synthetic strategies for the preparation of phenazine derivatives have attracted great attention from organic methodology. Herein, we comprehensively review and summarize a series of sustainable and facile synthetic strategies of phenazine derivatives. Moreover, we further discuss the approach of preparation and the superiority of each strategy.

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“…1) is a secondary metabolite isolated from Pseudomonas , Streptomycetes , and a few other bacterial genera from soil or marine habitats [1–5]. The biological properties of PCA includes antimicrobial [6–9] antiviral [7], antitumorigenic [8–12] antitubercular and antileukemic activities [13, 14]. In China, PCA has been registered as a biofungicide against rice sheath blight caused by Rhizoctonia solani , and it is noted for its high efficacy, low toxicity, environmental friendliness and enhancement of crop production [15–18].…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis and biological activity of hydroxybenzoic acid ester conjugates of phenazine-1-carboxylic acid

Zhu

Zhang

et al. 2018

Chemistry Central Journal

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We prepared 16 novel hydroxybenzoic acid ester conjugates of phenazine-1-carboxylic acid (PCA) and investigated their biological activity. Most of the synthesized conjugates displayed some level of fungicidal activities in vitro against five phytopathogenic fungi. Nine conjugates 5b, 5c, 5d, 5e, 5h, 5i, 5m, 5n and 5o (EC50 between 3.2 μg/mL and 14.1 μg/mL) were more active than PCA (EC50 18.6 μg/mL) against Rhizoctonia solani. Especially conjugate 5c showed the higher fungicidal activity against Rhizoctonia solani which is 6.5-fold than PCA. And the results of the bioassay indicated that the fungicidal activity of conjugates was associated with their LogP, and the optimal LogP values of the more potent fungicidal activities within these conjugates ranged from 4.42 to 5.08. The systemic acquired resistance induced by PCA–SA ester conjugate 5c against rice sheath blight disease in rice seedlings was evaluated. The results revealed that PCA–SA ester conjugate 5c retained the resistance induction activity of SA against rice sheath blight.Electronic supplementary materialThe online version of this article (10.1186/s13065-018-0478-2) contains supplementary material, which is available to authorized users.

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Simple synthesis of endophenazine G and other phenazines and their evaluation as anti-methicillin-resistant Staphylococcus aureus agents

Cited by 20 publications

References 38 publications

Physiological Evidence for Isopotential Tunneling in the Electron Transport Chain of Methane-Producing Archaea

Physiological Evidence for Isopotential Tunneling in the Electron Transport Chain of Methane-Producing Archaea

Synthetic strategies of phenazine derivatives: A review

Design, synthesis and biological activity of hydroxybenzoic acid ester conjugates of phenazine-1-carboxylic acid

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