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On Biocatalysis as Resourceful Methodology for Complex Syntheses: Selective Catalysis, Cascades and Biosynthesis
Published in Peter Grunwald, Pharmaceutical Biocatalysis, 2019
Andreas Sebastian Klein, Thomas Classen, Jörg Pietruszka
The tripyrrole pigment prodigiosin (36), which in addition to its characteristic color is also known for its antibiotic effect against pathogenic microorganisms and antitumor activity. The native producer of prodigiosin is the opportunistically pathogenic bacterium Serratia marcescens. The pig-gene cluster, which comprises the prodigiosin biosynthesis genes pigA to pigN carries the genetic information for the enzymatic production of the monopyrrole MAP (39, 2-methyl-3-amyl-pyrrole) and the dipyrrole MBC (40, 4-methoxy-2,2’-bipyrrole-5-carbaldehyde), which are condensed to the tripyrrole prodigiosin (36) (Hu et al., 2016).
Where Cancer and Bacteria Meet
Published in Ananda M. Chakrabarty, Arsénio M. Fialho, Microbial Infections and Cancer Therapy, 2019
Alexandra Merlos, Ricardo Perez-Tomás, José López-López, Miguel Viñas
One of the most important families of anionophores consists of prodiginines, produced by microorganisms such as Streptomyces sp. and Serratia marcescens [59]. Prodigiosin (2-methyl-3-pentyl-6-methoxyprodiginine), within the red-pigmented prodiginines family, is an alkaloid secondary metabolite synthesized by Serratia marcescens, among other microorganisms [55], and located in the bacterial inner membrane [60]. The structure of prodigiosin (Fig. 12.3a) (C20H25N3O) was clarified in the early 1960s, when partial and total chemical synthesis revealed a pyrrolyl-dipyrromethene core skeleton. Prodigiosin occurs in solution in interconverting cis (or β) and trans (or α) conformations. The equilibrium between the two is dependent on the solution pH. The biological role of prodigiosin in producer organisms remains unclear [61], although the alkaloid is a very efficient anion exchanger that facilitates Cl−/HCO3− exchange across lipid bilayers. The antifungal, immunosuppressive, and anticancer activities of prodigiosin have been described in several studies [62, 63]. Its structural analog obatoclax mesylate (GX15-070MS) is currently in phase II clinical trials to test its efficacy in combination with first-line drugs for the treatment of hematological malignancies and solid tumors [64–66].
Serratia
Published in Dongyou Liu, Handbook of Foodborne Diseases, 2018
Naheed S. Kanji, Umesh Narsinghani, Ritu A. Kumar
A single Serratia bacterium can swim by using its flagellum and swarm in a group on agar of lower concentrations (0.5%–0.8%). The swarmer cells can range in length from 5 to 30 μm, have about 100–1000 flagella per swimmer cell, and are nonseptated (Figure 39.4).37 The organism can also form a biofilm made of secreted mucilaginous matrix that functions as a protective coating in which they are encased. Serratia produces special enzymes—proteases, DNase, lipase, and gelatinase—and is resistant to colistin, ampicillin, and cephalothin.38 Optimally, Serratia grows at 37°C, but it can grow in temperatures ranging from 5°C to 40°C and in pH levels that range from 5 to 9.39 The organism is known for the red pigmentation it produces called prodigiosin. Prodigiosin is made up of three pyrrole rings, and its production capability is not present in all strains.40 Pigment production in Serratia is influenced by several variables, including temperature, nutrient media, and exposure to ultraviolet (UV) light. Only some strains of Serratia are capable of producing prodigiosin that ranges in color from dark red to pale pink depending on the temperature, substrate, and age of the colonies.41 Most strains of S. marcescens are red under 27°C and white above 28°C.42S. marcescens turns “bloody” red and mucoid only under certain conditions: when the colonies age giving umbonate elevation and when the food or substrate has the proper amino acids (Figure 39.5).
Inhibitory effect of norharmane on Serratia marcescens NJ01 quorum sensing-mediated virulence factors and biofilm formation
Published in Biofouling, 2021
Huai-Zhi Luo, Jin-Wei Zhou, Bing Sun, Huan Jiang, Shi Tang, Ai-Qun Jia
To identify the anti-QS activity of ILEE on S. marcescens NJ01, the virulence factors and biofilm formation by S. marcescens were assayed. Intracellular prodigiosin pigment production is directly regulated by the QS-signaling mechanism of S. marcescens strains from environmental or clinical origins (Slater et al. 2003). Generally, the pigments produced by pathogenic microbes such as Staphylococcus aureus and Pseudomonas aeruginosa are necessary virulence factors for their invasion, survival and lethality, but the prodigiosin produced by S. marcescens is not an essential virulence factor (Liu and Nizet 2009; Zhou et al. 2016). In this study, the prodigiosin was significantly reduced from 87.6% to 94.3% at 0.5 and 2.0 mg ml−1 of ILEE, respectively (Figure 3a). Hemolysin, which is produced by various pathogenic bacteria and has been proposed to be responsible for their pathogenesis (Shimuta et al. 2009), was also significantly reduced from 63.9% to 78.3% (Figure 3d). In addition, the productions of protease, lipase, EPS and biofilm were inhibited by ∼ 38.9%, 37.1%, 39.8% and 54.7% after being exposed to 2.0 mg ml−1 ILEE (Figure 3b, c, e, f).
Novel thiazolinyl-picolinamide based palladium(II) complex-impregnated urinary catheters quench the virulence and disintegrate the biofilms of uropathogens
Published in Biofouling, 2020
Deeksha Rajkumar, Durairajan Rubini, M. Sudharsan, D. Suresh, Paramasivam Nithyanand
QS-controlled virulent genes in S. marcescens play a vital role in its pathogenesis. Fuqua et al. (1996) showed that prodigiosin is one of the QS mediated secondary metabolites produced by S. marcescens which is encoded by the smaI gene. Furthermore, there was increased biomass production in pigmented strains with rapid multiplication of cells. The results also show that the reduction in prodigiosin correlated well with the reduction in biofilms. Based on this it is speculated that the complexes suppressed the QS phenomenon which resulted in an orchestrated decrease of the virulence factors in S. marcescens and P. aeruginosa. The hemolysis activity exhibited by S. marcescens is due to the cytotoxin haemolysin ShlA. The target destabilizes the target cell membrane resulting in cell lysis. Both the complexes showed almost 40-60% haemolysin inhibition. Since haemolysin production is also QS mediated, the cells treated with the complexes prevented haemolysin production and thereby prevented cell lysis.
Quorum sensing pathways in Gram-positive and -negative bacteria: potential of their interruption in abating drug resistance
Published in Journal of Chemotherapy, 2019
Shafiul Haque, Dinesh K. Yadav, Shekhar C. Bisht, Neelam Yadav, Vineeta Singh, Kashyap Kumar Dubey, Arshad Jawed, Mohd Wahid, Sajad Ahmad Dar
Number of natural and synthetic structural analogs of various AHL molecules has been studied to evaluate their effects on the QS system of related bacterial strains. In P. aeruginosa, QS regulates the expression of virulence factors and the development of pathogenesis through AHL signalling. Thus, synthetic analogs which impede cell-to-cell signalling in P. aeruginosa cultures could inhibit its pathogenesis. N-(2-oxocyclohexyl)-3-oxododecanamide showed antagonistic activity towards the las QS system, and N-(2-hydroxyphenyl)-3-oxododecanamide was antagonistic towards both the Las and the Rhl QS systems in P. aeruginosa. Las and Rhl systems have also been reported to reduce the expression of virulence factors by N-butanoyl-SHL derivative, N-decanoylcyclopentylamide (C10-CPA).186 Promising inhibition of QS via AHL analogs in P. aeruginosa has led to evaluation of a series of N-acyl-CPA compounds with variable lengths of carbon side chains for their ability to interfere with QS-mediated virulence in Serratia marcescens. It has been reported that the production of prodigiosin is strongly inhibited by C9 (N-nonanoyl)-CPA molecule in Serratia.187