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Pyrrolnitrin
Published in Anton C. de Groot, Monographs in Contact Allergy, 2021
Pyrrolnitrin is a pyrrole antifungal agent isolated from several Pseudomonas species including Pseudomonas pyrrocinia. It is effective mainly against Trichophyton, Microsporum, Epidermophyton, and Penicillium. It was formerly marketed in Italy, Spain and Japan (10), but is nowadays probably hardly, if at all, used anymore in topical antifungal preparations (1).
Ultraviolet and Light Absorption Spectrometry
Published in Adorjan Aszalos, Modern Analysis of Antibiotics, 2020
Zoltan M. Dinya, Ferenc J. Sztaricskai
Of the antibiotics with a pyrrole skeleton, netropsin, coumermycins, prodigiosins, verrucarin E, anisomycin, and pyrrolnitrin are the most important. Among these compounds only pyrrolnitrin (107) achieved actual pharmaceutical use. Pyrrolnitrin exhibits absorption at 252 nm (ε max 750 m2/mol) in ethanol solution, and at the same time simple pyrrole derivatives usually display a more intense band in the range 240—270 nm. The antibiotics containing more than one pyrrole unit (such as prodigiosin) show intense absorption in the visible range: at 460—470 nm in alkaline solution and between 520 and 540 nm in acid medium.
Halogenases with Potential Applications for the Synthesis of Halogenated Pharmaceuticals
Published in Peter Grunwald, Pharmaceutical Biocatalysis, 2019
Georgette Rebollar-Pérez, Cynthia Romero-Guido, Antonino Baez, Eduardo Torres
Pyrrolnitrin is a broad-spectrum antifungal produced by Pseudomonas and Burkholderia bacteria. Sequencing and mutagenesis analysis identified a DNA fragment involved in pyrrolnitrin biosynthesis in Pseudomonas fluorescens. This DNA fragment contain four genes, prnA, prnB, prnC and prnD, arranged in a cluster (Hill et al., 1994). The prnABCD cluster is conserved in Pseudomonas pyromania, Pseudomonas fluorescens (BL915), Pseudomonas pyrrocinia, Burkholderia cepacia LT4-12-W and Myxococcus fulvus Mx f147 (Hammer et al., 1999). Expression of prnABCD cluster in Escherichia coli conferred this organism to produce pyrrolnitrin, while deletion mutations in any of the four genes compromised pyrrolnitrin production in P. fluorescens, demonstrating that prnABCD cluster confer pyrrolnitrin biosynthesis and all of the four genes are required for it (Hammer et al., 1997). Through functional analysis, Kirner et al. (1998) demonstrated the function of prnABCD cluster genes and proposed the pyrrolnitrin biosynthetic pathway in P. fluorescens (Fig. 16.4). PrnA catalyzes the chlorination of L-tryptophan to form 7-chloro-L-tryptophan (7-CLT) (Hammer et al., 1997; Kirner et al., 1998). PrnB catalyzes the rearrangement of indole ring to a phenylpyrrole and the decarboxylation of 7-CLT to form the monodechloroaminopyrrolnitrin (MDA) intermediate. PrnC catalyzes the chlorination of MDA at the 3 position to form aminopyrrolnitrin (APRN). PrnA and PrnC are flavin-dependent halogenases that require the activity of a nonspecific flavin reductase that reduces FAD to FADH2 by using NADH as reductant (Keller et al., 2000). PrnD is probably a class IA oxygenase that catalyzes the oxidation of the amino group of APRN to a nitro group forming pyrrolnitrin (Kirner et al., 1998).
Subtle relationships between Pseudomonas aeruginosa and fungi in patients with cystic fibrosis
Published in Acta Clinica Belgica, 2022
Kaicheng Yan, Hong Yin, Jin Wang, Yun Cai
Pyrrolidin is a secondary metabolite of Pseudomonas species, which has decarboxylation, halogenation in the pyrrole ring and oxidation of amino group [12]. Pyoluteorin is related to the pyrrolnitrin, an antibiotic from PA. The inhibition of electron transfer between substrates and coenzyme Q in a fungus occurs in the site of action of pyrrolnitrin as an antibiotic [49]. The antifungal activity of pyrrolnitrin, previously shown to be effective against superficial infections, is evaluated against experimental systemic mycoses. Gordee et al. have reported that pyrrolnitrin has an in vitro inhibitory effect on CA, Cryptococcus neoformans, Blastomyces dermatitidis, Sporotrichum schenckii and Histoplasma capsulatum, ranging from <0.78 to 100 μg/mL [50].
Drug discovery through the isolation of natural products from Burkholderia
Published in Expert Opinion on Drug Discovery, 2021
Adam Foxfire, Andrew Riley Buhrow, Ravi S. Orugunty, Leif Smith
Pyrrolnitrin and analogs of pyrrolnitrin: B. pyrrocinia No. 2327 was originally isolated from a soil sample collected in Japan and identified for its antibiotic properties during an antibiotic screening in 1965. After taxonomic evaluation the strain was classified as a new species, P. pyrrocinia, for its production of the novel antibiotic pyrrolnitrin [99]. This species was later classified as B. pyrrocinia, a member of the Bcc with greater than 20 identified strains [100,101]. Pyrrolnitrin, a pale-yellow crystalline substance, was isolated from the culture of B. pyrrocinia No. 2327 and its molecular formula and structure were elucidated (Figure 5) [102]. The initial study showed that pyrrolnitrin has growth inhibitory activity when tested against fungi, yeasts, and Gram-positive bacteria, while having a low toxicity [103]. Pyrrolnitrin was found to be effective against Trichophyton, Microsporum, Epidermophyton, and Penicillium while displaying weaker effectiveness against S. aureus, Bacillus subtilis, Proteus vulgaris, Aspergillus niger, and C. albicans. Some Gram-negative and Gram-positive bacteria were found to be naturally resistant [104]. Pyrrolnitrin is essentially a fungistatic antimicrobial. Its activity was not greatly influenced by addition of 10% rabbit serum in media. When orally administered it may lose its antimicrobial activity, probably due to chemical degradation in the stomach’s low pH environment. There is little to no absorption of pyrrolnitrin after subcutaneous injection. Moreover, when applied topically, this compound has no observable toxicity [104]. The strains of B. cepacia, J82rif and J51rif, have also been shown to produce analogs of pyrrolnitrin. These strains were reported to produce aminopyrrolnitrin and monochloroaminopyrrolnitrin [105]. In addition to standard pyrrolnitrin, B. cepacia K87 also produces two pyrrolnitrin analogs (3-chloro-4-(3-chloro-2-nitrophenyl)-5-methoxy-3-pyrrolin-2-one (2) and 4-chloro-3-(3-chloro-2-nitrophenyl)-5-methoxy-3-pyrrolin-2-one).