New Opportunities with the Duff Reaction

Masurier, Nicolas; Moreau, Emmanuel; Lartigue, Claire; Gaumet, Vincent; Chezal, Jean‐Michel; Heitz, Annie; Teulade, Jean‐Claude; Chavignon, Olivier

doi:10.1021/jo800700b

Cited by 36 publications

(11 citation statements)

References 59 publications

(19 reference statements)

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“…Afterward, the quinolone derivative (11) was prepared through Conrad–Umpach thermic cyclization in diphenyl ether at 270 °C. Formylation of the C-3 position through the Duff reaction 36 allowed us to obtain the quinolone derivative (12) as the precursor of the desired hapten. Concomitant hydrolysis of the methyl ester group occurred; however, this fact no longer affected the synthetic procedure.…”

Section: Resultsmentioning

confidence: 99%

An Immunochemical Approach to Quantify and Assess the Potential Value of the Pseudomonas Quinolone Signal as a Biomarker of Infection

2021

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Quorum sensing (QS) is a bacterial cell density-based communication system using low molecular weight signals called autoinducers (AIs). Identification and quantification of these molecules could provide valuable information related to the stage of colonization or infection as well as the stage of the disease. With this scenario, we report here for the first time the development of antibodies against the PQS (pseudomonas quinolone signal), the main signaling molecule from the pqs QS system of Pseudomonas aeruginosa , and the development of a microplate-based enzyme-linked immunosorbent assay (ELISA) able of quantifying this molecule in complex biological media in the low nanometer range (LOD, 0.36 ± 0.14 nM in culture broth media). Moreover, the PQS ELISA here reported has been found to be robust and reliable, providing accurate results in culture media. The technique allowed us to follow up the PQS profile of the release of bacterial clinical isolates obtained from patients of different disease status. A clear correlation was found between the PQS immunoreactivity equivalents and the chronic or acute infection conditions, which supports the reported differences on virulence and behavior of these bacterial strains due to their adaptation capability to the host environment. The results obtained point to the potential of the PQS as a biomarker of infection and to the value of the antibodies and the technology developed for improving diagnosis and management of P. aeruginosa infections based on the precise identification of the pathogen, appropriate stratification of the patients according to their disease status, and knowledge of the disease progression.

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Section: Resultsmentioning

confidence: 99%

An Immunochemical Approach to Quantify and Assess the Potential Value of the Pseudomonas Quinolone Signal as a Biomarker of Infection

2021

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“…Due to the heterogeneity of the heterocyclic scaffolds used to obtain KLK7 inhibition, 65 heterocyclic derivatives from our internal library were chosen for an initial screening (data not shown), including imidazo[1,2-a]pyridine (IP) and 1,3-thiazole derivatives, due to our particular interest in these heterocyclic scaffolds [25][26][27][28][29][30][31].…”

Section: Screening Of the Diazepinone Library And Rationale For The Smentioning

confidence: 99%

Pyrido-imidazodiazepinones as a new class of reversible inhibitors of human kallikrein 7

Arama

Soualmia

Lisowski

et al. 2015

European Journal of Medicinal Chemistry

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The human tissue kallikrein-7 (KLK7) is a chymotryptic serine protease member of tissue kallikrein family. KLK7 is involved in skin homeostasis and inflammation. Excess of KLK7 activity is also associated with tumor metastasis processes, especially in ovarian carcinomas, prostatic and pancreatic cancers. Development of Kallikrein 7 inhibitors is thus of great interest in oncology but also for treating skin diseases. Most of the developed synthetic inhibitors present several drawbacks such as poor selectivity and unsuitable physico-chemical properties for in vivo use. Recently, we described a practical sequence for the synthesis of imidazopyridine-fused [1,3]-diazepines. Here, we report the identification of pyrido-imidazodiazepinone core as a new potential scaffold to develop selective and competitive inhibitors of kallikrein-related peptidase 7. Structure-activity relationships (SAR), inhibition mechanisms and selectivity as well as cytotoxicity against selected cancer cell lines were investigated.

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“…Numerous formylation methods were developed to prepare diverse aromatic aldehydes from corresponding phenols [6], such as the Duff reaction [7][8][9], Vilsmeier-Haack reaction [10][11][12], Reimer-Tiemann reaction [13][14][15], Gattermann-Koch reaction [16,17], Gattermann reaction [18,19], Rieche reaction [20][21][22], and paraformaldehyde/MgCl 2 reaction [23,24]. These methods possess their individual advantages, however, low ortho-selectivity of the most of these methods and poor yields sharply limited their application in industry [25].…”

Section: Introductionmentioning

confidence: 99%