Fluorogenic L-alanylaminopeptidase substrates derived from 6-amino-2-hetarylquinolines and 7-amino-3-hetarylcoumarins and their potential applications in diagnostic microbiology

Marie Cellier-Rastit; Arthur L. James; Sylvain Orenga; John D. Perry; Shaun Robinson; Graeme Turnbull; Steven Stanforth

doi:10.1016/j.bmcl.2019.03.011

Fluorogenic L-alanylaminopeptidase substrates derived from 6-amino-2-hetarylquinolines and 7-amino-3-hetarylcoumarins and their potential applications in diagnostic microbiology

Marie Cellier-Rastit, Arthur L. James, Sylvain Orenga, John D. Perry, Shaun Robinson, Graeme Turnbull, Steven Stanforth

Research output: Contribution to journal › Article › peer-review

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Abstract

Six novel fluorogenic enzyme substrates for detecting L-alanylaminopeptidase activity in microorganisms have been prepared and evaluated in Columbia agar media. The substrates are L-alanyl derivatives of 6-amino-2-hetarylquinolines and 7-amino-3-hetarylcoumarins. Both the quinoline and coumarin series of substrates produced fluorescence in the presence of Gram-negative microorganisms. In contrast, fluorescence generation in the presence of the Gram-positive microorganisms and yeasts was limited or absent.

Original language	English
Pages (from-to)	1227-1231
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	29
Issue number	10
Early online date	9 Mar 2019
DOIs	https://doi.org/10.1016/j.bmcl.2019.03.011
Publication status	Published - 15 May 2019

Keywords

Fluorogenic substrates
L-alanylaminopeptidase
microorganism detection
quinolines
coumarins

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10.1016/j.bmcl.2019.03.011

final text for 'pure' BMCLAccepted author manuscript, 706 KBLicence: CC BY-NC-ND

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Cellier-Rastit, M., James, A. L., Orenga, S., Perry, J. D., Robinson, S., Turnbull, G., & Stanforth, S. (2019). Fluorogenic L-alanylaminopeptidase substrates derived from 6-amino-2-hetarylquinolines and 7-amino-3-hetarylcoumarins and their potential applications in diagnostic microbiology. Bioorganic and Medicinal Chemistry Letters, 29(10), 1227-1231. https://doi.org/10.1016/j.bmcl.2019.03.011

@article{6404464513f943099dd9ca021676b41c,

title = "Fluorogenic L-alanylaminopeptidase substrates derived from 6-amino-2-hetarylquinolines and 7-amino-3-hetarylcoumarins and their potential applications in diagnostic microbiology",

abstract = "Six novel fluorogenic enzyme substrates for detecting L-alanylaminopeptidase activity in microorganisms have been prepared and evaluated in Columbia agar media. The substrates are L-alanyl derivatives of 6-amino-2-hetarylquinolines and 7-amino-3-hetarylcoumarins. Both the quinoline and coumarin series of substrates produced fluorescence in the presence of Gram-negative microorganisms. In contrast, fluorescence generation in the presence of the Gram-positive microorganisms and yeasts was limited or absent.",

keywords = "Fluorogenic substrates, L-alanylaminopeptidase, microorganism detection, quinolines, coumarins",

author = "Marie Cellier-Rastit and James, \{Arthur L.\} and Sylvain Orenga and Perry, \{John D.\} and Shaun Robinson and Graeme Turnbull and Steven Stanforth",

year = "2019",

month = may,

day = "15",

doi = "10.1016/j.bmcl.2019.03.011",

language = "English",

volume = "29",

pages = "1227--1231",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier",

number = "10",

}

Cellier-Rastit, M, James, AL, Orenga, S, Perry, JD, Robinson, S, Turnbull, G & Stanforth, S 2019, 'Fluorogenic L-alanylaminopeptidase substrates derived from 6-amino-2-hetarylquinolines and 7-amino-3-hetarylcoumarins and their potential applications in diagnostic microbiology', Bioorganic and Medicinal Chemistry Letters, vol. 29, no. 10, pp. 1227-1231. https://doi.org/10.1016/j.bmcl.2019.03.011

Fluorogenic L-alanylaminopeptidase substrates derived from 6-amino-2-hetarylquinolines and 7-amino-3-hetarylcoumarins and their potential applications in diagnostic microbiology. / Cellier-Rastit, Marie; James, Arthur L.; Orenga, Sylvain et al.
In: Bioorganic and Medicinal Chemistry Letters, Vol. 29, No. 10, 15.05.2019, p. 1227-1231.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Fluorogenic L-alanylaminopeptidase substrates derived from 6-amino-2-hetarylquinolines and 7-amino-3-hetarylcoumarins and their potential applications in diagnostic microbiology

AU - Cellier-Rastit, Marie

AU - James, Arthur L.

AU - Orenga, Sylvain

AU - Perry, John D.

AU - Robinson, Shaun

AU - Turnbull, Graeme

AU - Stanforth, Steven

PY - 2019/5/15

Y1 - 2019/5/15

N2 - Six novel fluorogenic enzyme substrates for detecting L-alanylaminopeptidase activity in microorganisms have been prepared and evaluated in Columbia agar media. The substrates are L-alanyl derivatives of 6-amino-2-hetarylquinolines and 7-amino-3-hetarylcoumarins. Both the quinoline and coumarin series of substrates produced fluorescence in the presence of Gram-negative microorganisms. In contrast, fluorescence generation in the presence of the Gram-positive microorganisms and yeasts was limited or absent.

AB - Six novel fluorogenic enzyme substrates for detecting L-alanylaminopeptidase activity in microorganisms have been prepared and evaluated in Columbia agar media. The substrates are L-alanyl derivatives of 6-amino-2-hetarylquinolines and 7-amino-3-hetarylcoumarins. Both the quinoline and coumarin series of substrates produced fluorescence in the presence of Gram-negative microorganisms. In contrast, fluorescence generation in the presence of the Gram-positive microorganisms and yeasts was limited or absent.

KW - Fluorogenic substrates

KW - L-alanylaminopeptidase

KW - microorganism detection

KW - quinolines

KW - coumarins

UR - https://www.scopus.com/pages/publications/85062915763

U2 - 10.1016/j.bmcl.2019.03.011

DO - 10.1016/j.bmcl.2019.03.011

M3 - Article

SN - 0960-894X

VL - 29

SP - 1227

EP - 1231

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 10

ER -

Cellier-Rastit M, James AL, Orenga S, Perry JD, Robinson S, Turnbull G et al. Fluorogenic L-alanylaminopeptidase substrates derived from 6-amino-2-hetarylquinolines and 7-amino-3-hetarylcoumarins and their potential applications in diagnostic microbiology. Bioorganic and Medicinal Chemistry Letters. 2019 May 15;29(10):1227-1231. Epub 2019 Mar 9. doi: 10.1016/j.bmcl.2019.03.011

Fluorogenic L-alanylaminopeptidase substrates derived from 6-amino-2-hetarylquinolines and 7-amino-3-hetarylcoumarins and their potential applications in diagnostic microbiology

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