Synthetic analogues of cyanobacterial alkaloid cylindrospermopsin and their toxicological activity

Christopher  Cartmell; Daniel Evans; Jessica ML Elwood; Hisham Fituri; Patrick Murphy; Thomas Caspari; Barbara  Poniedziałekc; Piotr Rzymskic

doi:10.1016/j.tiv.2017.07.007

Synthetic analogues of cyanobacterial alkaloid cylindrospermopsin and their toxicological activity

Christopher Cartmell, Daniel Evans, Jessica ML Elwood, Hisham Fituri, Patrick Murphy, Thomas Caspari, Barbara Poniedziałekc, Piotr Rzymskic

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Abstract

Highlights
•
The role of the C7-OH group in the activity of cylindrospermopsin 1 is unknown.
•
Synthetic analogues (11a–c) of cylindrospermopsin 1 were prepared.
•
Toxicity of these analogues was compared with 1 using human neutrophils in vitro.
•
The greatest toxicity was found in 11c with a 6-carbon tether and an –OH group.
•
An analogue closely resembling 1 but lacking the C7-OH group had low toxicity.

Original language	English
Pages (from-to)	172-181
Journal	Toxicology in Vitro
Volume	44
Early online date	10 Jul 2017
DOIs	https://doi.org/10.1016/j.tiv.2017.07.007
Publication status	Published - Oct 2017

Keywords

Cylindrospermopsin;
Guanidine synthesis
Neutrophils
Oxidative stress
Reactive oxygen species
Superoxide dismutase
Catalase
Glutathione peroxidase

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10.1016/j.tiv.2017.07.007

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title = "Synthetic analogues of cyanobacterial alkaloid cylindrospermopsin and their toxicological activity",

abstract = "Highlights • The role of the C7-OH group in the activity of cylindrospermopsin 1 is unknown. • Synthetic analogues (11a–c) of cylindrospermopsin 1 were prepared. • Toxicity of these analogues was compared with 1 using human neutrophils in vitro. • The greatest toxicity was found in 11c with a 6-carbon tether and an –OH group. • An analogue closely resembling 1 but lacking the C7-OH group had low toxicity.",

keywords = "Cylindrospermopsin; , Guanidine synthesis, Neutrophils, Oxidative stress, Reactive oxygen species, Superoxide dismutase, Catalase, Glutathione peroxidase",

author = "Christopher Cartmell and Daniel Evans and Elwood, \{Jessica ML\} and Hisham Fituri and Patrick Murphy and Thomas Caspari and Barbara Poniedzia{\l}ekc and Piotr Rzymskic",

year = "2017",

month = oct,

doi = "10.1016/j.tiv.2017.07.007",

language = "English",

volume = "44",

pages = "172--181",

journal = "Toxicology in Vitro",

issn = "0887-2333",

publisher = "Elsevier",

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TY - JOUR

T1 - Synthetic analogues of cyanobacterial alkaloid cylindrospermopsin and their toxicological activity

AU - Cartmell, Christopher

AU - Evans, Daniel

AU - Elwood, Jessica ML

AU - Fituri, Hisham

AU - Murphy, Patrick

AU - Caspari, Thomas

AU - Poniedziałekc, Barbara

AU - Rzymskic, Piotr

PY - 2017/10

Y1 - 2017/10

N2 - Highlights • The role of the C7-OH group in the activity of cylindrospermopsin 1 is unknown. • Synthetic analogues (11a–c) of cylindrospermopsin 1 were prepared. • Toxicity of these analogues was compared with 1 using human neutrophils in vitro. • The greatest toxicity was found in 11c with a 6-carbon tether and an –OH group. • An analogue closely resembling 1 but lacking the C7-OH group had low toxicity.

AB - Highlights • The role of the C7-OH group in the activity of cylindrospermopsin 1 is unknown. • Synthetic analogues (11a–c) of cylindrospermopsin 1 were prepared. • Toxicity of these analogues was compared with 1 using human neutrophils in vitro. • The greatest toxicity was found in 11c with a 6-carbon tether and an –OH group. • An analogue closely resembling 1 but lacking the C7-OH group had low toxicity.

KW - Cylindrospermopsin;

KW - Guanidine synthesis

KW - Neutrophils

KW - Oxidative stress

KW - Reactive oxygen species

KW - Superoxide dismutase

KW - Catalase

KW - Glutathione peroxidase

U2 - 10.1016/j.tiv.2017.07.007

DO - 10.1016/j.tiv.2017.07.007

M3 - Article

SN - 0887-2333

VL - 44

SP - 172

EP - 181

JO - Toxicology in Vitro

JF - Toxicology in Vitro

ER -

Synthetic analogues of cyanobacterial alkaloid cylindrospermopsin and their toxicological activity

Abstract

Keywords

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