Natural product-inspired profluorophores for imaging NQO1 activity in tumour tissues

被引：18

作者：

Cheng, Zhiming ^{[1
]}

Valenca, Wagner O. ^{[2
]}

Dias, Gleiston G. ^{[2
]}

Scott, Jamie ^{[1
]}

Barth, Nicole D. ^{[1
]}

de Moliner, Fabio ^{[1
]}

Souza, Gabriela B. P. ^{[2
]}

Mellanby, Richard J. ^{[3
]}

Vendrell, Marc ^{[1
]}

da Silva Junior, Eufranio N. ^{[2
]}

机构：

[1] Univ Edinburgh, Ctr Inflammat Res, Edinburgh EH16 4TJ, Midlothian, Scotland

[2] Univ Fed Minas Gerais, Inst Exact Sci, Dept Chem, BR-31270901 Belo Horizonte, MG, Brazil

[3] Univ Edinburgh, Easter Bush Vet Ctr, Royal Dick Sch Vet Studies, Roslin Inst,Div Vet Clin Studies,Hosp Small Anim, Roslin EH25 9RG, Midlothian, Scotland

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2019年 / 27卷 / 17期

基金：

英国生物技术与生命科学研究理事会; 英国工程与自然科学研究理事会; 英国惠康基金;

关键词：

FLUORESCENCE-GUIDED SURGERY; TOPICAL APPLICATION; CANCER; PROBES; EXPRESSION; MECHANISM; LAPACHOL; COMPLEX; HYBRIDS; CELLS;

D O I：

10.1016/j.bmc.2019.07.017

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Herein we designed a collection of trimethyl-lock quinone profluorophores as activity-based probes for imaging NAD(P)H:quinone oxidoreductase (NQO1) in cancer cells and tumour tissues. Profluorophores were prepared via synthetic routes from naturally-occurring quinones and characterised in vitro using recombinant enzymes, to be further validated in cells and fresh frozen canine tumour tissues as potential new tools for cancer detection and imaging.

引用

页码：3938 / 3946

页数：9

共 52 条

[1] [Anonymous], J CHEM SOC
[2] The crystal structure of NAD(P)H quinone oxidoreductase 1 in complex with its potent inhibitor dicoumarol
Asher, Gad
Dym, Orly
Tsvetkov, Peter
Adler, Julia
Shaul, Yosef
[J]. BIOCHEMISTRY, 2006, 45 (20) : 6372 - 6378
[3] Efficacious fluorescence turn-on probe for high-contrast imaging of human cells overexpressing quinone reductase activity
Best, Quinn A.
Prasai, Bijeta
Rouillere, Alexandra
Johnson, Amanda E.
McCarley, Robin L.
[J]. CHEMICAL COMMUNICATIONS, 2017, 53 (04) : 783 - 786
[4] Environmentally Robust Rhodamine Reporters for Probe-based Cellular Detection of the Cancer-linked Oxidoreductase hNQO1
Best, Quinn A.
Johnson, Amanda E.
Prasai, Bijeta
Rouillere, Alexandra
McCarley, Robin L.
[J]. ACS CHEMICAL BIOLOGY, 2016, 11 (01) : 231 - 240
[5] Structure, function, and mechanism of cytosolic quinone reductases
Bianchet, Mario A.
Erdemli, Sabri Bora
Amzel, L. Mario.
[J]. VITAMIN K, 2008, 78 : 63 - +
[6] NQO1 Expression Correlates with Cholangiocarcinoma Prognosis
Buranrat, Benjaporn
Chau-in, Siri
Prawan, Auemduan
Puapairoj, Anucha
Zeekpudsa, Pornsilp
Kukongviriyapan, Veerapol
[J]. ASIAN PACIFIC JOURNAL OF CANCER PREVENTION, 2012, 13 : 131 - 136
[7] High expression of NQO1 is associated with poor prognosis in serous ovarian carcinoma
Cui, Xuelian
Li, Lianhua
Yan, Guanghai
Meng, Kai
Lin, Zhenhua
Nan, Yunze
Jin, Guang
Li, Chunyu
[J]. BMC CANCER, 2015, 15
[8] NAD(P)H:quinone oxidoreductase-1 overexpression predicts poor prognosis in small cell lung cancer
Cui, Xuelian
Jin, Tiefeng
Wang, Xiaoyan
Jin, Guang
Li, Zhuhu
Lin, Lijuan
[J]. ONCOLOGY REPORTS, 2014, 32 (06) : 2589 - 2595
[9] Synthesis of fused chromene-1,4-naphthoquinones via ring-closing metathesis and Knoevenagel-electrocyclization under acid catalysis and microwave irradiation
da Rocha, David R.
Mota, Kelly
da Silva, Illana M. C. B.
Ferreira, Vitor F.
Ferreira, Sabrina B.
da Silva, Fernando de C.
[J]. TETRAHEDRON, 2014, 70 (20) : 3266 - 3270
[10] Naphthoquinoidal [1,2,3]-triazole, a new structural moiety active against Trypanosoma cruzi
da Silva, Eufranio N., Jr.
Menna-Barreto, Rubem F. S.
Pinto, Maria do Carmo F. R.
Silva, Raphael S. F.
Teixeira, Daniel V.
de Souza, Maria Cecilia B. V.
De Simone, Carlos Alberto
De Castro, Solange L.
Ferreira, Vitor F.
Pinto, Antonio V.
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (08) : 1774 - 1780

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