Synthesis, Photophysical Properties and Biological Evaluation of New Conjugates BODIPY: Dinuclear Trithiolato-Bridged Ruthenium(II)-Arene Complexes

被引:8
作者
Desiatkina, Oksana [1 ]
Boubaker, Ghalia [2 ]
Anghel, Nicoleta [2 ]
Amdouni, Yosra [2 ,3 ]
Hemphill, Andrew [2 ]
Furrer, Julien [1 ]
Paunescu, Emilia [1 ]
机构
[1] Univ Bern, Dept Chem Biochem & Pharmaceut Sci, Freiestr 3, CH-3012 Bern, Switzerland
[2] Univ Bern, Vetsuisse Fac, Inst Parasitol, Langgassstr 122, CH-3012 Bern, Switzerland
[3] Univ Manouba, Inst Rech & Enseignement Super Agr, Lab Parasitol, Sidi Thabet 2020, Tunisia
关键词
antiparasitic activity; antiprotozoal agents; BODIPY; fluorescence; photophysical properties; Toxoplasma gondii; ARENE RUTHENIUM COMPLEXES; METAL-BASED DRUGS; IN-VITRO; ANTICANCER ACTIVITY; POLYPYRIDINE COMPLEXES; CELLULAR-LOCALIZATION; NEOSPORA-CANINUM; HOST-CELLS; TOXOPLASMA; DERIVATIVES;
D O I
10.1002/cbic.202200536
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
The synthesis, photophysical properties and antiparasitic efficacy against Toxoplasma gondii beta-gal (RH strain tachyzoites expressing beta-galactosidase) grown in human foreskin fibroblast monolayers (HFF) of a series of 15 new conjugates BODIPY-trithiolato-bridged dinuclear ruthenium(II)-arene complexes are reported (BODIPY=4,4-difluoro-4-bora-3a,4a-diaza-s-indacene, derivatives used as fluorescent markers). The influence of the bond type (amide vs. ester), as well as that of the length and nature (alkyl vs. aryl) of the spacer between the dye and the diruthenium(II) complex moiety, on fluorescence and biological activity were evaluated. The assessed photophysical properties revealed that despite an important fluorescence quenching effect observed after conjugating the BODIPY to the diruthenium unit, the hybrids could nevertheless be used as fluorescent tracers. Although the antiparasitic activity of this series of conjugates appears limited, the compounds demonstrate potential as fluorescent probes for investigating the intracellular trafficking of trithiolato-bridged dinuclear Ru(II)-arene complexes in vitro.
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页数:17
相关论文
共 103 条
[51]  
Liu I., 2014, ANGEW CHEM, V126, P4022
[52]   Near infrared BODIPY-Platinum conjugates for imaging, photodynamic therapy and chemotherapy [J].
Liu, Yang ;
Li, Zhensheng ;
Chen, Li ;
Xie, Zhigang .
DYES AND PIGMENTS, 2017, 141 :5-12
[53]   The Potent Oxidant Anticancer Activity of Organoiridium Catalysts [J].
Liu, Zhe ;
Romero-Canelon, Isolda ;
Qamar, Bushra ;
Hearn, Jessica M. ;
Habtemariam, Abraha ;
Barry, Nicolas P. E. ;
Pizarro, Ana M. ;
Clarkson, Guy J. ;
Sadler, Peter J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (15) :3941-3946
[54]   BODIPY dyes and their derivatives: Syntheses and spectroscopic properties [J].
Loudet, Aurore ;
Burgess, Kevin .
CHEMICAL REVIEWS, 2007, 107 (11) :4891-4932
[55]   Potential anticancer agent for selective damage to mitochondria or lysosomes: Naphthalimide-modified fluorescent biomarker half-sandwich iridium (III) and ruthenium (II) complexes [J].
Ma, Wenli ;
Zhang, Shumiao ;
Tian, Zhenzhen ;
Xu, Zhishan ;
Zhang, Yujiao ;
Xia, Xiaorong ;
Chen, Xiaobing ;
Liu, Zhe .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2019, 181
[56]   Rhodamine-modified fluorescent half-sandwich iridium and ruthenium complexes: potential application as bioimaging and anticancer agents [J].
Ma, Wenli ;
Guo, Lihua ;
Tian, Zhenzhen ;
Zhang, Shumiao ;
He, Xiangdong ;
Li, JuanJuan ;
Yang, Yuliang ;
Liu, Zhe .
DALTON TRANSACTIONS, 2019, 48 (15) :4788-4793
[57]   Effects of Concentration on Aggregation of BODIPY-Based Fluorescent Dyes Solution [J].
Marfin, Yuriy S. ;
Banakova, Elizaveta A. ;
Merkushev, Dmitry A. ;
Usoltsev, Sergey D. ;
Churakov, Andrei V. .
JOURNAL OF FLUORESCENCE, 2020, 30 (06) :1611-1621
[58]   Self-Assembly of a Carboxyl-Functionalized BODIPY Dye via Hydrogen Bonding [J].
Matarranz, Beatriz ;
Sampedro, Angel ;
Daniliuc, Constantin G. ;
Fernandez, Gustavo .
CRYSTALS, 2018, 8 (11)
[59]   Use of Toxoplasma gondii expressing beta-galactosidase for colorimetric assessment of drug activity in vitro [J].
McFadden, DC ;
Seeber, F ;
Boothroyd, JC .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1997, 41 (09) :1849-1853
[60]   Structure-activity relationships for ruthenium and osmium anticancer agents - towards clinical development [J].
Meier-Menches, Samuel M. ;
Gerner, Christopher ;
Berger, Walter ;
Hartinger, Christian G. ;
Keppler, Bernhard K. .
CHEMICAL SOCIETY REVIEWS, 2018, 47 (03) :909-928