Desferrioxamine and desferrioxamine-caffeine as carriers of aluminum and gallium to microbes via the Trojan Horse Effect

被引:21
作者
Alvarado Huayhuaz, Jesus Antonio [1 ]
Vitorino, Hector Aguilar [1 ]
Campos, Othon Souto [1 ]
Pires Serrano, Silvia Helena [1 ]
Kaneko, Telma Mary [2 ]
Esposito, Breno Pannia [1 ]
机构
[1] Univ Sao Paulo, Inst Chem, Dept Fundamental Chem, Av Prof Lineu Prestes 748, BR-05508000 Sao Paulo, SP, Brazil
[2] Univ Sao Paulo, Fac Pharmaceut Sci, Sao Paulo, SP, Brazil
基金
巴西圣保罗研究基金会;
关键词
Desferrioxamine; Aluminum; Gallium; Caffeine; Trojan horse; IRON CHELATORS; SIDEROPHORES; TRANSPORT; EQUILIBRIUM; DELIVERY; OVERLOAD; COMPLEX; CELLS;
D O I
10.1016/j.jtemb.2017.01.006
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
Iron acquisition by bacteria and fungi involves in several cases the promiscuous usage of siderophores. Thus, antibiotic resistance from these microorganisms can be circumvented through a strategy of loading toxic metals into siderophores (Trojan Horse Effect). Desferrioxamine (dfo) and its cell-permeant derivative desferrioxamine-caffeine (dfcaf) were complexed with aluminum or gallium for this purpose. The complexes Me(dfo) and Me(dfcaf) (Me = Al3+ and Ga3+) were synthesized and characterized by mass spectroscopy and cyclic voltammetry. Their relative stabilities were studied through competitive equilibria with fluorescent probes calcein, fluorescein-desferrioxamine and 8-hydroxyquinoline. Me(dfo) and Me(dfcaf) were consistently more toxic than free Me3+ against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Candida albicans, demonstrating the Trojan Horse Effect. Wide spectrum antimicrobial action can be obtained by loading non-essential or toxic metal ions to microbes via a convenient siderophore carrier. (C) 2017 Elsevier GmbH. All rights reserved.
引用
收藏
页码:16 / 22
页数:7
相关论文
共 35 条
[21]   The evolution of iron chelators for the treatment of iron overload disease and cancer [J].
Kalinowski, DS ;
Richardson, DR .
PHARMACOLOGICAL REVIEWS, 2005, 57 (04) :547-583
[22]   Spectroscopic study of the interaction between adenosine disodium triphosphate and gatifloxacin-Al3+ complex and its analytical application [J].
Kamruzzaman, Mohammad ;
Faruqui, A. Nayeem ;
Hossain, Mohammed Ifteker ;
Lee, Sang Hak .
LUMINESCENCE, 2015, 30 (07) :1077-1082
[23]  
MARTIN RB, 1987, CLIN CHEM, V33, P405
[24]   SIDEROPHORES - STRUCTURE AND FUNCTION OF MICROBIAL IRON TRANSPORT COMPOUNDS [J].
NEILANDS, JB .
JOURNAL OF BIOLOGICAL CHEMISTRY, 1995, 270 (45) :26723-26726
[25]   MECHANISM OF OXIDATION OF HYDROXAMIC ACIDS BY ALKALINE FERRICYANIDE [J].
OLIVER, TR ;
WATERS, WA .
JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1971, (04) :677-&
[26]   Desferrioxamine-caffeine (DFCAF) as a cell permeant moderator of the oxidative stress caused by iron overload [J].
Pastrana Alta, Elizabeth Carmen ;
Goswami, Dibakar ;
Machini, M. Teresa ;
Silvestre, Daniel Menezes ;
Nomura, Cassiana Seimi ;
Espsito, Breno Pannia .
BIOMETALS, 2014, 27 (06) :1351-1360
[27]   Iron acquisition and its control in Pseudomonas aeruginosa:: Many roads lead to Rome [J].
Poole, K ;
McKay, GA .
FRONTIERS IN BIOSCIENCE-LANDMARK, 2003, 8 :D661-D686
[28]   Iron metabolism in pathogenic bacteria [J].
Ratledge, C ;
Dover, LG .
ANNUAL REVIEW OF MICROBIOLOGY, 2000, 54 :881-941
[29]  
Raymond K. N., 2004, AM SOC MICROBIOL, P1
[30]   Studies and syntheses of siderophores, microbial iron chelators, and analogs as potential drug delivery agents [J].
Roosenberg, JM ;
Lin, YM ;
Lu, Y ;
Miller, MJ .
CURRENT MEDICINAL CHEMISTRY, 2000, 7 (02) :159-197