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

来源：

JOURNAL OF TRACE ELEMENTS IN MEDICINE AND BIOLOGY | 2017年 / 41卷

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

页码：16 / 22

页数：7

共 35 条

[21] The evolution of iron chelators for the treatment of iron overload disease and cancer
Kalinowski, DS
Richardson, DR
[J]. 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
Kamruzzaman, Mohammad
Faruqui, A. Nayeem
Hossain, Mohammed Ifteker
Lee, Sang Hak
[J]. LUMINESCENCE, 2015, 30 (07) : 1077 - 1082
[23] MARTIN RB, 1987, CLIN CHEM, V33, P405
[24] SIDEROPHORES - STRUCTURE AND FUNCTION OF MICROBIAL IRON TRANSPORT COMPOUNDS
NEILANDS, JB
[J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 1995, 270 (45) : 26723 - 26726
[25] MECHANISM OF OXIDATION OF HYDROXAMIC ACIDS BY ALKALINE FERRICYANIDE
OLIVER, TR
WATERS, WA
[J]. 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
Pastrana Alta, Elizabeth Carmen
Goswami, Dibakar
Machini, M. Teresa
Silvestre, Daniel Menezes
Nomura, Cassiana Seimi
Espsito, Breno Pannia
[J]. BIOMETALS, 2014, 27 (06) : 1351 - 1360
[27] Iron acquisition and its control in Pseudomonas aeruginosa:: Many roads lead to Rome
Poole, K
McKay, GA
[J]. FRONTIERS IN BIOSCIENCE-LANDMARK, 2003, 8 : D661 - D686
[28] Iron metabolism in pathogenic bacteria
Ratledge, C
Dover, LG
[J]. 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
Roosenberg, JM
Lin, YM
Lu, Y
Miller, MJ
[J]. CURRENT MEDICINAL CHEMISTRY, 2000, 7 (02) : 159 - 197

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