Alkylating ability of artemisinin after Cu(I)-induced activation

被引：8

作者：

Bousejra-El Garah, Fatima ^{[1
]}

Pitie, Marguerite ^{[1
]}

Vendier, Laure ^{[1
]}

Meunier, Bernard ^{[2
]}

Robert, Anne ^{[1
]}

机构：

[1] CNRS, Chim Coordinat Lab, F-31077 Toulouse 4, France

[2] Palumed, F-31320 Castanet Tolosan, France

来源：

JOURNAL OF BIOLOGICAL INORGANIC CHEMISTRY | 2009年 / 14卷 / 04期

关键词：

Alkylation; Artemisinin; Copper; Malaria; Non-heme complexes; ANTIMALARIAL-DRUG ARTEMISININ; QINGHAOSU ARTEMISININ; STRUCTURAL-CHARACTERIZATION; PLASMODIUM-FALCIPARUM; HEME MODEL; COPPER; REDUCTION; COMPLEXES; DERIVATIVES; DECOMPOSITION;

D O I：

10.1007/s00775-009-0474-z

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 reductive activation of artemisinin by copper(I)-dipyrrin or copper(I)-(2-Clip-Phen) complexes generates an artemisinin derived alkylating species leading to covalent artemisinin-copper complex adducts. The reactivity of the peroxide function of artemisinin toward Cu(I) complexes is similar to that of Fe(II) analogues, even though the reaction is more sluggish and product distribution slightly different.

引用

页码：601 / 610

页数：10

共 59 条

[41] Alkylation of heme by the antimalarial drug artemisinin
Robert, A
Coppel, Y
Meunier, B
[J]. CHEMICAL COMMUNICATIONS, 2002, (05) : 414 - 415
[42] From mechanistic studies on artemisinin derivatives to new modular antimalarial drugs
Robert, A
Dechy-Cabaret, O
Cazelles, J
Meunier, B
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (03) : 167 - 174
[43] Is alkylation the main mechanism of action of the antimalarial drug artemisinin?
Robert, A
Meunier, B
[J]. CHEMICAL SOCIETY REVIEWS, 1998, 27 (04) : 273 - 279
[44] Characterization of the first covalent adduct between artemisinin and a heme model
Robert, A
Meunier, B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (25) : 5968 - 5969
[45] Robert A, 1998, CHEM-EUR J, V4, P1287, DOI 10.1002/(SICI)1521-3765(19980710)4:7<1287::AID-CHEM1287>3.3.CO
[46] 2-A
[47] Near net-shaped, alkaline-earth-bearing ceramics for electronic and refractory applications via the oxidation of solid, metal-bearing precursors (the VIMOX process)
Sandhage, KH
Allameh, SM
Kumar, B
Schmutzler, HJ
Viers, D
Zhang, XD
[J]. MATERIALS AND MANUFACTURING PROCESSES, 2000, 15 (01) : 1 - 28
[48] Malaria chemotherapeutics part 1: History of antimalarial drug development, currently used therapeutics, and drugs in clinical development
Schlitzer, Martin
[J]. CHEMMEDCHEM, 2007, 2 (07) : 944 - 986
[49] Sheldrick G.M., 1998, SHELX97 INCLUDES SHE
[50] Dispiro-1,2,4-trioxane analogues of a prototype dispiro-1,2,4-trioxolane: Mechanistic comparators for artemisinin in the context of reaction pathways with iron(II)
Tang, YQ
Dong, YX
Wang, XF
Sriraghavan, K
Wood, JK
Vennerstrom, JL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (13) : 5103 - 5110

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