洗涤剂胶束中的抗疟药物与血红素：一项核磁共振研究。
Antimalarial drugs and heme in detergent micelles: An NMR study.
作者信息
Casabianca Leah B, Kallgren Joye B, Natarajan Jayakumar K, Alumasa John N, Roepe Paul D, Wolf Christian, de Dios Angel C
机构信息
Department of Chemistry, Georgetown University, NW Washington, DC 20057, United States.
出版信息
J Inorg Biochem. 2009 May;103(5):745-8. doi: 10.1016/j.jinorgbio.2009.01.013. Epub 2009 Jan 27.
Abstract
Proton nuclear magnetic resonance relaxation times were measured for the protons of micelles formed by the detergents sodium dodecyl sulfate, dodecyltrimethyl ammonium bromide, and polyethylene glycol sorbitan monolaureate in the presence of ferriprotoporphyrin IX and the antimalarial drugs chloroquine, 7-chloro-4-quinolyl 4-N,N-diethylaminobutyl sulfide, and primaquine. Diffusion coefficients were extracted from pulsed gradient NMR experiments to evaluate the degree of association of these drugs with the detergent micelles. Results indicate that at low or neutral pH when the quinolyl N is protonated, chloroquine does not associate with neutral or cationic detergent micelles. For this reason, chloroquine's interaction with heme perturbs the partitioning of heme between the aqueous medium and detergent micelles.
摘要
在高铁原卟啉IX以及抗疟药物氯喹、7-氯-4-喹啉基4-N，N-二乙氨基丁基硫醚和伯氨喹存在的情况下，测量了由去污剂十二烷基硫酸钠、十二烷基三甲基溴化铵和聚乙二醇山梨醇单月桂酸酯形成的胶束中质子的质子核磁共振弛豫时间。从脉冲梯度核磁共振实验中提取扩散系数，以评估这些药物与去污剂胶束的缔合程度。结果表明，在低pH或中性pH下，当喹啉基N质子化时，氯喹不与中性或阳离子去污剂胶束缔合。因此，氯喹与血红素的相互作用扰乱了血红素在水相介质和去污剂胶束之间的分配。
相似文献
1
Antimalarial drugs and heme in detergent micelles: An NMR study.洗涤剂胶束中的抗疟药物与血红素：一项核磁共振研究。
J Inorg Biochem. 2009 May;103(5):745-8. doi: 10.1016/j.jinorgbio.2009.01.013. Epub 2009 Jan 27.
2
Interaction of primaquine and chloroquine with ionic micelles as studied by 1H NMR and electronic absorption spectroscopy.通过核磁共振氢谱（¹H NMR）和电子吸收光谱研究伯氨喹和氯喹与离子型胶束的相互作用。
Physiol Chem Phys Med NMR. 1995;27(1):1-15.
3
Understanding the interaction between valsartan and detergents by NMR techniques and molecular dynamics simulation.通过 NMR 技术和分子动力学模拟理解缬沙坦与清洁剂之间的相互作用。
J Phys Chem B. 2012 Jun 28;116(25):7470-8. doi: 10.1021/jp304304v. Epub 2012 Jun 18.
4
Phospholipid containing mixed micelles. Characterization of diheptanoyl phosphatidylcholine (DHPC) and sodium dodecyl sulfate and DHPC and dodecyl trimethylammonium bromide.含磷脂的混合胶束。二庚酰磷脂酰胆碱（DHPC）与十二烷基硫酸钠以及DHPC与十二烷基三甲基溴化铵的特性。
Chem Phys Lipids. 2005 May;135(1):93-104. doi: 10.1016/j.chemphyslip.2005.02.004. Epub 2005 Mar 20.
5
NMR study of the tetrameric KcsA potassium channel in detergent micelles.在去污剂胶束中对四聚体KcsA钾通道的核磁共振研究。
Protein Sci. 2006 Apr;15(4):684-98. doi: 10.1110/ps.051954706. Epub 2006 Mar 7.
6
NMR study of the dynamics of cationic gemini surfactant 14-2-14 in mixed solutions with conventional surfactants.阳离子双子表面活性剂14-2-14与传统表面活性剂混合溶液动力学的核磁共振研究
J Phys Chem B. 2009 Jun 18;113(24):8357-61. doi: 10.1021/jp902419u.
7
Versatile interactions of the antimicrobial peptide novispirin with detergents and lipids.抗菌肽新螺旋霉素与去污剂和脂质的多种相互作用。
Biochemistry. 2006 Jan 17;45(2):481-97. doi: 10.1021/bi051876r.
8
Encapsulation of curcumin in cationic micelles suppresses alkaline hydrolysis.姜黄素在阳离子胶束中的包封可抑制碱性水解。
Langmuir. 2008 Jun 3;24(11):5672-5. doi: 10.1021/la800780w. Epub 2008 May 7.
9
Orienting the heterocyclic periphery: a structural model for chloroquine's antimalarial activity.
Chem Commun (Camb). 2014 Nov 18;50(89):13765-8. doi: 10.1039/c4cc05328a.
10
Heme coordination states of unfolded ferrous cytochrome C.未折叠亚铁细胞色素C的血红素配位状态
Biophys J. 2006 Oct 15;91(8):3022-31. doi: 10.1529/biophysj.105.079749. Epub 2006 Jul 28.
引用本文的文献
1
Quinoline-triazole hybrids inhibit falcipain-2 and arrest the development of at the trophozoite stage.喹啉 - 三唑杂化物抑制疟原虫蛋白酶2并使疟原虫在滋养体阶段的发育停滞。
RSC Adv. 2019 Nov 29;9(67):39410-39421. doi: 10.1039/c9ra06571g. eCollection 2019 Nov 27.
2
Cytostatic versus cytocidal activities of chloroquine analogues and inhibition of hemozoin crystal growth.氯喹类似物的细胞抑制与细胞杀伤活性及抑制血晶素晶体生长。
Antimicrob Agents Chemother. 2013 Jan;57(1):356-64. doi: 10.1128/AAC.01709-12. Epub 2012 Oct 31.
3
Investigating the activity of quinine analogues versus chloroquine resistant Plasmodium falciparum.研究奎宁类似物对氯喹耐药的恶性疟原虫的活性。
Bioorg Med Chem. 2012 May 15;20(10):3292-7. doi: 10.1016/j.bmc.2012.03.042. Epub 2012 Mar 29.
4
PfCRT-mediated drug transport in malarial parasites.疟原虫 PfCRT 介导的药物转运。
Biochemistry. 2011 Jan 18;50(2):163-71. doi: 10.1021/bi101638n. Epub 2010 Dec 22.
5
The hydroxyl functionality and a rigid proximal N are required for forming a novel non-covalent quinine-heme complex.羟基官能团和刚性的近端 N 是形成新型非共价奎宁-血红素配合物所必需的。
J Inorg Biochem. 2011 Mar;105(3):467-75. doi: 10.1016/j.jinorgbio.2010.08.011. Epub 2010 Sep 22.
6
Chloroquine transport in Plasmodium falciparum. 1. Influx and efflux kinetics for live trophozoite parasites using a novel fluorescent chloroquine probe.恶性疟原虫中的氯喹转运。1. 使用新型荧光氯喹探针研究活滋养体寄生虫的摄取和流出动力学。
Biochemistry. 2009 Oct 13;48(40):9471-81. doi: 10.1021/bi901034r.
7
Chloroquine transport in Plasmodium falciparum. 2. Analysis of PfCRT-mediated drug transport using proteoliposomes and a fluorescent chloroquine probe.恶性疟原虫中的氯喹转运。2. 使用蛋白脂质体和荧光氯喹探针分析PfCRT介导的药物转运。
Biochemistry. 2009 Oct 13;48(40):9482-91. doi: 10.1021/bi901035j.
8
Molecular and physiologic basis of quinoline drug resistance in Plasmodium falciparum malaria.恶性疟原虫对喹啉类药物耐药性的分子与生理基础
Future Microbiol. 2009 May;4(4):441-55. doi: 10.2217/fmb.09.15.
本文引用的文献
1
Quinine and chloroquine differentially perturb heme monomer-dimer equilibrium.奎宁和氯喹对血红素单体-二聚体平衡有不同的干扰作用。
Inorg Chem. 2008 Jul 7;47(13):6077-81. doi: 10.1021/ic800440d. Epub 2008 Jun 6.
2
4-N-, 4-S-, and 4-O-chloroquine analogues: influence of side chain length and quinolyl nitrogen pKa on activity vs chloroquine resistant malaria.4-N-、4-S-和4-O-氯喹类似物：侧链长度和喹啉氮pKa对氯喹耐药疟疾活性的影响
J Med Chem. 2008 Jun 26;51(12):3466-79. doi: 10.1021/jm701478a.
3
HDP-a novel heme detoxification protein from the malaria parasite.HDP——一种来自疟原虫的新型血红素解毒蛋白。
PLoS Pathog. 2008 Apr 25;4(4):e1000053. doi: 10.1371/journal.ppat.1000053.
4
The role of neutral lipid nanospheres in Plasmodium falciparum haem crystallization.中性脂质纳米球在恶性疟原虫血红蛋白结晶中的作用。
Biochem J. 2007 Feb 15;402(1):197-204. doi: 10.1042/BJ20060986.
5
Haemozoin (beta-haematin) biomineralization occurs by self-assembly near the lipid/water interface.疟色素（β-血红素）生物矿化通过在脂质/水界面附近的自组装过程发生。
FEBS Lett. 2006 Sep 18;580(21):5105-10. doi: 10.1016/j.febslet.2006.08.043. Epub 2006 Sep 1.
6
Relationship between NMR shielding and heme binding strength for a series of 7-substituted quinolines.
J Phys Chem A. 2006 Jun 29;110(25):7787-92. doi: 10.1021/jp061320t.
7
Inhibition assay of beta-hematin formation initiated by lecithin for screening new antimalarial drugs.用于筛选新型抗疟药物的卵磷脂引发的β-血红素形成抑制试验。
Anal Biochem. 2006 Feb 15;349(2):292-6. doi: 10.1016/j.ab.2005.11.022. Epub 2005 Dec 6.
8
Hemozoin formation in malaria: a two-step process involving histidine-rich proteins and lipids.疟疾中疟色素的形成：一个涉及富含组氨酸蛋白和脂质的两步过程。
Biochem Biophys Res Commun. 2003 Sep 5;308(4):736-43. doi: 10.1016/s0006-291x(03)01465-7.
9
The structure of malaria pigment beta-haematin.疟色素β-血红素的结构。
Nature. 2000 Mar 16;404(6775):307-10. doi: 10.1038/35005132.
10
Involvement of lipids in ferriprotoporphyrin IX polymerization in malaria.脂质在疟疾中铁原卟啉IX聚合反应中的作用
Biochim Biophys Acta. 1999 May 31;1454(1):31-7. doi: 10.1016/s0925-4439(99)00017-4.
Zotero 插件