抗疟药伯氨喹及其衍生物对血红蛋白电离势的影响：一项量子力学/分子力学研究
Effect of antimalarial drug primaquine and its derivatives on the ionization potential of hemoglobin: A QM/MM study.
作者信息
Liu Haining, Ding Yuanqing, Walker Larry A, Doerksen Robert J
机构信息
Department of Medicinal Chemistry, School of Pharmacy, University of Mississippi, University, MS 38677 USA.
出版信息
Medchemcomm. 2013 Aug 1;4(8):1145-1147. doi: 10.1039/C3MD00045A.
Abstract
We used quantum mechanics/molecular mechanics calculations to test if antimalarial primaquine (PQ) and its derivatives aid the conversion of hemoglobin to methemoglobin by binding to hemoglobin and merely lowering hemoglobin's ionization potential (IP). Our results showed that PQ and its derivatives do not significantly lower the hemoglobin IP, disproving the hypothesis.
摘要
我们采用量子力学/分子力学计算方法，来检验抗疟药伯氨喹（PQ）及其衍生物是否通过与血红蛋白结合并仅降低其电离势（IP），从而帮助血红蛋白转化为高铁血红蛋白。我们的结果表明，PQ及其衍生物不会显著降低血红蛋白的IP，这一假设不成立。
相似文献
1
Effect of antimalarial drug primaquine and its derivatives on the ionization potential of hemoglobin: A QM/MM study.抗疟药伯氨喹及其衍生物对血红蛋白电离势的影响：一项量子力学/分子力学研究
Medchemcomm. 2013 Aug 1;4(8):1145-1147. doi: 10.1039/C3MD00045A.
2
Methemoglobin generation by 8-aminoquinolines: effect of substitution at 5-position of primaquine.
Chem Res Toxicol. 2013 Dec 16;26(12):1801-9. doi: 10.1021/tx400067a. Epub 2013 Nov 13.
3
Methemoglobinemia Hemotoxicity of Some Antimalarial 8-Aminoquinoline Analogues and Their Hydroxylated Derivatives: Density Functional Theory Computation of Ionization Potentials.
Chem Res Toxicol. 2016 Jul 18;29(7):1132-41. doi: 10.1021/acs.chemrestox.6b00063. Epub 2016 Jul 1.
4
Computational Study on the Effect of Exocyclic Substituents on the Ionization Potential of Primaquine: Insights into the Design of Primaquine-Based Antimalarial Drugs with Less Methemoglobin Generation.关于环外取代基对伯氨喹电离电位影响的计算研究：对减少高铁血红蛋白生成的基于伯氨喹的抗疟药物设计的见解。
Chem Res Toxicol. 2015 Feb 16;28(2):169-74. doi: 10.1021/tx500230t. Epub 2015 Jan 27.
5
Primaquine hybrids as promising antimycobacterial and antimalarial agents.原硷类杂合物作为有前途的抗分枝杆菌和抗疟药物。
Eur J Med Chem. 2018 Jan 1;143:769-779. doi: 10.1016/j.ejmech.2017.11.083. Epub 2017 Dec 2.
6
Susceptibility of glucose-6-phosphate dehydrogenase deficient red cells to primaquine enantiomers and two putative metabolites--I. Effect on reduced glutathione, methemoglobin content and release of hemoglobin.
Biochem Pharmacol. 1988 Dec 15;37(24):4605-9. doi: 10.1016/0006-2952(88)90327-9.
7
Machine learning prioritizes synthesis of primaquine ureidoamides with high antimalarial activity and attenuated cytotoxicity.机器学习优先合成具有高抗疟活性和降低细胞毒性的伯氨喹脲酰胺。
Eur J Med Chem. 2018 Feb 25;146:651-667. doi: 10.1016/j.ejmech.2018.01.062. Epub 2018 Jan 31.
8
[Study on structure-activity relationships of hemolytic toxicity of primaquine derivatives].
Zhongguo Ji Sheng Chong Xue Yu Ji Sheng Chong Bing Za Zhi. 1991;9(3):173-7.
9
Model-based assessment of the safety of community interventions with primaquine in sub-Saharan Africa.基于模型的评估：在撒哈拉以南非洲地区使用伯氨喹进行社区干预的安全性。
Parasit Vectors. 2021 Oct 9;14(1):524. doi: 10.1186/s13071-021-05034-4.
10
Methemoglobin incites primaquine toxicity through single-electron oxidation and modification.高铁血红蛋白通过单电子氧化和修饰引发伯氨喹毒性。
J Basic Clin Physiol Pharmacol. 2013;24(2):105-14. doi: 10.1515/jbcpp-2012-0058.
引用本文的文献
1
Tafenoquine: A Step toward Malaria Elimination.泰法诺喹：迈向疟疾消除的一步。
Biochemistry. 2020 Mar 3;59(8):911-920. doi: 10.1021/acs.biochem.9b01105. Epub 2020 Feb 24.
2
Computational Study on the Effect of Exocyclic Substituents on the Ionization Potential of Primaquine: Insights into the Design of Primaquine-Based Antimalarial Drugs with Less Methemoglobin Generation.关于环外取代基对伯氨喹电离电位影响的计算研究：对减少高铁血红蛋白生成的基于伯氨喹的抗疟药物设计的见解。
Chem Res Toxicol. 2015 Feb 16;28(2):169-74. doi: 10.1021/tx500230t. Epub 2015 Jan 27.
3
Hydroxylated derivatives of NPC1161: theoretical insights into their potential toxicity and the feasibility and regioselectivity of their formation.NPC1161的羟基化衍生物：对其潜在毒性以及形成的可行性和区域选择性的理论见解
J Phys Chem A. 2014 Jul 24;118(29):5501-7. doi: 10.1021/jp502612t. Epub 2014 Jul 11.
本文引用的文献
1
Review: Improving the therapeutic index of 8-aminoquinolines by the use of drug combinations: review of the literature and proposal for future investigations.综述：通过联合用药提高 8-氨基喹啉类药物的治疗指数：文献回顾与未来研究建议。
Am J Trop Med Hyg. 2011 Dec;85(6):1010-4. doi: 10.4269/ajtmh.2011.11-0498.
2
Plasmodium vivax treatments: what are we looking for?疟原虫 vivax 治疗方法：我们在寻找什么？
Curr Opin Infect Dis. 2011 Dec;24(6):578-85. doi: 10.1097/QCO.0b013e32834c61e3.
3
DFT study on the radical anions formed by primaquine and its derivatives.基于密度泛函理论研究普喹酮及其衍生物形成的自由基阴离子。
Chem Res Toxicol. 2011 Sep 19;24(9):1476-85. doi: 10.1021/tx200094v. Epub 2011 Jul 7.
4
Glutathione reductase-catalyzed cascade of redox reactions to bioactivate potent antimalarial 1,4-naphthoquinones--a new strategy to combat malarial parasites.谷胱甘肽还原酶催化的氧化还原反应级联反应使强效抗疟 1,4-萘醌类化合物生物激活——一种对抗疟原虫的新策略。
J Am Chem Soc. 2011 Aug 3;133(30):11557-71. doi: 10.1021/ja201729z. Epub 2011 Jul 12.
5
Multireference and multiconfiguration ab initio methods in heme-related systems: what have we learned so far?多参考态和多组态从头算方法在血红素相关体系中的应用：迄今为止我们学到了什么？
J Phys Chem B. 2011 Mar 3;115(8):1727-42. doi: 10.1021/jp110016u.
6
Methemoglobinemia caused by 8-aminoquinoline drugs: DFT calculations suggest an analogy to H4B's role in nitric oxide synthase.8-氨基喹啉类药物导致的高铁血红蛋白血症：DFT 计算提示其与 H4B 在一氧化氮合酶中的作用类似。
J Am Chem Soc. 2011 Feb 9;133(5):1172-5. doi: 10.1021/ja107472c. Epub 2011 Jan 18.
7
Road towards new antimalarials - overview of the strategies and their chemical progress.迈向新型抗疟药物之路 - 策略概述及其化学进展。
Curr Med Chem. 2011;18(6):853-71. doi: 10.2174/092986711794927748.
8
Synthesis, antiprotozoal, antimicrobial, β-hematin inhibition, cytotoxicity and methemoglobin (MetHb) formation activities of bis(8-aminoquinolines).双（8-氨基喹啉）的合成、抗原生动物、抗微生物、β-血卟啉抑制、细胞毒性和高铁血红蛋白（MetHb）形成活性。
Bioorg Med Chem. 2011 Jan 1;19(1):197-210. doi: 10.1016/j.bmc.2010.11.036. Epub 2010 Nov 25.
9
Antimalarial activity of novel 5-aryl-8-aminoquinoline derivatives.新型 5-芳基-8-氨基喹啉衍生物的抗疟活性。
J Med Chem. 2011 Jan 13;54(1):131-42. doi: 10.1021/jm100911f. Epub 2010 Dec 8.
10
P450 enzymes: their structure, reactivity, and selectivity-modeled by QM/MM calculations.细胞色素P450酶：其结构、反应性和选择性——通过量子力学/分子力学计算建模
Chem Rev. 2010 Feb 10;110(2):949-1017. doi: 10.1021/cr900121s.
Zotero 插件