Labetalol (BioDeep_00000001485)

 

Secondary id: BioDeep_00000398790

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


3-Carboxamido-4-hydroxy-alpha-((1-methyl-3-phenylpropylamino)methyl)benzyl alcohol

化学式: C19H24N2O3 (328.1787)
中文名称: 拉贝洛尔
谱图信息: 最多检出来源 Viridiplantae(plant) 18.2%

分子结构信息

SMILES: CC(CCC1=CC=CC=C1)NCC(C2=CC(=C(C=C2)O)C(=O)N)O
InChI: InChI=1S/C19H24N2O3/c1-13(7-8-14-5-3-2-4-6-14)21-12-18(23)15-9-10-17(22)16(11-15)19(20)24/h2-6,9-11,13,18,21-23H,7-8,12H2,1H3,(H2,20,24)

描述信息

Labetalol is only found in individuals that have used or taken this drug. It is a blocker of both alpha- and beta-adrenergic receptors that is used as an antihypertensive (PubChem). Labetalol HCl combines both selective, competitive, alpha-1-adrenergic blocking and nonselective, competitive, beta-adrenergic blocking activity in a single substance. In man, the ratios of alpha- to beta- blockade have been estimated to be approximately 1:3 and 1:7 following oral and intravenous (IV) administration, respectively. The principal physiologic action of labetalol is to competitively block adrenergic stimulation of β-receptors within the myocardium (β1-receptors) and within bronchial and vascular smooth muscle (β2-receptors), and α1-receptors within vascular smooth muscle. This causes a decrease in systemic arterial blood pressure and systemic vascular resistance without a substantial reduction in resting heart rate, cardiac output, or stroke volume, apparently because of its combined α- and β-adrenergic blocking activity.
CONFIDENCE standard compound; INTERNAL_ID 220; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 7134; ORIGINAL_PRECURSOR_SCAN_NO 7131
CONFIDENCE standard compound; INTERNAL_ID 220; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 7100; ORIGINAL_PRECURSOR_SCAN_NO 7098
CONFIDENCE standard compound; INTERNAL_ID 220; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 7094; ORIGINAL_PRECURSOR_SCAN_NO 7091
CONFIDENCE standard compound; INTERNAL_ID 220; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 7132; ORIGINAL_PRECURSOR_SCAN_NO 7130
CONFIDENCE standard compound; INTERNAL_ID 220; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3398; ORIGINAL_PRECURSOR_SCAN_NO 3397
CONFIDENCE standard compound; INTERNAL_ID 220; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3392; ORIGINAL_PRECURSOR_SCAN_NO 3391
CONFIDENCE standard compound; INTERNAL_ID 220; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3400; ORIGINAL_PRECURSOR_SCAN_NO 3399
CONFIDENCE standard compound; INTERNAL_ID 220; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 7150; ORIGINAL_PRECURSOR_SCAN_NO 7149
CONFIDENCE standard compound; INTERNAL_ID 220; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3395; ORIGINAL_PRECURSOR_SCAN_NO 3393
CONFIDENCE standard compound; INTERNAL_ID 220; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3466; ORIGINAL_PRECURSOR_SCAN_NO 3465
CONFIDENCE standard compound; INTERNAL_ID 220; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3405; ORIGINAL_PRECURSOR_SCAN_NO 3404
CONFIDENCE standard compound; INTERNAL_ID 220; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 7142; ORIGINAL_PRECURSOR_SCAN_NO 7140
C - Cardiovascular system > C07 - Beta blocking agents > C07A - Beta blocking agents > C07AG - Alpha and beta blocking agents
C78272 - Agent Affecting Nervous System > C29747 - Adrenergic Agent > C72900 - Adrenergic Antagonist
D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D013566 - Sympathomimetics
D018377 - Neurotransmitter Agents > D018663 - Adrenergic Agents > D018674 - Adrenergic Antagonists
D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents
CONFIDENCE standard compound; INTERNAL_ID 2757
CONFIDENCE standard compound; INTERNAL_ID 8188
Labetalol (AH5158) is an orally active selective α1- and non-selective β-adrenergic receptors competitive antagonist. Labetalol, an anti-hypertensive agent, can be used for the research of cardiovascular disease, such as hypertension in pregnancy[1][2][3].

同义名列表

36 个代谢物同义名

3-Carboxamido-4-hydroxy-alpha-((1-methyl-3-phenylpropylamino)methyl)benzyl alcohol; 3-Carboxamido-4-hydroxy-α-((1-methyl-3-phenylpropylamino)methyl)benzyl alcohol; 3-Carboxamido-4-hydroxy-a-((1-methyl-3-phenylpropylamino)methyl)benzyl alcohol; 2-hydroxy-5-{1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl}benzamide; 5-(1-Hydroxy-2-(1-methyl-3-phenylpropylamino)ethyl)salicylamide; GlaxoSmithKline brand OF labetalol hydrochloride; glaxo Wellcome brand OF labetalol hydrochloride; Alphapharm brand OF labetalol hydrochloride; Celltech brand OF labetalol hydrochloride; Schering brand OF labetalol hydrochloride; Apotex brand OF labetalol hydrochloride; Leiras brand OF labetalol hydrochloride; Shire brand OF labetalol hydrochloride; Sigma brand OF labetalol hydrochloride; faro Brand OF labetalol hydrochloride; Kern brand OF labetalol hydrochloride; Hydrochloride, labetalol; Labetalol, (R,R)-isomer; Labetalol hydrochloride; apo-Labetalol; R,R-Labetalol; apo Labetalol; R,R Labetalol; ApoLabetalol; Labetalolum; Normodyne; labetalol; Labetolol; DILEVALOL; Kabetalol; Presolol; Trandate; Albetol; AH5158; Sch-15719W (free base); Labetalol



数据库引用编号

41 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

亚细胞结构定位 关联基因列表
Cytoplasm 8 ABCB1, ACE, ADRA1A, ALB, AXIN2, CYP2C19, CYP2D6, VEGFA
Endoplasmic reticulum membrane 4 CYP2C19, CYP2D6, UGT1A1, UGT2B7
Nucleus 4 ADRA1A, ALB, AXIN2, VEGFA
cytosol 3 ADRA1A, ALB, AXIN2
centrosome 2 ALB, AXIN2
nucleoplasm 1 ADRA1A
Cell membrane 5 ABCB1, ACE, ADRA1A, ADRB3, AGTR2
Multi-pass membrane protein 5 ABCB1, ADRA1A, ADRB3, AGTR2, CACNA1I
cell surface 2 ABCB1, VEGFA
Golgi apparatus 2 ALB, VEGFA
Golgi membrane 1 INS
Lysosome 1 ACE
endosome 1 ACE
plasma membrane 12 ABCB1, ACE, ADRA1A, ADRB3, AGTR2, AXIN2, CACNA1I, CYP2C19, EDNRA, GCG, REN, UGT1A1
Membrane 9 ABCB1, ACE, CACNA1I, CYP2D6, PGF, REN, UGT1A1, UGT2B7, VEGFA
apical plasma membrane 1 ABCB1
caveola 1 ADRA1A
extracellular exosome 3 ABCB1, ACE, ALB
endoplasmic reticulum 4 ALB, CYP2D6, UGT1A1, VEGFA
extracellular space 8 ACE, ALB, GCG, IL6, INS, PGF, REN, VEGFA
perinuclear region of cytoplasm 1 UGT1A1
adherens junction 1 VEGFA
mitochondrion 1 CYP2D6
protein-containing complex 1 ALB
intracellular membrane-bounded organelle 3 ADRA1A, CYP2C19, CYP2D6
Microsome membrane 1 CYP2D6
Single-pass type I membrane protein 1 ACE
Secreted 8 ACE, ALB, GCG, IL6, INS, PGF, REN, VEGFA
extracellular region 8 ACE, ALB, GCG, IL6, INS, PGF, REN, VEGFA
Single-pass membrane protein 3 CYP2D6, UGT1A1, UGT2B7
anchoring junction 1 ALB
Nucleus membrane 1 ADRA1A
nuclear membrane 1 ADRA1A
external side of plasma membrane 1 ACE
Secreted, extracellular space, extracellular matrix 1 VEGFA
beta-catenin destruction complex 1 AXIN2
apical part of cell 1 REN
Apical cell membrane 1 ABCB1
Cytoplasm, perinuclear region 1 UGT1A1
extracellular matrix 1 VEGFA
secretory granule 1 VEGFA
receptor complex 1 ADRB3
ciliary basal body 1 ALB
centriole 1 ALB
brush border membrane 1 ACE
spindle pole 1 ALB
blood microparticle 1 ALB
sperm midpiece 1 ACE
endosome lumen 1 INS
Membrane, caveola 1 ADRA1A
basal plasma membrane 1 ACE
secretory granule lumen 2 GCG, INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 4 ALB, GCG, IL6, INS
platelet alpha granule lumen 2 ALB, VEGFA
voltage-gated calcium channel complex 1 CACNA1I
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
external side of apical plasma membrane 1 ABCB1
[Glucagon-like peptide 1]: Secreted 1 GCG
interleukin-6 receptor complex 1 IL6
endoplasmic reticulum chaperone complex 1 UGT1A1
[Angiotensin-converting enzyme, soluble form]: Secreted 1 ACE
[Isoform Testis-specific]: Cell membrane 1 ACE
[N-VEGF]: Cytoplasm 1 VEGFA
[VEGFA]: Secreted 1 VEGFA
[Isoform L-VEGF189]: Endoplasmic reticulum 1 VEGFA
[Isoform VEGF121]: Secreted 1 VEGFA
[Isoform VEGF165]: Secreted 1 VEGFA
VEGF-A complex 1 VEGFA
cytochrome complex 1 UGT1A1
ciliary transition fiber 1 ALB


文献列表

  • Ting Wang, Ruoan Jiang, Yingsha Yao, Ting Xu, Na Li. Anti-hypertensive therapy for preeclampsia: a network meta-analysis and systematic review. Hypertension in pregnancy. 2024 Dec; 43(1):2329068. doi: 10.1080/10641955.2024.2329068. [PMID: 38488570]
  • Piya Chaemsaithong, Mohitosh Biswas, Waranyu Lertrut, Puntabut Warintaksa, Tuangsit Wataganara, Liona Cy Poon, Chonlaphat Sukasem. Pharmacogenomics of Preeclampsia therapies: Current evidence and future challenges for clinical implementation. Best practice & research. Clinical obstetrics & gynaecology. 2024 Feb; 92(?):102437. doi: 10.1016/j.bpobgyn.2023.102437. [PMID: 38103508]
  • Hao-Cho Ou, Jou-Fang Deng, Chen-Chang Yang, Chin-Sheng Lin, Yan-Chiao Mao, Shih-Hung Tsai, Cheng-Hsuan Ho. A successful experience using labetalol and hemodialysis to treat near-fatal caffeine poisoning: A case report with toxicodynamics. The American journal of emergency medicine. 2022 05; 55(?):224.e1-224.e4. doi: 10.1016/j.ajem.2021.11.049. [PMID: 34922795]
  • Onyinye Ohamadike, Stephanie L Lim, Anne Siegel, Gregory Zemtsov, Jeffrey A Kuller, Sarah Dotters-Katz. Hypertensive Disorders of Pregnancy: Common Clinical Conundrums. Obstetrical & gynecological survey. 2022 Apr; 77(4):234-244. doi: 10.1097/ogx.0000000000000996. [PMID: 35395093]
  • Brian Pearlman, Bereket T Lodebo. Renin secreting tumour: a rare cause of secondary hypertension. Lancet (London, England). 2021 09; 398(10305):1074. doi: 10.1016/s0140-6736(21)01696-2. [PMID: 34537092]
  • Hui Zhou, John J Sim, Jiaxiao Shi, Sally F Shaw, Ming-Sum Lee, Jonathan R Neyer, Csaba P Kovesdy, Kamyar Kalantar-Zadeh, Steven J Jacobsen. β-Blocker Use and Risk of Mortality in Heart Failure Patients Initiating Maintenance Dialysis. American journal of kidney diseases : the official journal of the National Kidney Foundation. 2021 05; 77(5):704-712. doi: 10.1053/j.ajkd.2020.07.023. [PMID: 33010357]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Robert H Friesen. In response. Journal of cardiothoracic and vascular anesthesia. 2020 12; 34(12):3480-3481. doi: 10.1053/j.jvca.2020.07.001. [PMID: 32753324]
  • Xiuling Zhu. Labetalol Infusion Controls Paradoxical Hypertension and Decreases Plasma Renin Activity Following Repair of Coarctation of the Aorta in Children. Journal of cardiothoracic and vascular anesthesia. 2020 12; 34(12):3480. doi: 10.1053/j.jvca.2020.07.014. [PMID: 32741614]
  • Gareth A Charlton, David R Ladd, Richard M Friesen, Robert H Friesen. Labetalol Infusion Attenuates Paradoxical Hypertension and Decreases Plasma Renin Activity After Repair of Coarctation of the Aorta in Children. Journal of cardiothoracic and vascular anesthesia. 2020 Dec; 34(12):3348-3351. doi: 10.1053/j.jvca.2020.05.027. [PMID: 32593586]
  • Fotini Tsofliou, Yannis P Pitsiladis, Jose Lara, Marios Hadjicharalambous, Ian A Macdonald, Mike A Wallace, Mike E J Lean. The effects of moderate alterations in adrenergic activity on acute appetite regulation in obese women: A randomised crossover trial. Nutrition and health. 2020 Dec; 26(4):311-322. doi: 10.1177/0260106020942117. [PMID: 32729763]
  • Pattraporn Chera-Aree, Pimrapat Tengtrakulcharoen, Jarunee Leetheeragul, Urai Sampaojarean, Supitchaya Surasereewong, Tuangsit Wataganara. Clinical Experiences of Intravenous Hydralazine and Labetalol for Acute Treatment of Severe Hypertension in Pregnant Thai Women. Journal of clinical pharmacology. 2020 12; 60(12):1662-1670. doi: 10.1002/jcph.1685. [PMID: 32598488]
  • Kelly A Machovec, Warwick A Ames. Recycle: Do It for the Kids. Journal of cardiothoracic and vascular anesthesia. 2020 12; 34(12):3352-3353. doi: 10.1053/j.jvca.2020.07.030. [PMID: 32753327]
  • Carli Weyers, Laura M K Dingle, Brendan S Wilhelmi, Adrienne L Edkins, Clinton G L Veale. Use of a non-hepatic cell line highlights limitations associated with cell-based assessment of metabolically induced toxicity. Drug and chemical toxicology. 2020 Nov; 43(6):656-662. doi: 10.1080/01480545.2019.1585869. [PMID: 30880486]
  • Zeid A ALOthman, Khalid M Alsheetan, Hassan Y Aboul-Enein, Imran Ali. Applications of shun shell column and nanocomposite sorbent for analysis of eleven anti-hypertensive in human plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2020 Jun; 1146(?):122125. doi: 10.1016/j.jchromb.2020.122125. [PMID: 32371329]
  • Y Wu, D-J Wang, Y Zhang, Y-X Zhang, R Zhang. Regulation of magnesium sulfate combined with nifedipine and labetalol on disease-related molecules in serum and placenta in the treatment of preeclampsia. European review for medical and pharmacological sciences. 2020 05; 24(9):5062-5070. doi: 10.26355/eurrev_202005_21199. [PMID: 32432770]
  • Marwa Zayed, Heba Nassar, Ahmed Hasanin, Amany H Saleh, Passaint Hassan, Dalia Saad, Sahar Mahmoud, Ghada Abo Bakr, Eman Fouad, Norhan Saleh, Maha Ismail, Hani El-Hadi. Effects of nitroglycerin versus labetalol on peripheral perfusion during deliberate hypotension for sinus endoscopic surgery: a randomized, controlled, double-blinded trial. BMC anesthesiology. 2020 04; 20(1):85. doi: 10.1186/s12871-020-01006-w. [PMID: 32303182]
  • Pradeep Singh Rawat, Punna Rao Ravi, Laxman Kaswan, Rajeev Singh Raghuvanshi. Development and validation of a bio-analytical method for simultaneous quantification of nebivolol and labetalol in aqueous humor and plasma using LC-MS/MS and its application to ocular pharmacokinetic studies. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2020 Jan; 1136(?):121908. doi: 10.1016/j.jchromb.2019.121908. [PMID: 31862675]
  • Aleksandra Walasek, Sounak Gupta, Samson Fine, Paul Russo. Juxtaglomerular Cell Tumor: A Rare, Curable Cause of Hypertension in a Young Patient. Urology. 2019 Dec; 134(?):42-44. doi: 10.1016/j.urology.2019.06.009. [PMID: 31233811]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Nikhil Agrawal, Nishita Tripathi, Neil Roy, Sreedhar Adapa, Venu Madhav Konala, Hemant Dhingra, Wilbert S Aronow. Labetalol or Amphetamine: A Case of Mistaken Identity With Clinical Consequence. American journal of therapeutics. 2019 Nov; 26(6):e748-e750. doi: 10.1097/mjt.0000000000000901. [PMID: 30562170]
  • Louise M Webster, Kate Reed, Jenny E Myers, Angela Burns, Pankaj Gupta, Prashnath Patel, Cornelia Wiesender, Paul T Seed, Catherine Nelson-Piercy, Lucy C Chappell. Quantifying adherence to antihypertensive medication for chronic hypertension during pregnancy. Pregnancy hypertension. 2019 Jul; 17(?):12-14. doi: 10.1016/j.preghy.2019.05.004. [PMID: 31487627]
  • Michelle C Starr, Joseph T Flynn. Neonatal hypertension: cases, causes, and clinical approach. Pediatric nephrology (Berlin, Germany). 2019 05; 34(5):787-799. doi: 10.1007/s00467-018-3977-4. [PMID: 29808264]
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  • Seth J Lichtenstein, Michael J Herring, Pravir V Baxi, Richard I Abrams, Stephen M Korbet. Without Warning: Scleroderma Renal Crisis. The American journal of medicine. 2019 02; 132(2):175-178. doi: 10.1016/j.amjmed.2018.09.024. [PMID: 30290189]
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  • Pablo Zambrano, Mario Suwalsky, Malgorzata Jemiola-Rzeminska, Kazimierz Strzalka. α1-and β-adrenergic antagonist labetalol induces morphological changes in human erythrocytes. Biochemical and biophysical research communications. 2018 09; 503(1):209-214. doi: 10.1016/j.bbrc.2018.06.004. [PMID: 29879427]
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