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| Activity Type | Activity Value -log(M) | Mechanism of Action | Activity Reference | Publications (PubMed IDs) |
|---|
Basic Description
| Synonyms | gamma-Linolenic acid | GAMOLENIC ACID | 506-26-3 | (6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid | (Z,Z,Z)-6,9,12-Octadecatrienoic acid | Ligla | (6,9,12)-linolenic acid | gamma Linolenic Acid | 6,9,12-Octadecatrienoic acid, (Z,Z,Z)- | CCRIS 7668 | .gamma.-Linolenic Acid | all-cis |
|---|---|
| Specifications & Purity | Moligand™, 10mM in DMSO |
| Biochemical and Physiological Mechanisms | Unsaturated fatty acid. Putative anticancer agent. Linoleic acid derivative. Induces ROS generation. Inactivates NFκB. May also act via peroxisome proliferator activated receptors (PPARs) by stimulating their phosphorylation and translocation |
| Storage Temp | Store at -80°C |
| Shipped In | Ice chest + Ice pads |
| Grade | Moligand™ |
| Product Description | Usually used as an analytical standard in gas chromatography,and also used in nutritional studies regarding weight regain and as a possible tumor suppression agent. γ-linolenic acid is used in studies on the mechanisms and prevention of oxidation/peroxidation of unsaturated fatty acids. |
Associated Targets(Human)
CASP6 Tchem Caspase-6 (1 Activities)
F2 Tclin Thrombin (11687 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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ESR1 Tclin Estrogen receptor alpha (17718 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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PGR Tclin Progesterone receptor (8562 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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AR Tclin Androgen Receptor (11781 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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VDR Tclin Vitamin D receptor (26531 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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GABRA1 Tclin GABA receptor alpha-1 subunit (399 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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MAOA Tclin Monoamine oxidase A (11911 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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DRD1 Tclin Dopamine D1 receptor (9720 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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ACHE Tclin Acetylcholinesterase (18204 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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SLC6A2 Tclin Norepinephrine transporter (10102 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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SRD5A2 Tclin Steroid 5-alpha-reductase 2 (937 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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SLC6A4 Tclin Serotonin transporter (12625 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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OPRM1 Tclin Mu opioid receptor (19785 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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DRD3 Tclin Dopamine D3 receptor (14368 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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SLC6A3 Tclin Dopamine transporter (10535 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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PPARA Tclin Peroxisome proliferator-activated receptor alpha (9197 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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KCNH2 Tclin HERG (29587 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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PDE3A Tclin Phosphodiesterase 3A (3309 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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TBXA2R Tclin Thromboxane A2 receptor (5717 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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PDE4A Tclin Phosphodiesterase 4A (1943 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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ADORA3 Tchem Adenosine A3 receptor (15931 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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HRH3 Tclin Histamine H3 receptor (10389 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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PLK1 Tchem Serine/threonine-protein kinase PLK1 (28605 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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KDR Tclin Vascular endothelial growth factor receptor 2 (20924 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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FASN Tchem Fatty acid synthase (3390 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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GLP1R Tclin Glucagon-like peptide 1 receptor (111429 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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CASP6 Tchem Caspase-6 (1213 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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PIN1 Tchem Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 (36611 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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HEK293 (82097 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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FFAR1 Tchem Free fatty acid receptor 1 (4763 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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POLK Tbio DNA polymerase kappa (8653 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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POLI Tchem DNA polymerase iota (116820 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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POLH Tchem DNA polymerase eta (21678 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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L3MBTL1 Tchem Lethal(3)malignant brain tumor-like protein 1 (14536 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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PMP22 Tbio Peripheral myelin protein 22 (699 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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USP1 Tchem Ubiquitin carboxyl-terminal hydrolase 1 (22556 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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RGS4 Tchem Regulator of G-protein signaling 4 (13867 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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IDH1 Tclin Isocitrate dehydrogenase [NADP] cytoplasmic (40980 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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F7 Tchem Coagulation factor VII/tissue factor (740 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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GLS Tchem Glutaminase kidney isoform, mitochondrial (16997 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Associated Targets(non-human)
ampC Beta-lactamase AmpC (62480 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Trypsin (394 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Ppard Peroxisome proliferator-activated receptor delta (358 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Hdac6 Histone deacetylase 6 (222 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Plasmodium falciparum (966862 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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GCN5 Histone acetyltransferase GCN5 (89 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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rep Replicase polyprotein 1ab (378 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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TGR Thioredoxin glutathione reductase (28579 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
|---|
Names and Identifiers
| IUPAC Name | (6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid |
|---|---|
| INCHI | InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10,12-13H,2-5,8,11,14-17H2,1H3,(H,19,20)/b7-6-,10-9-,13-12- |
| InChi Key | VZCCETWTMQHEPK-QNEBEIHSSA-N |
| Canonical SMILES | CCCCCC=CCC=CCC=CCCCCC(=O)O |
| Isomeric SMILES | CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O |
| WGK Germany | 3 |
| PubChem CID | 5280933 |
| Molecular Weight | 278.43 |
| Beilstein | 1712253 |
Certificates
Certificate of Analysis(COA)
Enter Lot Number to search for COA:
Chemical and Physical Properties
| Sensitivity | Light & Air & Heat sensitive |
|---|---|
| Refractive Index | 1.48 |
| Flash Point(°F) | 230.0 °F |
| Flash Point(°C) | 110°C |
Safety and Hazards(GHS)
| Pictogram(s) | GHS07 |
|---|---|
| Signal | Warning |
| Hazard Statements | H315:Causes skin irritation H319:Causes serious eye irritation H335:May cause respiratory irritation |
| Precautionary Statements | P261:Avoid breathing dust/fume/gas/mist/vapors/spray. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do - continue rinsing. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of water. P321:Specific treatment (see ... on this label). P405:Store locked up. P501:Dispose of contents/container to ... P264:Wash hands [and …] thoroughly after handling. P271:Use only outdoors or in a well-ventilated area. P304+P340:IF INHALED: Remove person to fresh air and keep comfortable for breathing. P403+P233:Store in a well-ventilated place. Keep container tightly closed. P362+P364:Take off contaminated clothing and wash it before reuse. P264+P265:Wash hands [and …] thoroughly after handling. Do not touch eyes. P337+P317:If eye irritation persists: Get medical help. P332+P317:If skin irritation occurs: Get medical help. P319:Get medical help if you feel unwell. |
| WGK Germany | 3 |
| Merck Index | 5507 |
Related Documents
Citations of This Product
| 1. Hongshuai Lv, Weiping Jia, Li Yang, Peng Dong, Jiaojiao Liu, Si Wang, Xiaohai Li, Jinghua Hu, Ling Zhao, Yikang Shi. (2023) Influence of unsaturated fatty acids on the antitumor activity of polymeric conjugates grafted with cabazitaxel against prostate cancer. BIOMEDICINE & PHARMACOTHERAPY, 169 (115902). [PMID:37989031] [10.1016/j.biopha.2023.115902] |
| 2. Lei He, Qian Hu, Liyang Wei, Xuliyang Ge, Ning Yu, Ying Chen. (2023) Unravelling dynamic changes in non-volatile and volatile metabolites of pulses during soaking: An integrated metabolomics approach. FOOD CHEMISTRY, 422 (136231). [PMID:37141754] [10.1016/j.foodchem.2023.136231] |
| 3. Ge Tang, Kuaqian Deng, Panyang Li, Jiali Huang, Fanglin Dao, Hao Jiang, Jing Wang, Jianfang Jiang. (2023) One-pot method of recyclable lipase-nanocatalyst based on chitosan magnetic nanomaterial for ethyl levulinate synthesis. COMPOSITES SCIENCE AND TECHNOLOGY, 236 (110002). [PMID:] [10.1016/j.compscitech.2023.110002] |
| 4. Yang-Yang Li, Xin-Xin Ma, Xin-Yan Song, Lin-Lin Ma, Yu-Ying Li, Xin Meng, Yu-Jie Chen, Ke-Xin Xu, Ali Akbar Moosavi-Movahedi, Bao-Lin Xiao, Jun Hong. (2023) Glucose Biosensor Based on Glucose Oxidase Immobilized on BSA Cross-Linked Nanocomposite Modified Glassy Carbon Electrode. SENSORS, 23 (6): (3209). [PMID:36991919] [10.3390/s23063209] |
References
| 1. Hongshuai Lv, Weiping Jia, Li Yang, Peng Dong, Jiaojiao Liu, Si Wang, Xiaohai Li, Jinghua Hu, Ling Zhao, Yikang Shi. (2023) Influence of unsaturated fatty acids on the antitumor activity of polymeric conjugates grafted with cabazitaxel against prostate cancer. BIOMEDICINE & PHARMACOTHERAPY, 169 (115902). [PMID:37989031] [10.1016/j.biopha.2023.115902] |
| 2. Lei He, Qian Hu, Liyang Wei, Xuliyang Ge, Ning Yu, Ying Chen. (2023) Unravelling dynamic changes in non-volatile and volatile metabolites of pulses during soaking: An integrated metabolomics approach. FOOD CHEMISTRY, 422 (136231). [PMID:37141754] [10.1016/j.foodchem.2023.136231] |
| 3. Ge Tang, Kuaqian Deng, Panyang Li, Jiali Huang, Fanglin Dao, Hao Jiang, Jing Wang, Jianfang Jiang. (2023) One-pot method of recyclable lipase-nanocatalyst based on chitosan magnetic nanomaterial for ethyl levulinate synthesis. COMPOSITES SCIENCE AND TECHNOLOGY, 236 (110002). [PMID:] [10.1016/j.compscitech.2023.110002] |
| 4. Yang-Yang Li, Xin-Xin Ma, Xin-Yan Song, Lin-Lin Ma, Yu-Ying Li, Xin Meng, Yu-Jie Chen, Ke-Xin Xu, Ali Akbar Moosavi-Movahedi, Bao-Lin Xiao, Jun Hong. (2023) Glucose Biosensor Based on Glucose Oxidase Immobilized on BSA Cross-Linked Nanocomposite Modified Glassy Carbon Electrode. SENSORS, 23 (6): (3209). [PMID:36991919] [10.3390/s23063209] |