Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-05-22 14:17:53 UTC |
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Update Date | 2023-02-21 17:16:23 UTC |
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HMDB ID | HMDB0002428 |
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Secondary Accession Numbers | - HMDB0061917
- HMDB02428
- HMDB61917
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Metabolite Identification |
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Common Name | Terephthalic acid |
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Description | Terephthalic acid is a benzenedicarboxylic acid carrying carboxy groups at positions 1 and 4. One of three possible isomers of benzenedicarboxylic acid, the others being phthalic and isophthalic acids. It is a conjugate acid of a terephthalate(1-). Terephthalic acid is one isomer of the three phthalic acids. It finds important use as a commodity chemical, principally as a starting compound for the manufacture of polyester (specifically PET), used in clothing and to make plastic bottles. It is also known as 1,4-benzenedicarboxylic acid, and it has the chemical formula C6H4(COOH)2. |
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Structure | OC(=O)C1=CC=C(C=C1)C(O)=O InChI=1S/C8H6O4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h1-4H,(H,9,10)(H,11,12) |
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Synonyms | Value | Source |
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1,4-Benzenedicarboxylic acid | ChEBI | p-Benzenedicarboxylic acid | ChEBI | Para-benzenedicarboxylic acid | ChEBI | TPA | ChEBI | 1,4-Benzenedicarboxylate | Generator | p-Benzenedicarboxylate | Generator | Para-benzenedicarboxylate | Generator | Terephthalate | Generator | Benzene-P-dicarboxylate | HMDB | Benzene-P-dicarboxylic acid | HMDB | Kyselina terftalova | HMDB | P-Dicarboxybenzene | HMDB | P-Phthalate | HMDB | P-Phthalic acid | HMDB | P-Phthelate | HMDB | P-Phthelic acid | HMDB | Disodium terephthalate | MeSH, HMDB | Terephthalic acid | KEGG |
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Chemical Formula | C8H6O4 |
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Average Molecular Weight | 166.1308 |
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Monoisotopic Molecular Weight | 166.02660868 |
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IUPAC Name | benzene-1,4-dicarboxylic acid |
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Traditional Name | terephthalic acid |
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CAS Registry Number | 100-21-0 |
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SMILES | OC(=O)C1=CC=C(C=C1)C(O)=O |
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InChI Identifier | InChI=1S/C8H6O4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h1-4H,(H,9,10)(H,11,12) |
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InChI Key | KKEYFWRCBNTPAC-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as p-phthalic acid and derivatives. P-phthalic acid and derivatives are compounds containing a benzene ring bearing a carboxylic acid group at ring carbon atoms 1 and 4. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Benzoic acids and derivatives |
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Direct Parent | P-phthalic acid and derivatives |
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Alternative Parents | |
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Substituents | - Para_phthalic_acid
- Benzoic acid
- Benzoyl
- Dicarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | Not Available |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | > 300 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.015 mg/mL at 20 °C | Not Available | LogP | 2.00 | HANSCH,C ET AL. (1995) |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - Terephthalic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0udj-1960000000-c2ce285b39dcfaade068 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Terephthalic acid EI-B (Non-derivatized) | splash10-014j-9500000000-6b6ec61e945c382eed89 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Terephthalic acid EI-B (Non-derivatized) | splash10-014j-6900000000-1a7e017001fe0602a248 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Terephthalic acid EI-B (Non-derivatized) | splash10-014j-4900000000-95e39c2780c93f2f98fd | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Terephthalic acid GC-EI-TOF (Non-derivatized) | splash10-0udj-1960000000-c2ce285b39dcfaade068 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Terephthalic acid GC-EI-TOF (Non-derivatized) | splash10-0udj-1960000000-27e0381620f64e37fcad | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Terephthalic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-014j-1900000000-a84aff968bc81936616c | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Terephthalic acid GC-MS (2 TMS) - 70eV, Positive | splash10-00di-8290000000-755c4a3b1fe10891e0bc | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Terephthalic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Terephthalic acid Quattro_QQQ 10V, Negative-QTOF (Annotated) | splash10-00di-0900000000-95fdf5f4fdee61197dc8 | 2012-07-25 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Terephthalic acid Quattro_QQQ 25V, Negative-QTOF (Annotated) | splash10-00b9-9800000000-2b52539a11193ccec082 | 2012-07-25 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Terephthalic acid Quattro_QQQ 40V, Negative-QTOF (Annotated) | splash10-00b9-8900000000-197587f1e6a9e594c5b3 | 2012-07-25 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Terephthalic acid EI-B (JEOL JMS-AX-505-H) , Positive-QTOF | splash10-014j-9500000000-aafffbb19047f4caf673 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Terephthalic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF | splash10-014i-0900000000-b445c3bf5a9a7a5579fc | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Terephthalic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF | splash10-00di-0900000000-63c35cbaa3dcd73735c8 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Terephthalic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF | splash10-00di-4900000000-2e7d3b96b81c41872945 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Terephthalic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF | splash10-004i-9300000000-2d9c49fdd3573a453a1b | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Terephthalic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF | splash10-00fr-9000000000-999fd340fed30a63e4dd | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Terephthalic acid LC-ESI-QQ , negative-QTOF | splash10-014i-0900000000-b445c3bf5a9a7a5579fc | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Terephthalic acid LC-ESI-QQ , negative-QTOF | splash10-00di-0900000000-63c35cbaa3dcd73735c8 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Terephthalic acid LC-ESI-QQ , negative-QTOF | splash10-00di-4900000000-2e7d3b96b81c41872945 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Terephthalic acid LC-ESI-QQ , negative-QTOF | splash10-004i-9300000000-df1f4a76d59c66d5070d | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Terephthalic acid LC-ESI-QQ , negative-QTOF | splash10-00fr-9000000000-999fd340fed30a63e4dd | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Terephthalic acid 75V, Negative-QTOF | splash10-00di-0900000000-b7eddea80c1efd3740d5 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Terephthalic acid 90V, Negative-QTOF | splash10-00di-4900000000-395fdb86c134d67a782b | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Terephthalic acid 45V, Negative-QTOF | splash10-00di-0900000000-8eabec3ef384835097ef | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Terephthalic acid 60V, Negative-QTOF | splash10-00di-0900000000-a28fdef9c1c00d45c3ff | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Terephthalic acid 30V, Negative-QTOF | splash10-00di-0900000000-17c7a2e06ddf58f100a3 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Terephthalic acid 10V, Positive-QTOF | splash10-014j-0900000000-384b938e005844d386b8 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Terephthalic acid 20V, Positive-QTOF | splash10-0002-0900000000-736a9cc29426a85f2dbc | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Terephthalic acid 40V, Positive-QTOF | splash10-0a4j-4900000000-be05d9e5afe70d40b269 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Terephthalic acid 10V, Negative-QTOF | splash10-014i-0900000000-eaf8e1fadaf0331df52f | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Terephthalic acid 20V, Negative-QTOF | splash10-00xr-2900000000-69d77e7980f3f93873c2 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Terephthalic acid 40V, Negative-QTOF | splash10-00b9-9700000000-23275ad46308b76fb7c9 | 2017-09-01 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | 2012-12-05 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Blood | Expected but not Quantified | Not Quantified | Not Available | Not Available | Normal | | details | Saliva | Detected and Quantified | 5.01 +/- 1.19 uM | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected and Quantified | 0.0785 +/- 0.0591 uM | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected and Quantified | 3.72 +/- 1.60 uM | Adult (>18 years old) | Female | Normal | | details | Saliva | Detected and Quantified | 0.546 +/- 0.381 uM | Adult (>18 years old) | Female | Normal | | details | Saliva | Detected and Quantified | 3.94 +/- 1.61 uM | Adult (>18 years old) | Female | Normal | | details | Saliva | Detected and Quantified | 3.95 +/- 1.89 uM | Adult (>18 years old) | Female | Normal | | details | Urine | Detected and Quantified | 75.3 umol/mmol creatinine | Newborn (0-30 days old) | Both | Normal | | details | Urine | Detected and Quantified | 30.5 umol/mmol creatinine | Infant (0-1 year old) | Both | Normal | | details |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB023000 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 7208 |
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KEGG Compound ID | C06337 |
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BioCyc ID | TEREPHTHALATE |
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BiGG ID | Not Available |
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Wikipedia Link | Terephthalic_acid |
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METLIN ID | 6676 |
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PubChem Compound | 7489 |
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PDB ID | Not Available |
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ChEBI ID | 15702 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | rw1285651 |
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References |
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Synthesis Reference | Emerson, Wm. S.; Shafer, Theodore C.; Heimsch, Robert A. A study of the conversion of p-toluic acid to terephthalic acid with high-pressure oxygen. Journal of Organic Chemistry (1951), 16 1839-45. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
- Iwasaki Y, Yamasaki A, Ishihara K: Platelet compatible blood filtration fabrics using a phosphorylcholine polymer having high surface mobility. Biomaterials. 2003 Sep;24(20):3599-604. [PubMed:12809789 ]
- Bot I, von der Thusen JH, Donners MM, Lucas A, Fekkes ML, de Jager SC, Kuiper J, Daemen MJ, van Berkel TJ, Heeneman S, Biessen EA: Serine protease inhibitor Serp-1 strongly impairs atherosclerotic lesion formation and induces a stable plaque phenotype in ApoE-/-mice. Circ Res. 2003 Sep 5;93(5):464-71. Epub 2003 Aug 14. [PubMed:12919945 ]
- Yepes M, Sandkvist M, Moore EG, Bugge TH, Strickland DK, Lawrence DA: Tissue-type plasminogen activator induces opening of the blood-brain barrier via the LDL receptor-related protein. J Clin Invest. 2003 Nov;112(10):1533-40. [PubMed:14617754 ]
- Kawakami O, Miyamoto S, Hatano T, Yamada K, Hashimoto N, Tabata Y: Accelerated embolization healing of aneurysms by polyethylene terephthalate coils seeded with autologous fibroblasts. Neurosurgery. 2005 May;56(5):1075-81; discussion 1075-81. [PubMed:15854257 ]
- Kim YH, Park JH, Hong SH, Koh JY: Nonproteolytic neuroprotection by human recombinant tissue plasminogen activator. Science. 1999 Apr 23;284(5414):647-50. [PubMed:10213688 ]
- Patel JD, Iwasaki Y, Ishihara K, Anderson JM: Phospholipid polymer surfaces reduce bacteria and leukocyte adhesion under dynamic flow conditions. J Biomed Mater Res A. 2005 Jun 1;73(3):359-66. [PubMed:15800952 ]
- Tremaine LM, Quebbemann AJ: The renal handling of terephthalic acid. Toxicol Appl Pharmacol. 1985 Jan;77(1):165-74. [PubMed:3966238 ]
- Klomp AJ, Engbers GH, Mol J, Terlingen JG, Feijen J: Adsorption of proteins from plasma at polyester non-wovens. Biomaterials. 1999 Jul;20(13):1203-11. [PubMed:10395389 ]
- Roald HE, Barstad RM, Bakken IJ, Roald B, Lyberg T, Sakariassen KS: Initial interactions of platelets and plasma proteins in flowing non-anticoagulated human blood with the artificial surfaces Dacron and PTFE. Blood Coagul Fibrinolysis. 1994 Jun;5(3):355-63. [PubMed:8075307 ]
- Gappa-Fahlenkamp H, Lewis RS: Improved hemocompatibility of poly(ethylene terephthalate) modified with various thiol-containing groups. Biomaterials. 2005 Jun;26(17):3479-85. [PubMed:15621237 ]
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