Tetrac (BioDeep_00000184255)

 

Secondary id: BioDeep_00000271376

human metabolite PANOMIX_OTCML-2023 blood metabolite


代谢物信息卡片


2-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]acetic acid

化学式: C14H8I4O4 (747.6602)
中文名称: 3,3,5,5-四碘甲腺-乙酸
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 100%

分子结构信息

SMILES: C1=C(C=C(C(=C1I)OC2=CC(=C(C(=C2)I)O)I)I)CC(=O)O
InChI: InChI=1S/C14H8I4O4/c15-8-4-7(5-9(16)13(8)21)22-14-10(17)1-6(2-11(14)18)3-12(19)20/h1-2,4-5,21H,3H2,(H,19,20)

描述信息

D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones
Tetrac (Tetraiodothyroacetic acid), a derivative of L-thyroxine (T4), is a thyrointegrin receptor antagonist. Tetrac blocks the actions of T4 and 3,5,3'-triiodo-L-thyronine (T3) at the cell surface receptor for thyroid hormone on integrin αvβ3. Tetra has anti-angiogenic and anti-tumor activities[1][2].

同义名列表

12 个代谢物同义名

2-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]acetic acid; 3,5-Diiodo-4-(4-hydroxy-3,5-diiodophenoxy)benzeneacetic acid; 3,5-Diiodo-4-(4-hydroxy-3,5-diiodophenoxy)benzeneacetate; Tetraiodothyroacetic acid, monosodium salt; Acide 3,5,3,5-tetraiodothyroacetique; 3,5,3,5-Tetraiodothyroacetic acid; 3,3,5,5-Tetraiodothyroacetate; Tetraiodothyroacetic acid; Tetraiodothyroacetate; Tetrac; TA(4); 3,3',5,5'-Tetraiodothyroacetic acid



数据库引用编号

10 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


文献列表

  • Kavitha Godugu, Shaker A Mousa, Gennadi V Glinsky, Hung-Yun Lin, Paul J Davis. In Vivo Clearance of Apoptotic Debris From Tumor Xenografts Exposed to Chemically Modified Tetrac: Is There a Role for Thyroid Hormone Analogues in Efferocytosis?. Frontiers in endocrinology. 2022; 13(?):745327. doi: 10.3389/fendo.2022.745327. [PMID: 35311239]
  • Kavitha Godugu, Thangirala Sudha, Paul J Davis, Shaker A Mousa. Nano Diaminopropane tetrac and integrin αvβ3 expression in different cancer types: Anti-cancer efficacy and Safety. Cancer treatment and research communications. 2021; 28(?):100395. doi: 10.1016/j.ctarc.2021.100395. [PMID: 34034044]
  • Ozlem Ozen Karakus, Kavitha Godugu, Mehdi Rajabi, Shaker A Mousa. Dual Targeting of Norepinephrine Transporter (NET) Function and Thyrointegrin αvβ3 Receptors in the Treatment of Neuroblastoma. Journal of medicinal chemistry. 2020 07; 63(14):7653-7662. doi: 10.1021/acs.jmedchem.0c00537. [PMID: 32571015]
  • Lucas Solla Mathias, Bruna Moretto Rodrigues, Bianca Mariani Gonçalves, Fernanda Cristina Fontes Moretto, Regiane Marques Castro Olimpio, Igor Deprá, Maria Teresa De Sibio, Helena Paim Tilli, Célia Regina Nogueira, Miriane de Oliveira. Triiodothyronine activated extranuclear pathways upregulate adiponectin and leptin in murine adipocytes. Molecular and cellular endocrinology. 2020 03; 503(?):110690. doi: 10.1016/j.mce.2019.110690. [PMID: 31874199]
  • Weikun Li, Murat Yalcin, Dhruba J Bharali, Qishan Lin, Kavitha Godugu, Kazutoshi Fujioka, Kelly A Keating, Shaker A Mousa. Pharmacokinetics, Biodistribution, and Anti-Angiogenesis Efficacy of Diamino Propane Tetraiodothyroacetic Acid-conjugated Biodegradable Polymeric Nanoparticle. Scientific reports. 2019 06; 9(1):9006. doi: 10.1038/s41598-019-44979-6. [PMID: 31227723]
  • Susanne Neumann, Christine C Krieger, Marvin C Gershengorn. Letter to the Editor: 'Elevated Serum Tetrac in Graves Disease: Potential Pathogenic Role in Thyroid-Associated Ophthalmopathy'. The Journal of clinical endocrinology and metabolism. 2019 04; 104(4):1075-1076. doi: 10.1210/jc.2018-02103. [PMID: 30561709]
  • John T Leith, Aleck Hercbergs, Susan Kenney, Shaker A Mousa, Paul J Davis. Activation of tumor cell integrin αvβ3 by radiation and reversal of activation by chemically modified tetraiodothyroacetic acid (tetrac). Endocrine research. 2018 Nov; 43(4):215-219. doi: 10.1080/07435800.2018.1456550. [PMID: 29611723]
  • Keren Cohen, Uri Abadi, Aleck Hercbergs, Paul J Davis, Martin Ellis, Osnat Ashur-Fabian. The induction of myeloma cell death and DNA damage by tetrac, a thyroid hormone derivative. Endocrine-related cancer. 2018 01; 25(1):21-34. doi: 10.1530/erc-17-0246. [PMID: 29018054]
  • Roshini Fernando, Ekaterina Placzek, Edmund A Reese, Andrew T Placzek, Samantha Schwartz, Aaron Trierweiler, Leslie M Niziol, Nupur Raychaudhuri, Stephen Atkins, Thomas S Scanlan, Terry J Smith. Elevated Serum Tetrac in Graves Disease: Potential Pathogenic Role in Thyroid-Associated Ophthalmopathy. The Journal of clinical endocrinology and metabolism. 2017 03; 102(3):776-785. doi: 10.1210/jc.2016-2762. [PMID: 27768856]
  • Thangirala Sudha, Dhruba J Bharali, Murat Yalcin, Noureldien He Darwish, Melis Debreli Coskun, Kelly A Keating, Hung-Yun Lin, Paul J Davis, Shaker A Mousa. Targeted delivery of paclitaxel and doxorubicin to cancer xenografts via the nanoparticle of nano-diamino-tetrac. International journal of nanomedicine. 2017; 12(?):1305-1315. doi: 10.2147/ijn.s123742. [PMID: 28243091]
  • Sanjun Shi, Min Zhou, Xin Li, Min Hu, Chenwen Li, Min Li, Fangfang Sheng, Zhuoheng Li, Guolin Wu, Minghe Luo, Huanhuan Cui, Ziwei Li, Ruoqiu Fu, Mingfeng Xiang, Jing Xu, Qian Zhang, Laichun Lu. Synergistic active targeting of dually integrin αvβ3/CD44-targeted nanoparticles to B16F10 tumors located at different sites of mouse bodies. Journal of controlled release : official journal of the Controlled Release Society. 2016 08; 235(?):1-13. doi: 10.1016/j.jconrel.2016.05.050. [PMID: 27235150]
  • Paul J Davis, Gennadi V Glinsky, Hung-Yun Lin, Shaker A Mousa. Actions of Thyroid Hormone Analogues on Chemokines. Journal of immunology research. 2016; 2016(?):3147671. doi: 10.1155/2016/3147671. [PMID: 27493972]
  • Rosalba Senese, Federica Cioffi, Pieter de Lange, Fernando Goglia, Antonia Lanni. Thyroid: biological actions of 'nonclassical' thyroid hormones. The Journal of endocrinology. 2014 May; 221(2):R1-12. doi: 10.1530/joe-13-0573. [PMID: 24464019]
  • Tamar Barbakadze, Nino Natsvlishvili, David Mikeladze. Thyroid hormones differentially regulate phosphorylation of ERK and Akt via integrin αvβ3 receptor in undifferentiated and differentiated PC-12 cells. Cell biochemistry and function. 2014 Apr; 32(3):282-6. doi: 10.1002/cbf.3013. [PMID: 24214887]
  • Murat Yalcin, Hung-Yun Lin, Thangirala Sudha, Dhruba J Bharali, Ran Meng, Heng-Yuan Tang, Faith B Davis, Steven C Stain, Paul J Davis, Shaker A Mousa. Response of human pancreatic cancer cell xenografts to tetraiodothyroacetic acid nanoparticles. Hormones & cancer. 2013 Jun; 4(3):176-85. doi: 10.1007/s12672-013-0137-y. [PMID: 23456390]
  • Ana Paula Zanatta, Leila Zanatta, Renata Gonçalves, Ariane Zamoner, Fátima Regina Mena Barreto Silva. Integrin participates in the effect of thyroxine on plasma membrane in immature rat testis. Biochimica et biophysica acta. 2013 Mar; 1830(3):2629-37. doi: 10.1016/j.bbagen.2012.10.022. [PMID: 23137442]
  • Sangbin Lee, Jiyeon Kim, Gayong Shim, Sunil Kim, Su Eun Han, Kwangmeyung Kim, Ick Chan Kwon, Yongseok Choi, Young Bong Kim, Chan-Wha Kim, Yu-Kyoung Oh. Tetraiodothyroacetic acid-tagged liposomes for enhanced delivery of anticancer drug to tumor tissue via integrin receptor. Journal of controlled release : official journal of the Controlled Release Society. 2012 Dec; 164(2):213-20. doi: 10.1016/j.jconrel.2012.05.043. [PMID: 22664473]
  • Hung-Yun Lin, Vivian Cody, Faith B Davis, Aleck A Hercbergs, Mary K Luidens, Shaker A Mousa, Paul J Davis. Identification and functions of the plasma membrane receptor for thyroid hormone analogues. Discovery medicine. 2011 Apr; 11(59):337-47. doi: NULL. [PMID: 21524387]
  • Hung-Yun Lin, Faith B Davis, Mary K Luidens, Shaker A Mousa, James H Cao, Min Zhou, Paul J Davis. Molecular basis for certain neuroprotective effects of thyroid hormone. Frontiers in molecular neuroscience. 2011; 4(?):29. doi: 10.3389/fnmol.2011.00029. [PMID: 22016721]
  • Paul J Davis, Faith B Davis, Shaker A Mousa, Mary K Luidens, Hung-Yun Lin. Membrane receptor for thyroid hormone: physiologic and pharmacologic implications. Annual review of pharmacology and toxicology. 2011; 51(?):99-115. doi: 10.1146/annurev-pharmtox-010510-100512. [PMID: 20868274]
  • Ran Meng, Heng-Yuan Tang, Jennifer Westfall, David London, James H Cao, Shaker A Mousa, Mary Luidens, Aleck Hercbergs, Faith B Davis, Paul J Davis, Hung-Yun Lin. Crosstalk between integrin αvβ3 and estrogen receptor-α is involved in thyroid hormone-induced proliferation in human lung carcinoma cells. PloS one. 2011; 6(11):e27547. doi: 10.1371/journal.pone.0027547. [PMID: 22132110]
  • Anita Kinne, Gunnar Kleinau, Carolin S Hoefig, Annette Grüters, Josef Köhrle, Gerd Krause, Ulrich Schweizer. Essential molecular determinants for thyroid hormone transport and first structural implications for monocarboxylate transporter 8. The Journal of biological chemistry. 2010 Sep; 285(36):28054-63. doi: 10.1074/jbc.m110.129577. [PMID: 20628049]
  • Isabel Zvibel, Dikla Atias, Adam Phillips, Zamir Halpern, Ran Oren. Thyroid hormones induce activation of rat hepatic stellate cells through increased expression of p75 neurotrophin receptor and direct activation of Rho. Laboratory investigation; a journal of technical methods and pathology. 2010 May; 90(5):674-84. doi: 10.1038/labinvest.2010.48. [PMID: 20231820]
  • Sheue-Yann Cheng, Jack L Leonard, Paul J Davis. Molecular aspects of thyroid hormone actions. Endocrine reviews. 2010 Apr; 31(2):139-70. doi: 10.1210/er.2009-0007. [PMID: 20051527]
  • Paul J Davis, Min Zhou, Faith B Davis, Larry Lansing, Shaker A Mousa, Hung-Yun Lin. Mini-review: Cell surface receptor for thyroid hormone and nongenomic regulation of ion fluxes in excitable cells. Physiology & behavior. 2010 Feb; 99(2):237-9. doi: 10.1016/j.physbeh.2009.02.015. [PMID: 19248795]
  • Anna B Glinskii, Gennadi V Glinsky, Hung-Yun Lin, Heng-Yuan Tang, Mingzeng Sun, Faith B Davis, Mary K Luidens, Shaker A Mousa, Aleck H Hercbergs, Paul J Davis. Modification of survival pathway gene expression in human breast cancer cells by tetraiodothyroacetic acid (tetrac). Cell cycle (Georgetown, Tex.). 2009 Nov; 8(21):3562-70. doi: 10.4161/cc.8.21.9963. [PMID: 19838061]
  • M Yalcin, D J Bharali, L Lansing, E Dyskin, S S Mousa, A Hercbergs, F B Davis, P J Davis, S A Mousa. Tetraidothyroacetic acid (tetrac) and tetrac nanoparticles inhibit growth of human renal cell carcinoma xenografts. Anticancer research. 2009 Oct; 29(10):3825-31. doi: NULL. [PMID: 19846915]
  • Leonardo M Cortez, Ricardo N Farías, Rosana N Chehín. Protective effect of 3,5,3'-triiodothyroacetic and 3,5,3',5'-tetraiodothyroacetic acids on serum albumin fibrillation. European biophysics journal : EBJ. 2009 Sep; 38(7):857-63. doi: 10.1007/s00249-009-0448-7. [PMID: 19381627]
  • H James Cao, Hung-Yun Lin, Mary K Luidens, Faith B Davis, Paul J Davis. Cytoplasm-to-nucleus shuttling of thyroid hormone receptor-beta1 (Trbeta1) is directed from a plasma membrane integrin receptor by thyroid hormone. Endocrine research. 2009; 34(1-2):31-42. doi: 10.1080/07435800902911810. [PMID: 19557589]
  • Maria Moreno, Pieter de Lange, Assunta Lombardi, Elena Silvestri, Antonia Lanni, Fernando Goglia. Metabolic effects of thyroid hormone derivatives. Thyroid : official journal of the American Thyroid Association. 2008 Feb; 18(2):239-53. doi: 10.1089/thy.2007.0248. [PMID: 18279024]
  • Hung-Yun Lin, Heng-Yuan Tang, Travis Keating, Yun-Hsuan Wu, Ai Shih, Douglas Hammond, Mingzeng Sun, Aleck Hercbergs, Faith B Davis, Paul J Davis. Resveratrol is pro-apoptotic and thyroid hormone is anti-apoptotic in glioma cells: both actions are integrin and ERK mediated. Carcinogenesis. 2008 Jan; 29(1):62-9. doi: 10.1093/carcin/bgm239. [PMID: 17984113]
  • Shaker A Mousa, Joel J Bergh, Emie Dier, Abdelhadi Rebbaa, Laura J O'Connor, Murat Yalcin, Ahmad Aljada, Evgeny Dyskin, Faith B Davis, Hung-Yung Lin, Paul J Davis. Tetraiodothyroacetic acid, a small molecule integrin ligand, blocks angiogenesis induced by vascular endothelial growth factor and basic fibroblast growth factor. Angiogenesis. 2008; 11(2):183-90. doi: 10.1007/s10456-007-9088-7. [PMID: 18080776]
  • Hung-Yun Lin, Heng-Yuan Tang, Ai Shih, Travis Keating, Gary Cao, Paul J Davis, Faith B Davis. Thyroid hormone is a MAPK-dependent growth factor for thyroid cancer cells and is anti-apoptotic. Steroids. 2007 Feb; 72(2):180-7. doi: 10.1016/j.steroids.2006.11.014. [PMID: 17174366]
  • S A Mousa, F B Davis, S Mohamed, P J Davis, X Feng. Pro-angiogenesis action of thyroid hormone and analogs in a three-dimensional in vitro microvascular endothelial sprouting model. International angiology : a journal of the International Union of Angiology. 2006 Dec; 25(4):407-13. doi: NULL. [PMID: 17164749]
  • Faith B Davis, Heng-Yuan Tang, Ai Shih, Travis Keating, Lawrence Lansing, Aleck Hercbergs, Robert A Fenstermaker, Ahmed Mousa, Shaker A Mousa, Paul J Davis, Hung-Yun Lin. Acting via a cell surface receptor, thyroid hormone is a growth factor for glioma cells. Cancer research. 2006 Jul; 66(14):7270-5. doi: 10.1158/0008-5472.can-05-4365. [PMID: 16849576]
  • Shaker A Mousa, Laura O'Connor, Faith B Davis, Paul J Davis. Proangiogenesis action of the thyroid hormone analog 3,5-diiodothyropropionic acid (DITPA) is initiated at the cell surface and is integrin mediated. Endocrinology. 2006 Apr; 147(4):1602-7. doi: 10.1210/en.2005-1390. [PMID: 16384862]
  • Shaker A Mousa, Laura J O'Connor, Joel J Bergh, Faith B Davis, Thomas S Scanlan, Paul J Davis. The proangiogenic action of thyroid hormone analogue GC-1 is initiated at an integrin. Journal of cardiovascular pharmacology. 2005 Sep; 46(3):356-60. doi: 10.1097/01.fjc.0000175438.94906.a0. [PMID: 16116342]
  • Joel J Bergh, Hung-Yun Lin, Lawrence Lansing, Seema N Mohamed, Faith B Davis, Shaker Mousa, Paul J Davis. Integrin alphaVbeta3 contains a cell surface receptor site for thyroid hormone that is linked to activation of mitogen-activated protein kinase and induction of angiogenesis. Endocrinology. 2005 Jul; 146(7):2864-71. doi: 10.1210/en.2005-0102. [PMID: 15802494]
  • Faith B Davis, Shaker A Mousa, Laura O'Connor, Seema Mohamed, Hung-Yun Lin, H James Cao, Paul J Davis. Proangiogenic action of thyroid hormone is fibroblast growth factor-dependent and is initiated at the cell surface. Circulation research. 2004 Jun; 94(11):1500-6. doi: 10.1161/01.res.0000130784.90237.4a. [PMID: 15117822]
  • Ai Shih, Shenli Zhang, H James Cao, Heng-Yuan Tang, Faith B Davis, Paul J Davis, Hung-Yun Lin. Disparate effects of thyroid hormone on actions of epidermal growth factor and transforming growth factor-alpha are mediated by 3',5'-cyclic adenosine 5'-monophosphate-dependent protein kinase II. Endocrinology. 2004 Apr; 145(4):1708-17. doi: 10.1210/en.2003-0742. [PMID: 14691008]
  • F A Verhoeven, H H A G M Van der Putten, G Hennemann, J M J Lamers, T J Visser, M E Everts. Uptake of triiodothyronine and triiodothyroacetic acid in neonatal rat cardiomyocytes: effects of metabolites and analogs. The Journal of endocrinology. 2002 May; 173(2):247-55. doi: 10.1677/joe.0.1730247. [PMID: 12010632]
  • L Oziol, P Faure, C Vergely, L Rochette, Y Artur, P Chomard, P Chomard. In vitro free radical scavenging capacity of thyroid hormones and structural analogues. The Journal of endocrinology. 2001 Jul; 170(1):197-206. doi: 10.1677/joe.0.1700197. [PMID: 11431152]
  • A Shih, H Y Lin, F B Davis, P J Davis. Thyroid hormone promotes serine phosphorylation of p53 by mitogen-activated protein kinase. Biochemistry. 2001 Mar; 40(9):2870-8. doi: 10.1021/bi001978b. [PMID: 11258898]
  • N Lameloise, C Siegrist-Kaiser, M O'Connell, A Burger. Differences between the effects of thyroxine and tetraiodothyroacetic acid on TSH suppression and cardiac hypertrophy. European journal of endocrinology. 2001 Feb; 144(2):145-54. doi: 10.1530/eje.0.1440145. [PMID: 11182751]
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  • M E Everts, T J Visser, E P Moerings, A M Tempelaars, H van Toor, R Docter, M de Jong, E P Krenning, G Hennemann. Uptake of 3,3',5,5'-tetraiodothyroacetic acid and 3,3',5'-triiodothyronine in cultured rat anterior pituitary cells and their effects on thyrotropin secretion. Endocrinology. 1995 Oct; 136(10):4454-61. doi: 10.1210/endo.136.10.7664665. [PMID: 7664665]
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