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MedKoo Cat#: 596256 | Name: Diiodotyrosine
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Diiodotyrosine (DIT) is a precursor in the production of thyroid hormone, and results from iodization of monoiodotyrosine at the other meta- position on the phenol ring.

Chemical Structure

Diiodotyrosine
CAS#66-02-4

Theoretical Analysis

MedKoo Cat#: 596256

Name: Diiodotyrosine

CAS#: 66-02-4

Chemical Formula: C9H9I2NO3

Exact Mass: 432.8672

Molecular Weight: 432.98

Elemental Analysis: C, 24.97; H, 2.10; I, 58.62; N, 3.23; O, 11.09

Price and Availability

Size Price Availability Quantity
100mg USD 250.00 2 Weeks
250mg USD 450.00 2 Weeks
1g USD 950.00 2 Weeks
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Related CAS #
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Synonym
Diiodotyrosine; NSC 208959; NSC-208959; NSC208959; NSC 97936; NSC97936; NSC-97936; Agontan; Flaianina; Iodogorgoic acid; Iodogorgonic acid; Jodgorgon; Cemiod; H-DL-Tyr(3,5-DiI)-OH
IUPAC/Chemical Name
2-amino-3-(4-hydroxy-3,5-diiodophenyl)propanoic acid
InChi Key
NYPYHUZRZVSYKL-UHFFFAOYSA-N
InChi Code
InChI=1S/C9H9I2NO3/c10-5-1-4(2-6(11)8(5)13)3-7(12)9(14)15/h1-2,7,13H,3,12H2,(H,14,15)
SMILES Code
O=C(O)C(N)CC1=CC(I)=C(O)C(I)=C1
Appearance
Solid powder
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
2-Amino-3-(4-hydroxy-3,5-diiodophenyl)propanoic acid is a tyrosine derivative.
In vitro activity:
This study also evaluates the interaction between 3, 5-diiodotyrosine and APOBEC3B in cancer cells. KYSE150 cell line with low expression of APOBEC3B was selected (online supplemental figure S4A) for construction of a doxycycline (dox) inducible APOBEC3B overexpression cell line KYSE150-APOBEC3B (online supplemental figure S4B). A 4 ng/mL dox could induce APOBEC3B overexpression. Results in online supplemental figure S4C showed that 3, 5-diiodotyrosine had high affinity to KYSE150-APOBEC3B cells (KD=6.14 ± 7.93 µM), but it had no affinity to KYSE150-vector cells by MST assay. Furthermore, 3, 5-diiodotyrosine could strongly inhibit the deaminase activity of APOBEC3B in KYSE150-APOBEC3B cells (online supplemental figure S4D). These results further demonstrated that 3, 5-diiodotyrosine could interact with APOBEC3B and inhibit the deaminase activity of APOBEC3B. Reference: J Immunother Cancer. 2022 Nov;10(11):e005503. https://pubmed.ncbi.nlm.nih.gov/36323433/
In vivo activity:
Next, 3, 5-diiodotyrosine was used to treat ESCC mice (i.p.) at a low dose (0.5 mg/kg) and a high dose (2 mg/kg), respectively (figure 3A). Results showed that the number and length of ESCC tumor tissue were significantly reduced compared with normal saline (NS) group (figure 3B). Both low and high dose of 3, 5-diiodotyrosine group could significantly prolong the overall survival of mice, and slow down the loss trend of body weight (figure 3C and online supplemental figure S8A). Reference: J Immunother Cancer. 2022 Nov;10(11):e005503. https://pubmed.ncbi.nlm.nih.gov/36323433/

Preparing Stock Solutions

The following data is based on the product molecular weight 432.98 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Chen C, Sui X, Ning H, Sun Y, Du J, Chen X, Zhou X, Chen G, Shen W, Pang L, Zhou X, Shi R, Li W, Wang H, Zhao W, Zhai W, Qi Y, Wu Y, Gao Y. Identification of natural product 3, 5-diiodotyrosine as APOBEC3B inhibitor to prevent somatic mutation accumulation and cancer progression. J Immunother Cancer. 2022 Nov;10(11):e005503. doi: 10.1136/jitc-2022-005503. PMID: 36323433; PMCID: PMC9639148.
In vitro protocol:
1. Chen C, Sui X, Ning H, Sun Y, Du J, Chen X, Zhou X, Chen G, Shen W, Pang L, Zhou X, Shi R, Li W, Wang H, Zhao W, Zhai W, Qi Y, Wu Y, Gao Y. Identification of natural product 3, 5-diiodotyrosine as APOBEC3B inhibitor to prevent somatic mutation accumulation and cancer progression. J Immunother Cancer. 2022 Nov;10(11):e005503. doi: 10.1136/jitc-2022-005503. PMID: 36323433; PMCID: PMC9639148.
In vivo protocol:
1. Chen C, Sui X, Ning H, Sun Y, Du J, Chen X, Zhou X, Chen G, Shen W, Pang L, Zhou X, Shi R, Li W, Wang H, Zhao W, Zhai W, Qi Y, Wu Y, Gao Y. Identification of natural product 3, 5-diiodotyrosine as APOBEC3B inhibitor to prevent somatic mutation accumulation and cancer progression. J Immunother Cancer. 2022 Nov;10(11):e005503. doi: 10.1136/jitc-2022-005503. PMID: 36323433; PMCID: PMC9639148.
1: Ngambenjawong C, Sylvestre M, Gustafson HH, Pineda JMB, Pun SH. Reversibly Switchable, pH-Dependent Peptide Ligand Binding via 3,5-Diiodotyrosine Substitutions. ACS Chem Biol. 2018 Apr 20;13(4):995-1002. doi: 10.1021/acschembio.8b00171. Epub 2018 Mar 5. PubMed PMID: 29481044. 2: Mughal BB, Leemans M, Lima de Souza EC, le Mevel S, Spirhanzlova P, Visser TJ, Fini JB, Demeneix BA. Functional Characterization of Xenopus Thyroid Hormone Transporters mct8 and oatp1c1. Endocrinology. 2017 Aug 1;158(8):2694-2705. doi: 10.1210/en.2017-00108. PubMed PMID: 28591769. 3: Phatarphekar A, Rokita SE. Functional analysis of iodotyrosine deiodinase from drosophila melanogaster. Protein Sci. 2016 Dec;25(12):2187-2195. doi: 10.1002/pro.3044. Epub 2016 Sep 26. PubMed PMID: 27643701; PubMed Central PMCID: PMC5119571. 4: Wilson RA, Yanes EG, Kemppainen RJ. Iodine speciation in dog foods and treats by high performance liquid chromatography with inductively coupled plasma mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 Jun 1;1022:183-190. doi: 10.1016/j.jchromb.2016.04.002. Epub 2016 Apr 2. PubMed PMID: 27107244. 5: Tou WI, Chang KL, Chang TT, Lee CC, Chen CY. Residue-based design of small molecule inhibitor for H1N1, H5N1 and H7N1 mutants. J Mol Model. 2016 Jan;22(1):4. doi: 10.1007/s00894-015-2875-y. Epub 2015 Dec 8. PubMed PMID: 26645808. 6: Di Jeso B, Arvan P. Thyroglobulin From Molecular and Cellular Biology to Clinical Endocrinology. Endocr Rev. 2016 Feb;37(1):2-36. doi: 10.1210/er.2015-1090. Epub 2015 Nov 23. Review. PubMed PMID: 26595189; PubMed Central PMCID: PMC4740344. 7: Liu D, Lin X, Yu F, Zhang M, Chen H, Bao W, Wang X. Effects of 3,5-Diiodotyrosine and Potassium Iodide on Thyroid Function and Oxidative Stress in Iodine-Excess Wistar Rats. Biol Trace Elem Res. 2015 Dec;168(2):447-52. doi: 10.1007/s12011-015-0371-y. Epub 2015 May 24. PubMed PMID: 26002813. 8: Chen KC, Lee WY, Chen HY, Chen CY. In silico investigation of potential TRAF6 inhibitor from traditional Chinese medicine against cancers. Biomed Res Int. 2014;2014:429486. doi: 10.1155/2014/429486. Epub 2014 Jun 25. PubMed PMID: 25089269; PubMed Central PMCID: PMC4096009. 9: Hung TC, Lee WY, Chen KB, Chen CY. Lead screening for CXCR4 of the human HIV infection receptor inhibited by traditional Chinese medicine. Biomed Res Int. 2014;2014:809816. doi: 10.1155/2014/809816. Epub 2014 Jun 5. PubMed PMID: 24999477; PubMed Central PMCID: PMC4066726. 10: Li P, Hu B, He M, Chen B. Ion pair hollow fiber liquid-liquid-liquid microextraction combined with capillary electrophoresis-ultraviolet detection for the determination of thyroid hormones in human serum. J Chromatogr A. 2014 Aug 22;1356:23-31. doi: 10.1016/j.chroma.2014.06.046. Epub 2014 Jun 21. PubMed PMID: 24997114. 11: Cetrangolo GP, Arcaro A, Lepore A, Graf M, Mamone G, Ferranti P, Palumbo G, Gentile F. Hormonogenic donor Tyr2522 of bovine thyroglobulin. Insight into preferential T3 formation at thyroglobulin carboxyl terminus at low iodination level. Biochem Biophys Res Commun. 2014 Jul 18;450(1):488-93. doi: 10.1016/j.bbrc.2014.05.144. Epub 2014 Jun 6. PubMed PMID: 24911556. 12: Tóth G, Noszál B. [Thyroid hormones and their precursors. II. Species-specific properties]. Acta Pharm Hung. 2014;84(1):21-37. Review. Hungarian. PubMed PMID: 24809164. 13: Iglesias A, García-Nimo L, Cocho de Juan JA, Moreno JC. Towards the pre-clinical diagnosis of hypothyroidism caused by iodotyrosine deiodinase (DEHAL1) defects. Best Pract Res Clin Endocrinol Metab. 2014 Mar;28(2):151-9. doi: 10.1016/j.beem.2013.10.009. Epub 2013 Oct 29. Review. PubMed PMID: 24629858. 14: Phatarphekar A, Buss JM, Rokita SE. Iodotyrosine deiodinase: a unique flavoprotein present in organisms of diverse phyla. Mol Biosyst. 2014 Jan;10(1):86-92. doi: 10.1039/c3mb70398c. PubMed PMID: 24153409; PubMed Central PMCID: PMC3858845. 15: Romarís-Hortas V, Bermejo-Barrera P, Moreda-Piñeiro A. Ultrasound-assisted enzymatic hydrolysis for iodinated amino acid extraction from edible seaweed before reversed-phase high performance liquid chromatography-inductively coupled plasma-mass spectrometry. J Chromatogr A. 2013 Sep 27;1309:33-40. doi: 10.1016/j.chroma.2013.08.022. Epub 2013 Aug 9. PubMed PMID: 23972456. 16: Paul KB, Hedge JM, Macherla C, Filer DL, Burgess E, Simmons SO, Crofton KM, Hornung MW. Cross-species analysis of thyroperoxidase inhibition by xenobiotics demonstrates conservation of response between pig and rat. Toxicology. 2013 Oct 4;312:97-107. doi: 10.1016/j.tox.2013.08.006. Epub 2013 Aug 17. PubMed PMID: 23959146. 17: Tóth G, Noszál B. [Thyroid hormones and their precursors I. Biochemical properties]. Acta Pharm Hung. 2013;83(2):35-45. Review. Hungarian. PubMed PMID: 23926648. 18: Clinckspoor I, Verlinden L, Mathieu C, Bouillon R, Verstuyf A, Decallonne B. Vitamin D in thyroid tumorigenesis and development. Prog Histochem Cytochem. 2013 Aug;48(2):65-98. doi: 10.1016/j.proghi.2013.07.001. Epub 2013 Jul 26. Review. PubMed PMID: 23890557. 19: Tóth G, Mazák K, Hosztafi S, Kökösi J, Noszál B. Species-specific lipophilicity of thyroid hormones and their precursors in view of their membrane transport properties. J Pharm Biomed Anal. 2013 Mar 25;76:112-8. doi: 10.1016/j.jpba.2012.12.010. Epub 2012 Dec 20. PubMed PMID: 23298914. 20: Fujimoto K, Matsuura K, Das B, Fu L, Shi YB. Direct activation of Xenopus iodotyrosine deiodinase by thyroid hormone receptor in the remodeling intestine during amphibian metamorphosis. Endocrinology. 2012 Oct;153(10):5082-9. Epub 2012 Aug 3. PubMed PMID: 22865369; PubMed Central PMCID: PMC3512013.