T1775

Sigma-Aldrich

L-Thyroxine

powder, BioReagent, suitable for cell culture

Synonym(s):
3-[4-(4-Hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]-L-alanine, 3,3′,5,5″-Tetraiodo-L-thyronine, T4
Linear Formula:
HOC6H2(I)2OC6H2(I)2CH2CH(NH2)CO2H
CAS Number:
Molecular Weight:
776.87
Beilstein/REAXYS Number:
2228515
EC Number:
MDL number:
eCl@ss:
32190102
PubChem Substance ID:
NACRES:
NA.77

Quality Level

biological source

synthetic

product line

BioReagent

assay

≥98% (HPLC)

form

powder

potency

5-50 ng/mL

application(s)

cell culture | mammalian: suitable

mp

223 °C (dec.) (lit.)

solubility

4 M NH4OH in methanol: 50 mg/mL, clear to hazy, yellow

shipped in

ambient

storage temp.

room temp

SMILES string

N[C@@H](Cc1cc(I)c(Oc2cc(I)c(O)c(I)c2)c(I)c1)C(O)=O

InChI

1S/C15H11I4NO4/c16-8-4-7(5-9(17)13(8)21)24-14-10(18)1-6(2-11(14)19)3-12(20)15(22)23/h1-2,4-5,12,21H,3,20H2,(H,22,23)/t12-/m0/s1

InChI key

XUIIKFGFIJCVMT-LBPRGKRZSA-N

Gene Information

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General description

Thyroxine (T4) is a tetraiodo derivative of the p-hydroxyphenyl ether of tyrosine, which functions as growth factors or cell growth inhibitors. T4 is used to treat hypothyroidism and thyroid carcinoma. It regulates energy metabolism.

Application

L-Thyroxine has been used to investigate its role in colorectal cancer cell lines HCT 116 (APC wild type) and HT-29 (APC mutant). It has also been used to evaluate its effects on pro-inflammatory tumor necrosis factor-α (TNF-α), interleukin-6 (IL-6), angiogenic vascular endothelial growth factor (VEGF), leukocyte adhesion, intercellular adhesion molecule 1 (ICAM-1) and E-selectin in human umbilical vein endothelial cells (HUVECs).

Biochem/physiol Actions

L-Thyroxine (T4) and triiodo-L-thyronine (T3) are iodine-containing hormones produced from thyroglobulin in the thyroid follicular cells. The stimulation of metabolic rate and regulation of growth and development by these hormones appear to be due to their effects on DNA transcription and, thus, protein synthesis.

Preparation Note

For long term storage, keep stock solutions at -20° in working aliquots and avoid repeated freeze/thaw cycles. Solutions stored at 2-8 °C are stable for up to 30 days.

Reconstitution

To prepare 20 μg/ml stock solution, dissolve in 50 ml sterile culture medium per mg thyroxine.

storage_class_code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

The
Clinical Chemistry, 331(3), 174-180 (2008)
Chemistry of thyroxine. III. Constitution and synthesis of thyroxine
Harrington CR and Barger G
The Biochemical Journal, 21(6), 169-183 (1927)
Effects of thyroxine as compared with thyroxine plus triiodothyronine in patients with hypothyroidism
Bunevivcius R, et al.
The New England Journal of Medicine, 340(6), 424-429 (1999)
Thyroxine therapy
Toft AD
The New England Journal of Medicine, 331(3), 174-180 (1994)
Effects of thyroid-stimulating hormone on adhesion molecules and pro-inflammatory cytokines secretion in human umbilical vein endothelial cells
Milani AT, et al.
Research in Pharmaceutical Sciences, 13(6), 546-546 (2018)

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