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Merck

T1775

L-Thyroxine

powder, BioReagent, suitable for cell culture

Synonym(s):

3,3′,5,5″-Tetraiodo-L-thyronine, 3-[4-(4-Hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]-L-alanine, T4

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About This Item

Linear Formula:
HOC6H2(I)2OC6H2(I)2CH2CH(NH2)CO2H
CAS Number:
51-48-9
Molecular Weight:
776.87
NACRES:
NA.77
PubChem Substance ID:
24899990
eCl@ss:
32190102
UNSPSC Code:
12352209
EC Number:
200-101-1
MDL number:
MFCD00002595
Beilstein/REAXYS Number:
2228515
biological source:
synthetic
form:
powder
assay:
≥98% (HPLC)

Product Name

L-Thyroxine, powder, BioReagent, suitable for cell culture

InChI key

XUIIKFGFIJCVMT-LBPRGKRZSA-N

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

SMILES string

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

biological source

synthetic

product line

BioReagent

assay

≥98% (HPLC)

form

powder

potency

5-50 ng/mL

technique(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

Quality Level

200

Gene Information

human ... THRA(7067), THRB(7068), TTR(7276)
mouse ... Cnr2(12802)
rat ... Cnr1(25248)

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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.

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.

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

pictograms

Health hazard
GHS08

signalword

Danger

hcodes

H372

Hazard Classifications

STOT RE 1

target_organs

Thyroid,Cardio-vascular system,Kidney

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCP0039
BCCM6294
BCCK9809
BCCJ6599
BCCH3589

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Thyroid hormones (T3 and T4): dual effect on human cancer cell proliferation
Moriggi G, et al.
Anticancer Research, 31(1), 89-96 (2011)
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)
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)
Thyroid hormone promotes beta-catenin activation and cell proliferation in colorectal cancer
Lee YS, et al.
Hormones & Cancer, 9(3), 156-165 (2018)
Chemistry of thyroxine. III. Constitution and synthesis of thyroxine
Harrington CR and Barger G
The Biochemical Journal, 21(6), 169-183 (1927)
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