3,5-diiodothyronine

from Wikipedia, the free encyclopedia
Structural formula
Structural formula of 3,5-diiodo-L-thyronine
Structural formula of 3,5-diiodo- L -thyronine
General
Surname 3,5-diiodothyronine
other names
  • 3,5-T 2
  • 3,5-diiodothyronine
Molecular formula C 15 H 13 I 2 NO 4
Brief description

colorless to yellow solid

External identifiers / databases
CAS number
  • 534-51-0 ( racemate )
  • 1041-01-6 [( S ) form]
  • 5563-89-3 [( R ) -form]
PubChem 123675
ChemSpider 110252
Wikidata Q20888848
properties
Molar mass 525.08 g · mol -1
Physical state

firmly

Melting point

255 ° C

solubility

slightly soluble in water, methanol and DMSO

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 302
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

3,5-Diiodothyronine (3,5-T 2 ) in its L -form is an active thyroid hormone from the class of iodothyronines with an L - thyroxine -like effect. In the thyroid gland, 3,5-diiodo- L- thyronine is deactivated by deiodinases . It is produced in vivo by type 1 and type 2 de-iodination from triiodothyronine (T 3 ).

Whenever “3,5-diiodothyronine” is mentioned in this text or in the scientific literature without any additional name ( descriptor ), it means 3,5-diiodo- L- thyronine.

Occurrence

The ( S ) -form (= L -form) of the compound occurs in marine algae. 3.5 T 2 may in the serum of healthy subjects and patients after Schilddrüsenresektion receiving replacement therapy with LT 4 found.

Biological effects

3,5-T 2 stimulates the TR beta receptor for thyroid hormones and thus the basal metabolic rate . It has agonistic effects on the myocardium and pituitary gland so that it is able to suppress TSH secretion. 3,5-T 2 is also an allosteric regulator of cytochrome c oxidase , complex IV of the respiratory chain .

Clinical significance

In the case of non-thyroidal illness syndrome (NTIS), increased 3.5 T 2 levels are observed. This could explain why giving thyroid hormones to the severely ill with NTIS is of no use.

Individual evidence

  1. ↑ a b Entry on 3,5-diiodo- L -thyronine. In: Römpp Online . Georg Thieme Verlag, accessed on November 10, 2015.
  2. ↑ a b c d e data sheet 3,5-Diiodo-L-thyronine, thyroid hormone analog from Sigma-Aldrich , accessed on November 10, 2015 ( PDF ).
  3. ↑ scbio.de: 3,5-Diiodo-L-thyronine (CAS number: 1041-01-6). Santa Cruz Biotechnology, accessed January 1, 2016.
  4. ^ John Buckingham: Dictionary of Natural Products . CRC Press, 1993, ISBN 0-412-46620-1 , pp. 1837 ( limited preview in Google Book search).
  5. ↑ I. Lehmphul, G. Brabant, H. Wallaschofski, M. Ruchala, CJ Strasburger, J. Köhrle, Z. Wu: Detection of 3,5-diiodothyronine in sera of patients with altered thyroid status using a new monoclonal antibody-based chemiluminescence immunoassay. In: Thyroid. 24 (9), Sep 2014, pp. 1350-1360. doi: 10.1089 / thy.2013.0688 . PMID 24967815 .
  6. ^ F. Goglia: The effects of 3,5-diiodothyronine on energy balance . In: Frontiers in Physiology . tape 5 , p. 528 , doi : 10.3389 / fphys.2014.00528 , PMID 25628573 .
  7. ^ A. Lombardi, R. Senese, R. De Matteis, RA Busiello, F. Cioffi, F. Goglia, A. Lanni: 3,5-Diiodo-L-thyronine activates brown adipose tissue thermogenesis in hypothyroid rats . In: PloS One . tape 10 , no. 2 , p. e0116498 , doi : 10.1371 / journal.pone.0116498 , PMID 25658324 .
  8. ↑ AS Padron, RA Neto, RL Araujo, TU Pantaleão, MC de Souza dos Santos, BM de Andrade, M. da Silva Leandro, JP de Castro, AC Ferreira, DP de Carvalho: Administration of 3,5-diiodothyronine (3, 5-T2) causes central hypothyroidism and stimulates thyroid-sensitive tissues . In: The Journal of Endocrinology . tape 221 , no. 3 , June 2014, p. 415-427 , doi : 10.1530 / JOE-13-0502 , PMID 24692290 .
  9. ↑ W. Jonas, J. Lietzow, F. Wohlgemuth, CS Hoefig, P. Wiedmer, U. Schweizer, J. Köhrle, A. Schürmann: 3,5-Diiodo-L-thyronine (3,5-t2) exerts thyromimetic effects on hypothalamus-pituitary-thyroid axis, body composition, and energy metabolism in male diet-induced obese mice . In: Endocrinology . tape 156 , no. 1 , January 2015, p. 389-399 , doi : 10.1210 / en.2014-1604 , PMID 25322465 .
  10. ^ S. Arnold, F. Goglia, B. Kadenbach: 3,5-Diiodothyronine binds to subunit Va of cytochrome-c oxidase and abolishes the allosteric inhibition of respiration by ATP. In: Eur J Biochem. tape 252 , no. 2 , 1998, p. 325-330 , doi : 10.1046 / j.1432-1327.1998.2520325.x , PMID 9523704 .
  11. ↑ G. Pinna, H. Meinhold, L. Hiedra, R. Thoma, T. Hoell, KJ Gräf, G. Stoltenburg-Didinger, M. Eravci, H. Prengel, O. Brödel, R. Finke, A. Baumgartner: Elevated 3,5-diiodothyronine concentrations in the sera of patients with nonthyroidal illnesses and brain tumors . In: The Journal of Clinical Endocrinology and Metabolism . tape 82 , no. 5 , May 1997, pp. 1535-1542 , doi : 10.1210 / jcem.82.5.3939 , PMID 9141546 .
  12. ↑ a b J. W. Dietrich, P. Müller, F. Schiedat, M. Schlömicher, J. Strauch, A. Chatzitomaris, HH Klein, A. Mügge, J. Köhrle, E. Rijntjes, I. Lehmphul: Nonthyroidal Illness Syndrome in Cardiac Illness Involves Elevated Concentrations of 3,5-Diiodothyronine and Correlates with Atrial Remodeling . In: European Thyroid Journal . tape 4 , no. 2 , June 2015, p. 129-137 , doi : 10.1159 / 000381543 , PMID 26279999 .
  13. ↑ L Langouche, I Lehmphul, SV Perre, J Köhrle, G, Van den Berghe: Circulating 3-T1AM and 3,5-T2 in Critically Ill Patients: A Cross-Sectional Observational Study. . In: Thyroid: official journal of the American Thyroid Association . 26, No. 12, December 2016, pp. 1674–1680. PMID 27676423 .