2614-06-4 Usage
Description
(R)-(+)-THALIDOMIDE, also known as the optically active isomer of Thalidomide, is a 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione with R-configuration at the chiral center. It is characterized by its needle-like chemical properties and has been widely studied for its various biological effects and applications.
Uses
1. Used in Pharmaceutical Industry:
(R)-(+)-THALIDOMIDE is used as an inhibitor for FGF-induced angiogenesis, which is a process that plays a crucial role in the growth and metastasis of solid tumors. By inhibiting this process, it can potentially limit the progression of cancer.
2. Used in Antiviral Applications:
In the pharmaceutical industry, (R)-(+)-THALIDOMIDE is also used as an inhibitor of the replication of human immunodeficiency virus type 1 (HIV-1), making it a potential therapeutic agent for the treatment of HIV.
3. Used in Teratogenic Studies:
(R)-(+)-THALIDOMIDE is used as a teratogenic sedative in the field of embryology and developmental biology. It has been used to study its teratogenic effects in chicken embryos and human embryonic cells, providing valuable insights into the mechanisms of limb defects and other developmental abnormalities.
4. Used in Apoptosis Research:
(R)-(+)-THALIDOMIDE is used to study the stabilization of PTEN, inhibition of Akt expression, and activation of caspase-dependent apoptosis. These studies contribute to the understanding of the molecular mechanisms underlying the teratogenic effects of thalidomide and its potential applications in therapeutic interventions.
5. Used in Glutathione Research:
In the field of biochemistry, (R)-(+)-THALIDOMIDE has been used to study glutathione-mediated teratogenic resistance in mouse embryos, which can help in understanding the protective mechanisms against teratogenic agents and their potential applications in drug development and safety assessments.
Biochem/physiol Actions
(-)-Thalidomide selectively inhibits biosynthesis of tumor necrosis factor α (TNF-α). (R)-Thalidomide is called "safe enantiomer", but it can be converted in the body to (S)-isomer.
Check Digit Verification of cas no
The CAS Registry Mumber 2614-06-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,6,1 and 4 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 2614-06:
(6*2)+(5*6)+(4*1)+(3*4)+(2*0)+(1*6)=64
64 % 10 = 4
So 2614-06-4 is a valid CAS Registry Number.
InChI:InChI=1/C13H10N2O4/c16-10-6-5-9(11(17)14-10)15-12(18)7-3-1-2-4-8(7)13(15)19/h1-4,9H,5-6H2,(H,14,16,17)/t9-/m1/s1
2614-06-4Relevant articles and documents
Chiral inversion and hydrolysis of thalidomide: Mechanisms and catalysis by bases and serum albumin, and chiral stability of teratogenic metabolites
Reist, Marianne,Carrupt, Pierre-Alain,Francotte, Eric,Testa, Bernard
, p. 1521 - 1528 (2007/10/03)
The chiral inversion and hydrolysis of thalidomide and the catalysis by bases and human serum albumin were investigated by using a stereoselective HPLC assay. Chiral inversion was catalyzed by albumin, hydroxyl ions, phosphate, and amino acids. Basic amino acids (Arg and Lys) had a superior potency in cataLyzing chiral inversion compared to acid and neutral ones. The chiral inversion of thalidomide is thus subject to Specific and general base catalysis, and it is suggested that the ability of HSA to catalyze the reaction is due to the basic groups of the amino acids Arg and Lys and not to a single catalytic site on the macromolecule. The hydrolysis of thalidomide was also base-catalyzed. However, albumin had no effect on hydrolysis, and there was no difference between the catalytic potencies of acidic, neutral, and basic amino acids. This may be explained by different reaction mechanisms of the chiral inversion and hydrolysis of thalidomide. Chiral inversion is deduced to occur by electrophilic substitution involving specific and general base catalysis, whereas hydrolysis is thought to occur by nucleophilic substitution involving specific and general base as well as nucleophilic catalysis. As nucleophilic attack is sensitive to steric properties of the catalyst, steric hindrance might be the reason albumin is not able to catalyze hydrolysis. 1H NMR experiments revealed that the three teratogenic metabolites of thalidomide, in sharp contrast to the drug itself, had complete chiral stability. This leads to the speculation that, were some enantioselectivity to exist in the teratogenicity of thalidomide, it could result from fast hydrolysis to chirally stable teratogenic metabolites.