Absolute configuration of the thyroid hormone analog KAT-2003 as determined by the1H NMR anisotropy method with a novel chiral auxiliary, M?NP acid

Chirality ◽  
2003 ◽  
Vol 16 (1) ◽  
pp. 13-21 ◽  
Author(s):  
Toshihiro Nishimura ◽  
Hiromi Taji ◽  
Nobuyuki Harada
Keyword(s):  
Thyroid Hormone ◽  
Absolute Configuration ◽  
Chiral Auxiliary ◽  
Hormone Analog

Pilot Studies on the Use of 3,5-Diiodothyropropionic Acid, a Thyroid Hormone Analog, in the Treatment of Congestive Heart Failure

Cardiology ◽  
2002 ◽  
Vol 97 (4) ◽  
pp. 218-225 ◽  
Author(s):  
Eugene Morkin ◽  
Gregory Pennock ◽  
Peter H. Spooner ◽  
Joseph J. Bahl ◽  
Katherine Underhill Fox ◽  
...  
Keyword(s):  
Heart Failure ◽  
Congestive Heart Failure ◽  
Thyroid Hormone ◽  
Pilot Studies ◽  
Hormone Analog

DITPA, A Thyroid Hormone Analog, Reduces Infarct Size and Attenuates the Inflammatory Response Following Myocardial Ischemia

2011 ◽  
Vol 171 (2) ◽  
pp. 379-385 ◽  
Author(s):  
Abdelrahman A. Abohashem-Aly ◽  
Xianzhong Meng ◽  
Jilin Li ◽  
Miral R. Sadaria ◽  
Lihua Ao ◽  
...  
Keyword(s):  
Thyroid Hormone ◽  
Myocardial Ischemia ◽  
Inflammatory Response ◽  
Infarct Size ◽  
Hormone Analog

The Theoretical Basis for Assignment by NMR

2015 ◽  
Author(s):  
Josi M. Seco ◽  
Emilio Quiqoa ◽  
Ricardo Riguera
Keyword(s):  
Absolute Configuration ◽  
Chiral Auxiliary ◽  
Primary Amines ◽  
Primary Alcohols ◽  
Chiral Reagent ◽  
Chiral Compounds ◽  
Configurational Assignment ◽  
Derivatizing Agent ◽  
Chiral Derivatizing Agent ◽  
Diastereomeric Complexes

The nuclear magnetic resonance (NMR) spectra of two enantiomers are identical. Thus, the first step in using NMR to distinguish between two enantiomers should be to produce different spectra that eventually can be associated with their different stereochemistry (i.e., the assignment of their absolute configuration). Therefore, it is necessary to introduce a chiral reagent in the NMR media. There are two ways to address this problem. One is to use a chiral solvent, or a chiral agent, that combines with each enantiomer of the substrate to produce diastereomeric complexes/associations that lead to different spectra. This is the so-called chiral solvating agent (CSA) approach; it will not be further discussed here [33–34]. The second approach is to use a chiral auxiliary reagent [13–15] (i.e., a chiral derivatizing agent; CDA) that bonds to the substrate by a covalent linkage. Thus, in the most general method, the two enantiomers of the auxiliary CDA react separately with the substrate, giving two diastereomeric derivatives whose spectral differences carry information that can be associated with their stereochemistry. The CDA method that employs arylalcoxyacetic acids as auxiliaries is the most frequently used. It can be applied to a number of monofunctionals [14–15] (secondary alcohols [35–43], primary alcohols [44–46], aldehyde [47] and ketone cyanohydrins [48–49], thiols [50–51], primary amines [52–56], and carboxylic acids [57–58]), difunctional [13] (sec/sec-1,2-diols [59–61], sec/sec-1,2-amino alcohols [62], prim/sec-1,2-diols [63–65], prim/sec-1,2-aminoalcohols, and sec/prim-1,2-aminoalcohols [66–68]), and trifunctional (prim/sec/sec-1,2,3-triols [13, 69–70]) chiral compounds. Its scope and limitations are well established, and its theoretical foundations are well known, making it a reliable tool for configurational assignment. Figure 1.1 shows a summary of the steps to be followed for the assignment of absolute configuration of a chiral compound with just one asymmetric carbon and with substituents that, for simplicity, are assumed to resonate as singlets. Step 1 (Figure 1.1a): A substrate of unknown configuration (?) is separately derivatized with the two enantiomers of a chiral auxiliary reagent, (R)-Aux and (S)-Aux, producing two diastereomeric derivatives.

The thyroid hormone analog DITPA restoresI to in rats after myocardial infarction

2000 ◽  
Vol 278 (4) ◽  
pp. H1105-H1116 ◽  
Author(s):  
Alan D. Wickenden ◽  
Roger Kaprielian ◽  
Xiao-Mang You ◽  
Peter H. Backx
Keyword(s):  
Myocardial Infarction ◽  
Thyroid Hormone ◽  
Action Potential ◽  
Ventricular Myocytes ◽  
Monophasic Action Potential ◽  
Mrna Levels ◽  
Hormone Analog ◽  
Life Threatening ◽  
The Right

Previous studies have established that reductions in repolarizing currents occur in heart disease and can contribute to life-threatening arrhythmias in myocardium. In this study, we investigated whether the thyroid hormone analog 3,5-diiodothyropropionic acid (DITPA) could restore repolarizing transient outward K+ current ( I to) density and gene expression in rat myocardium after myocardial infarction (MI). Our findings show that I to density was reduced after MI (14.0 ± 1.0 vs. 10.2 ± 0.9 pA/pF, sham vs. post-MI at +40 mV). mRNA levels of Kv4.2 and Kv4.3genes were decreased but Kv1.4 mRNA levels were increased post-MI. Corresponding changes in Kv4.2 and Kv1.4 protein were also observed. Chronic treatment of post-MI rats with 10 mg/kg DITPA restored I to density (to 15.2 ± 1.1 pA/pF at +40 mV) as well as Kv4.2 and Kv1.4 expression to levels observed in sham-operated controls. Other membrane currents (Na+, L-type Ca2+, sustained, and inward rectifier K+ currents) were unaffected by DITPA treatment. Associated with the changes in I toexpression, action potential durations (current-clamp recordings in isolated single right ventricular myocytes and monophasic action potential recordings from the right free wall in situ) were prolonged after MI and restored with DITPA treatment. Our results demonstrate that DITPA restores I to density in the setting of MI, which may be useful in preventing complications associated with I to downregulation.

Thyroid hormone analog inhibition of hepatic 5′-iodothyrohine deiodinase activity

1988 ◽  
Vol 11 (9) ◽  
pp. 657-661 ◽  
Author(s):  
B. L. Shulkin ◽  
M. B. Bolger ◽  
R. D. Utiger
Keyword(s):  
Thyroid Hormone ◽  
Deiodinase Activity ◽  
Hormone Analog

scholarly journals DITPA (3,5-Diiodothyropropionic Acid), a Thyroid Hormone Analog to Treat Heart Failure

Circulation ◽  
2009 ◽  
Vol 119 (24) ◽  
pp. 3093-3100 ◽  
Author(s):  
Steven Goldman ◽  
Madeline McCarren ◽  
Eugene Morkin ◽  
Paul W. Ladenson ◽  
Robert Edson ◽  
...  
Keyword(s):  
Heart Failure ◽  
Thyroid Hormone ◽  
Treat Heart Failure ◽  
Hormone Analog
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