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Cited by 20Chemical Reaction MechanismsMuscle metabolism and nutritionAnalytical Methods in Pharmaceuticals

Non-enzymatic hydrolysis of creatine ethyl ester

Katseres, Nicholas S., Reading, David W., Shayya, Luay, DiCesare, John C., Purser, Gordon H.·2009·Biochemical and Biophysical Research Communications
DOI 10.1016/j.bbrc.2009.06.037
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Abstract

The rate of the non-enzymatic hydrolysis of creatine ethyl ester (CEE) was studied at 37 degrees C over the pH range of 1.6-7.0 using (1)H NMR. The ester can be present in solution in three forms: the unprotonated form (CEE), the monoprotonated form (HCEE(+)), and the diprotonated form (H(2)CEE(2+)). The values of pK(a1) and pK(a2) of H(2)CEE(2+) were found to be 2.30 and 5.25, respectively. The rate law is found to be Rate=-dCCEE/dt=k++[H2CEE2+][OH-]+k+[HCEE+][OH-]+k0[CEE][OH-] where the rate constants k(++), k(+), and k(0) are (3.9+/-0.2)x10(6)L mol(-1)s(-1), (3.3+/-0.5)x10(4)L mol(-1)s(-1), and (4.9+/-0.3)x10(4)L mol(-1)s(-1), respectively. Calculations performed at the density functional theory level support the hypothesis that the similarity in the values of k(+) and k(0) results from intramolecular hydrogen bonding that plays a crucial role. This study indicates that the half-life of CEE in blood is on the order of one minute, suggesting that CEE may hydrolyze too quickly to reach muscle cells in its ester form.

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  • Prior studies have shown that CEE degrades rather quickly to creatinine when exposed to low pH levels as would be found in the stomach.

    “However, prior studies have shown that it degrades rather quickly to creatinine when exposed to low pH levels as would be found in the stomach (Giese and Lecher 2009a; Katseres et al. 2009).”

    From Analysis of the efficacy, safety, and regulatory status of novel forms of creatine (2011) · cites this paper as Katseres et al. 2009

  • CEE rapidly degrades to creatinine when exposed to stomach acid; under physiological conditions, CEE non-enzymatically converts to creatinine with no measurable conversion to creatine; and the half-life of CEE is about one minute, suggesting it may hydrolyze too quickly to reach muscle cells in its ester form.

    “Childs and Tallon reported that CEE rapidly degrades to creatinine when exposed to stomach acid [34].”

    From Bioavailability, Efficacy, Safety, and Regulatory Status of Creatine and Related Compounds: A Critical Review (2022) · cites this paper as [193]

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Authors
Katseres, N. S., Reading, D. W., Shayya, L., DiCesare, J. C., & Purser, G. H.
Affiliations
University of Tulsa (US)
Corresponding author
Purser, Gordon H.
Venue
Biochemical and Biophysical Research Communications
Publisher
Elsevier BV
Published
2009-08
Volume
386
Issue
2
Pages
363-367
ISSN
0006-291X (ISSN-L)
DOI
10.1016/j.bbrc.2009.06.037
OpenAlex
W2138449327
Cited by
20
References
5
Citations by year
2023: 1 · 2022: 1 · 2021: 1 · 2019: 1 · 2016: 1 · 2015: 3 · 2014: 1 · 2013: 3
FWCI
1.07
Type
journal article
Language
en
Open access
closed
Licence
www.elsevier.com/tdm/userlicense/1.0/ (tdm)
Locations
  • Biochemical and Biophysical Research Communications (publishedVersion)
  • PubMed (publishedVersion)
Topics
  • Physical Sciences › Chemistry › Organic Chemistry › Chemical Reaction Mechanisms
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Cell Biology › Muscle metabolism and nutrition
  • Physical Sciences › Chemistry › Analytical Chemistry › Analytical Methods in Pharmaceuticals
Keywords
non-enzymatic hydrolysis, ester hydrolysis kinetics, protonation states, pKa determination, rate law, intramolecular hydrogen bonding, DFT calculations
MeSH terms
Creatine, Hydrogen-Ion Concentration, Hydrolysis, Kinetics, Magnetic Resonance Spectroscopy, Temperature

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