cis-Urocanic acid as a potential nickel( ii ) binding molecule in the human skin
Abstract
cis -Urocanic acid, a component of human skin, is an efficient ligand for allergenic Ni 2+ ions, forming high spin complexes.
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Urocanic acid can bind Ni(II) ions.
“We have previously shown that UCA can bind Ni(II) ions [17].”
From Ternary Cu(II) Complex with GHK Peptide and Cis-Urocanic Acid as a Potential Physiologically Functional Copper Chelate (2020) · cites this paper as [17]
The authors previously characterised the interaction of cis- and trans-UCA with Ni(II) ions and found the complexes sufficiently stable to be of potential biological relevance.
“We have previously characterised the interaction of cis- and trans-UCA with Ni(II) ions and found out that the complexes were sufficiently stable to be of potential biological relevance [17].”
From Ternary Cu(II) Complex with GHK Peptide and Cis-Urocanic Acid as a Potential Physiologically Functional Copper Chelate (2020) · cites this paper as [17]
Of the two urocanic acid isomers, cis-UCA binds Ni(II) ions more strongly owing to the chelate effect of its imidazole nitrogen and carboxyl oxygen.
“Of the two isomers, cis-UCA binds Ni(II) ions more strongly owing to the chelate effect of its imidazole nitrogen and carboxyl oxygen.”
From Ternary Cu(II) Complex with GHK Peptide and Cis-Urocanic Acid as a Potential Physiologically Functional Copper Chelate (2020) · cites this paper as [17]
The logβ value of Cu(cis-UCA) is higher than that of Ni(cis-UCA) (4.941 vs 3.406).
“As expected based on the Irving–Williams series [36], the logβ value of Cu(cis-UCA) is higher than that of Ni(cis-UCA) (4.941 vs 3.406) [17].”
From Ternary Cu(II) Complex with GHK Peptide and Cis-Urocanic Acid as a Potential Physiologically Functional Copper Chelate (2020) · cites this paper as [17]
The imidazole pKa of cis-UCA is 6.74 and that of trans-UCA is 5.83.
“(pKa values of 6.74 and 5.83, respectively) [17].”
From Ternary Cu(II) Complex with GHK Peptide and Cis-Urocanic Acid as a Potential Physiologically Functional Copper Chelate (2020) · cites this paper as [17]
The observed difference in pH sensitivity can be attributed to higher basicity of the imidazole moiety in cis-UCA than trans-UCA.
“The observed difference in pH sensitivity can be attributed to higher basicity of the imidazole moiety in cis-UCA than trans-UCA”
From Ternary Cu(II) Complex with GHK Peptide and Cis-Urocanic Acid as a Potential Physiologically Functional Copper Chelate (2020) · cites this paper as [17]
Cites
Moisturization and skin barrier function
Rawlings, A. V., & Harding, C. R. (2004) · Dermatologic Therapy · doi:10.1111/j.1396-0296.2004.04s1005.x · Cited by 924 · see citing works
Beissert, S., Rühlemann, D., Mohammad, T., Grabbe, S., El-Ghorr, A., Norval, M., Morrison, H., Granstein, R. D., & Schwarz, T. (2001) · The Journal of Immunology · doi:10.4049/jimmunol.167.11.6232 · Cited by 77 · see citing works
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Bossak-Ahmad, K., Wiśniewska, M. D., Bal, W., Drew, S. C., & Frączyk, T. (2020) · International Journal of Molecular Sciences · doi:10.3390/ijms21176190 · Cited by 25 · see citing works
Self-citation
- Authors
- Wezynfeld, N. E., Goch, W., Bal, W., & Frączyk, T.
- Affiliations
- Polish Academy of Sciences (PL)
- Corresponding author
- Frączyk, Tomasz
- Venue
- Dalton Trans.
- Publisher
- Royal Society of Chemistry (RSC)
- Published
- 2014
- Volume
- 43
- Issue
- 8
- Pages
- 3196-3201
- ISSN
- 1477-9226 (ISSN-L)
- 1477-9234
- OpenAlex
- W2127074225
- Cited by
- 22
- References
- 2
- Citations by year
- 2023: 2 · 2022: 4 · 2021: 3 · 2020: 3 · 2018: 4 · 2017: 1 · 2016: 2 · 2015: 1 · 2014: 2
- FWCI
- 0.89
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Dalton Transactions (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Health Sciences › Medicine › Oncology › Metal complexes synthesis and properties
- Physical Sciences › Environmental Science › Health, Toxicology and Mutagenesis › Heavy Metal Exposure and Toxicity
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Protein Interaction Studies and Fluorescence Analysis
- Keywords
- cis-urocanic acid, nickel(II) binding, metal ion binding, human skin, histidine derivatives, pH-dependent binding, dissociation constant, metal homeostasis
- MeSH terms
- Histidine, Humans, Hydrogen-Ion Concentration, Ions, Isomerism, Nickel, Skin, Thermodynamics, Ultraviolet Rays, Urocanic Acid
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