Vibrational spectral studies of l-citrullinium perchlorate

Jinnah, M. Mohamed Ali; Sasirekha, V.; Ramakrishnan, V.

doi:10.1016/j.saa.2005.03.013

Cited by 6 publications

(3 citation statements)

References 16 publications

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“…As expected, the non‐resonance Raman spectra of NCitGAILSS share very similar characteristics to those of NRGAILSS (data not shown) because the urea group of citrulline is an isostere of the guanidino group of arginine. This is consistent with the published non‐resonance Raman data for both citrulline and arginine 37,48 . An analysis of the spectra obtained when NWGAILSS was co‐incubated with NCitGAILSS revealed peak perturbations in the regions ca.…”

Section: Resultssupporting

confidence: 90%

“…This is consistent with the published nonresonance Raman data for both citrulline and arginine. 37,48 An analysis of the spectra obtained when NWGAILSS was co-incubated with NCitGAILSS revealed peak perturbations in the regions ca. 1180, 1460, and 1554 cm À1 (Figure 2, plot B), similar to those observed when NWGAILSS was co-incubated with NRGAILSS (Figure 2, plot C).…”

Section: Potential Indole Ring Interactionsmentioning

confidence: 99%

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π‐π stacking interactions mediate molecular recognition between arginine and tryptophan containing peptides derived from human islet polypeptide

Vedad,

Bilog,

Chamorro

et al. 2024

J Raman Spectroscopy

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Cation‐π interactions, often found in protein assemblies, are characterized by favorable electrostatic interactions between an aromatic π‐electron surface and a positively charged species. There are evidences that reveal the importance of cation‐π interactions between arginine and aromatic residues in protein structure and function. In this paper, the effect of cation‐π interactions on the aggregation propensity of peptides derived from human islet polypeptide (hIAPP) was explored using UV resonance Raman and fluorescence spectroscopy. By employing an analog of hIAPP22–29 in which Phe‐23 is replaced with tryptophan (NWGAILSS), we were able to demonstrate an increase in the amyloidogenic propensity of this mutant in the presence of Zn2+ that is attributable to cation‐π interactions. In contrast, no cation‐π interactions were observed when the cationic F23R analog of hIAPP22–29 (NRGAILSS) was allowed to interact with NWGAILSS. From these observations, it was surmised that in these peptides, the dominant interaction between arginine and tryptophan involves the π‐cloud of the guanidino group and the indole ring, not cation‐π interactions. The spectroscopic data, supported by density functional theory‐based simulation results, suggest that arginine‐tryptophan interaction involves π‐π stacking where the guanidino group is oriented parallel to the indole ring. These hydrophobic interactions, coupled with the hydrotropic effect of the guanidine functionality of arginine, led to a delay in the aggregation kinetics of NWGAILSS. These unique interactions were further exploited to design a peptide inhibitor of full‐length amylin self‐assembly.

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Section: Resultssupporting

confidence: 90%

Section: Potential Indole Ring Interactionsmentioning

confidence: 99%

π‐π stacking interactions mediate molecular recognition between arginine and tryptophan containing peptides derived from human islet polypeptide

Vedad,

Bilog,

Chamorro

et al. 2024

J Raman Spectroscopy

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“…In the same way as the IR analysis, the theoretical Raman spectrum agrees with the experimental values obtained in this work (Figure 8). The typical bands of Bipyridine complexes are 3077 cm −1 for the rings C-H and 766 cm −1 , corresponding to the C-H out-of-plane bending mode [45]. Most of the other bands overlap with the bands of Citrulline and are difficult to assign.…”

Section: Raman Spectroscopymentioning

confidence: 99%

D,L-Citrullinato-bipyridine Copper Complex: Experimental and Theoretical Characterization

Ramírez-Contreras,

García-García,

Mendoza

et al. 2023

Crystals

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Citrulline is a non-protein amino acid that acts as a metabolic intermediate in the urea cycle and arginine synthesis. It is present in some foods, although its name derives from watermelon (Citrullus vulgaris), from which it was first identified. Under normal conditions, Citrulline exists as a zwitterion in aqueous solutions since its carboxylic and amine groups can act as Lewis donors to chelate metal cations. In addition, Citrulline possesses in the aliphatic chain a terminal ureide group, which could also coordinate. Although Citrulline is comparable to other classical amino acids, its coordination chemistry has yet to be explored. Only two metal complexes have been reported, and the copper complex is a polymeric and insoluble material. As part of our search for active Casiopeina® analogs, we created a more soluble complex by combining 2,2′-Bipyridine into a new mixed material, resulting in the mononuclear complex [Cu(Bipy)(Citr)(H2O)(NO3)]·H2O. Single-crystal X-ray diffraction, spectroscopic methods (FT-IR, UV-Vis, Raman), and mass spectrometry characterized the material. Interestingly, both isomers of Citrulline, R(D), and S(L) are present in the same crystal. In addition, the molecular structure and electronic properties of the complex were calculated using density functional theory (DFT). Non-covalent interactions were characterized using the atoms-in-molecules (AIM) approach and Hirshfeld surface (HS) analysis. This ternary complex containing Citrulline and 2,2′-Bipyridine will be used for docking calculations and preliminary biological studies using calf thymus DNA (CT-DNA) and plasmid pUC19 as a first approximation to cytotoxic activity against cancer cell lines.

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Citrulline malate transdermal delivery through integrating into polyvinyl alcohol (PVA) nanofibers

López-Ramírez

González

Martínez-Pérez

et al. 2021

Journal of Drug Delivery Science and Technology

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Vibrational spectral studies of l-citrullinium perchlorate

Cited by 6 publications

References 16 publications

π‐π stacking interactions mediate molecular recognition between arginine and tryptophan containing peptides derived from human islet polypeptide

π‐π stacking interactions mediate molecular recognition between arginine and tryptophan containing peptides derived from human islet polypeptide

D,L-Citrullinato-bipyridine Copper Complex: Experimental and Theoretical Characterization

Citrulline malate transdermal delivery through integrating into polyvinyl alcohol (PVA) nanofibers

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