Residence Time of Polaprezinc (Zinc L-Carnosine Complex) in the Rat Stomach and Adhesiveness to Ulcerous Sites

Furuta, Shigeru; Toyama, Seiji; Miwa, Masahiro; Itabashi, Takeshi; Sano, Hiroshi; Yoneta, Tomoyuki

doi:10.1254/jjp.67.271

Cited by 22 publications

(12 citation statements)

References 24 publications

(27 reference statements)

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“…Polaprezinc is an insoluble zinc complex that dissolves in acid and seems to act directly on mucosal lesions. It is retained in the stomach longer and adheres to ulcerous sites more than zinc or carnosine, possibly because of its insolubility 15…”

Section: Introductionmentioning

confidence: 99%

Raman and IR spectroscopic investigation of zinc(II)-carnosine complexes

2000

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The zinc(II)–L‐carnosine system was investigated at different pH and metal/ligand ratios by Raman and IR spectroscopy. The Raman and IR spectra present some marker bands useful to identify the sites involved in metal chelation at a specific pH value. In particular, the neutral imidazole group gives rise to some Raman bands, such as the νC4C5 band, that change in wave number, depending on whether the imidazole ring takes the tautomeric form I or II. Even if tautomer I is predominant in the free ligand, metal coordination can upset tautomeric preference and Nτ‐ and Nπ‐ligated complexes can be identified. Although weak compared to those of aromatic residues, these Raman marker bands may be useful in analyzing metal–histidine interaction in peptides and proteins. On the basis of the vibrational results, conclusions can be drawn on the species existing in the system. Depending on the available nitrogen atoms, various complexes can be formed and the prevalent form of the species depends mainly on the pH. At basic pH carnosine gives rise to two different neutral complexes: a water‐insoluble polymeric species, [ZnH−1L] 0italicn, and a dimer, [Zn2H−2L2]0. The first is predominant and involves the tautomeric I form of the imidazole ring in metal chelation; the second contains tautomer II and increases its percentage by going from a 2 to 0.25 metal/ligand ratio. Conversely, the dimeric species dominates at pH 7, whereas two charged species, [ZnHL]2+ and [ZnL]+, are formed under slightly acidic conditions. In the [ZnHL]2+ complex the imidazole ring takes part in the Zn(II) coordination in the tautomeric I form, whereas in [ZnL]+ the ring is protonated and not bound to the Zn(II) ion. In addition, the curve fitting analysis of the 1700–1530 cm−1 Raman region was helpful in indicating the predominant species at each pH. © 2000 John Wiley & Sons, Inc. Biopolymers (Biospectroscopy) 57: 352–364, 2000

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Section: Introductionmentioning

confidence: 99%

Raman and IR spectroscopic investigation of zinc(II)-carnosine complexes

2000

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“…In the present study, we investigated the effect of polaprezinc on the inflammatory response to HPE in vitro. It has been reported that polaprezinc exhibits antiulcer effects by acting mainly on mucosal lesions (18). Polaprezinc shows a long term adhesive and permeable action on the gastric mucosa in acetic acid ulcer rats at the concentration of 10 -7 M to 10 -5 M, and it has a comparable high affinity at the ulcerous site.…”

Section: Discussionmentioning

confidence: 94%

Inhibitory Effects of Polaprezine on the Inflammatory Response toHelicobacter pylori

Handa

Yoshida

Tanaka

et al. 2002

Canadian Journal of Gastroenterology

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Helicobacter pylori-infected gastrointestinal mucosa is frequently infiltrated by polymorphonuclear leukocytes (PMN) and monocytes, and these invading cells have been implicated in gastrointestinal mucosal inflammation. To clarify the efficacy of polaprezinc, a chelate compound consisting of zinc and L-carnosine, against H pylori-induced inflammation including PMN infiltration, the in vitro effects of this drug on interleukin (IL)-8 production by an established gastric cancer cell line (MKN 45 cells) and on PMN-endothelial cell adhesive interactions was investigated. Polaprezinc and zinc sulphate inhibited IL-8 production by MKN 45 cells in response to stimulation with H pylori water extract (HPE) in a dose-dependent manner from 10(-7) M to 10(-5) M. In addition, the expression of CD11b and CD18 on PMN and PMN-dependent adhesion to endothelial cells elicited by HPE was inhibited by polaprezinc and zinc sulphate in a concentration-dependent manner. L-carnosine did not have any effects on IL-8 production or PMN-endothelial cell interactions. These results suggest that polaprezinc, mainly the zinc component, may inhibit H pylori-induced PMN-mediated gastric inflammation by attenuating CD11b/CD18 expression on PMN and IL-8 production from gastric epithelial cells.

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“…The antiulcer drug Polaprezinc consists of the Zn(II)-carnosine complex. Its biological function is still not fully understood [17][18][19][20][21][22]. Recently, the pH-dependent aggregation of Car with Zn(II) and Cu(II) was investigated by ESI-MS and carnosine to metal complexes have been identified [23].…”

Section: Introductionmentioning

confidence: 99%

The Interaction of the Dipeptide Carnosine With Alkali Metal Ions Studied by Ion Trap Mass Spectrometry

Menges

Riehn

Niedner‐Schatteburg³

2011

Zeitschrift Für Physikalische Chemie

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The complexation of alkali metal ions and the proton X + (X = H, Li, Na, K, Rb, Cs) by β-alanyl-L-histidine (carnosine, Car) was investigated by electrospray ionization mass spectrometry (ESI-MS) and MS/MS fragmentation studies. Collision-induced dissociation (CID) breakdown curves were recorded and the resulting apparent activation energies were compared to DFT calculations of binding energies at the B3LYP/cc-pVDZ level of theory. Additionally, the influence of metal complexation on hydrogen/deuterium exchange of CarX + with D 2 O was tested. Our investigations characterize the structures of Car-alkali complexes and elucidate the interaction with the differently sized solvated metal cations.

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Residence Time of Polaprezinc (Zinc L-Carnosine Complex) in the Rat Stomach and Adhesiveness to Ulcerous Sites

Cited by 22 publications

References 24 publications

Raman and IR spectroscopic investigation of zinc(II)-carnosine complexes

Raman and IR spectroscopic investigation of zinc(II)-carnosine complexes

Inhibitory Effects of Polaprezine on the Inflammatory Response toHelicobacter pylori

The Interaction of the Dipeptide Carnosine With Alkali Metal Ions Studied by Ion Trap Mass Spectrometry

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