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1

Statherin SV2 and Its Analogue. Synthesis and Evaluation of Antimicrobial Activity

Kamysz W., Kochańska B., Kędzia A., Ochocińska J., Maćkiewicz Z., Kupryszewski G.

Polish Journal of Chemistry

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2002

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Vol. 76 / nr 6

801-806

EN

Statherins are natural peptides derived from human saliva. They may take part in transport of calcium and phosphate and most probably are partly responsible for protection and recalcification of tooth enamel. The solid phase synthesis of statherin SV2 and its dephosphorylated analogue, their purification by solid phase extraction (SPE), as well as the evaluation of their antibacterial activity are presented.

2

New Analogues of Cucurbita maxima Trypsin Inhibitor III (CMTI-III) Substituted with D-Arg or D-Lys in Position 5 (P1)

Frąszczak P., Rolka K., Kupryszewski G.

Polish Journal of Chemistry

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2002

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Vol. 76 / nr 4

519-523

EN

Two new analogues of trypsin inhibitor CMTI-III substituted with D-Arg or D-Lys in position 5 (P1) were synthesized by the solid-phase method. The first analogue ([D-Arg5] CMTI-III) displayed association equilibrium constants (Ka) with bovine -trypsin by about three orders of magnitude lower than did wild CMTI-III. The second analogue ([D-Lys5] CMTI-III) displayed Ka by about four orders of magnitude lower than [Lys5] CMTI-III. The configuration of basic amino acid residue (Arg or Lys) in the reactive site (position P1) of CMTI-III and its analogues played an important role for the stabilization of the inhibitors active structure.

3

Interaction of a Transcription Factor IIIA Peptide Containing Two Zinc Fingers with 5S rRNA

Giel-Pietraszuk M., Mucha P., Rekowski P., Kupryszewski G., Barciszewska M. Z.

Polish Journal of Chemistry

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2002

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Vol. 76 / nr 6

815-822

EN

The interaction of lupin ribosomal 5S RNA with a chemically synthesized peptide containing 60 amino acid, derived from Xenopus laevis transcription factor IIIA, is analyzed. The results show that such short fragment retains the ability of binding to 5S rRNA molecule, as shown by electrophoretic gel shift and RNase footprint assay. The peptide protects from hydrolysis with specific nucleases helix II and V of 5S rRNA.

4

Analogues of Ecballium elaterium Trypsin Inhibitor II (EETI-II) with L-Cysteine Residues Substituted by L-Penicillamine (Pen) and L-Homocysteine (Hcy) in Positions 19, 21 and 27

Frąszczak P., Kaźmierczak K., Stawikowski M., Jaśkiewicz A., Kupryszewski G., Rolka K.

Polish Journal of Chemistry

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2002

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Vol. 76 / nr 10

1441-1446

EN

Two analogues of peptidic trypsin inhibitor isolated from seeds of Ecballium elaterium (EETI-II): [Pen19,21,27] EETI-II (1) and [Hcy19,21,27] EETI-II (2) were synthesized by the solid-phase method using the Fmoc/But procedure. Their inhibitory activity was determined by the calculation of association equilibrium constants (Ka) with bovine _-trypsin. In comparison with the parent compound, both analogues showed reduced trypsin inhibitory activity more than 7 and 18 times, respectively. We postulate that the observed differences may reflect the role of disulfide bridges in the interaction of inhibitors with trypsin or the introduced modifications change the conformational equilibrium of the analogues synthesized towards conformation(s) less favorable for the interaction with the enzyme.

5

Specific Interactions of Cu2+ Ions with Enantiomers of Hepatitis B Virus Surface Antigen 140-146 Region

Świątek-Kozłowska J., Brasuń J., Maćkiewicz Z., Kupryszewski G.

Polish Journal of Chemistry

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2001

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Vol. 75, nr 6

813-822

EN

Potentiometric and spectroscopic studies on Cu(II) interactions with 140-146 fragment of the hepatitis B virus antigen have shown that the basic binding sites of metal ion are centered at a peptide N-terminal donor system and the side chain donor atoms are not competing in the metal ion coordination.

6

Low Molecular Mass Inhibitors of Bovine beta-Trypsin Containing Binding Loop Fragment of CMTI-III. Synthesis and Evaluation of Inhibitory Activity

Frąszczak P., Lis K., Jaśkiewicz A., Miecznikowska H., Rolka K., Kupryszewski G.

Polish Journal of Chemistry

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2001

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Vol. 75, nr 12

1863-1868

EN

Three peptides with sequences related to the binding loop of Cucurbita maxima trypsin inhibitor III were obtained: [G3,GIO]CMTI-HI (1-10) (1), [A1,G3,A9,G10]MTlII (1-10) (2) and c(K-A-A-P-R-I-L-M-K-Y-A-E) (3). All peptides were synthesized by the solid-phase methodusing the Fmoc/Bu t procedure. Peptide 1 revealed a relatively high inhibitory activity (association equilibrium constant with bovine beta-trypsin Ka = 4 x 10 9 [M -1]). Significantly lower activity (Ka = 3.6x l O4 [M -1) was obtained for peptide 3. Peptide 2 appeared to be inactive.

7

Cyclic Analogue of Human Heat Shock Protein 70(29-42) Fragment. Synthesis, Conformational Studies and Evaluation of Its Immunogenicity

Karawajczyk B., Wirkus-Romanowska I., Wysocki J., Rolka K., Maćkiewicz Z., Głośnicka R., Kupryszewski G.

Polish Journal of Chemistry

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2001

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Vol. 75, nr 2

265-273

EN

The cyclic hexadecapeptide containing human heat shock protein 70(29-42) fragment cyclized by the disulfide bridge between two L-cysteine residues introduced at the N- and C-termini was synthesized by the solid phase method. It was established that the cyclic analogue, contrary to its linear counterpart, had much lower ability to generate immune response in rabbits. Conformational studies of cyclic peptide performed using 1D and 2D 1H-NMR spectroscopy in conjunction with theoretical conformational analysis revealed that the cyclization constrained the 3D structure of this peptide, reflected by the observed rate of cis/trans isomerization of Arg9-Thr10 peptide bond and the presence of Gly7-Asn8 peptide bond in cis geometry.We, therefore, postulate that the conformational flexibility in the case of Human Heat Shock Protein fragments is a key element for their immunogenicity.

8

The effect of humic substances isolated from a variety of marine and lacustrine environments on different microorganisms [commun.]

Kupryszewski G., Pempkowiak J., Kędzia A.

Oceanologia

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2001

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No. 43 (2)

257-261

EN

The antimicrobial activity of twelve preparations of humic substances isolated from sea water, marine bottom sediments and lake water was examined. Humic substances from marine bottom sediment samples were fractionated into humic and/or fulvic acids. The susceptibility of 11 strains of anaerobic, 8 strains of aerobic bacteria and 2 strains of yeast-like fungi to preparations of humic substances, humic and/or fulvic acids was determined employing the plate dilution technique in Brucella agar (anaerobic bacteria), Mueller-Hinton agar (aerobic bacteria) and Sabouraud agar (yeast-like fungi). Concentrations from 150 to 600 žg ml-1 of the preparations examined inhibited the growth of numerous microorganisms (Table). The results obtained seem to indicate that humic substances are involved in the self-purification of sea and lake waters.

9

New Analogues of Proline-Rich Protein Fragments : Synthesis and Their Effect on Resistance of Murine Thymocytes to Hydrocortisone

Wirkus-Romanowska I., Miecznikowska H., Janusz M., Szymaniec S., Fortuna W., Międzybrodzki R., Zablocka M., Lisowski J., Kupryszewski G.

Polish Journal of Chemistry

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2000

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Vol. 74, nr 7

979-984

EN

New analogues of proline-rich protein (PRP) fragment were synthezed by the solid phase method using Boc/Bzl procedure. Dimer of the nonapeptide as well as dimer, trimer and tetramer of hexapeptide fragments of PRP possesing immunotropic activity were obtained.

10

Fragments of a Proline-Rich Polypeptide Settled on a Hexapeptide Carcass Constructed of Glycine and L-Lysine Residues : Synthesis and Biological Properties

Wirkus-Romanowska I., Miecznikowska H., Zablocka M., Rybka K., Fortuna W., Międzybrodzki R., Szymaniec S., Janusz M., Lisowski J., Kupryszewski G.

Polish Journal of Chemistry

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2000

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Vol. 74, nr 2

219-225

EN

Proline-rich polypeptide fragments settled on a hexapeptide constructed od L-lysine and glycine residues were synthesized by the solid phase method: X-Lys(X)-Gly-Lys(X)-Gly-Lys(X)-Gly-OH, X= Tyr-Val-Pro-Leu-Phe-Pro and Y-Lys(Y)-Gly-Lys(Y)-Gly-Lys(Y)-Gly-OH, Y=Val-Glu-Ser-Tyr-Val-Pro-Leu-Phe-Pro. Imunotropic activity of the analogues was determined in a murine syste using resistance to hydrocortisone and in human cell cultures using induction of cytokines as indicators.

11

Enantiomers of Hepatitis B Virus (HBV) Surface Antigen (140-146) S Region Fragment : Synthesis and Studies on Immunological Properties

Kunikowska D., Dera-Tomaszewska B., Dziadziuszko H., Wysocki J., Wolańska I., Maćkiewicz A., Głosnicka R., Kupryszewski G.

Polish Journal of Chemistry

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1999

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Vol. 73, nr 11

1803-1809

12

Cyclic Analogues of Proline-Rich Protein Fragments : Part II : Conformational Studies Using NMR Spectroscopy and Theoretical Conformational Analysis

Rodziewicz S., Wirkus-Romanowska I., Ciurak M., Miecznikowska H., Kupryszewski G., Czaplewski C., Liwo A., Rolka K.

Polish Journal of Chemistry

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1999

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Vol. 73, nr 10

1697-1710

EN

These peptides were designed based on the immunoregulatory activity of linear peptides obtained after chymotrypsin digestion of PRP. Despite the fact that the structures of both analogues cannot be interpreted in terms of a single conformation, the superposition of the most populated conformations of the cyclic peptides studied revealed a similar geometry for the Tyr-Val-pro-Leu-Phe-Pro fragment (RMSD=1.6 A) in both peptides and therefore might be considered to be responsible for the biological activity.

13

Identification of selected siderophores in the Baltic Sea environment by the use of capillary electrophoresis

Kosakowska A., Kupryszewski G., Mucha P., Rekowski P., Lewandowska J., Pazdro K.

Oceanologia

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1999

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No. 41 (4)

573-587

EN

Extracts from seawater and sediment pore water samples were characterised by capillary electrophoresis (CE). Siderophores of the ferrioxamine family were identified. Ferrioxamine E is the dominant siderophore in both seawater and sediment pore water samples from different regions of the Baltic Sea. Ferrioxamine G was identified in subsurface seawater samples from the Gdansk Deep. Rhodotorulic acid was also identified in seawater samples from the euphotic zone (0-30 m) of Puck Bay and in sediment pore water from Puck Bay and the Bornholm Deep. Ferrioxamine B was not found. The presence of catechol siderophores was not investigated.

14

Synthesis of human heat shock protein 70 (29-42) fragment and evaluation of its immunogenicity

Karawajczyk B., Wysocki J., Kunikowska D., Maćkiewicz Z., Głośnicka R., Korzeniowski A., Górski J., Kupryszewski G.

Polish Journal of Chemistry

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1998

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Vol. 72, nr 6

1017-1020

EN

The 29-42 fragment of human heat shock protein 70 (hsp 70) was synthesized by the solid phase method. As determined by enzyme-linked immunosorbent assay (ELISA), the synthetic hsp 70(29-42) peptide generated relatively strong immune response in immunized rabbits. Antibody titers were comparable with anti hsp 70 antibody serum level that was induced by immunization with recombinant protein (hsp 70). It was established that antibodies directed against hsp 70(29-42) peptide could be applied in ELISA for detecting hsp 70 in body fluids and tissues.

15

Synthesis of hepatitic C virus protein fragments and evaluation of their immunogenicity

Karawajczyk B., Maćkiewicz Z., Kunikowska D., Dziadziuszko H., Dera-Tomaszewska B., Głośnicka R., Kupryszewski G.

Polish Journal of Chemistry

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1998

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Vol. 72, nr 1

84-88

EN

Three polypeptide fragments of Hepatitis C virus protein (130-140)C, (133-142)C and (1406-1415)NS3 were synthesized using the solid-phase method. The immunogenicity of the peptides was tested on rabbits. All the peptides studied revealed homoral and cell response.

16

Statherin and its shortened analogues

Wojciechowska I., Kochańska B., Stelmańska E., Knap N., Maćkiewicz Z., Kupryszewski G.

Polish Journal of Chemistry

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1998

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Vol. 72, nr 9

2098-2102

EN

Statherin is a 43-amino acid residue phosphominiprotein present in human parotid and submandibular saliva. It may take part in transport of calcium and phosphate and most probably is partly responsible for the protection and recalcification of tooth enamel. The solid phase synthesis of statherin and its three shorttened analoques: (1-15)statherin, [Ser(2), Ser(3)](1-15) statherin and [Asp(2), Asp(3)](1-15) statherin is presented. It was established that polyclonal antibodies directed against three shortened analoques showed affinity to synthetic statherin and statherin in saliva.

17

Cyclic analogues of proline-rich protein fragments. Part 1. Synthesis and evaluation of immunotropic activity

Wirkus-Romanowska I., Ciurak M., Miecznikowska H., Rolka K., Janusz M., Szymaniec S., Krukowska K., Lisowski J., Kupryszewski G.

Polish Journal of Chemistry

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1998

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Vol. 72, nr 11

2394-2398

EN

Proline-rich protein (PRP), isolated from ovine colostrum, possesses strong immunotropic activity. The nonapeptide (Val-Glu-Ser-Tyr-Val-Pro-Leu-Phe-Pro) and the hexapeptide (Tyr-Val-Pro-Leu-Phe-Pro) PRP fragments reveled biological activity similar to that of the native protein. Seeking for analogues of PRP fragments with costrained structure, two cyclic peptides were synthesized by the solid phase method: Cys-Val-Glu-Ser-Tyr-Val-Pro-Leu-Phe-Pro-Cys and Ac-Glu-Tyr-Val-Pro-Leu-Phe-Pro-Lys-NH2. Immunotropic activity of both peptides in murine system was the same as for linear nonapeptide, whereas all three peptides were practically inactive in human system, where resistance to hydrocortisone and induction of two cytokinins IFN and TNF were used as indicators, respectively.

18

Analogue of Cucurbita maxima trypsin inhibitor III (CMTI-III) with AII L-cysteine residues substituted by L-penicillamine (Pen). Synthesis and evaluation of trypsin inhibitory activity

Jaśkiewicz A., Lesner A., Różycki J., Kupryszewski G., Rolka K.

Polish Journal of Chemistry

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1998

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Vol. 72, nr 12

2537-2540

EN

A 29-peptide, [ Pen(3,10,16,20,22,28) ] CMTI-III, an analogue of Cucurbita maxima trypsin inhibitor from squash seeds was synthesized by the solid phase method using the Fmoc chemistry. The inhibitory activity of the analogue, as measured by the association equilibrium constant (K-a) with bovine beta-trypsin, is of the same order of magnitude as that for the wild CMTI-III.