Amino and Deamino Analogs of 8-D-Homoarginin-vasopressin with Modified Tyrosine in Position 2: Synthesis and Some Biological Properties

1992 ◽  
Vol 57 (3) ◽  
pp. 604-613 ◽  
Author(s):  
Miroslava Žertová ◽  
Zdenko Procházka ◽  
Jiřina Slaninová ◽  
Jana Škopková ◽  
Tomislav Barth ◽  
...  
Keyword(s):  
Amino Acid ◽  
Solid Phase ◽  
Biological Properties ◽  
Antidiuretic Activity

Solid phase methodology on benzhydrylamine or p-methylbenzhydrylamine resin was used for the synthesis of seven analogs of amino or deamino vasopressin with non-coded amino acid, D-homoarginine, in position 8 and D- or L- O-methyl or O-ethyl tyrosine in position 2. [L-Tyr-(Me)2, D-Har8]vasopressin (I), [D-Tyr(Me)2, D-Har8]vasopressin (II), [L-Tyr(Et)2, D-Har8]vasopressin (III), [D-Tyr(Et)2, D-Har8]vasopressin (IV), [Mpr1, L-Tyr(Me)2, D-Har8]vasopressin (V), [Mpr1, D-Tyr(Me)2, D-Har8]vasopressin (VI) and [Mpr1, D-Tyr(Et)2, D-Har8]vasopressin (VII) were synthesized. All analogs have very low antidiuretic activity. Analogs containing O-methyltyrosine of D-configuration or O-ethyltyrosine of both D- and L-configuration are low pressor inhibitors. All analogs were found to be uterotonic inhibitors, the most potent one in vitro being [Mpr1, D-Tyr(Me)2, D-Har8]vasopressin (VI) with pA2 = 9.0 and [Mpr1, D-Tyr(Et)2, D-Har8]vasopressin (VII) with pA2 = 8.8.

The Analogs of [D-Har8]Vasopressin with Di- and Trisubstituted Phenylalanine in Position 2; Synthesis and Some Biological Properties

1993 ◽  
Vol 58 (11) ◽  
pp. 2751-2760 ◽  
Author(s):  
Miroslava Žertová ◽  
Zdenko Procházka ◽  
Jiřina Slaninová ◽  
Tomislav Barth ◽  
Pavel Majer ◽  
...  
Keyword(s):  
Amino Acids ◽  
Solid Phase ◽  
Biological Properties ◽  
Phase Method ◽  
Antidiuretic Activity ◽  
Solid Phase Method

Four analogs of vasopressin with non-coded amino acids D-homoarginine (in position 8) and 2,6-di- or 2,4,6-trisubstituted L- or D-phenylalanine (in position 2) were synthesized using the solid phase method on p-methylbenzhydrylamine resin. All the analogs were found to be uterotonic inhibitors, the most potent one in vitro and in vivo being [D-Phe(2,4,6-triMe)2,D-Har8]vasopressin with pA2 values equal to 8.1 and 7.5, respectively. All of them had negligible antidiuretic activity and were weak pressor inhibitors.

The Analogs of 8-D-Homoarginin-vasopressin with O-Substituted Phenylalanine in Position 2: Synthesis and Some Biological Properties

1992 ◽  
Vol 57 (5) ◽  
pp. 1103-1110 ◽  
Author(s):  
Miroslava Žertová ◽  
Zdenko Procházka ◽  
Jiřina Slaninová ◽  
Tomislav Barth ◽  
Pavel Majer ◽  
...  
Keyword(s):  
Amino Acids ◽  
Solid Phase ◽  
Biological Properties ◽  
Antidiuretic Activity

Solid phase methodology on p-methylbenzhydrylamine resin was used for the synthesis of four analogs of vasopressin with the non coded amino acids, D-homoarginine (in position 8) and o-substituted L- or D-phenylalanine (in position 2). [L-Phe(o-Me)2,D-Har8]vasopressin (I), [D-Phe(o-Me)2,D-Har8]vasopressin (II), [L-Phe(o-Et)2,D-Har8]vasopressin (III) and [D-Phe(o-Et)2,D-Har8]vasopressin (IV) were synthesized. All analogs had very low antidiuretic activity. Analogs I and IV were low pressor inhibitors. All analogs were found to be the uterotonic inhibitors, the most potent on in vitro being [D-Phe(o-Et)2,D-Har8]vasopressin with a pA2 = 8.4.

Oxytocin analogues with non-coded amino acid residues in position 8: [8-Neopentylglycine]oxytocin and [8-cycloleucine]oxytocin

1987 ◽  
Vol 52 (9) ◽  
pp. 2317-2325 ◽  
Author(s):  
Jan Hlaváček ◽  
Jan Pospíšek ◽  
Jiřina Slaninová ◽  
Walter Y. Chan ◽  
Victor J. Hruby
Keyword(s):  
Amino Acid ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
The Other ◽  
Amino Acid Residues ◽  
Phase Synthesis ◽  
Other Hand ◽  
Fragment Condensation

[8-Neopentylglycine]oxytocin (II) and [8-cycloleucine]oxytocin (III) were prepared by a combination of solid-phase synthesis and fragment condensation. Both analogues exhibited decreased uterotonic potency in vitro, each being about 15-30% that of oxytocin. Analogue II also displayed similarly decreased uterotonic potency in vivo and galactogogic potency. On the other hand, analogue III exhibited almost the same potency as oxytocin in the uterotonic assay in vivo and in the galactogogic assay.

Vasopressin analogues modified in positions 2, 3 and 8. Synthesis and biological effects

1983 ◽  
Vol 48 (5) ◽  
pp. 1341-1351 ◽  
Author(s):  
Ivo Bláha ◽  
Danuta Konopinska ◽  
Milan Zaoral
Keyword(s):  
Amino Acid ◽  
Solid Phase ◽  
Biological Effects ◽  
Solution Synthesis ◽  
Antidiuretic Activity ◽  
Pressor Activity ◽  
Vasopressin Analogues

Four vasopressin analogues, modified in positions 2, 3 and 8 were prepared by solid phase as well as solution synthesis. Analogues, containing a D-amino acid in position 3, exhibit a low but markedly specific antidiuretic activity. Analogues with a D-substituent in position 2 show a more specific pressor activity.

[MeArg1, NLe10]-apelin-12: Optimization of solid-phase synthesis and evaluation of biological properties in vitro and in vivo

Peptides ◽  
2020 ◽  
Vol 129 ◽  
pp. 170320 ◽  
Author(s):  
Maria Sidorova ◽  
Irina Studneva ◽  
Valery Bushuev ◽  
Marina Pal’keeva ◽  
Alexander Molokoedov ◽  
...  
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Biological Properties ◽  
Phase Synthesis

scholarly journals Brushite cement containing gelatin: evaluation of mechanical strength and in vitro degradation

Cerâmica ◽  
2019 ◽  
Vol 65 (374) ◽  
pp. 261-266 ◽  
Author(s):  
L. P. Silva ◽  
M. D. P. Ribeiro ◽  
E. S. Trichês ◽  
M. Motisuke
Keyword(s):  
Mechanical Properties ◽  
Weight Loss ◽  
Compressive Strength ◽  
Solid Phase ◽  
Setting Time ◽  
Biological Properties ◽  
Solubility In Water ◽  
Ringer’S Solution ◽  
Weight Loss Data

Abstract Calcium phosphate cements (CPCs) are potential materials for repairing bone defects, mainly due to their excellent biocompatibility and osteoconductivity. Nevertheless, their low mechanical properties limit their usage in clinical applications. The gelatin addition may improve the mechanical and biological properties of CPCs, but their solubility in water may increase the porosity of the cement during degradation. Thus, the aim of this work was to investigate the influence of gelatin on the setting time, compressive strength and degradation rate of a brushite cement. CPCs were prepared with the addition of 0, 5, 10 and 20 wt% of gelatin powder in the solid phase of the cement. The results indicated that the setting time increased with gelatin. Furthermore, cement with 20 wt% of gelatin had an initial compressive strength of 14.1±1.8 MPa while cement without gelatin had 4.5±1.2 MPa. The weight loss, morphology and compressive strength were evaluated after degradation in Ringer’s solution. According to the weight loss data, gelatin was eliminated of samples during degradation. It was concluded that the presence of gelatin improved CPCs mechanical properties; however, as degradation in Ringer’s solution evolved, cement compressive strength decreased due to gelatin dissolution and, consequently, an increase in sample porosity.

Synthesis and biological properties of vasopressin analogues containing 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

1990 ◽  
Vol 55 (4) ◽  
pp. 1099-1105 ◽  
Author(s):  
Zdenko Procházka ◽  
Juris E. Ancans ◽  
Jiřina Slaninová ◽  
Alena Machová ◽  
Tomislav Barth ◽  
...  
Keyword(s):  
Amino Acid ◽  
Carboxylic Acid ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Biological Activities ◽  
Biological Properties ◽  
Phase Synthesis ◽  
Aromatic Residues ◽  
Synthesis Methodology ◽  
Vasopressin Analogues

Solid phase synthesis methodology on a benzhydrylamine resin was used for the synthesis of three analogues of vasopressin with the non-coded amino acid, 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic), in the position 2 ([Tic2, Lys8]VP (I)) and in the position 3 ([Tic3, Lys8]VP (II)). The analogue containing only one Tic in place of both aromatic residues was also isolated (des-Tyr2-[Tic3, Lys8]VP (III)). The biological activities of all analogues were negligible.

scholarly journals New Chemovariety of Lippia alba From Colombia: Compositional Analysis of the Volatile Secondary Metabolites and Some in vitro Biological Activities of the Essential Oil From Plant Leaves

2019 ◽  
Vol 14 (7) ◽  
pp. 1934578X1986290
Author(s):  
Amner Muñoz-Acevedo ◽  
María C. González ◽  
Juan D. Rodríguez ◽  
Yurina Sh. De Moya
Keyword(s):  
Secondary Metabolites ◽  
Essential Oil ◽  
Solid Phase ◽  
Biological Activities ◽  
Biological Properties ◽  
Northern Region ◽  
Chemical Diversity ◽  
Gas Chromatography Mass Spectrometry ◽  
Lippia Alba

Lippia alba is a plant widely studied due to both chemical diversity and bioactivities related to its ethnobotanical uses. In this work, the composition of the volatile secondary metabolites (volatile fractions/essential oil, EO) of the flower/leaves of L. alba (from northern region of Colombia) was determined by solid phase micro-extraction/distillation-solvent extraction/microwave-hydrodistillation/gas chromatography-mass spectrometry (MWHD/GC-MS), along with some in vitro biological properties (cytotoxicity and acetylcholinesterase enzyme [AChe] inhibition) from leaf EO. Outstanding results were found: (i) cis-piperitone oxide (~13%-46%), germacrene D (~11%-30%), and limonene (~10%-22%) characterized the volatile secondary metabolites from different parts of the plant; (ii) leaf EO showed a moderate hemolytic activity (HC50: 580 ± 1 µg/mL), a significant cytotoxicity on lymphocytes (LC50: 127 ± 3 µg/mL), a high cytotoxicity on HEp2 cell line (LC50: 38 ± 2 µg/mL), and a moderate inhibitory effect on AChE (IC50: 28 ± 2 µg/mL). Based on these results, a new chemovar of L. alba is reported (represented by cis-piperitone oxide) along with its promising cytotoxic and AChE inhibiting properties.

Synthesis and Properties of "Hormonogene" and "Inhibitorogene" Type Oxytocin Analogs

1992 ◽  
Vol 57 (6) ◽  
pp. 1345-1351 ◽  
Author(s):  
B. C. Pal ◽  
Jiřina Slaninová ◽  
Tomislav Barth ◽  
Jerzy Trojnar ◽  
Michal Lebl
Keyword(s):  
Amino Acid ◽  
Inhibitory Action ◽  
Time Course ◽  
Solid Phase ◽  
Prolonged Time ◽  
Prolonged Effect ◽  
In Vivo Tests

Nα-Glycyl, diglycyl and triglycyl [2-D and [2-L-p-ethylphenylalanine]oxytocin analogs were synthesized by the solid phase technology utilizing racemic p-ethylphenylalanine. Analogs containing this amino acid of D-configuration were shown to be weak uterotonic antagonists both in vitro and in vivo tests; the compound containing triglycyl residue in position 1 was shown to have prolonged time course of inhibitory action. Analogs containing the L-amino acid were shown to be inhibitors of uterotonic activity of oxytocin in vitro, but uterotonic agonists with prolonged effect in vivo.

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