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.

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.

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 1- and 2-Naphthylalanine Analogs of Oxytocin and Vasopressin

1995 ◽  
Vol 60 (12) ◽  
pp. 2170-2177 ◽  
Author(s):  
Zdenko Procházka ◽  
Jiřina Slaninová
Keyword(s):  
Amino Acids ◽  
Solid Phase ◽  
Pressor Test

Solid phase technique on p-methylbenzhydrylamine resin was used for the synthesis of four analogs of oxytocin and four analogs of vasopressin with the non-coded amino acids L- or D- and 1- or 2-naphthylalanine and D-homoarginine. [L-1-Nal2]oxytocin, [D-1-Nal2]oxytocin, [L-2-Nal2]oxytocin, [D-2-Nal2]oxytocin, [L-1-Nal2, D-Har8]vasopressin, [D-1-Nal2, D-Har8]vasopressin, [L-2-Nal2, D-Har8]vasopressin and [D-2-Nal2, D-Har8]vasopressin were synthesized. All eight analogs were found to be uterotonic inhibitors in vitro and in vivo. Analogs with 2-naphthylalanine are stronger inhibitors, particularly in the vasopressin series than the analogs with 1-naphthylalanine. Analogs with 1-naphthylalanine have no activity in the pressor test, analogs with 2-naphthylalanine are weak pressor inhibitors.

[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.

scholarly journals Oxytocin analogues with amide groups substituted by tetrazole groups in position 4, 5 or 9.

2007 ◽  
Vol 54 (4) ◽  
pp. 805-811 ◽  
Author(s):  
Michał Manturewicz ◽  
Zbigniew Grzonka ◽  
Lenka Borovicková ◽  
Jirina Slaninová
Keyword(s):  
Amino Acids ◽  
Solid Phase ◽  
Biological Activities ◽  
Synthesis Method ◽  
Oxytocin Receptor ◽  
Amide Group ◽  
Biologically Active ◽  
Side Chain ◽  
Electronic Effects

Eleven oxytocin analogues substituted in position 4, 5 or 9 by tetrazole analogues of amino acids were prepared using solid-phase peptide synthesis method and tested for rat uterotonic in vitro and pressor activities, as well as for their affinity to human oxytocin receptor. The tetrazolic group has been used as a bioisosteric substitution of carboxylic, ester or amide groups in structure-activity relationship studies of biologically active compounds. Replacement of the amide groups of Gln(4) and Asn(5) in oxytocin by tetrazole analogues of aspartic, glutamic and alpha-aminoadipic acids containing the tetrazole moiety in the side chains leads to analogues with decreased biological activities. Oxytocin analogues in which the glycine amide residue in position 9 was substituted by tetrazole analogues of glycine had diminished activities as well. The analysis of differences in rat uterotonic activity and in the affinity to human oxytocin receptors of analogues containing either an acidic 5-substituted tetrazolic group or a neutral 1,5- or 2,5-tetrazole nucleus makes it possible to draw some new conclusions concerning the role of the amide group of amino acids in positions 4, 5 and 9 of oxytocin for its activity. The data suggest that the interaction of the side chain of Gln(4) with the oxytocin receptor is influenced mainly by electronic effects and the hydrogen bonding capacity of the amide group. Steric effects of the side chain are minor. Substitution of Asn(5) by its tetrazole derivative gave an analogue of very low activity. The result suggests that in the interaction between the amide group of Asn(5) and the binding sites of oxytocic receptor hydrogen bonds are of less importance than the spatial requirements for this group.

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.

4-THREONINE ANALOGUES OF NEUROHYPOPHYSIAL HORMONES WITH SELECTIVELY ENHANCED OXYTOCIN-LIKE ACTIVITIES

1971 ◽  
Vol 49 (1) ◽  
pp. 151-165 ◽  
Author(s):  
W. H. SAWYER ◽  
M. MANNING
Keyword(s):  
Amino Acids ◽  
Solid Phase ◽  
Biological Activities ◽  
Molecular Structures ◽  
Natural Hormone ◽  
Equal Dose ◽  
Rabbit Milk ◽  
Natural Hormones

SUMMARY The 4-threonine analogues of oxytocin and of mesotocin and isotocin were prepared by solid-phase synthesis. [4-Threonine]-oxytocin is about twice as active as oxytocin in rat uterus assays in vitro and in vivo and about three times as active in fowl vasodepressor assays. It is slightly more active than oxytocin in rat or rabbit milk-ejection assays. When infused intravenously into water-loaded rats it causes much less depression of diuresis than does an equal dose of oxytocin. [4-Threonine]-oxytocin has much less vasopressor activity than oxytocin. [4-Threonine]-mesotocin also shows enhanced oxytocin-like properties. Its oxytocic activity is equal to or greater than that of oxytocin and its fowl vasodepressor potency is about the same as that of [4-threonine]-oxytocin, 1500 u./mg. It also has less antidiuretic and vasopressor activities than mesotocin. Thus 4-threonine analogues, containing nothing but common l-amino acids, appear to have more of the specific oxytocin-like properties and less of the vasopressin-like properties than do oxytocin or mesotocin. Thus they may be considered improvements on the natural hormones. In this respect they are unique among the reported synthetic analogues of natural peptide hormones. Substitution of 4-threonine in the weakly-active analogue [3-leucine]-oxytocin also increases its oxytocic and fowl vasodepressor activities. Thus a threonine in the 4-position appears to endow oxytocin-like peptides with greater specific activities than do the amino acids that occur naturally in this position, glutamine and serine. These observations may be of interest when considered (a) from an evolutionary viewpoint, (b) in attempting to interpret relations between molecular structures and biological activities, and (c) as describing peptides with more of the desired properties of oxytocin and less of the undesired properties which might have therapeutic advantages over the natural hormone.

Sulfur-free parathyroid hormone analogs containing D-amino acids: biological properties in vitro and in vivo

Biochemistry ◽  
1981 ◽  
Vol 20 (25) ◽  
pp. 7246-7250 ◽  
Author(s):  
Michael Rosenblatt ◽  
Marc D. Coltrera ◽  
Gary L. Shepard ◽  
D. A. Gray ◽  
John A. Parsons ◽  
...  
Keyword(s):  
Amino Acids ◽  
Parathyroid Hormone ◽  
Biological Properties ◽  
Hormone Analogs

scholarly journals In Vitro and In Silico Evaluation of Biological Properties of Some 1, 3, 4-Oxadiazole Derivatives Against Streptococcus mutans and Their Interaction With Gbp-C by Molecular Docking

2021 ◽  
Vol 13 (4) ◽  
pp. 142-147
Author(s):  
Behin Omidi ◽  
Yasin SarveAhrabi
Keyword(s):  
Amino Acids ◽  
Molecular Docking ◽  
Hydrogen Bonds ◽  
Streptococcus Mutans ◽  
In Silico ◽  
Antibacterial Properties ◽  
Inhibition Zone ◽  
Biological Properties ◽  
High Concentrations

Background: The need to replace new drug structures for the treatment of resistant strains has become essential. Streptococcus mutans is one of the most important factors in causing tooth decay. Glucan binding protein-C (Gbp-C) is a crucial mobileular floor protein that is worried in biofilm formation, and 1, 3, 4-oxadiazoles are new antibacterial structures. Accordingly, this study focused on assessing in vitro and in silico activity of our previously synthesized compounds of 1, 3, 4-oxadiazole against S. mutans. Methods: To this end, our previously synthesized derivatives were re-synthesized and prepared, and then antibacterial susceptibility tests were used for inhibition zone, minimum inhibitory concentration (MIC), and minimum bactericidal concentration (MBC) test values. The molecular docking method was also applied to confirm the effect of compounds in interaction with the Gbp-C of S. mutans. Results: All compounds showed different effects against the bacterial sample. Among these, the most effective ones were related to naphthalene (4d), fluorophenyl (4e), and dimethoxyphenyl (4h) derivatives against S. mutans, respectively. Other compounds also had antibacterial properties but to a lesser extent. In the molecular part, compounds 4d and 4h had the highest affinity to inhibit the GbpC-protein. compound 4d with amino acids ASP and GLN established 402 and 391 hydrogen bonds, respectively, and compound 4h with amino acids SER, GLU, THR, and TRP established 347, 360, 449, and 451 hydrogen bonds, respectively. Conclusions: In general, 1, 3, 4-oxadiazoles containing naphthalene and dimethoxy phenyl functional groups in high concentrations can be good alternatives to the existing drugs for eliminating caries-causing tooth mutants that have drug resistance. It seems that more inhibitory effects can be observed on clinical specimens by adding different purposeful groups and increasing the destructive power of oxadiazole-based compounds.

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