Muramyl-dipeptide analogues: Synthesis and biological activities

1988 ◽  
Vol 53 (11) ◽  
pp. 2897-2906 ◽  
Author(s):  
Jan Ježek ◽  
Milan Zaoral ◽  
Miloš Buděšínský ◽  
Jiří Günther ◽  
Jiří Rotta
Keyword(s):  
Biological Activities ◽  
Muramyl Dipeptide ◽  
Delayed Hypersensitivity ◽  
Test Compound ◽  
Active Compounds ◽  
Dipeptide Analogues ◽  
Pyrogenic Activity

In the search for immunoadjuvant active compounds without pyrogenic activity we prepared N-Ac-norMur-L-Abu-D-Gln-O-Bu (V), N-Ac-Mur-L-Abu-D-Gln-O-Bu (VII) and their respective α-benzylglycosides VI and VIII. All the prepared compounds are nonpyrogenic. In the delayed hypersensitivity test, compound V is inactive, VI is comparable to MDP, VII is more and VIII is less active than MDP.

scholarly journals Muramyl peptides. Variation of somnogenic activity with structure.

1984 ◽  
Vol 159 (1) ◽  
pp. 68-76 ◽  
Author(s):  
J M Krueger ◽  
J Walter ◽  
M L Karnovsky ◽  
L Chedid ◽  
J P Choay ◽  
...  
Keyword(s):  
Slow Wave Sleep ◽  
Biological Activities ◽  
Muramyl Dipeptide ◽  
Response Relationship ◽  
Dose Response Relationship ◽  
Structural Requirements ◽  
Naturally Occurring ◽  
Muramyl Peptide ◽  
S Factor ◽  
Pyrogenic Activity

Sleep-promoting activities of muramyl dipeptide (MDP) (NAc-Mur-L-ala-D-isogln) and the naturally occurring muramyl peptide(s), factor S, have recently been demonstrated. We now have amplified our understanding of structural requirements for somnogenic activity. The effects of several analogs of MDP on rabbit slow-wave sleep are presented and these results are compared to the dose-response relationship for MDP. Some tentative conclusions as to structural requirements for somnogenic activity are presented; most notably, amidation of the free gamma-carboxyl of MDP and several of its analogs resulted in the loss of somnogenic activity. MDP also can induce febrile and immunostimulatory responses. In the present paper, we show that some analogs possess immunostimulatory and pyrogenic activity but not somnogenic activity, thus suggesting that these biological activities of muramyl peptides may, in part, be mediated by separate mechanisms.

Combinatorial Design of Molecule using Activity-Linked Substructural Topological Information as Applied to Antitubercular Compounds

2018 ◽  
Vol 15 (1) ◽  
pp. 67-81 ◽  
Author(s):  
Chandan Raychaudhury ◽  
Md. Imbesat Hassan Rizvi ◽  
Debnath Pal
Keyword(s):  
Biological Activities ◽  
Combinatorial Design ◽  
Combinatorial Structure ◽  
Potential Drug ◽  
Structure Generation ◽  
Topological Information ◽  
Active Compounds ◽  
Antitubercular Drugs ◽  
Topological Distance ◽  
Drug Molecules

Background: Generating a large number of compounds using combinatorial methods increases the possibility of finding novel bioactive compounds. Although some combinatorial structure generation algorithms are available, any method for generating structures from activity-linked substructural topological information is not yet reported. Objective: To develop a method using graph-theoretical techniques for generating structures of antitubercular compounds combinatorially from activity-linked substructural topological information, predict activity and prioritize and screen potential drug candidates. </P><P> Methods: Activity related vertices are identified from datasets composed of both active and inactive or, differently active compounds and structures are generated combinatorially using the topological distance distribution associated with those vertices. Biological activities are predicted using topological distance based vertex indices and a rule based method. Generated structures are prioritized using a newly defined Molecular Priority Score (MPS). Results: Studies considering a series of Acid Alkyl Ester (AAE) compounds and three known antitubercular drugs show that active compounds can be generated from substructural information of other active compounds for all these classes of compounds. Activity predictions show high level of success rate and a number of highly active AAE compounds produced high MPS score indicating that MPS score may help prioritize and screen potential drug molecules. A possible relation of this work with scaffold hopping and inverse Quantitative Structure-Activity Relationship (iQSAR) problem has also been discussed. The proposed method seems to hold promise for discovering novel therapeutic candidates for combating Tuberculosis and may be useful for discovering novel drug molecules for the treatment of other diseases as well.

scholarly journals Green Synthesis andIn VitroBiological Evaluation of Heteroaryl Chalcones and Pyrazolines of Medicinal Interest

2013 ◽  
Vol 2013 ◽  
pp. 1-4 ◽  
Author(s):  
Vishal Banewar
Keyword(s):  
Green Synthesis ◽  
Elemental Analysis ◽  
Broad Spectrum ◽  
Spectroscopic Data ◽  
Heterocyclic Compounds ◽  
Biological Activities ◽  
Biological Evaluation ◽  
Active Compounds

Pyrazolines are well known and important nitrogen containing 5-membered heterocyclic compounds. In the present investigation, a series of various heteroaryl chalcones and pyrazolines were synthesized by condensing formylquinolines with diverse ketones. The newly synthesized 2-pyrazolines were characterized on the basis of elemental analysis and spectroscopic data. All of the newly synthesized target compounds were selected by the NCI forin vitrobiological evaluation. These active compounds exhibited broad spectrum of various biological activities. Most of the compounds showed potent activity.

scholarly journals Activity-relevant similarity values for fingerprints and implications for similarity searching

F1000Research ◽  
2016 ◽  
Vol 5 ◽  
pp. 591 ◽  
Author(s):  
Swarit Jasial ◽  
Ye Hu ◽  
Martin Vogt ◽  
Jürgen Bajorath
Keyword(s):  
Characteristic Feature ◽  
Success Rate ◽  
Similarity Search ◽  
Unsolved Problem ◽  
Biological Activities ◽  
Similarity Searching ◽  
Search Performance ◽  
General Activity ◽  
Active Compounds ◽  
Scientific Foundation

A largely unsolved problem in chemoinformatics is the issue of how calculated compound similarity relates to activity similarity, which is central to many applications. In general, activity relationships are predicted from calculated similarity values. However, there is no solid scientific foundation to bridge between calculated molecular and observed activity similarity. Accordingly, the success rate of identifying new active compounds by similarity searching is limited. Although various attempts have been made to establish relationships between calculated fingerprint similarity values and biological activities, none of these has yielded generally applicable rules for similarity searching. In this study, we have addressed the question of molecular versus activity similarity in a more fundamental way. First, we have evaluated if activity-relevant similarity value ranges could in principle be identified for standard fingerprints and distinguished from similarity resulting from random compound comparisons. Then, we have analyzed if activity-relevant similarity values could be used to guide typical similarity search calculations aiming to identify active compounds in databases. It was found that activity-relevant similarity values can be identified as a characteristic feature of fingerprints. However, it was also shown that such values cannot be reliably used as thresholds for practical similarity search calculations. In addition, the analysis presented herein helped to rationalize differences in fingerprint search performance.

scholarly journals Co-Microencapsulation of Anthocyanins from Black Currant Extract and Lactic Acid Bacteria in Biopolymeric Matrices

Molecules ◽  
2020 ◽  
Vol 25 (7) ◽  
pp. 1700 ◽  
Author(s):  
Iuliana Maria Enache ◽  
Aida Mihaela Vasile ◽  
Elena Enachi ◽  
Vasilica Barbu ◽  
Nicoleta Stănciuc ◽  
...  
Keyword(s):  
Lactic Acid ◽  
Lactic Acid Bacteria ◽  
Biological Activities ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Confocal Laser ◽  
In Vitro Digestibility ◽  
Black Currant ◽  
Active Compounds ◽  
Food Ingredients

Anthocyanins from black currant extract and lactic acid bacteria were co-microencapsulated using a gastro-intestinal-resistant biocomposite of whey protein isolate, inulin, and chitosan, with an encapsulation efficiency of 95.46% ± 1.30% and 87.38% ± 0.48%, respectively. The applied freeze-drying allowed a dark purple stable powder to be obtained, with a satisfactory content of phytochemicals and 11 log colony forming units (CFU)/g dry weight of powder (DW). Confocal laser microscopy displayed a complex system, with several large formations and smaller aggregates inside, consisting of biologically active compounds, lactic acid bacteria cells, and biopolymers. The powder showed good storage stability, with no significant changes in phytochemicals and viable cells over 3 months. An antioxidant activity of 63.64 ± 0.75 mMol Trolox/g DW and an inhibitory effect on α-amylase and α-glucosidase of 87.10% ± 2.08% and 36.96% ± 3.98%, respectively, highlighted the potential biological activities of the co-microencapsulated powder. Significantly, the in vitro digestibility profile showed remarkable protection in the gastric environment, with controlled release in the intestinal simulated environment. The powder was tested by addition into a complex food matrix (yogurt), and the results showed satisfactory stability of biologically active compounds when stored for 21 d at 4 °C. The obtained results confirm the important role of microencapsulation in ensuring a high degree of protection, thus allowing new approaches in developing food ingredients and nutraceuticals, with enhanced functionalities.

Biological activities of Pseudevernia furfuracea (L.) Zopf extracts and isolation of the active compounds

2012 ◽  
Vol 144 (3) ◽  
pp. 726-734 ◽  
Author(s):  
Ayşegül Güvenç ◽  
Esra Küpeli Akkol ◽  
İpek Süntar ◽  
Hikmet Keleş ◽  
Sulhiye Yıldız ◽  
...  
Keyword(s):  
Biological Activities ◽  
Active Compounds ◽  
Pseudevernia Furfuracea

Festphasensynthese von Muramyldipeptidderivaten und Untersuchung ihrer biologischen Aktivität / Solid Phase Synthesis of Muramyl Dipeptide Derivatives and Investigations on their Biological Activities

1994 ◽  
Vol 49 (5) ◽  
pp. 702-716 ◽  
Author(s):  
Jochen Tschakert ◽  
Wolfgang Voelter
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Biological Activities ◽  
Muramyl Dipeptide ◽  
Phase Synthesis ◽  
Opsonized Zymosan ◽  
Muramyl Dipeptide Derivatives

New muramyl dipeptide derivatives with exchanged carbohydrate residues are described. Each derivative is synthesized via a solid phase synthesis using an aminomethyl anchor resin. All synthetic products can be isolated in good yields. Their biological activities are tested by the luminol-dependent chemiluminescence associated with the phagocytosis of opsonized zymosan by granulocytes.

scholarly journals Activity-relevant similarity values for fingerprints and implications for similarity searching

F1000Research ◽  
2016 ◽  
Vol 5 ◽  
pp. 591 ◽  
Author(s):  
Swarit Jasial ◽  
Ye Hu ◽  
Martin Vogt ◽  
Jürgen Bajorath
Keyword(s):  
Characteristic Feature ◽  
Success Rate ◽  
Similarity Search ◽  
Unsolved Problem ◽  
Biological Activities ◽  
Similarity Searching ◽  
Search Performance ◽  
General Activity ◽  
Active Compounds ◽  
Scientific Foundation

A largely unsolved problem in chemoinformatics is the issue of how calculated compound similarity relates to activity similarity, which is central to many applications. In general, activity relationships are predicted from calculated similarity values. However, there is no solid scientific foundation to bridge between calculated molecular and observed activity similarity. Accordingly, the success rate of identifying new active compounds by similarity searching is limited. Although various attempts have been made to establish relationships between calculated fingerprint similarity values and biological activities, none of these has yielded generally applicable rules for similarity searching. In this study, we have addressed the question of molecular versus activity similarity in a more fundamental way. First, we have evaluated if activity-relevant similarity value ranges could in principle be identified for standard fingerprints and distinguished from similarity resulting from random compound comparisons. Then, we have analyzed if activity-relevant similarity values could be used to guide typical similarity search calculations aiming to identify active compounds in databases. It was found that activity-relevant similarity values can be identified as a characteristic feature of fingerprints. However, it was also shown that such values cannot be reliably used as thresholds for practical similarity search calculations. In addition, the analysis presented herein helped to rationalize differences in fingerprint search performance.

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