Comparative study of dG affinity vs. DNA methylation modulating properties of side chain derivatives of procainamide: insight into its DNA hypomethylating effect

RSC Advances ◽  
2016 ◽  
Vol 6 (7) ◽  
pp. 5350-5358 ◽  
Author(s):  
R. L. Gawade ◽  
D. K. Chakravarty ◽  
J. Debgupta ◽  
E. Sangtani ◽  
S. Narwade ◽  
...  
Keyword(s):  
Dna Methylation ◽  
Comparative Study ◽  
Structural Features ◽  
Side Chain ◽  
Side Chains ◽  
Hypomethylating Agents ◽  
Derivatives Of ◽  
Insight Into

Structural features of side-chains govern the association of procainamide and its derivatives with dG base of CpG rich DNA, which may differentially hinder the activity of DNMT-1, thereby they act as DNA hypomethylating agents.

scholarly journals Unusual Structural Features in the Adduct of Dirhodium Tetraacetate with Lysozyme

2021 ◽  
Vol 22 (3) ◽  
pp. 1496
Author(s):  
Domenico Loreto ◽  
Giarita Ferraro ◽  
Antonello Merlino
Keyword(s):  
Anticancer Agents ◽  
Structural Features ◽  
Side Chain ◽  
Side Chains ◽  
Valuable Insight ◽  
Experimental Conditions ◽  
Egg White Lysozyme ◽  
Potential Applications ◽  
Model Protein ◽  
Hen Egg White

The structures of the adducts formed upon reaction of the cytotoxic paddlewheel dirhodium complex [Rh2(μ-O2CCH3)4] with the model protein hen egg white lysozyme (HEWL) under different experimental conditions are reported. Results indicate that [Rh2(μ-O2CCH3)4] extensively reacts with HEWL:it in part breaks down, at variance with what happens in reactions with other proteins. A Rh center coordinates the side chains of Arg14 and His15. Dimeric Rh–Rh units with Rh–Rh distances between 2.3 and 2.5 Å are bound to the side chains of Asp18, Asp101, Asn93, and Lys96, while a dirhodium unit with a Rh–Rh distance of 3.2–3.4 Å binds the C-terminal carboxylate and the side chain of Lys13 at the interface between two symmetry-related molecules. An additional monometallic fragment binds the side chain of Lys33. These data, which are supported by replicated structural determinations, shed light on the reactivity of dirhodium tetracarboxylates with proteins, providing useful information for the design of new Rh-containing biomaterials with an array of potential applications in the field of catalysis or of medicinal chemistry and valuable insight into the mechanism of action of these potential anticancer agents.

scholarly journals Synthesis of New Derivatives of BEDT-TTF: Installation of Alkyl, Ethynyl, and Metal-Binding Side Chains and Formation of Tris(BEDT-TTF) Systems

2021 ◽  
Vol 7 (8) ◽  
pp. 110
Author(s):  
Songjie Yang ◽  
Matteo Zecchini ◽  
Andrew Brooks ◽  
Sara Krivickas ◽  
Desiree Dalligos ◽  
...  
Keyword(s):  
Metal Binding ◽  
Tricarboxylic Acid ◽  
Metal Salts ◽  
Side Chain ◽  
Side Chains ◽  
Ethynyl Group ◽  
X Ray ◽  
Transition Metal Salts ◽  
Alkyl Side Chains ◽  
Derivatives Of

The syntheses of new BEDT-TTF derivatives are described. These comprise BEDT-TTF with one ethynyl group (HC≡C-), with two (n-heptyl) or four (n-butyl) alkyl side chains, with two trans acetal (-CH(OMe)2) groups, with two trans aminomethyl (-CH2NH2) groups, and with an iminodiacetate (-CH2N(CH2CO2−)2 side chain. Three transition metal salts have been prepared from the latter donor, and their magnetic properties are reported. Three tris-donor systems are reported bearing three BEDT-TTF derivatives with ester links to a core derived from benzene-1,3,5-tricarboxylic acid. The stereochemistry and molecular structure of the donors are discussed. X-ray crystal structures of two BEDT-TTF donors are reported: one with two CH(OMe)2 groups and with one a -CH2N(CH2CO2Me)2 side chain.

scholarly journals Structural Features Defining NF-κB Inhibition by Lignan-Inspired Benzofurans and Benzothiophenes

Biomolecules ◽  
2020 ◽  
Vol 10 (8) ◽  
pp. 1131
Author(s):  
Toan Dao-Huy ◽  
Simone Latkolik ◽  
Julia Bräuer ◽  
Andreas Pfeil ◽  
Hermann Stuppner ◽  
...  
Keyword(s):  
Significant Influence ◽  
Inhibitory Activity ◽  
Structure Activity Relationship ◽  
Structural Features ◽  
Activity Relationship ◽  
Side Chain ◽  
Side Chains ◽  
Substitution Pattern ◽  
Structure Activity

A series of 2-arylbenzofurans and 2-arylbenzothiophenes was synthesized carrying three different side chains in position five. The synthesized compounds were tested for NF-κB inhibition to establish a structure activity relationship. It was found that both, the side chain in position five and the substitution pattern of the aryl moiety in position two have a significant influence on the inhibitory activity.

scholarly journals Peptide/Peptoid Hybrid Oligomers: The Influence of Hydrophobicity and Relative Side-Chain Length on Antibacterial Activity and Cell Selectivity

Molecules ◽  
2019 ◽  
Vol 24 (24) ◽  
pp. 4429 ◽  
Author(s):  
Nicki Frederiksen ◽  
Paul R. Hansen ◽  
Fredrik Björkling ◽  
Henrik Franzyk
Keyword(s):  
Antibacterial Activity ◽  
Chain Length ◽  
Hydrophobic Surface ◽  
Structural Features ◽  
Side Chain ◽  
Side Chains ◽  
Side Chain Length ◽  
E Coli ◽  
Cell Selectivity ◽  
Wide Range

Previous optimisation studies of peptide/peptoid hybrids typically comprise comparison of structurally related analogues displaying different oligomer length and diverse side chains. The present work concerns a systematically constructed series of 16 closely related 12-mer oligomers with an alternating cationic/hydrophobic design, representing a wide range of hydrophobicity and differences in relative side-chain lengths. The aim was to explore and rationalise the structure–activity relationships within a subclass of oligomers displaying variation of three structural features: (i) cationic side-chain length, (ii) hydrophobic side-chain length, and (iii) type of residue that is of a flexible peptoid nature. Increased side-chain length of cationic residues led to reduced hydrophobicity till the side chains became more extended than the aromatic/hydrophobic side chains, at which point hydrophobicity increased slightly. Evaluation of antibacterial activity revealed that analogues with lowest hydrophobicity exhibited reduced activity against E. coli, while oligomers with the shortest cationic side chains were most potent against P. aeruginosa. Thus, membrane-disruptive interaction with P. aeruginosa appears to be promoted by a hydrophobic surface of the oligomers (comprised of the aromatic groups shielding the cationic side chains). Peptidomimetics with short cationic side chains exhibit increased hemolytic properties as well as give rise to decreased HepG2 (hepatoblastoma G2 cell line) cell viability. An optimal hydrophobicity window could be defined by a threshold of minimal hydrophobicity conferring activity toward E. coli and a threshold for maximal hydrophobicity, beyond which cell selectivity was lost.

Use of malonic acid derivatives for the construction of substituted side chains in the position 17β of steroids

1982 ◽  
Vol 47 (4) ◽  
pp. 1240-1251 ◽  
Author(s):  
Pavel Drašar ◽  
Vladimír Pouzar ◽  
Ivan Černý ◽  
Miroslav Havel ◽  
Sofia N. Ananchenko ◽  
...  
Keyword(s):  
Malonic Acid ◽  
Ethyl Cyanoacetate ◽  
Diethyl Malonate ◽  
Side Chain ◽  
Knoevenagel Reaction ◽  
Side Chains ◽  
Condensation Products ◽  
Malonic Acid Derivatives ◽  
Derivatives Of ◽  
Dioxane Ring

Using the Knoevenagel reaction condensation products of 3β-acetoxyandrost-5-en-17-one with diethyl malonate, ethyl cyanoacetate and malononitrile were prepared which converted to derivatives of 3β-hydroxypregn-5-en-21-oic acid. Reductions and oxidations of the double bonds in the positions 5,6 and 17,20 and the stereochemistry at atoms C(17) and C(20) of some derivatives were also investigated. From derivatives of 23,24-dinorchola-5,17(20)-diene-21,22-diol compounds with a 1,3-dioxane ring in the side chain were prepared.

Comparison of the structural motifs and packing arrangements of six novel derivatives and one polymorph of 2-(1-phenyl-1H-1,2,3-triazol-4-yl)pyridine

2014 ◽  
Vol 70 (2) ◽  
pp. 379-389 ◽  
Author(s):  
Kinaan M. Tawfiq ◽  
Gary J. Miller ◽  
Mohamad J. Al-Jeboori ◽  
Paul S. Fennell ◽  
Simon J. Coles ◽  
...  
Keyword(s):  
Crystal Structures ◽  
Structural Features ◽  
Melting Points ◽  
Intermolecular Contact ◽  
Contact Patterns ◽  
Intermolecular Contacts ◽  
Packing Efficiency ◽  
Derivatives Of ◽  
Insight Into ◽  
Carboxylic Acid Derivative

The crystal structures of a new polymorph and seven new derivatives of 2-(1-phenyl-1H-1,2,3-triazol-4-yl)pyridine have been characterized and examined along with three structures from the literature to identify trends in their intermolecular contact patterns and packing arrangements in order to develop an insight into the crystallization behaviour of this class of compound. Seven unique C—H...Xcontacts were identified in the structures and three of these are present in four or more structures, indicating that these are reliable supramolecular synthons. Analysis of the packing arrangements of the molecules usingXPacidentified two closely related supramolecular constructs that are present in eight of the 11 structures; in all cases, the structures feature at least one of the three most common intermolecular contacts, suggesting a clear relationship between the intermolecular contacts and the packing arrangements of the structures. Both the intermolecular contacts and packing arrangements appear to be remarkably consistent between structures featuring different functional groups, with the expected exception of the carboxylic acid derivative 4-(4-(pyridin-2-yl)-1H-1,2,3-triazol-1-yl) benzoic acid (L11), where the introduction of a strong hydrogen-bonding group results in a markedly different supramolecular structure being adopted. The occurrence of these structural features has been compared with the packing efficiency of the structures and their melting points in order to assess the relative favourability of the supramolecular structural features in stabilizing the crystal structures.

Conformational analysis in aqueous solution and estimation of the persistence length of exopolysaccharides produced by Lactobacillus helveticus Lh59 and Streptococcus macedonicus Sc136

2006 ◽  
Vol 84 (4) ◽  
pp. 730-742 ◽  
Author(s):  
J Albert van Kuik ◽  
Sébastien JF Vincent ◽  
Bas R Leeflang ◽  
Loes MJ Kroon-Batenburg ◽  
Johannis P Kamerling
Keyword(s):  
Conformational Analysis ◽  
Molecular Modelling ◽  
Persistence Length ◽  
Lactobacillus Helveticus ◽  
Side Chain ◽  
Side Chains ◽  
Structural Elements ◽  
Monosaccharide Residue ◽  
A Value ◽  
Insight Into

The conformations of two exopolysaccharides, one produced by Lactobacillus helveticus Lh59 and one by Streptococcus macedonicus Sc136, were investigated by molecular modelling to get insight into their physical properties. In particular, the influence of side chains and glycosidic linkage types on the overall shapes and persistence lengths of the polysaccharides were studied. It appeared that the side chains had only minor effects on the persistence lengths of the polysaccharides, with the exception of the monosaccharide residue directly attached to the backbone. The extensiveness of the backbone is enhanced by β-D-Hexp-(1→4) structural elements, whereas α-D-Hexp-(1→3) and α-D-Hexp-(1→4) elements create structural variability by introducing bends. The occurrence of either (1→5)- or (1→6)-linked monosaccharides, resulting in one extra bond between monosaccharide units, causes the overall flexibility of the polysaccharide chain to be enhanced and extensiveness to be reduced. The presence of such flexible linkages in the backbone leads to a shorter persistence length than when present in the side chain: a value of only 4.5 nm was found for the L. helveticus Lh59 EPS with a (1→5) linkage in the backbone, and a value of 8.5 nm for the S. macedonicus Sc136 EPS with two (1→6) linkages in the side chain.Key words: conformational analysis, exopolysaccharide, Lactobacillus helveticus, molecular modelling, persistence length, Streptococcus macedonicus.

Contribution of Side Chains to Karbutilate Mode of Action

Weed Science ◽  
1975 ◽  
Vol 23 (5) ◽  
pp. 425-427 ◽  
Author(s):  
R. S. Hammerschlag ◽  
J. L. Hilton ◽  
P. G. Bartels ◽  
D. E. Moreland
Keyword(s):  
Seedling Growth ◽  
Mode Of Action ◽  
Acid Ester ◽  
Specific Inhibitor ◽  
Side Chain ◽  
Side Chains ◽  
Inhibiting Action ◽  
Alkyl Carbamate ◽  
Derivatives Of ◽  
Growth Inhibiting

Inhibition of seedling growth and four assays for inhibition of photosynthesis were used to compare karbutilate [tert-butylcarbamic acid ester with 3-(m-hydroxyphenyl)-1,1-dimethylurea] with derivatives of karbutilate in which either the urea or carbamate side chain was missing. Karbutilate was a more potent, more presistent, and more specific inhibitor of photosynthesis than the phenylurea derivative fenuron (1,1-dimethyl-3-phenylurea) that would be formed by removal of the carbamate side chain. However, karbutilate did not exert the growth-inhibiting action observed for the alkyl carbamate derivative phenyl-N-tert-butylcarbamate, formed by removal of the urea side chain, which does not affect photosynthesis at concentrations below 10-3M.

The Chemistry of Pyrrolic Compounds. LXV. Intramolecular Cyclization of Porphyrins With Acetic Acid Side Chains: Hydroxy Derivatives of Deoxophylloerythroaetioporphyrin (DPEP)

1990 ◽  
Vol 43 (5) ◽  
pp. 857 ◽  
Author(s):  
PS Clezy ◽  
AH Mirza ◽  
JK Prashar
Keyword(s):  
Acetic Acid ◽  
Intramolecular Cyclization ◽  
Extraction Process ◽  
Ring System ◽  
Side Chain ◽  
Side Chains ◽  
Hydroxy Groups ◽  
Derivatives Of

The intramolecular cyclization of porphyrins substituted with an acetic acid side chain has been studied under a range of conditions but the yield of product bearing a fused five- membered ketonic ring system was disappointingly low. Deoxophylloerythroaetioporphyrin (DPEP) derivatives with hydroxy groups at either C 13′ or C 15′ have been prepared by reduction of the corresponding ketones. 1H n.m.r . data for the latter alcohol matches well that reported for a porphyrin obtained from Marl Slate and which is probably derived from DPEP, by oxidation, during the extraction process.

Skeletal elements of crinoid echinoderms: High-resolution structural and microanalytical results

1983 ◽  
Vol 41 ◽  
pp. 194-195
Author(s):  
D. F. Blake ◽  
L. F. Allard ◽  
D. R. Peacor
Keyword(s):  
High Resolution ◽  
Marine Invertebrates ◽  
Sea Urchins ◽  
Structural Features ◽  
Sea Stars ◽  
High Resolution Tem ◽  
Relationship Of ◽  
The Relationship ◽  
Insight Into

Echinodermata is a phylum of marine invertebrates which has been extant since Cambrian time (c.a. 500 m.y. before the present). Modern examples of echinoderms include sea urchins, sea stars, and sea lilies (crinoids). The endoskeletons of echinoderms are composed of plates or ossicles (Fig. 1) which are with few exceptions, porous, single crystals of high-magnesian calcite. Despite their single crystal nature, fracture surfaces do not exhibit the near-perfect {10.4} cleavage characteristic of inorganic calcite. This paradoxical mix of biogenic and inorganic features has prompted much recent work on echinoderm skeletal crystallography. Furthermore, fossil echinoderm hard parts comprise a volumetrically significant portion of some marine limestones sequences. The ultrastructural and microchemical characterization of modern skeletal material should lend insight into: 1). The nature of the biogenic processes involved, for example, the relationship of Mg heterogeneity to morphological and structural features in modern echinoderm material, and 2). The nature of the diagenetic changes undergone by their ancient, fossilized counterparts. In this study, high resolution TEM (HRTEM), high voltage TEM (HVTEM), and STEM microanalysis are used to characterize tha ultrastructural and microchemical composition of skeletal elements of the modern crinoid Neocrinus blakei.

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