Structural and biological evaluation of some loloatin C analogues

Tuin, Adriaan W.; Grotenbreg, Gijsbert M.; Spalburg, Emile; Neeling, Albert J. de; Mars-Groenendijk, Roos H.; Marel, Gijsbert A. van der; Noort, Daan; Overkleeft, Herman S.; Overhand, Mark

doi:10.1016/j.bmc.2009.07.049

Cited by 14 publications

(8 citation statements)

References 10 publications

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“…This fit alignment in the hypothesized 3Dpharmacophore preserves the lead potency of this compound among the other synthesized macrocycles (MIC = 14.08, 15.65 nM for observed and estimated activity, fit value = 5.52). Compound 4k which is considered the second most potent synthesized macrocycle exhibits a relatively similar alignment to that exhibited by compound 4a (MIC = 15.01, 19.56 nM for observed and estimated activity, fit value = 5.43). Where, the pyridinyl N-21 is aligned with HBA-1, and the cyclic amidic N-3 with HBD.…”

Section: D-pharmacophore Modelingmentioning

confidence: 73%

“…Reiss showed significant antimicrobial activity against K. pneumoniae, S. aureus, Escherichia coli, Salmonella setubal, Staphylococcus epidermidis, and Micrococcus luteus. 18 Loloatin C and its analogues are cyclic cationic antimicrobial peptides active against Gram-positive bacteria like S. aureus, S. epidermidis and Enterococcus faecalis as well as certain Gram negative bacteria such as E. coli, P. aeruginosa, Bacillus cereus, as reported by Tuin et al 19 The enopeptins are cyclic acyldepsipeptides showing antibacterial activity against multidrug-resistant bacterial strains such as methicillinresistant S. aureus 1 (MRSA) while the syringopeptins SP508 and SP22 are cyclic lipodepsipeptides produced by several plant associated pseudomonads. Both of them displayed growth-inhibitory activities against Mycobacterium smegmatis, S. aureus, Bacillus megaterium, E. coli, P. vulgaris, P. aeruginosa, Serratia marcescens, Salmonella enterica (serovar typhimurium), Citrobacter freundii, Rhodotorula rubra, C. albicans and Rhodotorula pilimanae.…”

Section: Fungal Infectionsmentioning

confidence: 89%

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Macrocyclic peptidomimetics with antimicrobial activity: synthesis, bioassay, and molecular modeling studies

et al. 2015

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Novel, cyclic peptidomimetics were synthesized by facile acylation reactions using benzotriazole chemistry. Microbiological testing of the synthesized compounds revealed an exceptionally high activity against Candida albicans with a minimum inhibitory concentration (MIC) two orders of magnitude lower than the MIC of the antifungal reference drug amphotericin B. A strikingly high activity was also observed against three Gram-negative bacterial strains (Pseudomonas aeruginosa, Klebsiella pneumoniae and Proteus vulgaris), two of which are known human pathogens. Thus the discovered chemotype is a potential polypharmacological agent. The toxicity against mammalian tumor cells was found to be low, as demonstrated in five different human cell lines (HeLa, cervical; PC-3, prostate; MCF-7, breast; HepG2, liver; and HCT-116, colon). The internal consistency of the experimental data was studied using 3D-pharmacophore and 2D-QSAR.

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Section: D-pharmacophore Modelingmentioning

confidence: 73%

Section: Fungal Infectionsmentioning

confidence: 89%

Macrocyclic peptidomimetics with antimicrobial activity: synthesis, bioassay, and molecular modeling studies

et al. 2015

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“…Later loloatin A was isolated from a strain of Gram-positive sporeforming bacteria Brevibacillus laterosporus [54]. Loloatins A-D possess in vitro activity against methycyclineresistant Staphylococcus aureus, vancomycin-resistant enterococcus, and drug-resistant Streptococcus pneumoniae [53], activity against cyanobacteria [54], and also activity against Gram-negative bacteria [55]. Koshikamide B (27), isolated from two different collections of the marine sponge Theonella sp., is a cyclopeptidolactone consisting of 17 amino acid residues: six proteinogenic amino acids, two D-isomers of proteinogenic amino acids, seven N-methylated amino acids, N(δ)-carbamoyl Asn, and 2-(3-amino-2-hydroxy-5-oxopyrrolidin-2-yl)propionic acid.…”

Section: Cyclic Peptides With Fragments Of Asn (Asp) and β 23 -Unsubmentioning

confidence: 99%

Biologically active cyclic polypeptides with fragments of β-amino acid derivatives isolated from marine organisms (review)

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Tallo

Rybalko

et al. 2011

Chem Heterocycl Comp

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Published data on the structure, stereochemistry, and biological activity of natural cyclic polypeptides containing fragments of β-amino acids are reviewed, and an attempt is made to relate the structure to the biological activity.According to available estimates [1], there are more β-amino acids in the nature than the 22 proteinogenic α-amino acids that take part in ribosomal protein synthesis. The β-amino acids exist either as such or as fragments of the molecules of natural compounds with various degrees of complexity [2] and most often as linear or cyclic peptides that are, in all probability, formed by such microorganisms as bacteria and fungi as a result of non-ribosomal protein synthesis [3].Before 1996 nothing was known about the structure of the simplest β-peptides in the crystal and in solution. Today there are numerous papers and reviews on natural, semisynthetic, and fully synthetic β-peptides, the most comprehensive of which are the papers [4][5][6]. For this reason we will not dwell on these aspects here.The aim of our review is to classify published data on the structure, stereochemistry, and biological activity and also to study the structure-activity relationship of cyclic β-peptides, which have shown greater resistance to the action of enzymes than their linear analogs and α-peptides and therefore exhibit biological selectivity.

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“…Loloatins A-D exhibited in vitro antimicrobial activity against MRSA (MICs respectively: 4 μg/mL, 2 μg/mL, 0.5 μg/mL and 8μg/mL) as well as VRE (MICs: 4 μg/mL, 2 μg/mL, 1 μg/mL and 8 μg/mL). A number of reports have subsequently discussed the solution phase conformation of the loloatins and described the synthesis of loloatin anlogues [70–74]. …”

Section: Anti-methicillin-resistant Staphylococcus Aureus (Mrsa) Amentioning

confidence: 99%

Novel Anti-Infective Compounds from Marine Bacteria

et al. 2010

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As a result of the continuous evolution of microbial pathogens towards antibiotic-resistance, there have been demands for the development of new and effective antimicrobial compounds. Since the 1960s, the scientific literature has accumulated many publications about novel pharmaceutical compounds produced by a diverse range of marine bacteria. Indeed, marine micro-organisms continue to be a productive and successful focus for natural products research, with many newly isolated compounds possessing potentially valuable pharmacological activities. In this regard, the marine environment will undoubtedly prove to be an increasingly important source of novel antimicrobial metabolites, and selective or targeted approaches are already enabling the recovery of a significant number of antibiotic-producing micro-organisms. The aim of this review is to consider advances made in the discovery of new secondary metabolites derived from marine bacteria, and in particular those effective against the so called “superbugs”, including methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin resistant enterococci (VRE), which are largely responsible for the increase in numbers of hospital acquired, i.e., nosocomial, infections.

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Structural and biological evaluation of some loloatin C analogues

Cited by 14 publications

References 10 publications

Macrocyclic peptidomimetics with antimicrobial activity: synthesis, bioassay, and molecular modeling studies

Macrocyclic peptidomimetics with antimicrobial activity: synthesis, bioassay, and molecular modeling studies

Biologically active cyclic polypeptides with fragments of β-amino acid derivatives isolated from marine organisms (review)

Novel Anti-Infective Compounds from Marine Bacteria

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