Cyclic dipeptides exhibit potency for scavenging radicals

Furukawa, Tadashi; Akutagawa, Takashi; Funatani, Hitomi; Uchida, Toshikazu; Hotta, Yoshihiro; Niwa, Masayuki; Takaya, Yoshiaki

doi:10.1016/j.bmc.2012.01.050

Cited by 69 publications

(30 citation statements)

References 20 publications

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“…The Boc protecting group was removed with HCl in dioxane yielding 3 using N‐ methylmorpholine (NMM) and AcOH (Scheme ). Reduction of the nitro groups was carried out by using catalytic hydrogenation in AcOH to afford 4 …”

Section: Resultsmentioning

confidence: 99%

“…Reduction of the nitro groups was carried out by using catalytic hydrogenation in AcOH to afford 4. 42 The 1,4-diacetylpiperazine-2,5-dione 5 was condensed with biphenyl-4-carboxaledhyde to obtain the monoacetyl derivative according to Katritzky et al 43 Further deprotection of the acetyl group was carried out with hydrazine hydrate 44 to yield 6 (Scheme 2). The 3,6-dibenzylpiperazine-2,5-dione 7, prepared according to Yang and Birman, 45 was deprotonated with NaH and further alkylated with 4-nitrobenzyl bromide 46 to afford 8 (Scheme 3).…”

Section: Chemistrymentioning

confidence: 99%

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Development and evaluation of cationic amphiphilic antimicrobial 2,5‐diketopiperazines

Labriere

Kondori

Caous

et al. 2018

Journal of Peptide Science

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Both pathogenic bacteria and fungi are developing resistance to common antimicrobial treatment at an alarming rate. To counteract this development, it is of essence to develop new classes of antimicrobial agents. One such class is antimicrobial peptides, most of which are derived from the innate immune system. In this study, a series of novel 2,5‐diketopiperazines were designed, synthesized, and evaluated for their antimicrobial abilities. The compounds were designed to probe the pharmacophore dictated for short linear mimics of antimicrobial cationic peptides, and as such, the compounds contain a range of cationic and hydrophobic functionalities. Several of the prepared compounds displayed high antimicrobial activities toward bacteria and also against human pathogenic fungi. Of particular interest was the high activity toward fungal strains with an inherent increased resistance toward conventional antifungal agents. The most effective compounds displayed inhibition of Candida glabrata and Candida krusei growth at concentrations between 4 and 8 μg/mL, which is comparable to commercial antifungal agents in use. Structure activity relationship studies revealed a similar dependence on cationic charge and the volume of the hydrophobic bulk as for linear cationic antimicrobial peptides. Finally, the hemolytic activity of selected compounds was evaluated, which revealed a potential to produce active compounds with attenuation of unwanted hemolysis. The findings highlight the potential of cyclic cationic amphiphilic peptidomimetics as a class of promising compounds for the treatment of infections caused by microorganisms with an increased resistance to conventional antimicrobial agents.

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Section: Resultsmentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Development and evaluation of cationic amphiphilic antimicrobial 2,5‐diketopiperazines

Labriere

Kondori

Caous

et al. 2018

Journal of Peptide Science

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“…The CDP cyclo(L-Phe-L-Pro) isolated from Lactobacillus plantarum exhibited an antifungal effect against Fusarium sporotrichioides and Aspergillus fumigatus [ 15 ], while the CDPs cyclo(L-Leu-L-Pro), cyclo(L-Phe-L-Pro), cyclo(L-Val-L-Pro), cyclo(L-Trp-L-Pro), and cyclo(L-Leu-L-Val) isolated from the deep-sea bacterium Streptomyces fungicidicus showed antifouling effects [ 16 ]. Moreover, synthetic CDPs such as cyclo(Phe-Pro) induced apoptosis in the HT-29 colon cancer cell line [ 17 ], and cyclo(L-Cys-L-Leu) exhibited potential for scavenging free radicals [ 18 ]. Recently, it was reported that P. aeruginosa is capable of interacting with the plant Arabidopsis thaliana via the secretion of CDPs such as cyclo(L-Pro-L-Tyr), cyclo(L-Pro-L-Val), and cyclo(L-Pro-L-Phe), appearing to mimic the biological role of auxin, a natural plant hormone [ 12 ] ( Figure 1(b) ).…”

Section: Introductionmentioning

confidence: 99%

Cytotoxicity of Cyclodipeptides fromPseudomonas aeruginosaPAO1 Leads to Apoptosis in Human Cancer Cell Lines

Vázquez-Rivera

González

Guzmán-Rodríguez

et al. 2015

BioMed Research International

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Pseudomonas aeruginosa is an opportunistic pathogen of plants and animals, which produces virulence factors in order to infect or colonize its eukaryotic hosts. Cyclodipeptides (CDPs) produced by P. aeruginosa exhibit cytotoxic properties toward human tumor cells. In this study, we evaluated the effect of a CDP mix, comprised of cyclo(L-Pro-L-Tyr), cyclo(L-Pro-L-Val), and cyclo(L-Pro-L-Phe) that were isolated from P. aeruginosa, on two human cancer cell lines. Our results demonstrated that the CDP mix promoted cell death in cultures of the HeLa cervical adenocarcinoma and Caco-2 colorectal adenocarcinoma cell lines in a dose-dependent manner, with a 50% inhibitory concentration (IC50) of 0.53 and 0.66 mg/mL, for HeLa and Caco-2 cells, respectively. Flow cytometric analysis, using annexin V and propidium iodide as apoptosis and necrosis indicators, respectively, clearly showed that HeLa and Caco-2 cells exhibited apoptotic characteristics when treated with the CDP mix at a concentration <0.001 mg/mL. IC50 values for apoptotic cells in HeLa and Caco-2 cells were 6.5 × 10−5 and 1.8 × 10−4 mg/mL, respectively. Our results indicate that an apoptotic pathway is involved in the inhibition of cell proliferation caused by the P. aeruginosa CDP mix.

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“…On the basis of comparison of the NMR and specific rotation data with the literature, ten known compounds were identified to be (+)‐(7 S ,11 S )‐12‐hydroxysydonic acid ( 2 ), sydonic acid ( 3 ), hydroxysydonic acid ( 4 ), ascotrichic acid ( 5 ), trinorcyclonerodiol‐7,10‐lactone ( 6 ), 5 α ,8 α ‐epidioxyergosta‐6,22‐dien‐3 β ‐ol ( 7 ), cyclo‐( l ‐Leu‐ l ‐Trp) ( 8 ), cyclo‐( l ‐Trp‐Gly) ( 9 ), cyclo‐( l ‐Phe‐ l ‐Leu) ( 10 ), and cyclo‐( l ‐Leu‐ l ‐Tyr) ( 11 ) …”

Section: Resultsmentioning

confidence: 99%

A New Pimarane Diterpenoid from the Botryotinia fuckeliana Fungus Isolated from Deep‐Sea Water

Niu

Peng

Xia

et al. 2019

Chemistry & Biodiversity

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A new pimarane diterpenoid, named botryopimarene A (1), was discovered from the fungus Botryotinia fuckeliana MCCC 3 A00494 isolated from the deep-sea water, together with ten known compounds. The planar structure of 1 was established based on the extensive spectroscopic analyses. The absolute configurations of tricyclic system in 1 were resolved by the theoretical ECD calculation, while the 15,16-diol moiety in the side chain was resolved by the Mo 2 (OAc) 4 -induced ECD spectrum. Compound 1, featuring a Δ 9(11) double bond, was rarely discovered in pimarane family. Compounds 1-11 were tested for their cytotoxic activities using six human cancer cell lines by the MTT method. However, none of the compounds exhibited detectable cytotoxicities (IC 50 > 20 μM).

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Cyclic dipeptides exhibit potency for scavenging radicals

Cited by 69 publications

References 20 publications

Development and evaluation of cationic amphiphilic antimicrobial 2,5‐diketopiperazines

Development and evaluation of cationic amphiphilic antimicrobial 2,5‐diketopiperazines

Cytotoxicity of Cyclodipeptides fromPseudomonas aeruginosaPAO1 Leads to Apoptosis in Human Cancer Cell Lines

A New Pimarane Diterpenoid from the Botryotinia fuckeliana Fungus Isolated from Deep‐Sea Water

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