One‐pot synthesis and antiproliferative activity of novel double‐modified derivatives of the polyether ionophore monensin A

Klejborowska, Greta; Maj, Ewa; Wietrzyk, Joanna; Stefańska, Joanna; Huczyński, Adam

doi:10.1111/cbdd.13320

Cited by 5 publications

(7 citation statements)

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“…It is worth noting that none of the esters described in literature have been tested for their anticancer properties, although MON as well as its amide, double‐modified, and conjugate derivatives showed activity against various cancer cell lines (Antoszczak, Rutkowski, et al, ; Antoszczak, Klejborowska, et al., ; Huczyński, Klejborowska, Antoszczak, Maj, & Wietrzyk, ; Ketola, Vainio, Fey, Kallioniemi, & Iljin, ; Klejborowska, Ewa, Wietrzyk, Stefańska, & Huczyński, ; Park, Kim, Jung, Kim, & Lee, ; Park, Kim, Kim, & Lee, ; Park et al., ; Skiera et al., ; Wood, Rumsby, & Warr, ). MON inhibits the growth of colon cancer, lymphoma, and myeloma cells by inducing cell cycle arrest and apoptosis as well as overcomes the multidrug resistance.…”

Section: Introductionsupporting

confidence: 89%

“…The esters of MON ( 1 – 16 ) with different substituents such as alkyl chains, unsaturated alkyl chains, alkyl chains containing oxygen, and halogen atoms, as well as aromatic rings, were prepared according to four different previously described methods (Figure ; Antoszczak et al., ; Klejborowska et al., ).…”

Section: Resultsmentioning

confidence: 99%

“…We chose drug‐resistant cell lines, because in our previous in vitro studies MON and its derivatives strongly overcame doxorubicin‐resistance and showed low values of resistance index (RI; Klejborowska et al., ). Also in recent in vitro and in vivo studies, Wang et al.…”

Section: Resultsmentioning

confidence: 99%

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Antiproliferative activity of ester derivatives of monensin A at the C‐1 and C‐26 positions

et al. 2019

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Monensin A (MON) is a polyether ionophore antibiotic, which shows a wide spectrum of biological activity, including anticancer activity. A series of structurally diverse monensin esters including its C‐1 esters (1–9), C‐26‐O‐acetylated derivatives (10–15), and lactone (16) was synthesized and for the first time evaluated for their antiproliferative activity against four human cancer cell lines with different drug‐sensitivity level. All of the MON derivatives exhibited in vitro antiproliferative activity against cancer cells at micromolar concentrations. The majority of the compounds was able to overcome the drug resistance of LoVo/DX and MES‐SA/DX5 cell lines. The most active compounds proved to be MON C‐26‐O‐acetylated derivatives (10–15) which exhibited very good resistance index and high selectivity index.

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Section: Introductionsupporting

confidence: 89%

Section: Resultsmentioning

confidence: 99%

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Antiproliferative activity of ester derivatives of monensin A at the C‐1 and C‐26 positions

et al. 2019

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“…Similarly double modified amide-carbonate derivative blocked the growth of S. aureus strains (MIC: 81.4-162.8µM) and S. epidermidis (MIC: 325.7µM). But these double modifications increased the concentration of antibi-otic needed to inhibit the growth of Staphylococcus strains in comparison to the unmodified monensin [7] Regio-selective chemical modification alters the ionic selectivity of monensin with differential killing effect on bacteria. An amide derivative, monensin N-phenylamide forms specific complex with Na + ions.…”

Section: Monensin As An Anti-bacterial Agentmentioning

confidence: 99%

Chemotherapeutic Potential of Monensin as an Anti-microbial Agent

Rajendran

Ilamathi

Dutt

et al. 2019

CTMC

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Monensin is a lipid-soluble naturally occurring bioactive ionophore produced by Streptomyces spp. Its antimicrobial activity is mediated by its ability to exchange Na + and K + ions across the cell membrane thereby disrupting ionic gradients and altering cellular physiology. It is approved by Food and Drug Administration as a veterinary antibiotic to treat coccidiosis. Besides veterinary applications, monensin exhibits a broad spectrum activity against opportunistic pathogens of humans such as bacteria, virus, fungi and parasites in both drug sensitive and resistant strains. This ionophore can selectively kill pathogens with negligible toxic effect on mammalian cells. In this review, we discuss the therapeutic potential of monensin as a new broad-spectrum anti-microbial agent that warrants further studies for clinical use.

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“…Benzoyloxymethyl-10-Methoxy-1,6,9-Trioxaspiro [4.5] decane (18) Bromide 16a (120 mg, 0.20 mmol) was dissolved in anhydrous methanol (10 mL) followed by the addition of silver carbonate (55 mg, 0.20 mmol) and freshly dried molecular sieve 4 Å (1 g). After the mixture was stirred for 20 minutes at room temperature and under the absence of light, the silver salts were removed by filtration through a pad of kieselguhr and the filter rewashed with dichloromethane.…”

Section: (−)-(2r3r4s5s10s)-34-bis-benzoyloxy-2-mentioning

confidence: 99%

Stereoselective Synthesis of 1,6,9-Tri-oxaspiro[4.5]decanes From d-Glucose: Novel Structural Motifs of Spiroacetal Natural Products

Cuny

2020

Natural Product Communications

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Spiroacetals are the central structural core element of numerous natural products and are essential for their biological activity. A typical structural representative of a spiroacetal is the bicyclic 1,6-dioxaspiro[4.5]decane ring system. It represents the complete or partial structure of many biologically potent natural products such as the Paravespula pheromone 1, the antibiotic (+)-monensin A 2, the anticancer agent (−)-berkelic acid 3, the antimitotic ingredient spirastrellolide F, characterized after methylation as (+)-methyl ester 4, and the marine toxin (−)-calyculin A 5. In these compounds, the 1,6-dioxaspiro[4.5]decane ring system is found in either spiro ( R)-6 or ( S) - 6 configuration. The corresponding 1,6,9-trioxaspiro[4.5]decane framework ( S)-7 and ( R)-7 with opposite chirality at the spiro center due to an additional oxygen atom at position 9 in the pyran portion has so far not been found in living organisms or been synthesized. To close this gap and enable structure–activity relationship studies, potentially leading to novel antibiotics and selective anticancer agents, we have developed an efficient and stereocontrolled route to the ( R)- and ( S)-configurated 1,6,9-trioxaspiro[4.5]decane ring system leading to oxa analog motifs of the above natural products.

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One‐pot synthesis and antiproliferative activity of novel double‐modified derivatives of the polyether ionophore monensin A

Cited by 5 publications

References 22 publications

Antiproliferative activity of ester derivatives of monensin A at the C‐1 and C‐26 positions

Antiproliferative activity of ester derivatives of monensin A at the C‐1 and C‐26 positions

Chemotherapeutic Potential of Monensin as an Anti-microbial Agent

Stereoselective Synthesis of 1,6,9-Tri-oxaspiro[4.5]decanes From d-Glucose: Novel Structural Motifs of Spiroacetal Natural Products

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