Synthesis of aspirin-curcumin mimic conjugates of potential antitumor and anti-SARS-CoV-2 properties

Srour, Aladdin M.; Panda, Siva S.; Mostafa, Ahmed; Fayad, Walid; El-Manawaty, May A.; Soliman, A. M.; Moatasim, Yassmin; Taweel, Ahmed El; Abdelhameed, Mohamed F.; Bekheit, Mohamed S.; Ali, Mohamed A.; Girgis, Adel S.

doi:10.1016/j.bioorg.2021.105466

Cited by 24 publications

(30 citation statements)

References 102 publications

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“…[58,59] Screening the synthesized agents against SARS-CoV-2 is supported by our recent publication exhibiting the antiviral properties of piperidone-containing compounds. [60] Reports mentioning the success of curing patients with colon cancer by antiviral drugs solely or in combination with antitumor drugs [61] support the assumption of the current study directed towards investigation of mutually effective agents against cancer and anti-SARS-CoV-2 with a special interest in safety profile towards normal cells.…”

Section: Chemistryselectmentioning

confidence: 80%

Novel Curcumin Mimics: Design, Synthesis, Biological Properties and Computational Studies of Piperidone‐Piperazine Conjugates

et al. 2022

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alkyl]piperidin-4-ones 7 aÀ k were synthesized through dehydrohalogenation of 1-(2-chloroacyl)piperidin-4-ones 5 aÀ k with N-methylpiperazine (6). High antiproliferation potencies were observed by most of the synthesized agents against both HCT116 (colon) and MCF7 (breast) cancer cell lines relative to the standard references (sunitinib and 5-fluorouracil). The synthesized agents are of dual activity against topoisomerases I and IIα however, with higher efficacy against topoisomerase IIα rather than topoisomerase I. Flow-cytometry cell cycle studies support the observed antiproliferation properties and exhibit the capability of 1-(2-chloroacetyl)-3,5-bis[(E)-4-chlorobenzylidene]piperidin-4-one (5 e) and 3,5-bis[(E)-4-bromobenzylidene]-1-[2-(4-methylpiperazin-1-yl)acetyl]piperidin-4-one (7 g) to arrest the HCT116 cell cycle progression at G1/S and G1 phases, respectively. Noticeable anti-SARS-CoV-2 properties were observed by many synthesized agents. 3,5-Bis[(E)-4-chlorobenzylidene]-1-[3-(4-methylpiperazin-1-yl)propanoyl]piperidin-4-one (7 f) is the most effective anti-SARS-CoV-2 synthesized with high SI. Applicability of the highly effective candidates synthesized as antitumor and anti-SARS-CoV-2 is due to the safety observations against normal (RPE1 and VERO-E6) cells. QSAR models validated internally and externally, support their possibility for optimizing more hits/leads.

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Section: Chemistryselectmentioning

confidence: 80%

Novel Curcumin Mimics: Design, Synthesis, Biological Properties and Computational Studies of Piperidone‐Piperazine Conjugates

et al. 2022

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“…The Vero-E6 cell viral infection model/technique was undertaken to determine the anti-SARS-CoV-2 inhibitory properties of the synthesized spiro-3-indolin-2-ones 6a‒o 44 . Favipiravir 89 , Hydroxychloroquine and Chloroquine 51 were considered as standard references (Table 5 , Fig. 9 ).…”

Section: Resultsmentioning

confidence: 99%

“…It is postulated that viral zoonotic jump (probably bat) to human was firstly recognized in Wuhan, China. The infection then spread worldwide causing a universal pandemic, according to WHO (World Health Organization) in March 2020 50 , 51 . Lack of an effective therapeutic was a major factor in the ensuing threat to human life.…”

Section: Introductionmentioning

confidence: 99%

Development of spiro-3-indolin-2-one containing compounds of antiproliferative and anti-SARS-CoV-2 properties

Fawazy

Panda

Mostafa

et al. 2022

Sci Rep

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A series of 1″-(alkylsulfonyl)-dispiro[indoline-3,2′-pyrrolidine-3′,3″-piperidine]-2,4″-diones 6a‒o has been synthesized through regioselective multi-component azomethine dipolar cycloaddition reaction of 1-(alkylsulfonyl)-3,5-bis(ylidene)-piperidin-4-ones 3a‒h. X-ray diffraction studies (6b‒d,h) confirmed the structures. The majority of the synthesized analogs reveal promising antiproliferation properties against a variety of human cancer cell lines (MCF7, HCT116, A431 and PaCa2) with good selectivity index towards normal cell (RPE1). Some of the synthesized agents exhibit potent inhibitory properties against the tested cell lines with higher efficacies than the standard references (sunitinib and 5-fluorouracil). Compound 6m is the most potent. Multi-targeted inhibitory properties against EGFR and VEGFR-2 have been observed for the synthesized agents. Flow cytometry supports the antiproliferation properties and shows the tested agents as apoptosis and necrosis forming. Vero cell viral infection model demonstrates the anti-SARS-CoV-2 properties of the synthesized agents. Compound 6f is the most promising (about 3.3 and 4.8 times the potency of the standard references, chloroquine and hydroxychloroquine). QSAR models explain and support the observed biological properties.

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“…There is an burning need to design and synthesis of novel prospective dual-active compounds, especially anticancer-antiviral [ [32] , [33] , [34] ]. Our interest is the design, synthesis, and pharmacological evaluation of the heterocyclic compounds, especially those derived from the Biginelli reaction [ [35] , [36] , [37] , [38] , [39] , [40] , [41] , [42] , [43] ].…”

Section: Introductionmentioning

confidence: 99%

A new class of half-sandwich ruthenium complexes containing Biginelli hybrids: anticancer and anti-SARS-CoV-2 activities

Janković

Milović

Jovanović

et al. 2022

Chemico-Biological Interactions

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Synthesis of aspirin-curcumin mimic conjugates of potential antitumor and anti-SARS-CoV-2 properties

Cited by 24 publications

References 102 publications

Novel Curcumin Mimics: Design, Synthesis, Biological Properties and Computational Studies of Piperidone‐Piperazine Conjugates

Novel Curcumin Mimics: Design, Synthesis, Biological Properties and Computational Studies of Piperidone‐Piperazine Conjugates

Development of spiro-3-indolin-2-one containing compounds of antiproliferative and anti-SARS-CoV-2 properties

A new class of half-sandwich ruthenium complexes containing Biginelli hybrids: anticancer and anti-SARS-CoV-2 activities

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