Synthesis and Cytotoxic Properties of Chalcones: An Interactive and Investigative Undergraduate Laboratory Project at the Interface of Chemistry and Biology

Dickson, John K.; Flores, Lloyd V.; Stewart, Michelle; LeBlanc, Regan M.; Pati, Hari N.; Lee, Moses; Holt, Herman L.

doi:10.1021/ed083p934

Cited by 12 publications

(10 citation statements)

References 7 publications

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“…The administrative structure at The Evergreen State College (TESC), enabling faculty to integrate disciplines without hurdles, made it possible for this investigation to be truly interdisciplinary. Other laboratory exercises created in this environment have been published. − The value of interdisciplinary education is gaining recognition. − …”

Section: Pedagogymentioning

confidence: 99%

An Interdisciplinary, Project-Based Inquiry into the Chemistry and Geology of Alkaline Surface Lake Waters in the General Chemistry Laboratory

Bopegedera

Coughenour

2020

J. Chem. Educ.

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A new project-based laboratory (PJBL) was developed for general chemistry students to tackle the steps involved in chemical water quality analysis using an accessible, real-world hydrologic system (the lakes of the Lower Grand Coulee, Washington). This PJBL was developed in a joint general chemistry and environmental geology course by a chemist–geologist teaching team, and it emphasized an interdisciplinary approach for a more complete understanding of the geochemistry of the lake system. Students worked through the project following industry protocols for sample collection in the field, chemical laboratory determination of dissolved solids, alkalinity, and dissolved metals, and interpretation of the results within the unique geological context of the lakes. Foundational concepts in solution chemistry, such as solubility product, pH, and alkalinity, were essential in the discussion of the lake water trends and broader geologic processes. In particular, students could relate chemical weathering of basaltic bedrock to the measured lake water constituents and could observe how the groundwater- and evaporation-controlled fluxes of water in the closed basin produced a downstream increase in alkalinity and dissolved load. Collectively, the steps involved in the project meet the essential criteria (as defined by other authors) for a complete chemistry PJBL. This PJBL can be readily adapted to a wide range of groundwater or surface water systems and can be framed in a more or less interdisciplinary context. Many students, without prompting and on confidential evaluations, rated this as the most valuable learning experience in the year-long academic coursework.

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Section: Pedagogymentioning

confidence: 99%

An Interdisciplinary, Project-Based Inquiry into the Chemistry and Geology of Alkaline Surface Lake Waters in the General Chemistry Laboratory

Bopegedera

Coughenour

2020

J. Chem. Educ.

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“…Chalcones are receiving lots of attention recently because they exhibit diverse biological activities. They can exist in two major isomeric forms, cis and trans ; the trans -chalcone (TChal) is considered to be more thermodynamically stable [ 1 ]. TChal has been shown to exert cytotoxic activity against many cancer cells via multiple mechanisms including cell cycle disruption, angiogenesis inhibition, tubulin polymerization inhibition, apoptosis induction, and blockade of the NF-κB signaling pathway [ 2 ].…”

Section: Introductionmentioning

confidence: 99%

Trans-chalcone increases p53 activity via DNAJB1/HSP40 induction and CRM1 inhibition

et al. 2018

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Naturally-occurring chalcones and synthetic chalcone analogues have been demonstrated to have many biological effects, including anti-inflammatory, anti-malarial, anti-fungal, and anti-oxidant/anti-cancerous activities. Compared to other chalcones, trans-chalcone exhibits superior inhibitory activity in cancer cell growth as shown via in vitro assays, and exerts anti-cancerous effects via the activation of the p53 tumor suppressor protein. Thus, characterization of the specific mechanisms, by which trans-chalcone activates p53, can aid development of new chemotherapeutic drugs that can be used individually or synergistically with other drugs. In this report, we found that trans-chalcone modulates many p53 target genes, HSP40 being the most induced gene in the RNA-Seq data using trans-chalcone-treated cells. CRM1 is also inhibited by trans-chalcone, resulting in the accumulation of p53 and other tumor suppressor proteins in the nucleus. Similar effects were seen using trans-chalcone derivatives. Overall, trans-chalcone could provide a strong foundation for the development of chalcone-based anti-cancer drugs.

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“…Compound 7c has also been reported, but its biological activity has not been examined (Al-Hajjar et al, 1979). Compounds 5j, 6a, c, e, and 7a, b were newly synthesized by reaction of the appropriate chalcone (Dickson et al, 2006;Pati et al, 2005) with 2.5 mol equivalents of thiourea and potassium carbonate in refluxing ethanol (overnight). A similar reaction was recently reported in the preparation of curcumin-based thioxopyrimidine analogs (Fadda et al, 2009).…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and antiprotozoal activity of 1,2,3,4-tetrahydro-2-thioxopyrimidine analogs of combretastatin A-4

et al. 2010

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Eighteen 1,2,3,4-tetrahydro-2-thioxopyrimidine analogs (5a-j, 6a-e, and 7a-c) of combretastatin A-4 were synthesized with the objective of discovering compounds capable of controlling the growth of Trypanosoma lewisii, Leishmania tarantole, Plasmodium falciparum, and Giardia lamblia. Even though the target compounds demonstrated differential cytotoxicity against mammalian cancer cells, with IC 50 values ranging from 0.5 to [100 lM, the range of activity against Trypanosoma, Leishmania, and Plasmodium, and to a good extent for Giardia, was narrow. The IC 50 values of ''active'' compounds against the parasites ranged from about 10 lM to slightly greater than 50 lL. Specifically, compounds 5a, 5g, 5h, 6c, 7a, and 7c were not cytotoxic against mammalian cancer cells (IC 50 [ 100 lM) but showed good activity against the parasites, except Giardia (e.g., compounds 6c and 7a), suggesting that these compounds may act in a similar mechanism in parasites. Compounds 5f and 6b were previously shown to promote microtubule depolymerization in mammalian cells.

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Synthesis and Cytotoxic Properties of Chalcones: An Interactive and Investigative Undergraduate Laboratory Project at the Interface of Chemistry and Biology

Cited by 12 publications

References 7 publications

An Interdisciplinary, Project-Based Inquiry into the Chemistry and Geology of Alkaline Surface Lake Waters in the General Chemistry Laboratory

An Interdisciplinary, Project-Based Inquiry into the Chemistry and Geology of Alkaline Surface Lake Waters in the General Chemistry Laboratory

Trans-chalcone increases p53 activity via DNAJB1/HSP40 induction and CRM1 inhibition

Synthesis and antiprotozoal activity of 1,2,3,4-tetrahydro-2-thioxopyrimidine analogs of combretastatin A-4

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