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Baerlocher, Felix J.; Baerlocher, Mark O.; Guckert, Kristal D.; Langler, Richard Francis; MacQuarrie, Stephanie; O’Connor, Paul; Sung, Gabriel Carl Yan

doi:10.1071/ch01046

Cited by 9 publications

(3 citation statements)

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“…The successful application of the rationale presented in Figure 5 not only led to the design of esters and sulfones having substantially enhanced antifungal activity [28] but also permitted the extension of our bioactive organosulfur compounds to include two new classes i.e. aryl methyl disulfides (e.g.…”

Section: Discussionmentioning

confidence: 99%

Characterization of the apoptotic response of human leukemia cells to organosulfur compounds

et al. 2010

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BackgroundNovel therapeutic agents that selectively induce tumor cell death are urgently needed in the clinical management of cancers. Such agents would constitute effective adjuvant approaches to traditional chemotherapy regimens. Organosulfur compounds (OSCs), such as diallyl disulfide, have demonstrated anti-proliferative effects on cancer cells. We have previously shown that synthesized relatives of dysoxysulfone, a natural OSC derived from the Fijian medicinal plant, Dysoxylum richi, possess tumor-specific antiproliferative effects and are thus promising lead candidates.MethodsBecause our structure-activity analyses showed that regions flanking the disulfide bond mediated specificity, we synthesized 18 novel OSCs by structural modification of the most promising dysoxysulfone derivatives. These compounds were tested for anti-proliferative and apoptotic activity in both normal and leukemic cells.ResultsSix OSCs exhibited tumor-specific killing, having no effect on normal bone marrow, and are thus candidates for future toxicity studies. We then employed mRNA expression profiling to characterize the mechanisms by which different OSCs induce apoptosis. Using Gene Ontology analysis we show that each OSC altered a unique set of pathways, and that these differences could be partially rationalized from a transcription factor binding site analysis. For example, five compounds altered genes with a large enrichment of p53 binding sites in their promoter regions (p < 0.0001).ConclusionsTaken together, these data establish OSCs derivatized from dysoxysulfone as a novel group of compounds for development as anti-cancer agents.

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Section: Discussionmentioning

confidence: 99%

Characterization of the apoptotic response of human leukemia cells to organosulfur compounds

et al. 2010

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“…I). Hence, relative to previous structural modifications [3,5], modest chain lengthening with and without branching is not competitive as a strategy to enhance a-ester disulfide fungitoxicity. As an aside, we have noticed that a-ester disulfide fungitoxicity is much shorter-lived than that of similar a-sulfone disulfides.…”

Section: (B) Antifungal Testingmentioning

confidence: 91%

“…Recently, we have established that three types of disulfides have significant fungitoxicity: a-sulfone disulfides [1][2][3], some substituted aryl disulfides [4] and a-ester disulfides in which the ester moiety is attached to the disulfide framework by a CO bond [1,3,5]. In contrast, related thiosulfonates had only modest fungitoxicity [6].…”

Section: Introductionmentioning

confidence: 96%

Optimizing disulfide fungitoxicity: Adjustment of hydrocarbon chain length

Baerlocher

Langler

et al. 2002

Sulfur Letters

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The Variable Strength of the Sulfur–Sulfur Bond: 78 to 41 kcal – G3, CBS‐Q, and DFT Bond Energies of Sulfur (S₈) and Disulfanes XSSX (X = H, F, Cl, CH₃, CN, NH₂, OH, SH)

Denk

2009

Eur J Inorg Chem

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Experimental values for the strength of the sulfur-sulfur bond scatter over a wide range and are frequently in disagreement with each other. For S 8 , reliable experimental data seem to lack entirely. To check experimental data and establish the strength of the sulfur-sulfur bond in S 8 , highprecision thermochemical calculations (G3, CBS-Q) and DFT methods were employed. The calculations confirm a stunning range for the strength of the sulfur-sulfur bond with energies between 77.7 kcal for FSSF and only 41.8 kcal for tetrasulfane, HSS-SSH. For the pivotal bond energy of ele-

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Cited by 9 publications

References 1 publication

Characterization of the apoptotic response of human leukemia cells to organosulfur compounds

Characterization of the apoptotic response of human leukemia cells to organosulfur compounds

Optimizing disulfide fungitoxicity: Adjustment of hydrocarbon chain length

The Variable Strength of the Sulfur–Sulfur Bond: 78 to 41 kcal – G3, CBS‐Q, and DFT Bond Energies of Sulfur (S₈) and Disulfanes XSSX (X = H, F, Cl, CH₃, CN, NH₂, OH, SH)

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Untitled

Cited by 9 publications

References 1 publication

Characterization of the apoptotic response of human leukemia cells to organosulfur compounds

Characterization of the apoptotic response of human leukemia cells to organosulfur compounds

Optimizing disulfide fungitoxicity: Adjustment of hydrocarbon chain length

The Variable Strength of the Sulfur–Sulfur Bond: 78 to 41 kcal – G3, CBS‐Q, and DFT Bond Energies of Sulfur (S8) and Disulfanes XSSX (X = H, F, Cl, CH3, CN, NH2, OH, SH)

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The Variable Strength of the Sulfur–Sulfur Bond: 78 to 41 kcal – G3, CBS‐Q, and DFT Bond Energies of Sulfur (S₈) and Disulfanes XSSX (X = H, F, Cl, CH₃, CN, NH₂, OH, SH)