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Reaction Mechanism of Aspirin Synthesis - The Student …

of the antioxidant properties of tocopherols ().

First synthesis of linoleic acid ()

Kurz H used ethyl alcohol to derivatize fatty acids (FA ethyl esters) beforetheir analysis ().

First data on cholesterol and fatty acid metabolism after using an isotope of hydrogen(deuterium) in mice and chicks ().

Using deuterated acetate, Sonderhoff R et al. have shown that it serves asa precursor for sterols including ergosterol in yeast ().

Paul Karrer received the

Reaction Mechanism of Aspirin Synthesis Watch

Girish and colleagues proposed that aspirin correctsthe production levels of maspin in human breast cells and in patients, regulating maspin to normal levelsthrough the stimulation of nitric oxide (NO) synthesis independentof the insulin receptor (). Anepidemiologic example of this previously mentioned concept, is astudy carried out in India, where the effect of aspirin and theincidence of metastasis in BC patients was determined (). In this work, 35 women participated,and the age range was from 41 to 64 years. All of the women werediagnosed with BC and had been previously treated (chemotherapy,radiation and/or surgery). The patients consumed a dose of aspirinof 75 mg/70 kg body weight daily for 3 years. During this period oftime, plasmatic levels of NO and maspin were measured, and amonthly surveillance of metastasis was performed by an oncologistand occasionally by biopsy. The control group consisted of 35healthy volunteers whose plasma maspin levels were measured. Theresults showed that maspin levels were higher after 24 h of aspirinadministration; such levels were maintained during the 3 years oftreatment (initially maspin levels were 0.95±0.04 nM increasing to4.63±0.05 nM at the end of treatment). Six patients developedmetastasis, and the rest of the patients were, apparently, free ofmetastasis after 3 years. Researchers suggest that daily intake ofaspirin in patients with previously treated BC may reduce theincidence of metastasis independent of the disease stage.

The synthesis of aspirin is a multi-billion dollar a year chemical

Synthesis Of Methyl Salicylate From Aspirin Mechanism …

described for the first time the synthesis of a naturalneutral lipid, tributyrin, by the direct esterification of glycerol and butyricacid ().

In summary, according to the aforementioned studies,there is not enough evidence yet to support aspirin as a possibledrug to lower BC risk. On one hand, some of the studies suggestthat aspirin could be a preventive treatment over long periods ofingestion (longer than 3 years). However, the main problem withlong periods of aspirin consumption is its adverse reactions, suchas peptic ulcers and gastrointestinal hemorrhage. These secondaryeffects are important to consider by physicians before prescribingto women with the possibility to develop BC.

Synthesis and biological activity of aspirin derivatives | …

Synthesis and biological activity of aspirin derivatives

These enzymes are responsible for catalyzing theconversion of arachidonic acid to prostaglandin endoperoxide(prostaglandin H2) and thromboxanes; both COX-1 and COX-2participate in maintaining physiological regulation in the stomach,platelets, kidneys and intestine (). The principal side effects of aspirinand NSAIDs such as gastropathy, renal insufficiency and impairedvascular homeostasis among others, are due to a reduction in theappropriate prostaglandins in these organs (). Prostaglandins are short-livedcompounds acting as local mediators of continuous importance innormal cellular reactions, but they appear to be increased inseveral pathological conditions, particularly inflammation(), and it has also been shownthat the level of prostaglandins in various tumors is greater thanthat of normal tissues ().

Additional experimental data suggest that COX-2 canbe induced by a mutation of the tumor-suppressor gene APC,subsequently increasing the expression of the nuclear transcriptionfactor PPAR-δ (). Induction ofCOX-2 expression in tumors can also occur by lipopolysaccharidethrough the mitogen-activated protein kinase (MAPK) and proteinkinase C-(PKC) pathways ().Ceramide-stimulated activation of MAPK can also activate c-JunN-terminal kinase (JNK), which in turn can lead to increased COX-2gene expression in human mammary epithelial cells (). In breast tissue, induction of COX-2expression can trigger prostaglandin production, which indirectlystimulates cellular proliferation increasing the local biosynthesisof estrogen and increasing the expression of the aromatase gene(,). In humans, high levels ofprostaglandins have been related with metastatic potential andreduced survival of patients ().Such a process could be reversible when COX-2 is inhibited usingNSAIDs with the purpose of reducing prostaglandin synthesis. Forthose women who present with tumors with positive hormonereceptors, the use of aspirin could contribute to the suppressionof aromatase activity, reducing the intra-mammary prostaglandinproduction, and thus, estrogen production (). In particular, it has been shown thatE2 prostaglandin (PGE) stimulates the transcription ofaromatase, increasing the estrogen levels and, moreover,contributing to the progression of estrogen-dependent BC ().

Name _____ Period _____ Date _____ SYNTHESIS OF ASPIRIN Purpose: The purpose of this ..
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Write a mechanism for the synthesis of aspirin

Bhattacharyya M, Girish GV, Ghosh R,Chakraborty S and Sinha AK: Acetylsalicylic acid (aspirin) improvessynthesis of maspin and lowers incidence of metastasis in breastcancer patients. Cancer Sci. 101:2105–2109. 2010. : :

Week #11: Synthesis of Aspirin and Oil of Wintergreen

They were correctly identified in 1961.

Discovery that mevalonic acid is incorporated quantitatively into cholesterol incell-free systems with loss of carbon dioxide ().

The chemical structure of the cord factor of was established as trehalose dimycolate ().

Discovery of the first polyisoprenoid alcohol, solanesol, in tobacco leaves

PDF Downloads : Oriental Journal of Chemistry

Evidence of the chemopreventive effect of aspirincited in this review, suggests that it is likely to lower BC riskwhen administrated at doses greater than 100 mg/day for 3 or moreyears. Such information suggests that aspirin may start beingfavorable after a long period of regular use. However, this dosageposes adverse reactions, such as, an increase in gastric ulcer riskand gastrointestinal bleeding. Cancer is a multifactorial disease,and its behavior is constantly being investigated toward a greaterunderstand and, at the same time, to propose less aggressive andmore effective therapies or, when possible, chemopreventivealternatives. Aspirin could yield beneficial results for a specificgroup of risk patients, but who should be monitored carefully ifthere are any contraindications to the medicine. In conclusion,aspirin is a suitable alternative in this non-stop search forcancer prevention and treatment.

Fish Oil (Extract) Omega-3 • Solal Vitamins & …

Regarding the possible anti-metastatic effect ofaspirin, it was demonstrated that the daily ingestion of aspirin inpatients previously treated with standard therapies indeed reducesmetastasis, assigning this effect to the maspin protein (). Maspin is a serine protease inhibitorof 42 kDa synthesized abundantly in normal mammary epithelialcells, and it has been shown that the expression of this protein isreduced in patients with breast cancer. Thus, the lack ofexpression of maspin in breast cancer has been suggested toindicate the presence of an aggressive and metastatic tumor(). Studies have revealed thatingestion of aspirin increases the levels of serum nitric oxide(NO) and maspin, both of which inhibited the growth of breastcancer cells , as well as invasion and metastaticprocesses in an animal model (,).This finding suggests that aspirin participates in the restorationof maspin synthesis at any stage of the disease, and also thatmaspin presents beneficial effects at any stage of tumoralprogression. It has been observed that maspin is reduced in BC, oreven absent in invasive cancer; hence, there is a correlationbetween the protein synthesis and its reduction according to cancertype and stage (). There is alsoevidence of maspin as an inhibitor of angiogenesis ().

Practice Questions | Biochemistry for Medics – Lecture …

The induction and overexpression of COX-2 and itsmain product PGE in human mammary tissue, have alsobeen associated with aromatase-catalyzed estrogen biosynthesis(). In addition, someepidemiologic studies have reported that hormone-receptor-positivebreast tumors are more responsive to aspirin (). The ability of aspirin and otherNSAIDs to protect against breast cancer might vary according tohormone receptor status. For instance, in 2004, a case-controlstudy, reported a reduction in risk only in women with hormonereceptor-positive tumors, but not in women with hormonereceptor-negative tumors ().Moreover, COX-2 is related to the activation of carcinogens,mutagenesis, angiogenesis, inhibition of apoptosis and metastasis(,,).In contrast, COX-2 inhibition may reverse these processes; aspirinand salicylates may also suppress NF-κB-related survival signalingby inhibiting IKKα activation, leading to apoptosis ().

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