Glucose–aspirin: Synthesis and in vitro anti-cancer activity studies

Jacob, James N.; Tazawa, Makio J.

doi:10.1016/j.bmcl.2012.03.053

Cited by 19 publications

(24 citation statements)

References 10 publications

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“…In the discovery of a superaspirin Jacob et al (2012) [110] synthesized by conjugation aspirin-glucose ( Figure 5) in order to study the solubility in water and anticancer activity as compared to aspirin and evaluated that aspirin-glucose was seven times more soluble in water than aspirin, and about 8 to 9 times more active in inhibiting cell growth than aspirin in its anticancer activity in cell culture breast, pancreatic, and cell lines prostate, while the activity was similar in a line benign non-cancer cells. According to the computer calculations performed to aspirin and aspirin-glucose in HF/6-31G** verified that the anticancer activity of aspirin-glucose was increased by the fact of presenting high value GAP = −0.43232 eV, having greater molecular stability and low chemical reactivity, being that the value of GAP to aspirin in HF/6-31G** was −0.43332 eV, having a variation of GAP = ±10 −3 eV (between aspirin and aspirin-glucose).…”

Section: Case Study On Aspirinmentioning

confidence: 99%

Application of Hartree-Fock Method for Modeling of Bioactive Molecules Using SAR and QSPR

Santos¹,

Lobato²,

Braga³

et al. 2014

CMB

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The central importance of quantum chemistry is to obtain solutions of the Schrödinger equation for the accurate determination of the properties of atomic and molecular systems that occurred from the calculation of wave functions accurate for many diatomic and polyatomic molecules, using Self Consistent Field method (SCF). The application of quantum chemical methods in the study and planning of bioactive compounds has become a common practice nowadays. From the point of view of planning it is important to note, when it comes to the use of molecular modeling, a collective term that refers to methods and theoretical modeling and computational techniques to mimic the behavior of molecules, not intend to reach a bioactive molecule simply through the use of computer programs. The choice of method for energy minimization depends on factors related to the size of the molecule, parameters of availability, stored data and computational resources. Molecular models generated by the computer are the result of mathematical equations that estimate the positions and properties of the electrons and nuclei, the calculations exploit experimentally, the characteristics of a structure, providing a new perspective on the molecule. In this work we show that studies of

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Section: Case Study On Aspirinmentioning

confidence: 99%

Application of Hartree-Fock Method for Modeling of Bioactive Molecules Using SAR and QSPR

Santos¹,

Lobato²,

Braga³

et al. 2014

CMB

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“…[4] [16] Sugar drug derivatives have opened a new gateway in the medical and pharmaceutical field and, currently, a great number of the drugs commonly in use rely on linkage of carbohydrates. [22] The ibuprofen-fructose ester showed extended stability in aqueous solution, and fewer adverse effects, enhanced tissue uptake in comparison with ibuprofen alone. [18] [19] Glycosidic conjugation also leads to better absorption [20] and penetration of drugs into the cell membranes, thus aiding delivery of drugs to the targeted site.…”

Section: Introductionmentioning

confidence: 99%

“…[22] The ibuprofen-fructose ester showed extended stability in aqueous solution, and fewer adverse effects, enhanced tissue uptake in comparison with ibuprofen alone. [26] Because the conjugation of drugs with saccharides presents multiple opportunities to improve bioavailability and pharmaceutical properties, [19] [22] monosaccharide derivatives of 5-ASA were prepared in this study to investigate the role of the glycoside conjugation on the biological properties of this drug. [24] For instance, galactose and fructose laurates have demonstrated excellent antibacterial effects against both Gram-positive and Gram-negative bacteria when compared with alternative analogues of synthesized fatty acid-carbohydrate esters.…”

Section: Introductionmentioning

confidence: 99%

“…[21] For example, the anticancer activity and water solubility of glucoseaspirin conjugate were improved eight to nine-fold and seven-fold, respectively, in comparison with unlinked aspirin. [22] The ibuprofen-fructose ester showed extended stability in aqueous solution, and fewer adverse effects, enhanced tissue uptake in comparison with ibuprofen alone. [23] Many carbohydrate-based compounds have also demonstrated antimicrobial activity comparable to currently available antimicrobials.…”

Section: Introductionmentioning

confidence: 99%

“…[25] Likewise, fructose derivatives of 1,2,3-triazole have displayed antibacterial activity toward initial compound. [26] Because the conjugation of drugs with saccharides presents multiple opportunities to improve bioavailability and pharmaceutical properties, [19] [22] monosaccharide derivatives of 5-ASA were prepared in this study to investigate the role of the glycoside conjugation on the biological properties of this drug. [27] Since the ester linkage is known to be stable in acidic environments such as the stomach, yet readily hydrolyses in the basic environment of the lower alimentary tract, [28] the ester derivatives of 5-ASA were prepared with the intention of permitting the active moiety of the drug to be released only when it arrives at the colon.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and in vitro Bioactivity Evaluation of New Galactose and Fructose Ester Derivatives of 5‐Aminosalicylic Acid

Yousefi

Bayat

Rahman

et al. 2017

Chemistry & Biodiversity

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Inflammatory bowel disease (IBD) is the main risk factor for developing colorectal cancer which is common in patients of all ages. 5-Aminosalicylic acid (5-ASA), structurally related to the salicylates, is highly active in the treatment of IBD with minor side effects. In this study, the synthesis of galactose and fructose esters of 5-ASA was planned to evaluate the role of glycoconjugation on the bioactivity of the parent drug. The antibacterial activity of the new compounds were evaluated against two Gram-negative and two Gram-positive species of bacteria, with a notable effect observed against Staphylococcus aureus and Escherichia coli in comparisons with the 5-ASA. Cytotoxicity testing over HT-29 and 3T3 cell lines indicated that the toxicity of the new products against normal cells was significantly reduced compared with the original drug, whereas their activity against cancerous cells was slightly decreased. The anti-inflammatory activity test in RAW264.7 macrophage cells indicated that the inhibition of nitric oxide by both of the monosaccharide conjugated derivatives was slightly improved in comparison with the non-conjugated drug.

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Complex roles of the old drug aspirin in cancer chemoprevention and therapy

Hua

Zhang

Kong

et al. 2018

Medicinal Research Reviews

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The nonsteroidal anti-inflammatory agent aspirin is widely used for preventing and treating cardiovascular and cerebrovascular diseases. In addition, epidemiologic evidences reveal that aspirin may prevent a variety of human cancers, while data on the association between aspirin and some kinds of cancer are conflicting. Preclinical studies and clinical trials also reveal the therapeutic effect of aspirin on cancer. Although cyclooxygenase is a well-known target of aspirin, recent studies uncover other targets of aspirin and its metabolites, such as AMP-activated protein kinase, cyclin-dependent kinase, heparanase, and histone. Accumulating evidence demonstrate that aspirin may act in different cell types, such as epithelial cell, tumor cell, endothelial cell, platelet, and immune cell. Therefore, aspirin acts on diverse hallmarks of cancer, such as sustained tumor growth, metastasis, angiogenesis, inflammation, and immune evasion. In this review, we focus on recent progress in the use of aspirin for cancer chemoprevention and therapy, and integratively analyze the mechanisms underlying the anticancer effects of aspirin and its metabolites. We also discuss mechanisms of aspirin resistance and describe some derivatives of aspirin, which aim to overcome the adverse effects of aspirin.

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Glucose–aspirin: Synthesis and in vitro anti-cancer activity studies

Cited by 19 publications

References 10 publications

Application of Hartree-Fock Method for Modeling of Bioactive Molecules Using SAR and QSPR

Application of Hartree-Fock Method for Modeling of Bioactive Molecules Using SAR and QSPR

Synthesis and in vitro Bioactivity Evaluation of New Galactose and Fructose Ester Derivatives of 5‐Aminosalicylic Acid

Complex roles of the old drug aspirin in cancer chemoprevention and therapy

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