Synthesis and characterization of novel PUFA esters exhibiting potential anticancer activities: An in vitro study

Khan, Azmat Ali; Alam, Muhammad Waqar; Tufail, Saba; Mustafa, Jamal; Owais, Mohammad

doi:10.1016/j.ejmech.2011.07.044

Cited by 24 publications

(16 citation statements)

References 26 publications

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“…2,6-Diisopropylphenol-Oleic acid (2,6P-OLA); is a novel oleic acid conjugate that possess potent antineoplastic properties. Because of its inhibitory and apoptotic action on cancer cells, in vitro [1], it has a potential of being characterised as a member of a new class of fatty acid based anticancer agents [2][3][4][5][6][7]. 2,6P-OLA as of now, has not been exploited for its interaction abilities with various biological targets.…”

Section: Introductionmentioning

confidence: 99%

Biophysical Interactions of Novel Oleic Acid Conjugate and its Anticancer Potential in HeLa Cells

et al. 2015

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Novel conjugate 2,6-Diisopropylphenol-Oleic acid (2,6P-OLA) has shown potent anticancer activity on various cancer cell lines (Khan et al. Lipids 47:973-986, 2012). In the present study, the protein-or/ and DNA-binding property of 2,6P-OLA was evaluated that could predict its potential toxic effect, in vitro. Preferential structural stability and interaction mechanism of 2,6P-OLA to human serum albumin (HSA) and calf thymus DNA (CT-DNA) was used as model molecules, employing fluorescence spectroscopy (FS) and circular dichroism (CD) methods. The binding and apoptotic activities of conjugate were determined on bacterial recombinant DNA, pBR322 and human cancer cell line, HeLa, respectively. FS studies showed a strong conjugate binding affinity to HSA with overall binding constant of K = 7.66 (±0.03) × 10(2) M(-1). Higher concentration induced detectable changes in the CD spectrum of HSA. The conjugate complexation altered HSA secondary conformation by an increase in α-helices and decrease in β-sheets. Flourescence quenching studies with CT-DNA exhibited K = 1.215 × 10(2) L mol(-1) where 2,6P-OLA efficiently displaced the ethidium bromide (EtBr) bound DNA indicating its strong competition with EtBr for intercalation. Similarly, 2,6P-OLA was able to partially bind pBR322, resulting in decrease the intensity of EtBr gradually. The conjugate significantly reduced survival of HeLa cells. Morphological studies revealed altered cell morphology, suggesting apoptotic death of HeLa cells. Overall, our data shows that 2,6P-OLA bind well with both HSA and DNA and possessed anticancer activities.

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Section: Introductionmentioning

confidence: 99%

Biophysical Interactions of Novel Oleic Acid Conjugate and its Anticancer Potential in HeLa Cells

et al. 2015

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“…27 Another interesting approach for the nanodelivery of ω-3 PUFAs was recently used to deliver ALA to diethylnitrosamine-induced hepatocarcinomas in mice. 41 In this case, ALA was conjugated with 2,6-di-isopropylphenol, an anesthetic agent being structurally similar to vitamin E. The chemical structure of this conjugate was reported in Khan et al 42 This compound, conjugated with DHA, was previously shown to possess antioxidant properties and the ability to induce apoptosis and decrease the metastatic potential of human cancer cells. 43 For an efficient delivery, the 2,6-di-isopropylphenol-linolenic acid conjugate was enclosed in nanoliposomes tagged with the tetrapeptide tuftsin (Thr-Lys-Pro-Arg), 44 a fraction of the immunoglobulin G molecule ( Table 2; Figure 2A).…”

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<p>Nanomedicine-based formulations containing ω-3 polyunsaturated fatty acids: potential application in cardiovascular and neoplastic diseases</p>

Serini¹,

Cassano²,

Trombino³

et al. 2019

IJN

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Omega-3 polyunsaturated fatty acids (ω-3 PUFAs) are dietary factors involved in the prevention of cardiovascular, inflammatory, and neoplastic diseases. A multidisciplinary approach -based on recent findings in nutritional science, lipid biochemistry, biotechnology, and biology of inflammation and cancer -has been recently employed to develop ω-3 PUFAcontaining nanoformulations with an aim to protect these fatty acids from degradation, increase their bioavailability and delivery to target tissues, and, thus, enhance their bioactivity. In some cases, these nanoformulations were designed to administer ω-3 PUFAs in combination with other nutraceuticals or conventional/innovative drugs. The aim of this strategy was to increase the activities of the compounds contained in the nanoformulation and to reduce the adverse effects often induced by drugs. We herein analyze the results of papers evaluating the potential use of ω-3 PUFA-containing nanomaterials in fighting cardiovascular diseases and cancer. Future directions in this field of research are also provided.

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“…The study formed esters of linoleic acid 249 and arachidonic acid 252 with propofol. 38 The esters were then evaluated against various cancer cell lines. Linoleic acid 249 was coupled to 2,4-propofol 237 and 2,6-propofol 1, respectively, in the presence of DCC and DMAP to yield esters 250 and 251 (Scheme 36).…”

Section: Scheme 34 Docosahexanoic Acid Ester Conjugates Of Propofol 37mentioning

confidence: 99%

Syntheses of Analogues of Propofol: A Review

Dimitrov

Suonio

2020

Synthesis

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Propofol (2,6-diisopropylphenol) is an intravenous sedative/hypnotic agent that is used extensively for introduction and maintenance of general anaesthesia, sedation of critically ill patients and procedural sedation (e.g., endoscopy). Propofol has a rapid onset and offset of action and shows only minimal accumulation upon prolonged use. Propofol is only sparingly soluble in water and is currently marketed in 10% soybean oil-based lipid emulsion. Propofol’s anaesthetic properties were discovered over forty years ago, and it has been in clinical use for over thirty years. The main use of propofol remains as an anaesthetic but, over the years, analogues have been developed with varying properties from anticancer, anticonvulsant and antioxidant. In addition, large synthetic efforts have been made towards improving propofol’s water-solubility, its activity, and elucidating its structure–activity relationship and exact mechanism of action have been made. This review provides an overview of the research pertaining to propofol-like molecules and covers the efforts of synthetic chemists towards propofol analogues over the last 40 years.1 Introduction2 History3 Early Work4 Improving Water Solubility5 The Importance of the Phenol6 Exploring the Structure–Activity Relationship and Attempts to Improve Activity7 Anticancer Activity8 Anticonvulsant Properties9 Antioxidant Activity10 Photoactive Labelling to Elucidate Mechanism of Action11 Photoregulation12 Conclusion

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Synthesis and characterization of novel PUFA esters exhibiting potential anticancer activities: An in vitro study

Cited by 24 publications

References 26 publications

Biophysical Interactions of Novel Oleic Acid Conjugate and its Anticancer Potential in HeLa Cells

Biophysical Interactions of Novel Oleic Acid Conjugate and its Anticancer Potential in HeLa Cells

<p>Nanomedicine-based formulations containing ω-3 polyunsaturated fatty acids: potential application in cardiovascular and neoplastic diseases</p>

Syntheses of Analogues of Propofol: A Review

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Synthesis and characterization of novel PUFA esters exhibiting potential anticancer activities: An in vitro study

Cited by 24 publications

References 26 publications

Biophysical Interactions of Novel Oleic Acid Conjugate and its Anticancer Potential in HeLa Cells

Biophysical Interactions of Novel Oleic Acid Conjugate and its Anticancer Potential in HeLa Cells

<p>Nanomedicine-based formulations containing &omega;-3 polyunsaturated fatty acids: potential application in cardiovascular and neoplastic diseases</p>

Syntheses of Analogues of Propofol: A Review

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<p>Nanomedicine-based formulations containing ω-3 polyunsaturated fatty acids: potential application in cardiovascular and neoplastic diseases</p>