β-Amino Acid and Amino-Alcohol Conjugation of a Nonsteroidal Anti-Inflammatory Drug (NSAID) Imparts Hydrogelation Displaying Remarkable Biostability, Biocompatibility, and Anti-Inflammatory Properties

Majumder, Joydeb; Das, Madhusweta; Deb, Jolly; Jana, Siddhartha S.; Dastidar, Parthasarathi

doi:10.1021/la401929v

Cited by 34 publications

(31 citation statements)

References 63 publications

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“…Based on their IC 50 values, except 3, rest of the derivatives were found to have a better killing property compared to their parent compound naproxen sodium (NS). It is of note that although 1 and 2 could exhibit better killing properties (IC 50 ~ 2 mM and ~3 mM, respectively) against the cancer cell lines, they also proved to be cytotoxic against the mouse macrophage cell line RAW 264.7 [13]. Because macrophages serve as the first line of defense during tumor establishment [16], a drug molecule with little to no toxic effect against macrophages would be advantageous.…”

Section: Resultsmentioning

confidence: 99%

“…Furthermore, we have showed that 4 can inhibit PGE 2 synthesis and delay tumor cell migration ( in vitro ). Since the derivative 4 is capable of forming hydrogel at room temperature [13] it can also be employed as the hydrogel drug-delivery system [23] for sustained release of the anti-cancer agent. However, it is also important to note the difference in the IC 50 vales of 4 against p53 wild type MCF-7 (~3 mM) and p53 null MDA-MB-231 (~6 mM) cells.…”

Section: Discussionmentioning

confidence: 99%

“…All the naproxen derivatives were synthesized according to the methods described in our previously published literature [13]. …”

Section: Methodsmentioning

confidence: 99%

“…To demonstrate the above hypothesis we chose to work with four naproxen-derivatives [13] 1 – 4 (Figure 1). In the present study we report that naproxen derivative 4 can be employed as an anti-cancer agent due to its enhanced cytotoxic activity against human breast cancer cell lines and also address the underlying mechanism of action by employing studies related to induction of apoptosis, activation of caspases, cell-cycle progression, synthesis of PGE 2 and cellular migration.

Figure 1 Naproxen and its derivatives (1–4).…”

Section: Introductionmentioning

confidence: 99%

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A novel naproxen derivative capable of displaying anti-cancer and anti-migratory properties against human breast cancer cells

et al. 2014

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BackgroundIncreasingly, the role of chronic inflammation and its mediators in tumor generation and progression is gaining importance in the field of cancer research. In this context, candidature of non steroidal anti-inflammatory drugs (NSAIDs) as potential anti-tumor therapeutic agent is being evaluated globally. In the present study we have evaluated the anti-cancer effect of a series of newly synthesized naproxen derivatives on human breast cancer cell lines.MethodsMCF-7 (poorly invasive) and MDA-MB-231 (highly invasive) cells were treated with different concentrations of naproxen sodium and its derivatives in vitro, and the underlying mechanism of action was monitored by employing studies related to induction of apoptosis, activation of caspases, cell-cycle progression, synthesis of PGE2 and cellular migration.ResultsAfter a preliminary screening using MCF-7 and MDA-MB-231 cells, it was evident that naproxen derivative 4 has a better killing property compared to its parent compound naproxen sodium (NS). On further investigation, it was apparent that the observed growth inhibitory activity on MDA-MB-231 cells after treatment with 4, was not due to cell cycle arrest but due to an early induction of apoptosis and subsequent induction of caspases 3 and 9. Derivative 4 could also inhibit COX activity in MDA-MB-231 cells as evidenced by reduction in prostaglandin E2 secretion. Moreover, 4 was capable of delaying the overall migration rate of MDA-MB-231 cells in vitro.ConclusionIn this study we report that a naproxen-derivative (4) has powerful anti-inflammatory and anti-tumor properties as it induces appreciable amount of apoptosis in breast cancer cell line, and can also delay migration of cancer cells (MDA-MB-231) which would in turn delay cancer cell invasion and formation of secondary tumours in primary breast cancer patients. Thus, we propose that 4 is worthy of further investigation due to its potential as a therapeutic agent in anti-tumor treatment regimen.

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Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

“…All the naproxen derivatives were synthesized according to the methods described in our previously published literature [13]. …”

Section: Methodsmentioning

confidence: 99%

Figure 1 Naproxen and its derivatives (1–4).…”

Section: Introductionmentioning

confidence: 99%

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A novel naproxen derivative capable of displaying anti-cancer and anti-migratory properties against human breast cancer cells

et al. 2014

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“…Through hydrolysis of the hydrazone bond, Nb was released from the PA gel over the course of a month. Other drugs, including naproxen, dexamethasone, and fenoprofen have also been released from PA gels using cleavable linkers to achieve long-term and localized release [148][149][150][151].…”

Section: Peptide Amphiphilesmentioning

confidence: 99%

Gasotransmitter delivery via self-assembling peptides: Treating diseases with natural signaling gases

Qian

Matson

2017

Advanced Drug Delivery Reviews

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Supramolecular Synthon Approach in Designing Molecular Gels for Advanced Therapeutics

Dastidar

Roy

Parveen

2018

Advanced Therapeutics

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Low‐molecular‐weight gelators (LMWGs) are an important class of soft materials that offer various potential applications including drug delivery. Structural diversities of the reported LMWGs and lack of molecular‐level understanding of the self‐assembly process of gelation make it difficult to design a gelator a priori. Most often gelators are discovered in a serendipitous manner and second‐generation gelators are designed by modifying known gelling scaffolds. Since gel network within which the solvent molecules are immobilized is often found to be crystalline, a supramolecular synthon approach in the context of crystal engineering is demonstrated to be quite effective in designing LMWGs for various applications including therapeutics. Self‐drug‐delivery systems, wherein the need for a delivery vehicle does not exist, are becoming an effective alternative to conventional drug delivery systems. In the form of a simple gel (for non‐invasive topical application) or injectable gel (for invasive subcutaneous applications), LMWGs derived from drugs provide an effective way to develop self‐drug‐delivery systems. This review article encompasses the early development of LMWG research, describes gradual transition from discovering just a gelator to a gelator having potential material applications including drug delivery, and highlights the merit of supramolecular synthon approach in designing LMWGs for self‐drug‐delivery applications.

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β-Amino Acid and Amino-Alcohol Conjugation of a Nonsteroidal Anti-Inflammatory Drug (NSAID) Imparts Hydrogelation Displaying Remarkable Biostability, Biocompatibility, and Anti-Inflammatory Properties

Cited by 34 publications

References 63 publications

A novel naproxen derivative capable of displaying anti-cancer and anti-migratory properties against human breast cancer cells

A novel naproxen derivative capable of displaying anti-cancer and anti-migratory properties against human breast cancer cells

Gasotransmitter delivery via self-assembling peptides: Treating diseases with natural signaling gases

Supramolecular Synthon Approach in Designing Molecular Gels for Advanced Therapeutics

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