An Easy Access to Organic Salt‐Based Stimuli‐Responsive and Multifunctional Supramolecular Hydrogels

Majumder, Joydeb; Dastidar, Parthasarathi

doi:10.1002/chem.201601136

Cited by 23 publications

(8 citation statements)

References 87 publications

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“…Compared with polymer gels, LMWGs have considerable mechanical properties; meanwhile, reversible non-covalent bonds and the functional groups of gelators confer to the gels more stimulus responsiveness (pH, light, magnetism, enzyme, ion, etc.) and better biodegradability [15,16]. Researchers have attempted to systematically modify and optimize existing gelators or to introduce diverse functional groups to form new compounds and construct progressive LMWGs [17].…”

Section: Introductionmentioning

confidence: 99%

RETRACTED: A Novel Drug Self-Delivery System from Fatty Alcohol Esters of Tranexamic Acid for Venous Malformation Sclerotherapy

et al. 2022

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Venous malformation (VM), which causes severe damage to patients’ appearance and organ function, is one of the most common vascular malformations. At present, many drugs in clinical treatment cause various adverse reactions. Herein, we synthesized cationic amphiphilic gelators (TA6, TA8, and TA9) by introducing saturated carbon chains of different lengths to tranexamic acid (TA), which could self-assemble into low-molecular-weight gels (LMWGs) as drug delivery carriers by hydrogen bonds, van der Waals forces, and hydrophobic interactions. The rheological properties, gelation driving force and drug release profiles of TA6, TA8, and TA9 hydrogels were characterized, and the results indicated that the hydrogels prepared in this study possessed the typical characteristics of a gel and could release drugs slowly. More importantly, the TA9 gelator showed significant pharmacological activity, in that it served as both an active drug compound and a drug carrier. The in vitro experiments demonstrated that TA9 induced HUVECs death and hemolysis by destroying cell membranes in a dose-dependent manner, and caused cell death and hemolysis at a concentration of 0.09 µM/mL. Meanwhile, we found TA9 could interact not only with fibrinogen, but also with other endogenous molecules in the blood. After the administration of TA9 hydrogel for 15 days, macroscopic imaging and histological evaluation in mice and rabbits displayed obvious thrombi, inflammatory reactions, and venous embolization, indicating that the mechanism of the TA9 hydrogel in treating VM was involved in two processes. Firstly, the TA9 hydrogel relied on its mechanical strength to physically block veins and continuously release TA9, in situ, for targeted therapy. Then, TA9 destroyed endothelial cells and damaged venous walls critically, causing thrombi. Most excitingly, TA9 was hydrolyzed to TA by enzymes that inhibited the degradation of thrombi by plasmin to prolong the embolization time and to promote venous fibrosis. Compared with other clinically available sclerosants, the degradation of TA9 also empowered a better biocompatibility and biodegradability for the TA9 hydrogel. In conclusion, we synthesized a potentially safe and effective derivative of TA and developed a low-molecular-weight gel as a self-delivery system for TA in treating VM.

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Section: Introductionmentioning

confidence: 99%

RETRACTED: A Novel Drug Self-Delivery System from Fatty Alcohol Esters of Tranexamic Acid for Venous Malformation Sclerotherapy

et al. 2022

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“…In the context of synthesis of gelator molecules, salt formation deserves special mention; it is the least time consuming high throughput, high yield process in comparison to typical covalent synthesis thereby providing means to generate a large library of potential LMWGs within a relatively short period of time. We demonstrated that such supramolecular approach was indeed useful in generating SGs for various applications such as synthesizing nanoparticles, sensing, dye adsorption, drug delivery via self‐delivery fashion etc.…”

Section: Introductionmentioning

confidence: 99%

Simple Organic Salts Having a Naphthalenediimide (NDI) Core Display Multifunctional Properties: Gelation, Anticancer and Semiconducting Properties

Parveen

Maity

Dastidar

2017

Chemistry An Asian Journal

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Following a supramolecular synthon rationale, a dicarboxylic acid derivative having a naphthalenediimide (NDI) core, namely, bis-N-carboxymethyl naphthalenediimide (NDI-G), was reacted with n-alkyl amines with varying alkyl chain lengths to generate a new series of primary ammonium dicarboxylate (PAD) salts. The majority of the salts (≈85 %) were found to gel various polar solvents. The gels were characterized by dynamic rheology and high-resolution electron microscopy. Single-crystal and powder X-ray diffraction analyses were used to study the supramolecular synthon present in one of the gelator salts (i.e., S8). Charge-transfer (CT)-induced gelation with donor molecules such as anthracene methanol (Ant) and pyrene (Py) was also possible with S8. The CT complex (S8.Ant) displayed anticancer activity as probed by cell migration assay on the highly aggresive breast cancer cell line MDA-MB-231. The DMSO gel of S8.Ant also displayed semiconducting behavior. To the best of our knowledge, simple organic salts with an NDI core that display such mulitifunctional properties are hitherto unknown.

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“…“The peasant who wants to harvest in his lifetime cannot wait for the ab initio theory of weather”—in keeping with the philosophy of Hans Georg von Schnering, the author’s group has been actively involved in designing supramolecular gelators following the crystal engineering approach and successfully developed many supramolecular gels that have displayed intriguing material properties, as applicable in containing oil spills [19], synthesizing metal nanoparticles [24], sensing hazardous gas [25] and dissolved glucose, and in the adsorption of dyes [25].…”

Section: Supramolecular Gels For Various Applicationsmentioning

confidence: 99%

Designing Supramolecular Gelators: Challenges, Frustrations, and Hopes

Dastidar

2019

Gels

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This article is a personal account of the author, who serendipitously entered the field of supramolecular gels nearly two decades ago. A supramolecular synthon approach in the context of crystal engineering was utilized to develop a working hypothesis to design supramolecular gelators derived from simple organic salts. The activity not only provided a way to occasionally predict gelation, but also afforded clear understanding of the structural landscape of such supramolecular materials. Without waiting for an ab initio approach for designing a gel, a large number of supramolecular gelators derived from organic salts were designed following the working hypothesis thus developed. Organic salts possess a number of advantages in terms of their ease of synthesis, purification, high yield and stability and, therefore, are suitable for developing materials for various applications. Organic salt-based gel materials for containing oil spills, synthesizing inorganic nanostructures and metal nanoparticles, sensing hazardous gas and dissolved glucose, adsorbing dyes, and facilitating drug delivery in self-delivery fashion have been developed. The journey through the soft world of gelators which was started merely by serendipity turned out to be rewarding, despite the challenges and frustrations in the field.

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An Easy Access to Organic Salt‐Based Stimuli‐Responsive and Multifunctional Supramolecular Hydrogels

Cited by 23 publications

References 87 publications

RETRACTED: A Novel Drug Self-Delivery System from Fatty Alcohol Esters of Tranexamic Acid for Venous Malformation Sclerotherapy

RETRACTED: A Novel Drug Self-Delivery System from Fatty Alcohol Esters of Tranexamic Acid for Venous Malformation Sclerotherapy

Simple Organic Salts Having a Naphthalenediimide (NDI) Core Display Multifunctional Properties: Gelation, Anticancer and Semiconducting Properties

Designing Supramolecular Gelators: Challenges, Frustrations, and Hopes

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