Phosphate bioisostere containing amphiphiles: a novel class of squaramide-based lipids

Saha, Abhishek; Panda, Subhankar; Paul, Soumen; Manna, Debasis

doi:10.1039/c6cc04089f

Cited by 19 publications

(45 citation statements)

References 20 publications

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“…The GUVs are widely used as simple model cell membrane because of their similar size to mammalian cells and their aptitude in acting as physical barriers for entrapped materials and used for imaging purpose . The ability of these TP‐lipids in forming giant unilamellar vesicles (GUVs) was examined by standard electroformation method . Fluorescence microscopic images reveal that the 100 % TP‐4 lipid is capable of forming excellent GUVs (Figure A and in the Supporting Information, Figure S3 and Movie S1).…”

Section: Resultsmentioning

confidence: 99%

“…The chain length and degree of unsaturation of the hydrophobic moiety also play a crucial role on the T m values of the lipids . Temperature dependent steady‐state fluorescence anisotropy measurement of 1,6‐diphenyl‐1,3,5‐hexatriene (DPH) was performed under the liposomal environment to calculate the phase transition temperature ( T m ) values of the TP‐lipids . The T m values of the TP‐2 , TP‐3 and TP‐4 lipids were 59, 45 and 62 °C, respectively (Figure A and Figure S4).…”

Section: Resultsmentioning

confidence: 99%

“…The T m values also suggest that the headgroups of these lipids may have inferior hydration abilities than the natural phospholipids. Broader melting ranges indicate less co‐operativity of the TP‐lipids during phase transition . Pre‐transitions of the lipids within 18–27 °C (Figure ) may be due to the interaction among the phosphonate‐ and triazole‐linked ammonium or trimethylammonium moieties.…”

Section: Resultsmentioning

confidence: 99%

“…The presence of phosphonate and triazole‐linked ammonium/trimethylammonium groups prompted us to measure the surface potential of the large unilamellar vesicles (LUV) of these TP‐lipids . Zeta potential measurements provide important information about net surface charge of the vesicles present in the solution and bilayer permeability of the charge molecules and ions.…”

Section: Resultsmentioning

confidence: 99%

“…Most of the reported synthetic lipids are comprised of modified hydrophobic tails, headgroups and the linker region between the tails and the headgroup without altering the phosphodiester bonds. Recently reported headgroup‐modified synthetic lipids with squaramide, sulfobetaine, sulfated quaternary amine, moieties and others displayed a number of exciting and complimentary properties of natural phospholipids.…”

Section: Introductionmentioning

confidence: 99%

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Azidophosphonate Chemistry as a Route for a Novel Class of Vesicle‐Forming Phosphonolipids

Saha

Panda

Pradhan

et al. 2017

Chemistry A European J

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Membrane forming synthetic lipids constitutes a new class of biomaterials with impressive applications in the field of biological and pharmaceutical sciences. Interestingly, alteration(s) in the headgroup region of the lipids offer a wide chemical space to investigate their specific properties. In this regard, we have utilized β-azidophosphonate chemistry to gain access to a novel class of triazole-phosphonate (TP) amphiphiles with fascinating physicochemical properties of lipids. TP lipids form stable vesicles that exhibit negative surface potential across a broad pH range. These anionic lipids have high phase-transition temperatures, phospholipase resistance, slow vesicle leakage profiles, and doxorubicin delivery efficacy. We hypothesize that these readily synthesizable phosphonolipids could find several applications as phospholipid substituents.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Azidophosphonate Chemistry as a Route for a Novel Class of Vesicle‐Forming Phosphonolipids

Saha

Panda

Pradhan

et al. 2017

Chemistry A European J

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Programmable and Multifunctional DNA‐Based Materials for Biomedical Applications

et al. 2018

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DNA encodes the genetic information; recently, it has also become a key player in material science. Given the specific Watson-Crick base-pairing interactions between only four types of nucleotides, well-designed DNA self-assembly can be programmable and predictable. Stem-loops, sticky ends, Holliday junctions, DNA tiles, and lattices are typical motifs for forming DNA-based structures. The oligonucleotides experience thermal annealing in a near-neutral buffer containing a divalent cation (usually Mg ) to produce a variety of DNA nanostructures. These structures not only show beautiful landscape, but can also be endowed with multifaceted functionalities. This Review begins with the fundamental characterization and evolutionary trajectory of DNA-based artificial structures, but concentrates on their biomedical applications. The coverage spans from controlled drug delivery to high therapeutic profile and accurate diagnosis. A variety of DNA-based materials, including aptamers, hydrogels, origamis, and tetrahedrons, are widely utilized in different biomedical fields. In addition, to achieve better performance and functionality, material hybridization is widely witnessed, and DNA nanostructure modification is also discussed. Although there are impressive advances and high expectations, the development of DNA-based structures/technologies is still hindered by several commonly recognized challenges, such as nuclease instability, lack of pharmacokinetics data, and relatively high synthesis cost.

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Squaramide‐Based 5’‐Phosphate Replacements Bind to the DNA Repair Exonuclease SNM1A

et al. 2018

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Phosphate groups are often crucial to biological activity and interactions of oligonucleotides, but confer poor membrane permeability. In addition, the group's lability to enzymatic hydrolysis is an obstacle to its use in therapeutics and in biological tools. We present the synthesis of N ‐oxyamide and squaramide modifications at the 5’‐end of oligonucleotides as phosphate replacements and their biological evaluation using the 5’‐exonuclease SNM1A. The squaryl diamide modification showed minimal recognition as a 5’‐phosphate mimic; however, modest inhibition of SNM1A, postulated to occur through metal coordination at the active site, was observed. Their facile incorporation after solid‐phase synthesis and recognition by the exonuclease makes squaryl diamides attractive neutral 5’‐phosphate replacements for oligonucleotides. This work is the first example of squaryl diamide modifications at the 5’‐terminal position of oligonucleotides and of the potential use of modified oligonucleotides to bind to the metal center of SNM1A.

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Phosphate bioisostere containing amphiphiles: a novel class of squaramide-based lipids

Cited by 19 publications

References 20 publications

Azidophosphonate Chemistry as a Route for a Novel Class of Vesicle‐Forming Phosphonolipids

Azidophosphonate Chemistry as a Route for a Novel Class of Vesicle‐Forming Phosphonolipids

Programmable and Multifunctional DNA‐Based Materials for Biomedical Applications

Squaramide‐Based 5’‐Phosphate Replacements Bind to the DNA Repair Exonuclease SNM1A

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