Fluorescent macrocycle-dye-anchor conjugates for sensing phospholipids in biomembranes

Oshchepkov, Alexander S.; Silva, Elisabete Cruz Da; Morozov, Boris S.; Aparin, Ilya O.; Kataev, Evgeny A.; Klymchenko, Andrey S.

doi:10.1016/j.snb.2023.133911

Cited by 5 publications

(2 citation statements)

References 75 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Nonetheless, the task of sensing and imaging lipid organization continues to present challenges [ 70 ]. Despite these difficulties, successful examples of studying cellular membranes have emerged recently, including sensor systems for detecting phospholipids [ 71 , 72 ], investigating membrane tension [ 73 ] and the cellular microenvironment [ 74 , 75 ]. Further development of sensors for exploring the features of bacterial membrane organization can be a promising direction in studying the mechanisms of antibiotic action.…”

Section: Sensing the Antibiotic Mechanism Of Actionmentioning

confidence: 99%

Sensing of Antibiotic–Bacteria Interactions

Baranova,

Tyurin,

Korshun

et al. 2023

Antibiotics

View full text Add to dashboard Cite

Sensing of antibiotic–bacteria interactions is an important area of research that has gained significant attention in recent years. Antibiotic resistance is a major public health concern, and it is essential to develop new strategies for detecting and monitoring bacterial responses to antibiotics in order to maintain effective antibiotic development and antibacterial treatment. This review summarizes recent advances in sensing strategies for antibiotic–bacteria interactions, which are divided into two main parts: studies on the mechanism of action for sensitive bacteria and interrogation of the defense mechanisms for resistant ones. In conclusion, this review provides an overview of the present research landscape concerning antibiotic–bacteria interactions, emphasizing the potential for method adaptation and the integration of machine learning techniques in data analysis, which could potentially lead to a transformative impact on mechanistic studies within the field.

show abstract

Section: Sensing the Antibiotic Mechanism Of Actionmentioning

confidence: 99%

Sensing of Antibiotic–Bacteria Interactions

Baranova,

Tyurin,

Korshun

et al. 2023

Antibiotics

View full text Add to dashboard Cite

show abstract

“…The first generation of our systems demonstrated an excellent ability to fold and unfold depending on the protonation and complexation states. The principle of binding event visualization is based on the supramolecular p K a shift induced by the complexation. , For instance, receptor 1 binds sulfate in a diprotonated state (at pH 3.6), leading to fluorescence quenching. The quenching results from the folding of the receptor, producing a naphthalimide–pyridine–naphthalimide stack (Figure a).…”

Section: Introductionmentioning

confidence: 99%

Macrocyclic Conformational Switch Coupled with Pyridinium-Induced PET for Fluorescence Detection of Adenosine Triphosphate

Morozov,

Gargiulo,

Ghule

et al. 2024

J. Am. Chem. Soc.

Self Cite

View full text Add to dashboard Cite

The binding of nucleotides is crucial for signal transduction as it induces conformational protein changes, leading to downstream cellular responses. Synthetic receptors that bind nucleotides and transduce the binding event into global conformational rearrangements are highly challenging to design, especially those that operate in an aqueous solution. Much work is focused on evaluating functionalized dyes to detect nucleotides, whereas coupling of a nucleotide-induced conformational switching to a sensing event has not been reported to date. We disclose synthetic receptors that undergo a global conformational rearrangement upon nucleotide binding. Integrating naphthalimide and the pyridinium ion into the structure enables stabilization of the folded conformation and efficient fluorescence quenching. The binding of a nucleotide rearranges the receptor conformation and alters the strong fluorescence enhancement. The methylpyridinium-containing receptor demonstrated high sensing selectivity for adenosine 5′-triphosphate (ATP) and a record 160-fold fluorescence enhancement. It can detect fluctuations of ATP in HeLa cells and possesses low cytotoxicity. The developed systems present an attractive approach for designing ATP-responsive artificial molecular switches that operate in water and integrate a strong fluorescence response.

show abstract

Cytosine‐Functionalized Macrocyclic Receptor for Nucleotides: Combining Three Recognition Motifs

Morozov,

Oshchepkov,

et al. 2023

Eur J Org Chem

Self Cite

View full text Add to dashboard Cite

Nucleoside monophosphates perform various essential functions and serve as second messengers in living systems. Despite the success of nucleotide‐selective probes based on proteins, the creation of synthetic receptors for nucleoside monophosphates remains a challenging task. In this paper, we explore the design of synthetic receptors based on a combination of three recognition motifs. We show that each binding motif contributes to the formation of the host‐guest complexes. The core macrocycle provides recognition of the phosphate residue of the nucleotide, while naphthalimide and the attached cytosine residue participate in the coordination of the nucleobase via π‐π and hydrogen bonding interactions. The presence of cytosine in the receptor structure substantially increases the overall affinity of receptors for nucleotides. A considerable increase (100‐fold) in binding affinities is observed for the tetranucleotide DNA sequences 5′‐GGGG ‐3′ and 5′‐CCCC‐3′, as compared to the previously reported system without the attached cytosine.

show abstract

Fluorescent macrocycle-dye-anchor conjugates for sensing phospholipids in biomembranes

Cited by 5 publications

References 75 publications

Sensing of Antibiotic–Bacteria Interactions

Sensing of Antibiotic–Bacteria Interactions

Macrocyclic Conformational Switch Coupled with Pyridinium-Induced PET for Fluorescence Detection of Adenosine Triphosphate

Cytosine‐Functionalized Macrocyclic Receptor for Nucleotides: Combining Three Recognition Motifs

Contact Info

Product

Resources

About