PL449497A1 - A receptor for transporting zwitterions across organic membranes and a method of transporting zwitterions across organic membranes using this receptor - Google Patents

A receptor for transporting zwitterions across organic membranes and a method of transporting zwitterions across organic membranes using this receptor

Info

Publication number
PL449497A1
PL449497A1 PL449497A PL44949724A PL449497A1 PL 449497 A1 PL449497 A1 PL 449497A1 PL 449497 A PL449497 A PL 449497A PL 44949724 A PL44949724 A PL 44949724A PL 449497 A1 PL449497 A1 PL 449497A1
Authority
PL
Poland
Prior art keywords
receptor
organic
membranes
zwitterions
zwiterions
Prior art date
Application number
PL449497A
Other languages
Polish (pl)
Inventor
Marta ZALESKAYA-HERNIK
Marcin WILCZEK
Jan Romański
Original Assignee
Uniwersytet Warszawski
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Uniwersytet Warszawski filed Critical Uniwersytet Warszawski
Priority to PL449497A priority Critical patent/PL449497A1/en
Priority to PCT/IB2025/058199 priority patent/WO2026038142A1/en
Publication of PL449497A1 publication Critical patent/PL449497A1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
    • C07C237/38—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
    • C07C225/20—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
    • C07C225/22—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/65—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D323/00—Heterocyclic compounds containing more than two oxygen atoms as the only ring hetero atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Separation Using Semi-Permeable Membranes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Przedmiotem zgłoszenia jest receptor do transportu zwiterjonów przez membrany organiczne i sposób transportu zwiterjonów przez membrany organiczne wykorzystujący ten receptor. Receptor do transportu zwiterjonów przez membrany organiczne, charakteryzuje się tym, że posiada w obrębie jednej cząsteczki domenę amidową koordynującą część anionową zwiterjonu, domenę eterową koordynującą część kationową zwiterjonu oraz domenę lipofilową, tworząc strukturę molekularną o wzorze ogólnym 1, gdzie ugrupowanie amidowe kwasu kwadratowego jest zdolne do odwracalnego wiązania części anionowej zwiterjonów poprzez jej koordynację protonami grup amidowych, ugrupowanie arylowe z podstawnikiem eterowym (Ar—Y) jest zdolne do odwracalnego wiązania części kationowej zwiterjonów poprzez jej koordynację wolnymi parami elektronowymi atomów tlenu eteru, ugrupowanie arylowe z podstawnikiem (Ar—X) ma właściwości lipofilowe i zapewnia lipofilowość receptora i możliwość jego rozpuszczenia w membranach organicznych, przy czym receptor ma charakter lipofilowy, wykazuje powinowactwo do membrany organicznej i jest rozpuszczalny w rozpuszczalnikach organicznych, mieszaninach rozpuszczalników organicznych i w błonach fosfolipidowych, a także ma zdolność do tworzenia kompleksu z zwiterjonem, rozpuszczalnego w rozpuszczalnikach organicznych lub mieszaninach rozpuszczalników organicznych, korzystnie niemieszających się z wodą, a także w błonach fosfolipidowych, przy czym receptor ma zdolność ekstrakcji zwiterjonów z fazy wodnej, o większym stężeniu zwiterjonów, do fazy organicznej, korzystnie niemieszającej się z wodą, a także ma zdolność ekstrakcji zwrotnej zwiterjonów, z fazy organicznej, korzystnie niemieszającej się z wodą, do fazy wodnej, o mniejszym stężeniu zwiterjonów. Receptor, według zgłoszenia wykazuje zdolność do odwracalnego wiązania zwiterjonów rozpuszczonych w fazie wodnej, w tym aminokwasów o znaczeniu biologicznym w postaci jonów obojnaczych w fizjologicznym pH i wykazuje zdolność ich przenoszenia przez membrany organiczne, także przez fosfolipidowe błony komórkowe. Receptor jest tani i prosty w syntezie i może potencjalnie znaleźć zastosowanie w badaniach nad przenoszeniem aminokwasów przez błony komórkowe w układach biologicznie czynnych.The subject of the application is a receptor for transporting zwitterions through organic membranes and a method of transporting zwitterions through organic membranes using this receptor. A receptor for the transport of zwitterions through organic membranes is characterized in that it has within one molecule an amide domain coordinating the anionic part of the zwiterion, an ether domain coordinating the cationic part of the zwiterion and a lipophilic domain, forming a molecular structure of the general formula 1, wherein the amide group of the squaric acid is capable of reversibly binding the anionic part of zwiterions through its coordination with protons of amide groups, an aryl group with an ether substituent (Ar—Y) is capable of reversibly binding the cationic part of zwiterions through its coordination with free electron pairs of ether oxygen atoms, an aryl group with a substituent (Ar—X) has lipophilic properties and ensures the lipophilicity of the receptor and the possibility of its dissolution in organic membranes, wherein the receptor is lipophilic in nature, has an affinity for the organic membrane and is soluble in organic solvents, mixtures of organic solvents and in Phospholipid membranes and also has the ability to form a complex with a zwitterion, soluble in organic solvents or mixtures of organic solvents, preferably water-immiscible, as well as in phospholipid membranes, wherein the receptor has the ability to extract zwiterions from an aqueous phase with a higher zwiterion concentration into an organic phase, preferably water-immiscible, and also has the ability to back-extract zwiterions from an organic phase, preferably water-immiscible, into an aqueous phase with a lower zwitterion concentration. According to the application, the receptor has the ability to reversibly bind zwiterions dissolved in the aqueous phase, including amino acids of biological significance in the form of zwitterions at physiological pH, and has the ability to transport them through organic membranes, including phospholipid cell membranes. The receptor is cheap and simple to synthesize and may potentially find application in research on the transfer of amino acids across cell membranes in biologically active systems.

PL449497A 2024-08-12 2024-08-12 A receptor for transporting zwitterions across organic membranes and a method of transporting zwitterions across organic membranes using this receptor PL449497A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PL449497A PL449497A1 (en) 2024-08-12 2024-08-12 A receptor for transporting zwitterions across organic membranes and a method of transporting zwitterions across organic membranes using this receptor
PCT/IB2025/058199 WO2026038142A1 (en) 2024-08-12 2025-08-12 Receptor for the transport of zwitterions through organic membranes and a method of transport of zwitterions through organic membranes using said receptor

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PL449497A PL449497A1 (en) 2024-08-12 2024-08-12 A receptor for transporting zwitterions across organic membranes and a method of transporting zwitterions across organic membranes using this receptor

Publications (1)

Publication Number Publication Date
PL449497A1 true PL449497A1 (en) 2026-02-16

Family

ID=98772950

Family Applications (1)

Application Number Title Priority Date Filing Date
PL449497A PL449497A1 (en) 2024-08-12 2024-08-12 A receptor for transporting zwitterions across organic membranes and a method of transporting zwitterions across organic membranes using this receptor

Country Status (2)

Country Link
PL (1) PL449497A1 (en)
WO (1) WO2026038142A1 (en)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL429164A1 (en) * 2019-03-06 2020-09-07 Uniwersytet Warszawski Receptor for removing oxoanions from the water phase, method of removing oxoanions from the water phase, sensor for detecting oxoanions, preparation for removing oxoanions from the water phase and improved process of disposal of aqueous solutions by glass transition

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL429164A1 (en) * 2019-03-06 2020-09-07 Uniwersytet Warszawski Receptor for removing oxoanions from the water phase, method of removing oxoanions from the water phase, sensor for detecting oxoanions, preparation for removing oxoanions from the water phase and improved process of disposal of aqueous solutions by glass transition

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DAMIAN JAGLENIEC, SYLWIA SIENNICKA, ŁUKASZ DOBRZYCKI, MARCIN KARBARZ, JAN ROMANSKI: "Inorganic Chemistry, 2018, 57, 20, 12941–12952", „RECOGNITION AND EXTRACTION OF SODIUM CHLORIDE BY A SQUARAMIDE-BASED ION PAIR RECEPTOR" *
MARTA ZALESKAYA, MARCIN KARBARZ, MARCIN WILCZEK, ŁUKASZ DOBRZYCKI, JAN ROMANSKI: "Inorganic Chemistry, 2020, 59, 13749−13759", „COOPERATIVE TRANSPORT AND SELECTIVE EXTRACTION OF SULFATES BY A SQUARAMIDE-BASED ION PAIR RECEPTOR: A CASE OF ADAPTABLE SELECTIVITY" *

Also Published As

Publication number Publication date
WO2026038142A1 (en) 2026-02-19

Similar Documents

Publication Publication Date Title
Shionoya et al. A new ternary zinc (II) complex with [12] aneN4 (= 1, 4, 7, 10-tetraazacyclododecane) and AZT (= 3'-azido-3'-deoxythymidine). Highly selective recognition of thymidine and its related nucleosides by a zinc (II) macrocyclic tetraamine complex with novel complementary associations
Molina et al. Anion recognition strategies based on combined noncovalent interactions
Shionoya et al. Novel" multipoint" molecular recognition of nucleobases by a new zinc (II) complex of acridine-pendant cyclen (cyclen= 1, 4, 7, 10-tetraazacyclododecane)
Aliakbar Tehrani et al. Functional molecules and materials by π‐interaction based quantum theoretical design
Cuthbert Importance of guanidinium groups for blocking sodium channels in epithelia
Sikkema et al. Cell fuelling and metabolic energy conservation in synthetic cells
Schmuck et al. N ‘-Alkylated Guanidiniocarbonyl Pyrroles: New Receptors for Amino Acid Recognition in Water
Hu et al. Stepwise folding and self-assembly of a merocyanine folda-pentamer
Wu et al. NO-to-[N2O2] 2–-to-N2O Conversion Triggered by {Fe (NO) 2} 10-{Fe (NO) 2} 9 Dinuclear Dinitrosyl Iron Complex
Xu et al. Rapid determination of telmisartan in pharmaceutical preparations and serum by linear sweep polarography
Brown et al. Improved access to linear tetrameric hydroxamic acids with potential as radiochemical ligands for zirconium (IV)-89 PET imaging
Kawai et al. Physicochemical and solution properties of quaternary-ammonium-salt-type amphiphilic gemini ionic liquids with spacers containing oxygen or nitrogen
Smukste et al. Structure− Function Relationship of Amino Acid−[2] Rotaxanes
Egorova et al. Biological activity, solvation properties and microstructuring of protic imidazolium ionic liquids
Joubert et al. Novel nitric oxide synthase inhibitors: a patent review
Ballester et al. Self-assembly, binding, and dynamic properties of heterodimeric porphyrin macrocycles
Vušurović et al. Interactions of protonated guanidine and guanidine derivatives with multiply deprotonated RNA probed by electrospray ionization and collisionally activated dissociation
Ludvı́k et al. Electrochemical reduction of metamitron
Buendia et al. Solvent-dependent disassembly of amphiphilic OPE-based tricarboxamides
Vincil et al. Effects of the number and placement of positive charges on viologen–cucurbit [n] uril interactions
Souto-Trinei et al. Biomimetic construction of phospholipid membranes by direct aminolysis ligations
CN113620883A (en) Preparation method of semi-proton type compound, product and application thereof
Schmuck et al. New guanidinium-based carboxylate receptors derived from 5-amino-pyrrole-2-carboxylate: synthesis and first binding studies
Tsopelas et al. Lipophilicity, biomimetic retention profile and antioxidant activity of selenium species
Çakir et al. Electrochemical and spectroscopic study of 4-(Phenyldiazenyl)-2-{[tris-(hydroxymethyl) methyl] aminomethylene} cyclohexa-3, 5-dien-1 (2H)-one: mechanism of the azo and imine electroreduction