NOVEL CATIONIC AND POLYCATIONIC AMPHOPHILIC COMPOUNDS, REAGENTS CONTAINING THEREOF AND THEIR USE Russian patent published in 2002 - IPC

Abstract RU 2179549 C2

FIELD: organic chemistry. SUBSTANCE: invention describes novel compounds of the general formula (I) given in the invention claim where R1 means saturated or nonsaturated C(O)-C1-23-chain or saturated or nonsaturated C1-24-chain; A1 means O-R2-group where R2 has value indicated for R1; A2 means NR3X- residue or -N+R3R4R5Y--residue where R3, R4 that can be similar or different and under condition that R3 and R4 can not mean hydrogen atom simultaneously mean hydrogen atom, alkyl group with 1-4 carbon atoms, (CH2)n-group where "n" = 2-6; R5 that can mean the same value or distinct from R3 and R4 means hydrogen atom, alkyl group with 1-4 carbon atoms, (CH2)n-OH-group or the group [(CH2)mNH]o-(CH2)n-NH2; "m" means whole number from 2 to 6 and can be the same or distinct from "n" or "o" being "n" can mean whole number from 2 to 6; "o" can mean whole number from 0 to 4; X can mean the following values additionally to R5: amide-bound amino acid. -C(O)-CHR6N(R7)2-group, -C(O)-CHR6N +(R7)3-group, -C(O)-CHR6N +(R7)2 R8- group or -C(O)-CHR6N R7 R8-group under condition that when R3 means hydrogen atom then X means amide-bound amino acid being R6 means -(CH2)m-NR7R8-residue where "m" can mean number from 1 to 5; R7 means hydrogen atom or alkyl group with 1-4 carbon atoms; R8 means (CH2)n-N(R7)2-group or -(CH2)n-N +(R7)3-group being "n" means whole number from 2 to 4; R7 can mean the above indicated value; Y means pharmaceutically acceptable anion; B1 means NH[C(O)-(CH2)p-NH]q-Z- residue being "p" means number from 1 to 6 and "q" means number from 0 to 2; Z means -C(O)-CHR6N(R7)2/ -group, -C(O)- CHR6N +(R7)3-group, -C(O)-CHR6N +(R7)2R8-group or -C(O)-CHR6N R7R8-group and R6...R8 and "m" have the above indicated values; B2 can mean value given for A1; value A1 is used with B1 only and value A2 is used with B2 only. Invention describes reagent eliciting ability for transfection as solution consisting of at least one compound of the general formula (I) and mixing with water as a solvent and also reagent containing except for one or some compounds of the formula (I) also other lipid compounds in the form of liposome or other aggregates. Invention describes method of incorporation of (bio)molecules into cells by contacting reagent of the formula (I) with ability to transfection firstly with anionic (bio)molecule and then with cells. New compounds are able for effective transfection, they show low toxicity, their use does not require the preliminary treatment of cells in order to enhance permeability of cellular membrane and they can be used in vivo. EFFECT: new compounds indicated above, valuable biological properties. 14 cl, 7 dwg, 24 ex

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RU 2 179 549 C2

Authors

Ehrkhard Fernkhol'Ts

Kherbert Fon Der Ehl'Tts

Mattias Khintspeter

Dates

2002-02-20Published

1996-06-12Filed