New transfection reagents

• US 20050164971A1
• Filed: 01/21/2005
• Published: 07/28/2005
• Est. Priority Date: 11/12/1998
• Status: Abandoned Application

• Current Assignee: Life Technologies Corporation (Thermo Fisher Scientific Incorporated)
• Original Assignee: Life Technologies Corporation (Thermo Fisher Scientific Incorporated)
• Inventors: Gebeyehu, Gulilat, Chu, Yongliang, Masoud, Malek
• Application Number:
  US11/040,449
• Publication Number:
  US 20050164971A1
• Time in Patent Office: Days
• US Class Current: 514/44.R
• CPC Class Codes: A61K 31/14 Quaternary ammonium compounds, e.g. edrophonium, choline betaines A61K31/205
• CPC Class Codes: A61K 38/28 Insulins
• CPC Class Codes: A61K 38/40 Transferrins, e.g. lactoferrins, ovotransferrins
• CPC Class Codes: A61K 47/543 Lipids, e.g. triglycerides; Polyamines, e.g. spermine or spermidine
• CPC Class Codes: A61K 9/16 Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction A61K9/20 takes precedence if the final form is a tablet; microspheres with drug-free outer coating, microcapsules A61K9/50; mixture of different granules, microcapsules, (coated) microparticles A61K9/5084; nanoparticles A61K9/51
• CPC Class Codes: C07C 211/21 Monoamines
• CPC Class Codes: C07C 211/63 having quaternised nitrogen atoms bound to acyclic carbon atoms
• CPC Class Codes: C07C 211/64 having quaternised nitrogen atoms bound to carbon atoms of six-membered aromatic rings
• CPC Class Codes: C07C 229/26 having more than one amino group bound to the carbon skeleton, e.g. lysine
• CPC Class Codes: C07D 209/48 with oxygen atoms in positions 1 and 3, e.g. phthalimide
• CPC Class Codes: C07D 241/12 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C12N 15/88 using microencapsulation, e.g. using amphiphile liposome vesicle
• CPC Class Codes: Y10S 435/81 Packaged device or kit

Abstract

Disclosed are compounds capable of facilitating transport of biologically active agents or substances into cells having the general structure: wherein

• • Q is selected from the group consisting of N, O and S; L is any bivalent organic radical capable of linking each Q, such as C, CH, (CH₂)l, or {(CH₂)i-Y—(CH₂)j}k, wherein Y is selected from the group consisting of CH₂, an ether, a polyether, an amide, a polyamide, an ester, a sulfide, a urea, a thiourea, a guanidyl, a carbamoyl, a carbonate, a phosphate, a sulfate, a sulfoxide, an imine, a carbonyl, and a secondary amino group and wherein Y is optionally substituted by —X₁-L′-X₂-Z or -Z; R₁-R₆, independently of one another, are selected from the group consisting of H, —(CH₂)p-D-Z, an alkyl, an alkenyl, an aryl, and an alkyl or alkyl ether optionally substituted by one or more of an alcohol, an aminoalcohol, an amine, an amide, an ether, a polyether, a polyamide, an ester, a mercaptan, an alkylthio, a urea, a thiourea, a guanidyl, or a carbamoyl group, and wherein at least one of R₁, R₃, R₄ and R₆ is a straight chain or branched, cyclic, alkyl, alkenyl, alkynyl or aryl group; and anyone of R₁, R₃, R₄ and/or R₆ may optionally be covalently linked with each other, with Y or with L when L is C or CH to form a cyclic moiety; Z is selected from the group consisting of amine, spermiyl, carboxyspermiyl, guanidyl, spermidinyl, putricinyl, diaminoalkyl, pyridyl, piperidinyl, pyrrolidinyl, polyamine, amino acid, peptide, and protein; X₁ and X₂, independently of one another, are selected from the group consisting of NH, O, S, alkylene, and arylene; L′ is selected from the group consisting of alkylene, alkenylene, alkynylene, arylene, alkylene ether, and polyether; D is Q or a bond; A₁ and A₂, independently of one another, are selected from the group consisting of CH₂O, CH₂S, CH₂NH, C(O), C{NH), C(S) and (CH₂)t; X is a physiologically acceptable anion; m, n, r, s, u, v, w and y are 0 or 1, with the proviso that when both m and n are 0 at least one of r, s, u and y is other than 0; i, j, k, l, p and are integers from 0 to about 100; q is an integer from 1 to about 1000; and a is the number of positive charge divided by the valence of the anion.

Claims

1. A compound having the formula:

2. The compound as claimed in claim 1, wherein at least one of R₁, R₃, R₄ and R₆ is a straight chain, branched, or cyclic alkyl, alkenyl, alkynyl or aryl having from about 8 to about 24 carbon atoms.

3. The compound as claimed in claim 1, wherein the alkyl ether optionally substituted by one or more alcohol groups comprises a carbohydrate.

4. The compound as claimed in claim 1, wherein said compound has the formula:

5. The compound as claimed in claim 4, wherein at least one of R₁, R₃, R₄ and R₆ is a straight-chain, branched, or cyclic alkyl, alkenyl, alkynyl or aryl having from about 8 to about 24 carbon atoms.

6. The compound as claimed in claim 4, wherein the alkyl ether optionally substituted by one or more alcohol groups comprises a carbohydrate.

7. The compound as claimed in claim 4 having the formula:

8. The compound as claimed in claim 1 having the formula:

9. The compound as claimed in claim 1 having the formula:

10. The compound as claimed in claim 1 having the formula:

11. The compound as claimed in claim 1 having the formula

12. The compound as claimed in claim 1 having the formula:

13. The compound as claimed in claim 1, having the formula:

14. The compound as claimed in claim 1 having the formula:

15. The compound as claimed in claim 1 having the formula:

16. The compound as claimed in claim 1 having the formula:

17. The compound as claimed in claim 1, wherein said compound has the formula:

18. The compound as claimed in claim 1 having the formula:

19. A composition comprising one or more compounds having the formula:

20. A kit comprising one or more container means wherein said container means comprises one or more compounds having the formula: