Light sensitive liposomes

• US 4,882,165 A
• Filed: 11/05/1986
• Issued: 11/21/1989
• Est. Priority Date: 11/09/1981
• Status: Expired due to Fees

• Current Assignee: Regents of the University of California (University of California)
• Original Assignee: Regents of the University of California (University of California)
• Inventors: Pidgeon, Charles, Hunt, Anthony C.
• Primary Examiner(s): Robinson, Douglas W.
• Application Number:
  US06/926,877
• Time in Patent Office: 1,112 Days
• Field of Search: 252/316, 252/30, 424/38, 428/402.2, 264/4.1, 264/4.3, 264/4.6
• US Class Current: 424/450
• CPC Class Codes: A61K 9/1271 Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers liposome as conjugate A61K47/6911
• CPC Class Codes: B01J 13/02 Making microcapsules or microballoons for medical preparations A61K9/50
• CPC Class Codes: C07F 9/10 Phosphatides, e.g. lecithin
• CPC Class Codes: Y10T 428/2984 Microcapsule with fluid core [includes liposome]

Abstract

Light sensitive liposomes are provided which release their contents on demand in response to irradiation with an appropriate wavelength of light. Substantially all the liposome contents can be released within about 60 seconds.

Preferred embodiments of the light sensitive liposomes include lipids having at least one retinoyl group and being a structural component of the lipid membrane.

Claims

1. A light sensitive liposome comprising:

a lipid membrane, said lipid membrane encapsulating a fluid, said lipid membrane including a light sensitive lipid in an amount from about 50 wt.% to about 100 wt.% of the lipid membrane and having a polar head region and a nonpolar tail region, said light sensitive lipid including one retinoyl group or two retinoyl groups covalently bonded in the nonpolar tail region of said light sensitive lipid, said light sensitive lipid having an absorptive of light at a predetermined wavelength between about 300 nm to about 400 nm, said light sensitive lipid providing release of said fluid from said lipid membrane in response to an effective amount of irradiation at said predetermined wavelength.

2. The light sensitive liposome as in claim 1 wherein:

said light sensitive lipid is a glycerol derivative defining a 1 position carbon and a 2 position carbon, said one retinoyl group esterified at said 1 position carbon or at said 2 position carbon and said two retinoyl groups esterified at both of said 1 and 2 position carbons.

3. The light sensitive liposome as in claim 1 wherein:

said retinoyl groups are derived in major part from transretinoic acid.

4. The light sensitive liposome as in claim 1 wherein:

said light sensitive lipid includes di-retinoyl-sn-glycero-3-phosphocholine, 1-palmitoyl, 2-retinoyl-sn-3-phosphocholine and mixtures thereof.

5. The light sensitive liposome as in claim 1 wherein said light sensitive lipid with one retinoyl group has the structure ##STR4## wherein n is from about 8 to about 18, and said light sensitive lipid with two retinoyl groups has the structure ##STR5##

6. The light sensitive liposome as in claim 1 wherein said fluid includes a polar liquid phase.

7. The light sensitive liposome as in claim 6 wherein said polar liquid phase is aqueous.

8. The light sensitive liposome as in claim 6 wherein said fluid includes a biologically active component.

9. The light sensitive liposome as in claim 6 wherein said fluid includes a pharmaceutical.

10. The light sensitive liposome as in claim 1 wherein:

said membrane in the releasing position permits substantially all of said fluid to leak therefrom.

11. The light sensitive liposome as in claim 1 wherein said light sensitive lipid is a structural component of said lipid membrane.

12. The light sensitive liposome as in claim 4 wherein said predetermined wavelength is about 360 nm.

13. The light sensitive liposome as in claim 12 wherein the effective amount of said irradiation permits substantially all of said fluid to leak from said membrane within about 60 seconds.

14. The light sensitive liposome as in claim 13 wherein said effective amount of irradiation is an irradiance of at least about 4 mW/cm² for at least about 15 seconds.

15. The light sensitive liposome as in claim 1 wherein said light sensitive lipid with one retinoyl group has the structure ##STR6## and said light sensitive lipid with two retinoyl groups has the structure ##STR7## wherein n is about 8 to about 18, and R is selected from the group consisting of --H, --CH₂ CH₂ NH₂, --CH₂ CH₂ N⁺ (CH₃)₃, --CH₂ CHNH₂ COOH, --CH₂ CHOHCH₂ OH, and ##STR8##