CA2164813A1 - Stabilized microbubble compositions for ultrasound - Google Patents

Stabilized microbubble compositions for ultrasound

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Publication number
CA2164813A1
CA2164813A1 CA002164813A CA2164813A CA2164813A1 CA 2164813 A1 CA2164813 A1 CA 2164813A1 CA 002164813 A CA002164813 A CA 002164813A CA 2164813 A CA2164813 A CA 2164813A CA 2164813 A1 CA2164813 A1 CA 2164813A1
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CA
Canada
Prior art keywords
gas
surfactant
preparation
microbubbles
liquid
Prior art date
Legal status (The legal status 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 status listed.)
Granted
Application number
CA002164813A
Other languages
French (fr)
Other versions
CA2164813C (en
Inventor
Ernest G. Schutt
David P. Evitts
Rene Alta Kinner
Jeffry G. Weers
Charles David Anderson
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Imcor Pharmaceutical Co
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Individual
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Application filed by Individual filed Critical Individual
Publication of CA2164813A1 publication Critical patent/CA2164813A1/en
Application granted granted Critical
Publication of CA2164813C publication Critical patent/CA2164813C/en
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Expired - Fee Related legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/22—Echographic preparations; Ultrasound imaging preparations ; Optoacoustic imaging preparations
    • A61K49/222—Echographic preparations; Ultrasound imaging preparations ; Optoacoustic imaging preparations characterised by a special physical form, e.g. emulsions, liposomes
    • A61K49/227—Liposomes, lipoprotein vesicles, e.g. LDL or HDL lipoproteins, micelles, e.g. phospholipidic or polymeric
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/22—Echographic preparations; Ultrasound imaging preparations ; Optoacoustic imaging preparations
    • A61K49/222—Echographic preparations; Ultrasound imaging preparations ; Optoacoustic imaging preparations characterised by a special physical form, e.g. emulsions, liposomes
    • A61K49/223—Microbubbles, hollow microspheres, free gas bubbles, gas microspheres
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B6/00—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings
    • G02B6/0001—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings specially adapted for lighting devices or systems
    • G02B6/0005—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings specially adapted for lighting devices or systems the light guides being of the fibre type
    • G02B6/0006—Coupling light into the fibre

Abstract

A microbubble formed of a plurality of a microbubbles comprising a first gas and a second gas surrounded by a membrane such as a surfactant, wherein the first gas and the second gas are present in a molar ratio of from about 1:100 to about 1000:1, and wherein the first gas has a vapor pressure of at least about (760 - x) mm Hg at 37 .degree.C, where x is the vapor pressure of the second gas at 37 .degree.C, and wherein the vapor pressure of each of the first and second gases is greater than about 75 mm Hg at 37 .degree.C; also disclosed are methods for preparing microbubble compositions, including compositions that rapidly shrink from a first average diameter to a second average diameter less than about 75 % of the first average diameter and are stabilized at the second average diameter; methods and kits for preparing microbubbles; and methods for using such microbubbles as contrast agents.

Claims (102)

1. A method for forming stabilized microbubbles in a liquid, said method comprising the steps of:
providing a first gas, a second gas, a membrane forming material, and a liquid, wherein said first gas and said second gas are present in a molar ratio of about 1:100 to about 1,000:1, and wherein said first gas has a vapor pressure of at least about (760 - x) mm Hg at 37°C, where x is the vapor pressure of the second gas at 37°C, and wherein said vapor pressure of each of said first and second gases is greater than about 75 mm Hg at 37°C, with the proviso that said first gas and said second gas are not water vapor; and surrounding said first and second gases with said membrane forming material to form microbubbles in said liquid.
2. The method of Claim 1, wherein said membrane forming material is a surfactant and one of said gases is a fluorocarbon with a vapor pressure less than 760 mm Hg at 37°C.
3. The method of Claim 2, wherein said surfactant comprises one or more phospholipids.
4. The method of Claim 2, wherein said membrane forming material comprises a non-Newtonian surfactant.
5. The method of Claim 1, further comprising the steps of:
initially forming microbubbles having a first average diameter wherein the initial ratio of said first gas to said second gas in said microbubbles is at least about 1:1;
contacting said microbubbles having a first average diameter with a liquid medium;
shrinking said microbubbles in said medium as a result of loss of said first gas through said membrane;
and then stabilizing said microbubbles at a second average diameter of less than about 75% of said first diameter for a period of at least one minute.
6. The method of claim 5, wherein said microbubbles are stabilized at said second diameter by providing a gas osmotic pressure differential across said membrane such that the tension of a gas or gases dissolved in said medium is equal to or greater than the partial pressure of the same gas or gases inside said microbubbles.
7. The method of Claim 5, wherein said first diameter is at least about 5 µm.
8. A method for converting solid microbubble precursors to stabilized microbubbles, said method comprising the steps of:
providing solid or semi-solid substantially liquid-soluble void-containing structures, said void-containing structures defining a plurality of voids having a diameter less than about 100 µm;
providing a gas in said voids;
providing a surfactant;
providing said void-containing structures, said gas, and said surfactant in admixture with a liquid in which said void-containing structures are soluble; and dissolving said void-containing structures in said liquid whereby the gas in said voids forms microbubbles that are surrounded by said surfactant.
9. The method of Claim 8, wherein said void-containing structures are microspheres and said gas is a fluorocarbon.
10. The method of Claim 8, wherein said microbubbles contain a first gas and a second gas respectively present in a molar ratio of from about 1:100 to about 1000:1.
11. The method of Claim 8 wherein said surfactant comprises one or more phospholipids.
12. A method for forming stabilized microbubbles in a liquid from a powder precursor, said method comprising the steps of:
providing a gas osmotic agent-permeated powder precursor; and combining said powder precursor with an aqueous phase whereby said stabilized microbubbles are formed.
13. The method of Claim 12 wherein said gas osmotic agent-permeated powder precursor further comprises a surfactant.
14. The method of Claim 13 wherein said surfactant is a non-Newtonian surfactant.
15. The method of Claim 13 wherein said non-Newtonian surfactant comprises one or more phospholipids.
16. The method of Claim 12 wherein said gas osmotic agent-permeated powder comprises a fluorocarbon.
17. The method of Claim 12 wherein said stabilized microbubbles have a half-life in vivo of at least about 20 seconds.
18. The method of Claim 12 further comprising the steps of:
spray drying a liquid formulation containing a biocompatible film-forming material to form a hollow microsphere powder therefrom;
combining said microsphere powder with a gas osmotic agent to produce said gas osmotic agent-permeated powder precursor.
19. The method of Claim 18, wherein said liquid formulation further comprises an inflating agent.
20. The method of Claim 19, wherein said inflating agent is selected from the group consisting of: methylene chloride, Freon 113, perfluorohexane and carbon dioxide.
21. The method of Claim 18, wherein said liquid formulation further comprises a sugar polyester.
22. The method of Claim 18, wherein said film forming material comprises a starch or derivatized starch.
23. The method of Claim 22, wherein said film forming material comprises a starch or derivatized starch having a molecular weight of greater than about 500,000 or a dextrose equivalency value less than about 12.
24. The method of Claim 23, wherein said starch is hydroxyethyl starch.
25. The method of Claim 18, wherein said film-forming material comprises a non-Newtonian surfactant.
26. The method of Claim 25, wherein said non-Newtonian surfactant comprises one or more phospholipids.
27. The method of Claim 18, wherein said gas osmotic agent comprises a fluorocarbon.
28. The method of Claim 18, wherein said film forming material comprises a sugar ester.
29. The method of Claim 28, wherein said sugar ester has a component with a hydrophilic-lipophilic balance less than about eight.
30. The method of Claim 29, wherein said sugar ester component is sucrose tristearate.
31. The method of claim 18 wherein said gas osmotic agent-permeated powder substantially dissolves in said aqueous phase to form microbubbles.
32. A method for imaging an object or body part, or body cavity providing enhanced contrast, said method comprising the steps of:
introducing into said object or body part or body cavity a stabilized liquid microbubble preparation; and imaging at least a portion of said body by ultrasound or magnetic resonance.
33. The method of Claim 32, wherein said body is a vertebrate and said preparation is introduced into the vasculature of said vertebrate.
34. The method of Claim 32, further comprising the step of preparing said stabilized liquid microbubble preparation according to the method of Claim 1 prior to said introduction.
35. The method of Claim 32, further comprising the step of preparing said stabilized microbubble preparation according to the method of Claim 8 prior to said introduction.
36. The method of Claim 32, further comprising the step of preparing said stabilized microbubble preparation according to the method of Claim 12 prior to said introduction.
37. The method of Claim 32, further comprising the step of preparing said stabilized microbubble preparation according to the method of Claim 18 prior to said introduction.
38. A spray dried hollow microsphere composition capable of forming stabilized microbubbles upon addition to liquid, said hollow microspheres having an average diameter of less than about 100 µm and comprising a surfactant in combination with one or more carbohydrates selected from the group consisting of starches, derivatized starches, dextrin and combinations thereof.
39. The hollow microsphere composition of Claim 38 wherein said surfactant is a sugar ester having a component with a hydrophilic/lipophilic balance of less than about 8.
40. The hollow microsphere composition of Claim 38 wherein said surfactant comprises one or more phospholipids.
41. The microsphere composition of Claim 38, further comprising a fluorocarbon gas in said hollow microspheres.
42. A stabilized gas filled microbubble preparation, comprising:
a mixture of a first gas or gases and a second gas or gases within generally spherical membranes to form microbubbles, wherein said first gas and said second gas are respectively present in a molar ratio of about 1:100 to about 1,000:1, and wherein said first gas has a vapor pressure of at least about (760 - x) mm Hg at 37°C, where x is the vapor pressure of the second gas at 37°C, and wherein said vapor pressure of each of said first and second gases is greater than about 75 mm Hg at 37°C, with the proviso that said first gas and said second gas are not water vapor.
43. The stabilized gas filled microbubble preparation of Claim 42 further comprising:
a container incorporating said stabilized microbubbles comprising a mixture of said first gas or gases and said second gas or gases.
44. The preparation of Claim 42, wherein said second gas comprises a fluorocarbon and said first gas is a nonfluorocarbon.
45. The preparation of Claim 42, wherein said first gas comprises nitrogen, oxygen, carbon dioxide, or a mixture thereof.
46. The preparation of Claim 42, wherein:
said stabilized microbubbles are in a liquid medium and have a first average diameter;
the ratio of said first gas to said second gas in said stabilized microbubbles is at least 1:1; and said stabilized microbubbles are adapted to shrink in said medium as a result of loss of said first gas through said membrane to a second average diameter of less than about 75% of said first diameter and then remain stabilized at or about said second diameter for at least about 1 minute as a result of a gas osmotic pressure differential across said membrane.
47. The preparation of Claim 46, wherein said medium is aqueous.
48. The preparation of Claim 46, wherein said medium is in a container and said microbubbles have been formed in said container.
49. The preparation of Claim 46, wherein said medium is blood in vivo.
50. The preparation of Claim 46, wherein said liquid medium contains gas or gases dissolved therein with a gas tension of at least about 700 mm Hg, wherein said first diameter is at least about 5 µm, and wherein the tension of the gas or gases dissolved in said medium is less than the pressure of the same gas or gases inside said microbubble.
51. The preparation of Claim 46, wherein said first diameter is at least about 10 µm and said second diameter is between about 1 µm and 6 µm.
52. The preparation of Claim 42, wherein said second gas has an average molecular weight at least about 4 times that of said first gas.
53. The preparation of Claim 42, wherein said second gas has a vapor pressure less than about 750 mm Hg at 37°C.
54. The preparation of Claim 53, wherein said molar ratio of said first gas to said second gas is from about 1:10 to about 500: 1.
55. The preparation of Claim 53, wherein said second gas comprises a fluorocarbon and said first gas is a nonfluorocarbon.
56. The preparation of Claim 55, wherein said second gas comprises at least two fluorocarbons.
57. The preparation of Claim 55, wherein said second gas comprises perfluorohexane.
58. The preparation of Claim 53, wherein both said first gas and said second gas comprise fluorocarbons.
59. The preparation of Claim 42, wherein said microbubbles contain as said first gas, or as said second gas, or respectively as said first and second gases, gaseous perfluorobutane and perfluorohexane in a ratio from about 1:10 to about 10:1.
60. The preparation of Claim 42, wherein said microbubbles contain as said first gas, or as said second gas, or respectively as said first and second gases, gaseous perfluorobutane and perfluoropentane in a ratio from about 1:10 to about 10:1.
61. The preparation of Claim 42, wherein said second gas has a water solubility of not more than about 0.5 mM at 25°C
and one atmosphere, and wherein said first gas has a water solubility at least 10 times grater than that of said second gas.
62. The preparation of Claim 42 wherein the permeability of the membrane to said first gas is at least about 5 times greater than the permeability of said membrane to said second gas.
63. The preparation of Claim 43, further comprising a liquid in said container in admixture with said microbubbles, wherein said container further comprises means for transmission of sufficient ultrasonic energy to said liquid to permit formation of said microbubbles by sonication.
64. The preparation of Claim 63, wherein said means for transmission comprises a flexible polymer material having a thickness less than about 0.5 mm.
65. The preparation of Claim 42, wherein said generally spherical membrane is a surfactant.
66. The preparation of Claim 65, wherein said surfactant comprises one or more phospholipids.
67. The preparation of Claim 65, wherein said surfactant comprises a non-Newtonian viscoelastic surfactant.
68. The preparation of Claim 65, wherein said surfactant is a carbohydrate.
69. The preparation of Claim 68, wherein said carbohydrate is a polysaccharide.
70. The preparation of Claim 65, wherein said surfactant is a fatty acid ester of a sugar.
71. The preparation of Claim 65, wherein said surfactant is sucrose stearate.
72. The preparation of Claim 65, wherein said surfactant is proteinaceous.
73. The preparation of Claim 42, wherein said membrane is solid or semi-solid.
74. The preparation of Claim 42, wherein said membrane is a proteinaceous material.
75. The preparation of Claim 74, wherein said proteinaceous material is albumin.
76. A system for forming stabilized microbubbles from a solid precursor, said system comprising:
a first chamber containing a gaseous phase and solid or semi-solid substantially water soluble void-containing structures defining a plurality of voids having an average diameter less than about 100 µm;
a second chamber containing an aqueous liquid;
a surfactant in said first chamber or said second chamber; and a seal interposed between said first and second chambers, wherein said gas, said void-containing structure, said aqueous liquid, and said surfactant are adapted to form microbubbles when combined together in said first or second chamber.
77. The system of Claim 76, wherein said gaseous phase comprises a gas osmotic agent having a water solubility of not more than about 0.5 mM at 25°C and one atmosphere.
78. The system of Claim 76, further comprising a container in which said first and second chambers are provided, and wherein said seal and said aqueous liquid are interposed between said gaseous phase and the exterior of said container.
79. The system of Claim 78, wherein said container is glass.
80. The system of Claim 78, wherein said container is a bottle and said first chamber has only one opening, which is closed by said seal.
81. The system of Claim 73, wherein said container is a syringe.
82. The system of Claim 81, wherein said syringe has a barrel in which said first and second chambers are located, and a plunger adjacent said second chamber but separated from said first chamber by said aqueous liquid and said seal.
83. The system of Claim 76, wherein said void-containing structure comprises a spray-dried starch or spray-dried derivatized starch.
84. The system of Claim 76, wherein said void-containing structure comprises a surfactant.
85. The system of Claim 84, wherein said surfactant comprises one or more phospholipids.
86. The system of Claim 84, wherein said surfactant is a non-Newtonian surfactant.
87. The system of Claim 84, wherein a component of said surfactant has a hydrophilic/lipophilic balance of at least 12.
88. The system of Claim 76, wherein said first chamber includes an amount of a sugar ester having a HLB of less than 8 effective to increase the in vivo half life of microbubbles formed therefrom.
89. The system of Claim 76, wherein said void-containing structure comprises spray dried microspheres.
90. The system of Claim 89, wherein said microspheres comprise a surfactant and either (a) a starch or derivatized starch or a dextrin or (b) a sugar ester.
91. A kit for use in preparing stabilized microbubbles directly in a liquid, said kit comprising:
a sealed container;
a liquid in said container;
a surfactant in said container; and a fluorocarbon gas in said container, wherein said liquid, said surfactant, and said fluorocarbon gas or vapor are together adapted to form microbubbles upon the application of energy thereto.
92. The kit of Claim 91, further comprising means in said container for permitting transmission of sufficient external energy to said liquid to form microbubbles in said container.
93. The kit of Claim 92, wherein said means for transmission comprises a flexible polymer membrane having a thickness less than about 0.5 mm.
94. The kit of Claim 91, further comprising a nonfluorocarbon gas in said container, wherein the molar ratio of said nonfluorocarbon gas to said fluorocarbon gas is from about 1:10 to about 1000:1, with the proviso that said nonfluorocarbon gas is not water vapor.
95. A kit for producing stabilized microbubbles from a solid microbubble precursor, comprising:
a container;
solid liquid-soluble void-containing structures in said container, said void-containing structures defining a plurality of voids having an average diameter less than about 100 µm;
a gas in said voids; and a surfactant, wherein said void-containing structures, said gas, and said surfactant are together adapted to form microbubbles upon addition to said container of a liquid in which said void-containing structures are soluble.
96. The kit of Claim 95, wherein said void-containing structures comprise at least in part said surfactant.
97. The kit of Claim 95 wherein said surfactant comprises one or more phospholipids.
98 The kit of Claim 95, wherein said surfactant is a non-Newtonian viscoelastic surfactant.
99. The kit of Claim 95, wherein said surfactant is a fatty acid ester of a sugar.
100. The kit of Claim 95, wherein said surfactant is sucrose stearate.
101. The kit of Claim 95, wherein said void-containing structures are proteinaceous.
102. The kit of Claim 95, wherein said void-containing structures are formed of a carbohydrate.
CA002164813A 1993-07-30 1994-08-01 Stabilized microbubble compositions for ultrasound Expired - Fee Related CA2164813C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US9995193A 1993-07-30 1993-07-30
US08/099,951 1993-07-30
PCT/US1994/008671 WO1995003835A1 (en) 1993-07-30 1994-08-01 Stabilized microbubble compositions for ultrasound

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CA2164813A1 true CA2164813A1 (en) 1995-02-09
CA2164813C CA2164813C (en) 2009-11-24

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US (17) US5605673A (en)
EP (2) EP0711179B2 (en)
JP (1) JP3559849B2 (en)
AT (1) ATE281183T1 (en)
AU (1) AU694135B2 (en)
CA (1) CA2164813C (en)
DE (1) DE69434119T3 (en)
DK (1) DK0711179T3 (en)
ES (1) ES2231775T5 (en)
HK (1) HK1013403A1 (en)
PT (1) PT711179E (en)
WO (1) WO1995003835A1 (en)

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