Permanent, removable tissue markings

• US 7,175,950 B2
• Filed: 11/09/2004
• Issued: 02/13/2007
• Est. Priority Date: 11/20/1998
• Status: Expired due to Fees

• Current Assignee: Craig A. Drill, Freedom-2, Inc., The General Hospital Corporation (Mass General Brigham, Inc.)
• Original Assignee: Freedom-2, Inc., The General Hospital Corporation (Mass General Brigham, Inc.)
• Inventors: Anderson, Richard Rox, Drill, Craig A., Mlynarczyk-Evans, Susanna K.
• Primary Examiner(s): WALKE, AMANDA C
• Application Number:
  US10/984,133
• Publication Number:
  US 20050178287A1
• Time in Patent Office: 826 Days
• Field of Search: 430/944, 430/947, 430/19, 430/138, 430/139, 106/31.03, 840/4, 428/403
• US Class Current: 430/19
• CPC Class Codes: A61K 2800/412 Microsized, i.e. having sizes between 0.1 and 100 microns
• CPC Class Codes: A61K 2800/438 Thermochromatic; Photochromic; Phototropic
• CPC Class Codes: A61K 2800/56 Compounds, absorbed onto or entrapped into a solid carrier, e.g. encapsulated perfumes, inclusion compounds, sustained release forms
• CPC Class Codes: A61K 2800/624 by macromolecular compounds
• CPC Class Codes: A61K 8/0241 Containing particulates characterized by their shape and/or structure see also A61K8/04, A61K8/11, and A61K8/14, further aspects are classified in A61K2800/40 and subcodes
• CPC Class Codes: A61Q 1/025 Semi-permanent tattoos, stencils, e.g. "permanent make-up"
• CPC Class Codes: A61Q 19/04 for chemically tanning the skin topical sun or radiation screening or tanning preparations A61Q17/04
• CPC Class Codes: C09D 11/00 Inks
• CPC Class Codes: C09D 11/02 Printing inks C09D11/30 takes precedence
• CPC Class Codes: C09D 11/037 characterised by the pigment
• CPC Class Codes: C09D 11/50 Sympathetic, colour changing or similar inks
• CPC Class Codes: Y10S 430/145 Infrared
• CPC Class Codes: Y10S 430/165 Thermal imaging composition
• CPC Class Codes: Y10T 428/2991 Coated
• CPC Class Codes: Y10T 428/2993 Silicic or refractory material containing [e.g., tungsten oxide, glass, cement, etc.]

Abstract

While the invention has been described in conjunction with the detailed description thereof, the foregoing description is intended to illustrate and not limit the scope of the invention, which is defined by the scope of the appended claims. Other aspects, advantages, and modifications are within the scope of the following claims.

Claims

1. A tissue marking ink comprising:

a particle comprising a chromophore, which is photobleachable upon exposure to a specific energy by being altered by the specific energy when the particle is within a tissue; and

a carrier.

2. The ink of claim 1, wherein the photobleachable chromophore comprises at least one of phthalocyanine, porphycene, chlorin, a rhodamine dye, porphyrin, Rose Bengal, a dye-paired ion compound, a cationic dye-borate anion complex, a coumarin compound, and a bis(diiminosuccinonitrilo)metal complex.

3. The ink of claim 2, wherein the chromophore comprises a 3-position-substituted coumarin compound.

4. The ink of claim 1, wherein the appearance of the chromophore changes when the specific energy is applied once.

5. The ink of claim 1, wherein the specific energy is infrared or near-infrared radiation.

6. The ink of claim 1, wherein the chromophore has an average particle size of less than about 50 nm.

7. The ink of claim 1, wherein the chromophore changes from an initial color to a different color upon exposure of the particle to the specific energy.

8. The ink of claim 1, wherein the particle is from about 50 nm to about 100 microns m size.

9. The ink of claim 1, wherein the particle is from about 15 nm to about 500 nm in size.

10. The ink of claim 1, wherein the particle is less than about 50 nm size.

11. The ink of claim 10, wherein the particle is less than about 5 rim in size.

12. The ink of claim 1, wherein the carrier comprises at least one of alcohol, water, or glycerin.

13. A tissue marking ink comprising:

a particle comprising chromophore, which is photobleachable only upon simultaneous absorption of multiple photons when the particle is within a tissue; and

a carrier.

14. A tissue marking ink comprising the particle of claim 13 and a carrier.

15. A tissue marking particle comprising:

(i) an indispersible, biologically inert coating; and

(ii) a core enveloped within the coating, wherein the core comprises a chromophore, which is photobleachable upon exposure to a specific energy by being altered by the specific energy when the particle is within a tissue.

16. The particle of claim 15, wherein the coating comprises a metal oxide, silica, glass, fluorocarbon resin, organic polymer, wax, or a combination thereof.

17. The particle of claim 15, wherein the coating is substantially visibly transparent and absorbs near-infrared radiation.

18. The particle of claim 15, wherein multiple cores are enveloped within the coating of a single particle.

19. The particle of claim 15, wherein the chromophore is detectable through the coating.

20. The particle of claim 15, wherein the coating comprises from about 10 to about 95 percent of the volume of the particle.

21. A method of applying a tissue marking, the method comprising:

providing a particle comprising a chromophore; and

implanting the particle into a tissue to form a tissue marking,

wherein the chromophore is photobleachable upon exposure to a specific energy by being altered by the specific energy when the chromophore is within the tissue.

22. The method of claim 21, wherein the photobleachable chromophore comprises at least one of phthalocyanine, porphycene, chlorin, a rhodamine dye, porphyrin, Rose Bengal, a dye-paired ion compound, a cationic dye-borate anion complex, a coumarin compound, and a bis(diiminosuccinonitrilo)metal complex.

23. The method of claim 22, wherein the chromophore comprises a 3-position-substituted coumarin compound.

24. The method of claim 21, wherein the chromophore is photobleachable only upon simultaneous absorption of multiple photons.

25. The method according claim 21, wherein the appearance of the chromophore changes when the specific energy is applied once.

26. The method of claim 21, wherein the specific energy is infrared or near-infrared radiation.

27. The method of claim 21, wherein the chromophore has an avenge particle size of less than about 50 nm.

28. The method of claim 21, wherein the chromophore changes from an initial color to a different color upon exposure of the particle to the specific energy.

29. The method of claim 21, wherein the particle further comprises:

(i) an indispersible, biologically inert coating; and

(ii) a core enveloped within the coating, wherein the core comprises the chromophore.

30. The method of claim 29, wherein the coating comprises a metal oxide, silica, glass, fluorocarbon resin, organic polymer, wax, or a combination thereof.

31. The method of claim 29, wherein the coating is substantially visibly transparent and absorbs near-infrared radiation.

32. The method of claim 29, wherein multiple cores are enveloped within the coating of a single particle.

33. The method of claim 29, wherein the chromophore is detectable through the coating.

34. The method of claim 29, wherein the coating comprises from about 10 to about 95 percent of the volume of the particle.

35. The method of claim 21, wherein the particle is from about 50 nm to about 100 microns in size.

36. The method of claim 21, wherein the particle is from about 15 nm to about 500 nm in size.

37. The method of claim 21, wherein the particle is less than about 50 nm in size.

38. The method of claim 37, wherein the particle is less than about 5 nm in size.

39. A method for rendering invisible a tissue marking implanted in tissue, the tissue marking comprising a particle comprising a chromophore, which is photobleachable upon exposure to a specific energy by being altered by the specific energy when the chromophore is within the tissue, the method comprising exposing the tissue marking to the specific energy for a sufficient time to photobleach the chromophore.

40. The method of claim 39, wherein the photobleachable chromophore comprises at least one of phthalocyanine, porphycene, chlorin, a rhodamine dye, porphyrin, Rose Bengal, a dye-paired ion compound, a cationic dye-borate anion complex, a coumarin compound, and a bis(diiminosuccinonitrilo)metal complex.

41. The method of claim 40, wherein the chromophore comprises a 3-position-substituted coumarin compound.

42. The method of claim 39, wherein the chromophore is photobleachable only upon absorption of multiple photons.

43. The method according claim 39, wherein the appearance of the chromophore changes when the specific energy is applied once.

44. The method of claim 39, wherein the specific energy is infrared or near-infrared radiation.

45. The method of claim 39, wherein the chromophore has an average particle size of less than about 50 nm.

46. The method of claim 39, wherein exposure of the particle to the specific energy changes a color of the chromophore.

47. The method of claim 39, wherein the particle further comprises:

(i) an indispersible, biologically inert coating; and

(ii) a core enveloped within the coating, wherein the core comprises the chromophore.

48. The method of claim 47, wherein multiple cores are enveloped within the coating of a single particle.

49. The method of claim 47, wherein the chromophore is detectable through the coating.

50. The method of claim 47, wherein the coating comprises from about 10 to about 95 percent of the volume of the particle.

51. The method of claim 47, wherein the coating comprises a metal oxide, silica, glass, fluorocarbon resin, organic polymer, wax, or a combination thereof.

52. The method of claim 47, wherein the coating is substantially visibly transparent and absorbs near-infrared radiation.

53. The method of claim 39, wherein the particle is from about 50 nm to about 100 microns in size.

54. The meted of claim 39, wherein the particle is from about 15 nm to about 500 nm in size.

55. The method of claim 39, wherein the particle is less than about 50 nm in size.

56. The method of claim 55, wherein the particle is less than about 5 nm in size.