Claims
- 1. A biologically active composition being fluorescent, photosensitizing, and having the capability of localizing in and being retained in tumor tissue as compared to normal tissues which composition comprises conjugates containing two or more covalently-linked porphyrin molecules wherein at least one porphyrin has the formula ##STR3## wherein the bond shown attaches said porphyrin to the conjugate or the pharmaceutically acceptable salts thereof;
- which conjugates form aggregates of >10 kd in aqueous environments but are sufficiently lipophilic so that said aggregates dissociate in tissue, said conjugates having triplet energy of >37.5 kcal/mol, being not readily oxidized, and not capable of physically quenching any required energy state.
- 2. A biologically active composition being fluorescent, photosensitizing, and having the capability of localizing in and being retained in tumor tissue as compared to normal tissues which composition comprises conjugates containing two or more covalently-linked chlorin molecules wherein at least one chlorin has the formula ##STR4## wherein the bond shown attaches said chlorin to the conjugate or the pharmaceutically acceptable salts thereof;
- which conjugates form aggregates of >10 kd in aqueous environments but are sufficiently lipophilic so that said aggregates dissociate in tissue, said conjugates having triplet energy of >37.5 kcal/mol, being not readily oxidized, and not capable of physically quenching any required energy state.
- 3. A biologically active composition being fluorescent, photosensitizing, and having the capability of localizing in and being retained in tumor tissues as compared to normal tissues which composition comprises conjugates containing two or more covalently-linked phlorin molecules wherein at least one phlorin has the formula ##STR5## wherein the bond shown attaches said phlorin to the conjugate or the pharmaceutically acceptable salts thereof;
- which conjugates form aggregates of >10 kd in aqueous environments but are sufficiently lipophilic so that said aggregates dissociate in tissue, said conjugates having triplet energy of >37.5 kcal/mol, being not readily oxidized, and not capable of physically quenching any required energy state.
- 4. A composition comprising porphyrins which are fluorescent, photosensitizing, and capable of localizing in and being retained in tumor cells for a longer time than in normal tissues, which composition contains porphyrin conjugates wherein at least one porphyrin has the formula ##STR6## wherein the bond shown attaches said porphyrin to the conjugate or the pharmaceutically acceptable salts thereof;
- which conjugates form aggregates of >10 kd in aqueous environments but are sufficiently lipophilic so that said aggregates dissociate in tissue, said conjugates having triplet energy of >37.5 kcal/mol, being not readily oxidized, and not capable of physically quenching any required energy state and wherein said composition has adsorption peaks in the visible spectrum in water at approximately 365, 505, 537, 575 and 615 nanometers, adsorption peaks in the infrared spectrum at approximately 3.0, 3.4, 6.4, 7.1, 8.1, 9.4, 12 and 15 microns, adsorption peaks in carbon-13 nuclear magnetic resonance study at approximately 9.0, 18.9, 24.7, 34.5, 62, 94.5, 130-145, 171.7 ppm and possibly 118 and 127 relative to a 37.5 ppm resonance peak of dimethyl sulfoxide and additional adsorption peaks in carbon-13 nuclear magnetic study at approximately 27.9 ppm and 68.4 ppm relative to the resonance peak of tetramethylsilane in deuterated chloroform solvent.
- 5. A drug comprising:
- a mixture of porphyrins;
- at least some of the molecules of said porphyrin mixture having conjugates of the molecular formula: ##STR7## wherein one or more hydroxyethyl substituent is replaced by a vinyl group, wherein said porphyrins are fluorescent, photosensitizing, and capable of localizing in and being retained in tumor cells for a longer time than in normal tissues, and wherein said composition has adsorption peaks in the visible spectrum in water at approximately 365, 505, 537, 575 and 615 nanometers, adsorption peaks in the infrared spectrum at approximately 3.0, 3.4, 6.4, 7.1, 8.1, 9.4, 12 and 15 microns, adsorption peaks in carbon-13 nuclear magnetic resonance study at approximately 9.0, 18.9, 24.7, 34.5, 62, 94.5, 130-145, 171.7 ppm and possibly 118 and 127 relative to a 37.5 ppm resonance peak of dimethyl sulfoxide and additional adsorption peaks in carbon-13 nuclear magnetic study at approximately 27.9 ppm and 68.4 ppm relative to the resonance peak of tetramethylsilane in deuterated chloroform solvent, and
- which conjugates form aggregates of >10 kd in aqueuos environments but are sufficiently lipophilic so that said aggregates dissociate in tissue, said conjugates having triplet energy of >37.5 kcal/mol, being not readily oxidized, and not capable of physically quenching any required energy state.
- 6. A pharmaceutical composition which consists essentially of the composition of claim 1 as active ingredient along with a pharmaceutically acceptable excipient.
- 7. A pharmaceutical composition which consists essentially of the composition of claim 2 as active ingredient along with a pharmaceutically acceptable excipient.
- 8. A pharmaceutical composition which consists essentially of the composition of claim 3 as active ingredient along with a pharmaceutically acceptable excipient.
RELATED CASES
This application is a continuation of U.S. Ser. No. 889,829 filed 24 July 1986 which issued 12 Sept. 1989 as U.S. Pat. No. 4,866,168 which is a continuation of U.S. Ser. No. 609,991 filed 14 May 1984 and has issued 10 Mar. 1987 as U.S. Pat. No. 4,649,151, which is a continuation-in-part of application Ser. No. 481,345, filed Apr. 1, 1983, now abandoned, which is a continuation-in-part of application Ser. No. 424,647, filed Sept. 27, 1982, now abandoned.
RIGHTS IN THE UNITED STATES GOVERNMENT
This invention was made with federal support under research grants CA 30940-01 and CA 16717 and contract NO1-CM-97311, awarded by the National Cancer Institute, U.S. Department of Health and Human Services. The Government has certain rights to this invention.
US Referenced Citations (2)
Number |
Name |
Date |
Kind |
4649151 |
Dougherty et al. |
Mar 1987 |
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4866168 |
Dougherty et al. |
Sep 1989 |
|
Continuations (2)
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Number |
Date |
Country |
Parent |
889829 |
Jul 1986 |
|
Parent |
609991 |
May 1984 |
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Continuation in Parts (2)
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Number |
Date |
Country |
Parent |
481345 |
Apr 1983 |
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Parent |
424647 |
Sep 1982 |
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