CA2358948A1 - Therapy for human cancers using cisplatin and other drugs or genes encapsulated into liposomes - Google Patents

Therapy for human cancers using cisplatin and other drugs or genes encapsulated into liposomes Download PDF

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Publication number
CA2358948A1
CA2358948A1 CA002358948A CA2358948A CA2358948A1 CA 2358948 A1 CA2358948 A1 CA 2358948A1 CA 002358948 A CA002358948 A CA 002358948A CA 2358948 A CA2358948 A CA 2358948A CA 2358948 A1 CA2358948 A1 CA 2358948A1
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cisplatin
encapsulated
effective amount
subject
micelles
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Granted
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CA002358948A
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French (fr)
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CA2358948C (en
Inventor
Teni Boulikas
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Regulon Inc
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Teni Boulikas
Regulon, Inc.
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    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N15/00—Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
    • C12N15/09—Recombinant DNA-technology
    • C12N15/87—Introduction of foreign genetic material using processes not otherwise provided for, e.g. co-transformation
    • C12N15/88—Introduction of foreign genetic material using processes not otherwise provided for, e.g. co-transformation using microencapsulation, e.g. using amphiphile liposome vesicle
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/337—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having four-membered rings, e.g. taxol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/475—Quinolines; Isoquinolines having an indole ring, e.g. yohimbine, reserpine, strychnine, vinblastine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
    • A61K31/573—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
    • A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
    • A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
    • A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
    • A61K31/7068—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid
    • A61K31/7072—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid having two oxo groups directly attached to the pyrimidine ring, e.g. uridine, uridylic acid, thymidine, zidovudine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K33/00—Medicinal preparations containing inorganic active ingredients
    • A61K33/24—Heavy metals; Compounds thereof
    • A61K33/243—Platinum; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/14—Peptides containing saccharide radicals; Derivatives thereof, e.g. bleomycin, phleomycin, muramylpeptides or vancomycin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
    • A61K47/6905—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being a colloid or an emulsion
    • A61K47/6907—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being a colloid or an emulsion the form being a microemulsion, nanoemulsion or micelle
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
    • A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/127—Liposomes
    • A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/04—Antineoplastic agents specific for metastasis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K48/00—Medicinal preparations containing genetic material which is inserted into cells of the living body to treat genetic diseases; Gene therapy
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/127—Liposomes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/127—Liposomes
    • A61K9/1277—Processes for preparing; Proliposomes
    • A61K9/1278—Post-loading, e.g. by ion or pH gradient

Abstract

A method for encapsulating cisplatin and other positively-charged drugs into liposomes having a different lipid composition between their inner and outer membrane bilayers is disclosed. The liposomes are able to reach primary tumo rs and their metastases after intravenous injection to animals and humans. The encapsulated cisplatin has a high therapeutic efficacy in eradicating a variety of solid human tumors including but not limited to breast carcinoma and prostate carcinoma. Combination of the encapsulated cisplatin with encapsulated doxorubicin or with other antineoplastic drugs are claimed to b e of therapeutic value. Also of therapeutic value in cancer eradication are claimed to be combinations of encapsulated cisplatin with a number of anticancer genes including but not limited to p53, IL-2, IL-12, angiostatin, and oncostatin encapsulated into liposomes as well as combinations of encapsulated cisplatin with HSV-tk plus encapsulated ganciclovir.

Claims (28)

1. A method for producing cisplatin micelles, comprising:
a) combining cisplatin and a phosphatidyl glycerol lipid derivative in a range of 1:1 to 1:2 to form a cisplatin mixture; and b) combining the mixture of step a) with an effective amount of at least a 30%
ethanol solution to form cisplatin micelles.
2. A method for producing cisplatin micelles, comprising:
a) combining cisplatin with an effective amount of at least a 30% ethanol solution to form a cisplatin/ethanol solution; and b) combining the solution with a phosphatidyl glycerol lipid derivative in a range of 1:1 to 1:2 to form cisplatin micelles.
3. The method of claim 1 or 2, wherein the phosphatidyl glycerol lipid derivative is selected from the group consisting of dipalmitoyl phosphatidyl glycerol (DPPG), dimyristoyl phosphatidyl glycerol (DMPG), dicaproyl phosphatidyl glycerol (DCPG), distearoyl phosphatidyl glycerol (DSPG) and dioleyl phosphatidyl glycerol (DOPG).
4. The method of claim 1 or 2, wherein the molar ratio is 1:1.
5. The method of claim 1 or 2, further comprising combining an effective amount of a free fusogenic peptide, a fusogenic peptide-lipid conjugate or a fusogenic peptide -PEG-HSPC conjugate to the mixture of step a) where the fusogenic peptide is derivatized with a stretch of 1-6 negatively-charged amino acids at the N or C- terminus and thus, able to bind electrostatically to aquaplatin.
6. The method of claim 5, wherein the free fusogenic peptide or fusogenic peptide lipid conjugate comprises DOPE or DOPE/cationic lipid.
7. The cisplatin micelle obtained by the method of claims 1 or 2.
8. The cisplatin micelle obtained by the method of claim 5.
9. A method for encapsulating cisplatin micelles, comprising mixing an effective amount of a vesicle-forming lipid with the cisplatin micelles of claim 1 or 2.
10. The encapsulated cisplatin obtainable by the method of claim 9.
11. The method of claim 10, wherein the lipid is selected from premade neutral liposomes, composed of cholesterol 10-60%, hydrogenated soy phosphatidylcholine (HSPC) 40-90% and polyethyleucglycol (PEG)-HSPC 1-7% or lipids in solution, lipids in powder and PEG-DSPE.
12. The method of claim 10, wherein the lipid comprises 10-60% cholesterol.
13. A method for obtaining a cisplatin/lipid complex capable of evading macrophages and cells of the immune system when administered to a subject, the method comprising mixing an effective amount of the cisplatin micelles of claim 9 with an effective amount of PEG-DSPE, PEG-DSPC or hyaluronic acid - DSPE.
14. The method of claim 1 or 2, further comprising removal of the ethanol from the cisplatin micelles.
15. The method of claim 14, wherein removal of the ethanol is by dialysis of the micelles through permeable membranes to remove the ethanol.
16. Encapsulated cisplatin obtainable by the method of claim 11.
17. Encapsulated cisplatin obtainable by the method of claim 13.
18. A method for delivering cisplatin to a cell comprising contacting the cell with the encapsulated cisplatin of claim 15.
19. A method for delivering cisplatin to a cell comprising contacting the cell with the encapsulated cisplatin of claim 17.
20. A method for inhibiting the growth of a tumor in a subject, comprising administering to the subject an effective amount of the encapsulated cisplatin of claim 16.
21. A method for inhibiting the growth of a tumor in a subject, comprising administering to the subject an effective amount of the encapsulated cisplatin of claim 17.
22. A method for targeting solid tumors and metastases in a subject comprising intravenous administration of an effective amount of the encapsulated cisplatin of claims 16 or 17.
23. A method for penetrating the cell membrane of a tumor in a subject comprising administering an effective amount of the cisplatin micelle obtainable by the method of claim 7.
24. A method for inhibiting tumor growth in a subject comprising administering to the subject an effective amount of the encapsulated cisplatin of claim 10 and a gene selected from the group consisting of p53, pax5 and HSV-tk genes.
25. The method of claim 24, wherein the method further comprises administering an effective amount of encapsulated ganciclovir.
26. The method of claim 24, wherein the genes to be combined with cisplatin are any of, or combinations of encapsulated IL-2, IL-4, IL-7, IL-12, GM-CSF, IFN-gamma, TNF-alpha, RB, BRCA1, E1A, cytosine deaminase in combination with encapsulated 5-fluorcytosine, bc1-2, MDR-1, p21, p16, bax, bcl-xs, E2F, IGFI, VEGF, TGF-beta and the like.
27. A composition comprising the encapsulated cisplatin of claim 10 and encapsulated oligonucleotides, ribozymes, triplex, or PNA.
28. A composition comprising the encapsulated cisplatin of claim 10 and a drug selected from the group consisting of doxorubicin, fluorodeoxyuridine, bleomycin, adriamycin, vinblastin, prednisone, vincristine, and taxol.
CA002358948A 1999-11-05 2000-10-27 Therapy for human cancers using cisplatin and other drugs or genes encapsulated into liposomes Expired - Fee Related CA2358948C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US09/434,345 1999-11-05
US09/434,345 US6511676B1 (en) 1999-11-05 1999-11-05 Therapy for human cancers using cisplatin and other drugs or genes encapsulated into liposomes
PCT/US2000/029723 WO2001034130A1 (en) 1999-11-05 2000-10-27 Therapy for human cancers using cisplatin and other drugs or genes encapsulated into liposomes

Publications (2)

Publication Number Publication Date
CA2358948A1 true CA2358948A1 (en) 2001-05-17
CA2358948C CA2358948C (en) 2010-01-05

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US (3) US6511676B1 (en)
EP (1) EP1156789B9 (en)
JP (2) JP2003513911A (en)
CN (1) CN100562311C (en)
AT (1) ATE321541T1 (en)
AU (1) AU777151B2 (en)
CA (1) CA2358948C (en)
CY (1) CY1105628T1 (en)
DE (1) DE60027039T2 (en)
DK (1) DK1156789T3 (en)
ES (1) ES2261251T3 (en)
GR (1) GR1004168B (en)
PT (1) PT1156789E (en)
TW (1) TWI259770B (en)
WO (1) WO2001034130A1 (en)

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