CA1262863A - Fusogenic liposomes and method of making same - Google Patents
Fusogenic liposomes and method of making sameInfo
- Publication number
- CA1262863A CA1262863A CA000505702A CA505702A CA1262863A CA 1262863 A CA1262863 A CA 1262863A CA 000505702 A CA000505702 A CA 000505702A CA 505702 A CA505702 A CA 505702A CA 1262863 A CA1262863 A CA 1262863A
- Authority
- CA
- Canada
- Prior art keywords
- ammonium hydroxide
- salt
- liposomes
- phospholipid
- quaternary ammonium
- 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.)
- Expired
Links
- 230000000799 fusogenic effect Effects 0.000 title claims description 32
- 239000002502 liposome Substances 0.000 title abstract description 136
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 35
- 239000000908 ammonium hydroxide Substances 0.000 claims abstract description 34
- 150000003904 phospholipids Chemical class 0.000 claims abstract description 33
- 239000012528 membrane Substances 0.000 claims abstract description 14
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 60
- 238000000034 method Methods 0.000 claims description 40
- 235000012000 cholesterol Nutrition 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- -1 sphingomyelin Chemical compound 0.000 claims description 7
- AWWSASBFOLSEEZ-UHFFFAOYSA-M benzyl-(2-ethoxyethyl)-dimethylazanium hydroxide Chemical compound [OH-].C(C)OCC[N+](CC1=CC=CC=C1)(C)C AWWSASBFOLSEEZ-UHFFFAOYSA-M 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- WJLUBOLDZCQZEV-UHFFFAOYSA-M hexadecyl(trimethyl)azanium;hydroxide Chemical compound [OH-].CCCCCCCCCCCCCCCC[N+](C)(C)C WJLUBOLDZCQZEV-UHFFFAOYSA-M 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000012634 fragment Substances 0.000 claims description 4
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 claims description 4
- BJAARRARQJZURR-UHFFFAOYSA-N trimethylazanium;hydroxide Chemical compound O.CN(C)C BJAARRARQJZURR-UHFFFAOYSA-N 0.000 claims description 4
- GWRHNZBWCXQDPH-UHFFFAOYSA-N 2-dodecyl-1,3,4-trimethylbenzene Chemical group CCCCCCCCCCCCC1=C(C)C=CC(C)=C1C GWRHNZBWCXQDPH-UHFFFAOYSA-N 0.000 claims description 3
- PVARMOHUPUUMOU-UHFFFAOYSA-M [OH-].C(C(C)C)C=1C(=C(C([N+](C)(C)CC)(OCC)OC2=CC=CC=C2)C=CC1)CC(C)C Chemical compound [OH-].C(C(C)C)C=1C(=C(C([N+](C)(C)CC)(OCC)OC2=CC=CC=C2)C=CC1)CC(C)C PVARMOHUPUUMOU-UHFFFAOYSA-M 0.000 claims description 3
- JCFOTQFHMCVCJR-UHFFFAOYSA-M [OH-].C(C)OC(C1=CC=CC=C1)[N+](C)(C)CC Chemical compound [OH-].C(C)OC(C1=CC=CC=C1)[N+](C)(C)CC JCFOTQFHMCVCJR-UHFFFAOYSA-M 0.000 claims description 3
- NRJAVPSFFCBXDT-HUESYALOSA-N 1,2-distearoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC NRJAVPSFFCBXDT-HUESYALOSA-N 0.000 claims description 2
- 229960003724 dimyristoylphosphatidylcholine Drugs 0.000 claims description 2
- 238000009877 rendering Methods 0.000 claims description 2
- 229940043379 ammonium hydroxide Drugs 0.000 claims 8
- 235000011114 ammonium hydroxide Nutrition 0.000 claims 8
- PDXWQZZCXIZRLR-UHFFFAOYSA-M benzyl-dimethyl-tetradecan-2-ylazanium hydroxide Chemical compound [OH-].CC([N+](C)(C)CC1=CC=CC=C1)CCCCCCCCCCCC PDXWQZZCXIZRLR-UHFFFAOYSA-M 0.000 claims 2
- LAUPTJWHHKNSCT-UHFFFAOYSA-M benzyl-hexadecyl-dimethylazanium;hydroxide Chemical compound [OH-].CCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 LAUPTJWHHKNSCT-UHFFFAOYSA-M 0.000 claims 2
- CITHEXJVPOWHKC-UUWRZZSWSA-N 1,2-di-O-myristoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCC CITHEXJVPOWHKC-UUWRZZSWSA-N 0.000 claims 1
- KILNVBDSWZSGLL-KXQOOQHDSA-N 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC KILNVBDSWZSGLL-KXQOOQHDSA-N 0.000 claims 1
- SNKAWJBJQDLSFF-NVKMUCNASA-N 1,2-dioleoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC SNKAWJBJQDLSFF-NVKMUCNASA-N 0.000 claims 1
- 210000004027 cell Anatomy 0.000 abstract description 60
- 239000003814 drug Substances 0.000 abstract description 15
- 229940079593 drug Drugs 0.000 abstract description 15
- 230000007910 cell fusion Effects 0.000 abstract description 10
- 210000000170 cell membrane Anatomy 0.000 abstract description 8
- 239000000463 material Substances 0.000 abstract description 4
- 210000004379 membrane Anatomy 0.000 abstract 2
- 241000196324 Embryophyta Species 0.000 description 24
- 229940067631 phospholipid Drugs 0.000 description 21
- 108010039491 Ricin Proteins 0.000 description 16
- 230000004927 fusion Effects 0.000 description 16
- 241001465754 Metazoa Species 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
- 108020004414 DNA Proteins 0.000 description 13
- 102000053602 DNA Human genes 0.000 description 13
- 238000000520 microinjection Methods 0.000 description 11
- 210000001938 protoplast Anatomy 0.000 description 11
- 239000000427 antigen Substances 0.000 description 10
- 102000036639 antigens Human genes 0.000 description 8
- 108091007433 antigens Proteins 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 238000010348 incorporation Methods 0.000 description 5
- 238000011534 incubation Methods 0.000 description 5
- 230000001404 mediated effect Effects 0.000 description 5
- 108090000623 proteins and genes Proteins 0.000 description 5
- 102000004169 proteins and genes Human genes 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 241000700605 Viruses Species 0.000 description 4
- 239000008351 acetate buffer Substances 0.000 description 4
- 230000004520 agglutination Effects 0.000 description 4
- 239000006285 cell suspension Substances 0.000 description 4
- 210000000805 cytoplasm Anatomy 0.000 description 4
- 229940088597 hormone Drugs 0.000 description 4
- 239000005556 hormone Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- 150000002632 lipids Chemical class 0.000 description 4
- 238000001243 protein synthesis Methods 0.000 description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 4
- 230000014616 translation Effects 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 241000282414 Homo sapiens Species 0.000 description 3
- 241000711408 Murine respirovirus Species 0.000 description 3
- XDMCWZFLLGVIID-SXPRBRBTSA-N O-(3-O-D-galactosyl-N-acetyl-beta-D-galactosaminyl)-L-serine Chemical compound CC(=O)N[C@H]1[C@H](OC[C@H]([NH3+])C([O-])=O)O[C@H](CO)[C@H](O)[C@@H]1OC1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 XDMCWZFLLGVIID-SXPRBRBTSA-N 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 210000004748 cultured cell Anatomy 0.000 description 3
- 210000003743 erythrocyte Anatomy 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 150000004679 hydroxides Chemical class 0.000 description 3
- 238000003780 insertion Methods 0.000 description 3
- 230000037431 insertion Effects 0.000 description 3
- 230000003834 intracellular effect Effects 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 230000035479 physiological effects, processes and functions Effects 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- 206010056740 Genital discharge Diseases 0.000 description 2
- 241000207748 Petunia Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 210000004102 animal cell Anatomy 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- 229940098773 bovine serum albumin Drugs 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 210000002421 cell wall Anatomy 0.000 description 2
- 230000001413 cellular effect Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 150000004665 fatty acids Chemical group 0.000 description 2
- 230000002163 immunogen Effects 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 210000004779 membrane envelope Anatomy 0.000 description 2
- 210000003463 organelle Anatomy 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000012384 transportation and delivery Methods 0.000 description 2
- 230000003612 virological effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CITHEXJVPOWHKC-UUWRZZSWSA-O 2-[[(2r)-2,3-di(tetradecanoyloxy)propoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium Chemical compound CCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCC CITHEXJVPOWHKC-UUWRZZSWSA-O 0.000 description 1
- NHSSTOSZJANVEV-UHFFFAOYSA-N 2-hydroxybutanenitrile Chemical compound CCC(O)C#N NHSSTOSZJANVEV-UHFFFAOYSA-N 0.000 description 1
- ZBFDAUIVDSSISP-UHFFFAOYSA-N 5-methoxy-2-[(4-methoxy-3,5-dimethyl-2-pyridinyl)methylsulfinyl]-1H-imidazo[4,5-b]pyridine Chemical compound N=1C2=NC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C ZBFDAUIVDSSISP-UHFFFAOYSA-N 0.000 description 1
- 101100230376 Acetivibrio thermocellus (strain ATCC 27405 / DSM 1237 / JCM 9322 / NBRC 103400 / NCIMB 10682 / NRRL B-4536 / VPI 7372) celI gene Proteins 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- 208000034423 Delivery Diseases 0.000 description 1
- 102000003886 Glycoproteins Human genes 0.000 description 1
- 108090000288 Glycoproteins Proteins 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 240000007377 Petunia x hybrida Species 0.000 description 1
- 229940096437 Protein S Drugs 0.000 description 1
- 102000029301 Protein S Human genes 0.000 description 1
- 108010066124 Protein S Proteins 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- SZKKRCSOSQAJDE-UHFFFAOYSA-N Schradan Chemical compound CN(C)P(=O)(N(C)C)OP(=O)(N(C)C)N(C)C SZKKRCSOSQAJDE-UHFFFAOYSA-N 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 230000004523 agglutinating effect Effects 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 229940046545 animal allergen extract Drugs 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 230000009830 antibody antigen interaction Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- CHUSNWLRHFMLMQ-UHFFFAOYSA-M benzyl-ethyl-dimethylazanium;hydroxide Chemical compound [OH-].CC[N+](C)(C)CC1=CC=CC=C1 CHUSNWLRHFMLMQ-UHFFFAOYSA-M 0.000 description 1
- 239000013060 biological fluid Substances 0.000 description 1
- 150000003842 bromide salts Chemical class 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- 210000003855 cell nucleus Anatomy 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 229960004132 diethyl ether Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- HBNYJWAFDZLWRS-UHFFFAOYSA-N ethyl isothiocyanate Chemical compound CCN=C=S HBNYJWAFDZLWRS-UHFFFAOYSA-N 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 238000001415 gene therapy Methods 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 206010073071 hepatocellular carcinoma Diseases 0.000 description 1
- XQSBLCWFZRTIEO-UHFFFAOYSA-N hexadecan-1-amine;hydrobromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[NH3+] XQSBLCWFZRTIEO-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000002625 immunotoxic effect Effects 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 229960003971 influenza vaccine Drugs 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000000386 microscopy Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 210000004940 nucleus Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- YHHSONZFOIEMCP-UHFFFAOYSA-O phosphocholine Chemical compound C[N+](C)(C)CCOP(O)(O)=O YHHSONZFOIEMCP-UHFFFAOYSA-O 0.000 description 1
- 102000040430 polynucleotide Human genes 0.000 description 1
- 108091033319 polynucleotide Proteins 0.000 description 1
- 239000002157 polynucleotide Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
Classifications
-
- 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—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
- A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes or liposomes coated or grafted with polymers
- A61K9/1272—Non-conventional liposomes, e.g. PEGylated liposomes or liposomes coated or grafted with polymers comprising non-phosphatidyl surfactants as bilayer-forming substances, e.g. cationic lipids or non-phosphatidyl liposomes coated or grafted with polymers
-
- 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
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/58—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
- G01N33/585—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances with a particulate label, e.g. coloured latex
- G01N33/586—Liposomes, microcapsules or cells
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- General Health & Medical Sciences (AREA)
- Biotechnology (AREA)
- Physics & Mathematics (AREA)
- Biochemistry (AREA)
- Hematology (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Microbiology (AREA)
- Zoology (AREA)
- Urology & Nephrology (AREA)
- Cell Biology (AREA)
- Wood Science & Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biophysics (AREA)
- Immunology (AREA)
- General Engineering & Computer Science (AREA)
- Dispersion Chemistry (AREA)
- Pathology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Plant Pathology (AREA)
- Animal Behavior & Ethology (AREA)
- General Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Food Science & Technology (AREA)
- Medicinal Preparation (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71986285A | 1985-04-04 | 1985-04-04 | |
| US719,862 | 1985-04-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1262863A true CA1262863A (en) | 1989-11-14 |
Family
ID=24891665
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000505702A Expired CA1262863A (en) | 1985-04-04 | 1986-04-02 | Fusogenic liposomes and method of making same |
Country Status (16)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5545412A (en) * | 1985-01-07 | 1996-08-13 | Syntex (U.S.A.) Inc. | N-[1, (1-1)-dialkyloxy]-and N-[1, (1-1)-dialkenyloxy]-alk-1-yl-n,n,n-tetrasubstituted ammonium lipids and uses therefor |
| US4897355A (en) * | 1985-01-07 | 1990-01-30 | Syntex (U.S.A.) Inc. | N[ω,(ω-1)-dialkyloxy]- and N-[ω,(ω-1)-dialkenyloxy]-alk-1-yl-N,N,N-tetrasubstituted ammonium lipids and uses therefor |
| US4818537A (en) * | 1986-10-21 | 1989-04-04 | Liposome Technology, Inc. | Liposome composition for treating dry eye |
| JPS63275522A (ja) * | 1987-05-01 | 1988-11-14 | Terumo Corp | 人工赤血球及びその製造方法 |
| JPH04283207A (ja) * | 1991-03-13 | 1992-10-08 | Kao Corp | ベシクル及び重合体ベシクル |
| CA2269725C (en) * | 1996-10-25 | 2010-01-05 | Monsanto Company | Composition and method for treating plants with exogenous chemicals |
| DK0936860T3 (da) * | 1996-10-25 | 2002-06-10 | Monsanto Technology Llc | Sammensætning og fremgangsmåde til behandling af planter med exogene kemikalier |
| US20150174068A1 (en) * | 2011-09-12 | 2015-06-25 | Cure Ip Holdings, Llc | Apparatus, Composition, and Related Methods for Transdermal Delivery of Active Ingredients |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4515736A (en) * | 1983-05-12 | 1985-05-07 | The Regents Of The University Of California | Method for encapsulating materials into liposomes |
| US4789633A (en) * | 1984-04-19 | 1988-12-06 | University Of Tennessee Research Corporation | Fused liposome and acid induced method for liposome fusion |
| ATE50983T1 (de) * | 1985-01-07 | 1990-03-15 | Syntex Inc | Oberflaechenaktive n-(omega, omega-1-dialkoxy)und n-(omega, omega-1-dialkenoxy)-alk-1-yl-n,n,ntrisubstituierte ammoniumverbindungen, deren herstellung und sie enthaltende pharmazeutische formulierungen. |
-
1986
- 1986-03-26 SE SE8601408A patent/SE464448B/sv not_active IP Right Cessation
- 1986-03-27 NL NL8600794A patent/NL8600794A/nl not_active Application Discontinuation
- 1986-03-31 IL IL78348A patent/IL78348A/xx unknown
- 1986-04-01 DE DE19863610873 patent/DE3610873A1/de not_active Withdrawn
- 1986-04-02 BE BE0/216489A patent/BE904536A/fr not_active IP Right Cessation
- 1986-04-02 CA CA000505702A patent/CA1262863A/en not_active Expired
- 1986-04-03 AU AU55622/86A patent/AU585330B2/en not_active Ceased
- 1986-04-03 ES ES553703A patent/ES8802401A1/es not_active Expired
- 1986-04-03 ZA ZA862466A patent/ZA862466B/xx unknown
- 1986-04-03 IT IT83340/86A patent/IT1189877B/it active
- 1986-04-03 NZ NZ215696A patent/NZ215696A/xx unknown
- 1986-04-03 JP JP61077505A patent/JPS61274739A/ja active Pending
- 1986-04-03 FR FR868604760A patent/FR2579891B1/fr not_active Expired - Fee Related
- 1986-04-03 CH CH1297/86A patent/CH668005A5/de not_active IP Right Cessation
- 1986-04-04 BR BR8601554A patent/BR8601554A/pt unknown
- 1986-04-08 GB GB8608468A patent/GB2188900B/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ES553703A0 (es) | 1988-05-16 |
| AU585330B2 (en) | 1989-06-15 |
| SE464448B (sv) | 1991-04-29 |
| DE3610873A1 (de) | 1986-10-09 |
| GB2188900B (en) | 1990-04-04 |
| SE8601408D0 (sv) | 1986-03-26 |
| NZ215696A (en) | 1989-07-27 |
| ZA862466B (en) | 1986-11-26 |
| ES8802401A1 (es) | 1988-05-16 |
| CH668005A5 (de) | 1988-11-30 |
| FR2579891B1 (enrdf_load_stackoverflow) | 1990-02-02 |
| FR2579891A1 (enrdf_load_stackoverflow) | 1986-10-10 |
| IL78348A (en) | 1989-08-15 |
| JPS61274739A (ja) | 1986-12-04 |
| BE904536A (fr) | 1986-07-31 |
| AU5562286A (en) | 1986-10-09 |
| IL78348A0 (en) | 1986-07-31 |
| NL8600794A (nl) | 1986-11-03 |
| SE8601408L (sv) | 1986-10-05 |
| IT8683340A0 (it) | 1986-04-03 |
| GB8608468D0 (en) | 1986-05-14 |
| IT1189877B (it) | 1988-02-10 |
| GB2188900A (en) | 1987-10-14 |
| BR8601554A (pt) | 1986-12-09 |
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