SG10201808315UA - Non-toxic adjuvant formulation comprising a monophosphoryl lipid a (mpla)-containing liposome composition and a saponin - Google Patents
Non-toxic adjuvant formulation comprising a monophosphoryl lipid a (mpla)-containing liposome composition and a saponinInfo
- Publication number
- SG10201808315UA SG10201808315UA SG10201808315UA SG10201808315UA SG10201808315UA SG 10201808315U A SG10201808315U A SG 10201808315UA SG 10201808315U A SG10201808315U A SG 10201808315UA SG 10201808315U A SG10201808315U A SG 10201808315UA SG 10201808315U A SG10201808315U A SG 10201808315UA
- Authority
- SG
- Singapore
- Prior art keywords
- saponin
- mol
- liposome composition
- mpla
- adjuvant formulation
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title abstract 8
- 229940035032 monophosphoryl lipid a Drugs 0.000 title abstract 5
- 239000002671 adjuvant Substances 0.000 title abstract 4
- 238000009472 formulation Methods 0.000 title abstract 4
- 239000002502 liposome Substances 0.000 title abstract 4
- 239000001397 quillaja saponaria molina bark Substances 0.000 title abstract 4
- 229930182490 saponin Natural products 0.000 title abstract 4
- 150000007949 saponins Chemical class 0.000 title abstract 4
- 231100000252 nontoxic Toxicity 0.000 title abstract 2
- 230000003000 nontoxic effect Effects 0.000 title abstract 2
- 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 abstract 2
- 239000000232 Lipid Bilayer Substances 0.000 abstract 1
- -1 QS-21) Chemical class 0.000 abstract 1
- 235000012000 cholesterol Nutrition 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- GZQKNULLWNGMCW-PWQABINMSA-N lipid A (E. coli) Chemical compound O1[C@H](CO)[C@@H](OP(O)(O)=O)[C@H](OC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC)[C@@H](NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)[C@@H]1OC[C@@H]1[C@@H](O)[C@H](OC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](NC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](OP(O)(O)=O)O1 GZQKNULLWNGMCW-PWQABINMSA-N 0.000 abstract 1
- 230000008018 melting Effects 0.000 abstract 1
- 238000002844 melting Methods 0.000 abstract 1
- 231100000324 minimal toxicity Toxicity 0.000 abstract 1
- 150000003904 phospholipids Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K39/12—Viral antigens
- A61K39/21—Retroviridae, e.g. equine infectious anemia virus
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K39/12—Viral antigens
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K39/39—Medicinal preparations containing antigens or antibodies characterised by the immunostimulating additives, e.g. chemical adjuvants
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- 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
- C12N7/00—Viruses; Bacteriophages; Compositions thereof; Preparation or purification thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K2039/555—Medicinal preparations containing antigens or antibodies characterised by a specific combination antigen/adjuvant
- A61K2039/55511—Organic adjuvants
- A61K2039/55555—Liposomes; Vesicles, e.g. nanoparticles; Spheres, e.g. nanospheres; Polymers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K2039/555—Medicinal preparations containing antigens or antibodies characterised by a specific combination antigen/adjuvant
- A61K2039/55511—Organic adjuvants
- A61K2039/55572—Lipopolysaccharides; Lipid A; Monophosphoryl lipid A
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K2039/555—Medicinal preparations containing antigens or antibodies characterised by a specific combination antigen/adjuvant
- A61K2039/55511—Organic adjuvants
- A61K2039/55577—Saponins; Quil A; QS21; ISCOMS
-
- 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
- C12N2740/00—Reverse transcribing RNA viruses
- C12N2740/00011—Details
- C12N2740/10011—Retroviridae
- C12N2740/16011—Human Immunodeficiency Virus, HIV
- C12N2740/16034—Use of virus or viral component as vaccine, e.g. live-attenuated or inactivated virus, VLP, viral protein
-
- 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
- C12N2740/00—Reverse transcribing RNA viruses
- C12N2740/00011—Details
- C12N2740/10011—Retroviridae
- C12N2740/16011—Human Immunodeficiency Virus, HIV
- C12N2740/16111—Human Immunodeficiency Virus, HIV concerning HIV env
- C12N2740/16134—Use of virus or viral component as vaccine, e.g. live-attenuated or inactivated virus, VLP, viral protein
-
- 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
- C12N2740/00—Reverse transcribing RNA viruses
- C12N2740/00011—Details
- C12N2740/10011—Retroviridae
- C12N2740/16011—Human Immunodeficiency Virus, HIV
- C12N2740/16111—Human Immunodeficiency Virus, HIV concerning HIV env
- C12N2740/16171—Demonstrated in vivo effect
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Virology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Communicable Diseases (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Preparation (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Abstract
NON-TOXIC ADJUVANT FORMULATION COMPRISING A MONOPHOSPHORYL LIPID A (MPLA)-CONTAINING LIPOSOME COMPOSITION AND A SAPONIN Provided herein is an adjuvant formulation comprising a monophosphoryl lipid A (MPLA)-containing liposome composition to saponin (e.g., QS-21), wherein the liposome composition comprises i) a lipid bilayer comprising phospholipids in which the hydrocarbon chains have a melting temperature in water of ≥ 23°C and ii) cholesterol at a mole percent concentration of greater than about 50% (mol/mol), preferably about 55% to about 71% (mol/mol), or more preferably about 55% (mol/mol). The adjuvant formulation displays minimal toxicity of either lipid A or saponin. (FIG. 2)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201461970118P | 2014-03-25 | 2014-03-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SG10201808315UA true SG10201808315UA (en) | 2018-10-30 |
Family
ID=52829375
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SG10201808315UA SG10201808315UA (en) | 2014-03-25 | 2015-03-25 | Non-toxic adjuvant formulation comprising a monophosphoryl lipid a (mpla)-containing liposome composition and a saponin |
| SG11201607396WA SG11201607396WA (en) | 2014-03-25 | 2015-03-25 | Non-toxic adjuvant formulation comprising a monophosphoryl lipid a (mpla)-containing liposome composition and a saponin |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SG11201607396WA SG11201607396WA (en) | 2014-03-25 | 2015-03-25 | Non-toxic adjuvant formulation comprising a monophosphoryl lipid a (mpla)-containing liposome composition and a saponin |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US10434167B2 (en) |
| EP (1) | EP3122380B1 (en) |
| JP (1) | JP6608422B2 (en) |
| KR (1) | KR102242875B1 (en) |
| CN (1) | CN107124869B (en) |
| AU (1) | AU2015236106A1 (en) |
| CA (1) | CA2943190A1 (en) |
| MX (1) | MX2016012168A (en) |
| RU (1) | RU2016141622A (en) |
| SG (2) | SG10201808315UA (en) |
| WO (1) | WO2015148648A1 (en) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA3015639A1 (en) * | 2016-03-09 | 2017-09-14 | Technion Research And Development Foundation Ltd. | Liposomal formulations and methods of using same in agriculture |
| JP6661454B2 (en) * | 2016-04-21 | 2020-03-11 | 株式会社東海理化電機製作所 | Display device and method of manufacturing display plate |
| EP3615005B1 (en) * | 2017-04-28 | 2025-07-30 | The Henry M. Jackson Foundation for the Advancement of Military Medicine, Inc. | Compositions and methods for vaccine delivery |
| CN107669692B (en) * | 2017-09-07 | 2020-09-29 | 中国人民解放军第二军医大学 | Application of MPLA in preparation of medicines for preventing and treating intestinal injury caused by ionizing radiation |
| AU2018330165B2 (en) * | 2017-09-08 | 2025-07-17 | Access To Advanced Health Institute | Liposomal formulations comprising saponin and methods of use |
| WO2020243166A1 (en) * | 2019-05-28 | 2020-12-03 | The Regents Of The University Of California | Th1-polarizing adjuvants for enhancing immunogenicity of hiv antigens |
| CN110613844B (en) * | 2019-10-23 | 2024-02-27 | 中国医学科学院生物医学工程研究所 | Mini combined adjuvant nanoparticle and preparation method and application thereof |
| AU2020407871A1 (en) | 2019-12-20 | 2022-06-30 | Nammi Therapeutics, Inc. | Formulated and/or co-formulated liposome compositions containing toll-like receptor ("TLR") agonist prodrugs useful in the treatment of cancer and methods thereof |
| EP3892296A1 (en) * | 2020-04-07 | 2021-10-13 | InnoMedica Holding AG | Immunogenic composition comprising an antigenic moiety and a liposomal formulation, method of producing the composition, the composition for use as a medicament, in particular for use as a vaccine |
| US20220287970A1 (en) * | 2020-06-30 | 2022-09-15 | Eyegene Inc | Composition for inhibiting saponin-induced hemolysis, containing cationic liposome |
| GB2600468A (en) * | 2020-10-30 | 2022-05-04 | Excivion Ltd | Adjuvant composition |
| CN112546233A (en) * | 2020-12-25 | 2021-03-26 | 常州大学 | Hyaluronic acid composite material loaded with water-insoluble immunoregulatory molecules and preparation method thereof |
| CN114366810B (en) * | 2022-02-15 | 2024-11-22 | 中国人民解放军陆军军医大学 | A natural microorganism and plant-derived composite dual adjuvant capable of efficiently inducing humoral and cellular immunity, and its preparation method and application |
| MX2024010416A (en) | 2022-03-14 | 2024-09-05 | Pfizer | Methods for producing an adjuvant. |
| KR20250054810A (en) | 2022-09-29 | 2025-04-23 | 화이자 인코포레이티드 | Immunogenic composition comprising RSV F protein trimer |
| AU2023403045A1 (en) | 2022-12-01 | 2025-06-12 | Pfizer Inc. | Pneumococcal conjugate vaccine formulations |
| US20240189410A1 (en) * | 2022-12-13 | 2024-06-13 | Pfizer Inc. | Immunogenic compositions and methods for eliciting an immune response against clostridioides (clostridium) difficile |
| WO2025057058A1 (en) * | 2023-09-13 | 2025-03-20 | Pfizer Inc. | Methods for producing an adjuvant |
| WO2025057078A1 (en) | 2023-09-14 | 2025-03-20 | Pfizer Inc. | Adjuvanted immunogenic compositions comprising conjugated pneumococcal capsular saccharide antigens and uses thereof |
| CN117771361B (en) * | 2024-02-27 | 2024-06-07 | 天津中逸安健生物科技有限公司 | Lipid nanoadjuvant of polyinosinic acid-polycytidylic acid compound, and preparation method and application thereof |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4186183A (en) | 1978-03-29 | 1980-01-29 | The United States Of America As Represented By The Secretary Of The Army | Liposome carriers in chemotherapy of leishmaniasis |
| US4302459A (en) | 1980-03-19 | 1981-11-24 | The United States Of America As Represented By The Secretary Of The Army | Liposome carriers in leishmaniasis chemotherapy with 8-aminoquinoline derivatives |
| US5916588A (en) | 1984-04-12 | 1999-06-29 | The Liposome Company, Inc. | Peptide-containing liposomes, immunogenic liposomes and methods of preparation and use |
| US5231112A (en) | 1984-04-12 | 1993-07-27 | The Liposome Company, Inc. | Compositions containing tris salt of cholesterol hemisuccinate and antifungal |
| US4684479A (en) | 1985-08-14 | 1987-08-04 | Arrigo Joseph S D | Surfactant mixtures, stable gas-in-liquid emulsions, and methods for the production of such emulsions from said mixtures |
| US6759057B1 (en) | 1986-06-12 | 2004-07-06 | The Liposome Company, Inc. | Methods and compositions using liposome-encapsulated non-steroidal anti-inflammatory drugs |
| CN1093255A (en) * | 1986-06-17 | 1994-10-12 | 恩特雷麦德有限公司 | Vaccines against sterols |
| IE60901B1 (en) | 1986-08-21 | 1994-08-24 | Vestar Inc | Improved treatment of systemic fungal infections with phospholipid particles encapsulating polyene antifungal antibiotics |
| US6406713B1 (en) | 1987-03-05 | 2002-06-18 | The Liposome Company, Inc. | Methods of preparing low-toxicity drug-lipid complexes |
| US5057540A (en) | 1987-05-29 | 1991-10-15 | Cambridge Biotech Corporation | Saponin adjuvant |
| AU598958B2 (en) | 1987-11-12 | 1990-07-05 | Vestar, Inc. | Improved amphotericin b liposome preparation |
| US5888519A (en) | 1988-06-02 | 1999-03-30 | The United States Of America As Represented By The Secretary Of The Army | Encapsulated high-concentration lipid a compositions as immunogenic agents to produce human antibodies to prevent or treat gram-negative bacterial infections |
| US5215680A (en) | 1990-07-10 | 1993-06-01 | Cavitation-Control Technology, Inc. | Method for the production of medical-grade lipid-coated microbubbles, paramagnetic labeling of such microbubbles and therapeutic uses of microbubbles |
| CA2138997C (en) * | 1992-06-25 | 2003-06-03 | Jean-Paul Prieels | Vaccine composition containing adjuvants |
| AU5959494A (en) * | 1992-12-29 | 1994-07-19 | Entremed, Inc | Vaccines against sterols |
| GB9320668D0 (en) * | 1993-10-07 | 1993-11-24 | Secr Defence | Liposomes containing particulare materials |
| UA56132C2 (en) * | 1995-04-25 | 2003-05-15 | Смітклайн Бічем Байолоджікалс С.А. | Vaccine composition (variants), method for stabilizing qs21 providing resistance against hydrolysis (variants), method for manufacturing vaccine |
| US6846489B1 (en) * | 1995-04-25 | 2005-01-25 | Smithkline Beecham Biologicals S.A. | Vaccines containing a saponin and a sterol |
| ES2208946T3 (en) | 1996-08-23 | 2004-06-16 | Sequus Pharmaceuticals, Inc. | LIPOSOMES CONTAINING A CISPLATIN COMPOUND. |
| US6056973A (en) | 1996-10-11 | 2000-05-02 | Sequus Pharmaceuticals, Inc. | Therapeutic liposome composition and method of preparation |
| AU4907897A (en) | 1996-10-11 | 1998-05-11 | Sequus Pharmaceuticals, Inc. | Therapeutic liposome composition and method |
| US6120797A (en) | 1996-10-15 | 2000-09-19 | The Liposome Company, Inc. | N-acyl phosphatidylethanolamine-mediated liposomal drug delivery |
| US6231859B1 (en) | 1996-12-02 | 2001-05-15 | Aquila Biopharmaceuticals, Inc. | Saponin adjuvant compositions |
| GB9817052D0 (en) * | 1998-08-05 | 1998-09-30 | Smithkline Beecham Biolog | Vaccine |
| TWI457133B (en) * | 2005-12-13 | 2014-10-21 | Glaxosmithkline Biolog Sa | Novel composition |
| CA2679765A1 (en) * | 2007-03-01 | 2008-09-12 | The Catholic University Of America | T4 bacteriophage bound to a substrate |
| GB0910046D0 (en) * | 2009-06-10 | 2009-07-22 | Glaxosmithkline Biolog Sa | Novel compositions |
| EP2654779B1 (en) | 2010-12-23 | 2018-02-28 | Ludwig Institute for Cancer Research, Ltd. | Liposomal formulation of nonglycosidic ceramides and uses thereof |
-
2015
- 2015-03-25 SG SG10201808315UA patent/SG10201808315UA/en unknown
- 2015-03-25 AU AU2015236106A patent/AU2015236106A1/en not_active Abandoned
- 2015-03-25 CN CN201580026334.9A patent/CN107124869B/en active Active
- 2015-03-25 EP EP15716264.5A patent/EP3122380B1/en active Active
- 2015-03-25 WO PCT/US2015/022461 patent/WO2015148648A1/en active Application Filing
- 2015-03-25 CA CA2943190A patent/CA2943190A1/en not_active Abandoned
- 2015-03-25 MX MX2016012168A patent/MX2016012168A/en unknown
- 2015-03-25 JP JP2017502920A patent/JP6608422B2/en active Active
- 2015-03-25 KR KR1020167026025A patent/KR102242875B1/en active Active
- 2015-03-25 US US15/127,081 patent/US10434167B2/en active Active
- 2015-03-25 RU RU2016141622A patent/RU2016141622A/en not_active Application Discontinuation
- 2015-03-25 SG SG11201607396WA patent/SG11201607396WA/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US20170182152A1 (en) | 2017-06-29 |
| RU2016141622A (en) | 2018-04-25 |
| KR102242875B1 (en) | 2021-04-20 |
| MX2016012168A (en) | 2017-04-25 |
| CA2943190A1 (en) | 2015-10-01 |
| US10434167B2 (en) | 2019-10-08 |
| SG11201607396WA (en) | 2016-10-28 |
| WO2015148648A1 (en) | 2015-10-01 |
| RU2016141622A3 (en) | 2018-10-26 |
| KR20170007242A (en) | 2017-01-18 |
| EP3122380B1 (en) | 2025-03-19 |
| EP3122380A1 (en) | 2017-02-01 |
| AU2015236106A1 (en) | 2016-10-20 |
| CN107124869B (en) | 2022-04-01 |
| JP6608422B2 (en) | 2019-11-20 |
| JP2017515889A (en) | 2017-06-15 |
| CN107124869A (en) | 2017-09-01 |
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