CA3072282A1 - Nanoemulsion of iodinated fatty acids for ct imaging - Google Patents
Nanoemulsion of iodinated fatty acids for ct imaging Download PDFInfo
- Publication number
- CA3072282A1 CA3072282A1 CA3072282A CA3072282A CA3072282A1 CA 3072282 A1 CA3072282 A1 CA 3072282A1 CA 3072282 A CA3072282 A CA 3072282A CA 3072282 A CA3072282 A CA 3072282A CA 3072282 A1 CA3072282 A1 CA 3072282A1
- Authority
- CA
- Canada
- Prior art keywords
- contrast agent
- emulsion
- vivo imaging
- nano
- fatty acids
- 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.)
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- 235000014113 dietary fatty acids Nutrition 0.000 title claims description 76
- 229930195729 fatty acid Natural products 0.000 title claims description 76
- 239000000194 fatty acid Substances 0.000 title claims description 76
- 150000004665 fatty acids Chemical class 0.000 title claims description 72
- 239000007908 nanoemulsion Substances 0.000 title claims description 65
- 238000003384 imaging method Methods 0.000 title abstract description 26
- 239000002872 contrast media Substances 0.000 claims abstract description 96
- 210000000577 adipose tissue Anatomy 0.000 claims abstract description 24
- 210000004185 liver Anatomy 0.000 claims abstract description 15
- 238000011002 quantification Methods 0.000 claims abstract description 14
- 238000012800 visualization Methods 0.000 claims abstract description 12
- 238000002591 computed tomography Methods 0.000 claims description 77
- 238000000034 method Methods 0.000 claims description 52
- 125000004432 carbon atom Chemical group C* 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 43
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 37
- 238000011503 in vivo imaging Methods 0.000 claims description 32
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- 150000003839 salts Chemical class 0.000 claims description 30
- 150000002148 esters Chemical class 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 229920006395 saturated elastomer Polymers 0.000 claims description 16
- 239000003995 emulsifying agent Substances 0.000 claims description 15
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 14
- 230000000694 effects Effects 0.000 claims description 14
- 238000001727 in vivo Methods 0.000 claims description 14
- 210000000056 organ Anatomy 0.000 claims description 13
- 229920000136 polysorbate Polymers 0.000 claims description 12
- 229910052740 iodine Inorganic materials 0.000 claims description 11
- 239000011630 iodine Substances 0.000 claims description 11
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims description 10
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- 150000002170 ethers Chemical class 0.000 claims description 8
- 238000011156 evaluation Methods 0.000 claims description 8
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims description 7
- 239000002202 Polyethylene glycol Substances 0.000 claims description 7
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical class CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 claims description 7
- 150000002191 fatty alcohols Chemical class 0.000 claims description 7
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- 229920001223 polyethylene glycol Polymers 0.000 claims description 7
- 208000004930 Fatty Liver Diseases 0.000 claims description 6
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- 230000006870 function Effects 0.000 claims description 3
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
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- 241000699666 Mus <mouse, genus> Species 0.000 description 13
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- 101150041968 CDC13 gene Proteins 0.000 description 11
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 11
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- 235000009518 sodium iodide Nutrition 0.000 description 10
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- 235000011152 sodium sulphate Nutrition 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 7
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- 235000019345 sodium thiosulphate Nutrition 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
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- 241000699670 Mus sp. Species 0.000 description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
- XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- 239000003925 fat Substances 0.000 description 6
- 235000019197 fats Nutrition 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 6
- 235000011007 phosphoric acid Nutrition 0.000 description 6
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 6
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 6
- 229910008066 SnC12 Inorganic materials 0.000 description 5
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
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- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 5
- 239000000546 pharmaceutical excipient Substances 0.000 description 5
- 235000011150 stannous chloride Nutrition 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
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- 238000006243 chemical reaction Methods 0.000 description 4
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
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- 238000003760 magnetic stirring Methods 0.000 description 4
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- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
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- HXYHOQMJIDZELE-UHFFFAOYSA-N ethyl 2,2,3,3-tetraiodoicosanoate Chemical compound CCCCCCCCCCCCCCCCCC(C(C(=O)OCC)(I)I)(I)I HXYHOQMJIDZELE-UHFFFAOYSA-N 0.000 description 1
- WARJIOFDHWCTOS-UHFFFAOYSA-N ethyl 2,2-diiodooctadecanoate Chemical compound CCCCCCCCCCCCCCCCC(I)(I)C(=O)OCC WARJIOFDHWCTOS-UHFFFAOYSA-N 0.000 description 1
- XYSWCJVTCOLTLI-UHFFFAOYSA-N ethyl 2-iodooctadecanoate Chemical compound CCCCCCCCCCCCCCCCC(I)C(=O)OCC XYSWCJVTCOLTLI-UHFFFAOYSA-N 0.000 description 1
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- PYIDGJJWBIBVIA-UYTYNIKBSA-N lauryl glucoside Chemical compound CCCCCCCCCCCCO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O PYIDGJJWBIBVIA-UYTYNIKBSA-N 0.000 description 1
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- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
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- YYELLDKEOUKVIQ-UHFFFAOYSA-N octaethyleneglycol monododecyl ether Chemical compound CCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCO YYELLDKEOUKVIQ-UHFFFAOYSA-N 0.000 description 1
- HEGSGKPQLMEBJL-RKQHYHRCSA-N octyl beta-D-glucopyranoside Chemical group CCCCCCCCO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HEGSGKPQLMEBJL-RKQHYHRCSA-N 0.000 description 1
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- 238000005457 optimization Methods 0.000 description 1
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- 235000019371 penicillin G benzathine Nutrition 0.000 description 1
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- 125000003367 polycyclic group Chemical group 0.000 description 1
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- ARIWANIATODDMH-UHFFFAOYSA-N rac-1-monolauroylglycerol Chemical compound CCCCCCCCCCCC(=O)OCC(O)CO ARIWANIATODDMH-UHFFFAOYSA-N 0.000 description 1
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- 239000012047 saturated solution Substances 0.000 description 1
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
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- NJGWOFRZMQRKHT-UHFFFAOYSA-N surfactin Natural products CC(C)CCCCCCCCCC1CC(=O)NC(CCC(O)=O)C(=O)NC(CC(C)C)C(=O)NC(CC(C)C)C(=O)NC(C(C)C)C(=O)NC(CC(O)=O)C(=O)NC(CC(C)C)C(=O)NC(CC(C)C)C(=O)O1 NJGWOFRZMQRKHT-UHFFFAOYSA-N 0.000 description 1
- NJGWOFRZMQRKHT-WGVNQGGSSA-N surfactin C Chemical compound CC(C)CCCCCCCCC[C@@H]1CC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)O1 NJGWOFRZMQRKHT-WGVNQGGSSA-N 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/04—X-ray contrast preparations
- A61K49/0433—X-ray contrast preparations containing an organic halogenated X-ray contrast-enhancing agent
- A61K49/0438—Organic X-ray contrast-enhancing agent comprising an iodinated group or an iodine atom, e.g. iopamidol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/0004—Screening or testing of compounds for diagnosis of disorders, assessment of conditions, e.g. renal clearance, gastric emptying, testing for diabetes, allergy, rheuma, pancreas functions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/04—X-ray contrast preparations
- A61K49/0433—X-ray contrast preparations containing an organic halogenated X-ray contrast-enhancing agent
- A61K49/0447—Physical forms of mixtures of two different X-ray contrast-enhancing agents, containing at least one X-ray contrast-enhancing agent which is a halogenated organic compound
- A61K49/0461—Dispersions, colloids, emulsions or suspensions
-
- 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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
Landscapes
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Biomedical Technology (AREA)
- Diabetes (AREA)
- Dispersion Chemistry (AREA)
- Gastroenterology & Hepatology (AREA)
- Pathology (AREA)
- Rheumatology (AREA)
- Toxicology (AREA)
- Engineering & Computer Science (AREA)
- Nutrition Science (AREA)
- Physiology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Apparatus For Radiation Diagnosis (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| EP17185185.0 | 2017-08-07 | ||
| EP17185185 | 2017-08-07 | ||
| PCT/EP2018/070501 WO2019030024A1 (en) | 2017-08-07 | 2018-07-27 | NANOEMULSION OF IODIZED FATTY ACIDS FOR COMPUTER-ASSISTED TOMOGRAPHY (CT) IMAGING |
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|---|---|
| CA3072282A1 true CA3072282A1 (en) | 2019-02-14 |
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|---|---|---|---|
| CA3072282A Pending CA3072282A1 (en) | 2017-08-07 | 2018-07-27 | Nanoemulsion of iodinated fatty acids for ct imaging |
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| US (1) | US11654202B2 (enExample) |
| EP (1) | EP3664855A1 (enExample) |
| JP (1) | JP7210542B2 (enExample) |
| CN (1) | CN111194225B (enExample) |
| AU (1) | AU2018314406B2 (enExample) |
| BR (1) | BR112020002619A2 (enExample) |
| CA (1) | CA3072282A1 (enExample) |
| EA (1) | EA202090139A1 (enExample) |
| WO (1) | WO2019030024A1 (enExample) |
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| CN113784734B (zh) * | 2019-02-13 | 2024-09-27 | 日内瓦大学 | 用于恶病质的检测的ct造影剂 |
| JP2023536358A (ja) * | 2020-08-06 | 2023-08-24 | アディポス エスエー | Ｐｅｔ－ｃｔ撮像方法、その撮像方法における使用のための造影剤および医薬組成物 |
| CN112933246A (zh) * | 2020-12-17 | 2021-06-11 | 太阳雨林（厦门）生物医药有限公司 | 一种可显影的油制剂及其制备方法 |
| US20240336552A1 (en) * | 2021-08-02 | 2024-10-10 | Microvention, Inc. | Compounds |
| EP4423211A1 (en) | 2021-10-28 | 2024-09-04 | Adiposs SA | Emulsions, compositions for emulsions, methods for making the same and uses thereof |
| WO2025079088A1 (en) * | 2023-10-11 | 2025-04-17 | Bioroot Exploration India Private Limited | A contrast agent for computed tomography and process of preparation thereof |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US5258172A (en) * | 1983-12-29 | 1993-11-02 | Rubin Daniel L | Iodinated aliphatic emulsions for X-ray contrast |
| DE3785849T2 (de) | 1987-06-11 | 1993-08-26 | Kabi Pharmacia Ab | Jod enthaltende emulsion. |
| US5861367A (en) | 1993-08-04 | 1999-01-19 | Colgate Palmolive Company | Cleaning and disinfecting composition in microemulsion/liquid crystal form comprising aldehyde and mixture of partially esterified, fully esterified and non-esterified polyhydric alcohols |
| FR2736549B1 (fr) | 1995-07-11 | 1997-10-10 | Louis Jung | Esters d'acides gras iodes, acides gras iodes et leurs derives, obtenus par iodohydrination faisant intervenir des derives alkylsilyles avec des iodures alcalins et leurs activites pharmacologiques |
| DE19936727A1 (de) | 1999-08-06 | 2001-02-08 | Henkel Kgaa | Niotensidbasiertes wäßriges mehrphasiges Reinigungsmittel |
| US20050079131A1 (en) * | 2003-08-08 | 2005-04-14 | Lanza Gregory M. | Emulsion particles for imaging and therapy and methods of use thereof |
| GB0408684D0 (en) | 2004-04-19 | 2004-05-19 | Guy S And St Thomas Hospital N | Diagnostic method |
| SG10201505948VA (en) | 2004-12-13 | 2015-09-29 | Amylin Pharmaceuticals Llc | Pancreatic Polypeptide Family Motifs, Polypeptides And Methods Comprising The Same |
| ATE496881T1 (de) | 2006-02-15 | 2011-02-15 | Ge Healthcare As | Kontrastmittel |
| US20080319315A1 (en) | 2007-06-07 | 2008-12-25 | Beth Israel Deaconess Medical Center | Method of reducing interferences in positron emission tomography |
| US20140065067A1 (en) | 2010-12-17 | 2014-03-06 | Universite De Strasbourg | Radiopaque iodinated products intended for use medical imaging and their methods |
| KR101263733B1 (ko) | 2011-03-22 | 2013-05-14 | 한국과학기술연구원 | 리피오돌을 함유하는 컴퓨터 단층촬영용 혈관 조영제 |
| CN102166365B (zh) | 2011-04-25 | 2012-10-24 | 东南大学 | 一种多模态碘油纳米乳造影剂的制备方法 |
| DE102012204378A1 (de) | 2012-03-20 | 2013-09-26 | Bernd Schwegmann Gmbh & Co. Kg | Reinigungsmittel auf Mikroemulsionsbasis |
| CN105592862B (zh) | 2013-09-30 | 2020-09-29 | 贝朗医疗有限公司 | 肝脏预饱和及其后造影剂的施用 |
| WO2015127347A1 (en) | 2014-02-24 | 2015-08-27 | The Regents Of The University Of California | Therapeutic hyperbranched polyglycerol encapsulated biomolecules |
| US10157462B2 (en) | 2016-06-27 | 2018-12-18 | University Of Central Florida Research Foundation, Inc. | System and method for image-based quantification of white and brown adipose tissue at the whole-body, organ and body-region levels |
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2018
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| EP3664855A1 (en) | 2020-06-17 |
| EA202090139A1 (ru) | 2020-08-06 |
| AU2018314406A1 (en) | 2020-02-20 |
| WO2019030024A1 (en) | 2019-02-14 |
| CN111194225B (zh) | 2023-01-13 |
| CN111194225A (zh) | 2020-05-22 |
| JP7210542B2 (ja) | 2023-01-23 |
| AU2018314406B2 (en) | 2024-08-15 |
| BR112020002619A2 (pt) | 2020-07-28 |
| US11654202B2 (en) | 2023-05-23 |
| US20210330820A1 (en) | 2021-10-28 |
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