GB2599535A - Magnetic resonance imaging contrast agents including an imidazole-comprising compound - Google Patents

Magnetic resonance imaging contrast agents including an imidazole-comprising compound Download PDF

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Publication number
GB2599535A
GB2599535A GB2117923.9A GB202117923A GB2599535A GB 2599535 A GB2599535 A GB 2599535A GB 202117923 A GB202117923 A GB 202117923A GB 2599535 A GB2599535 A GB 2599535A
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United Kingdom
Prior art keywords
contrast agent
imidazole
equal
agent according
mri contrast
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.)
Granted
Application number
GB2117923.9A
Other versions
GB202117923D0 (en
GB2599535B (en
Inventor
Geninatti Crich Simonetta
Aime Silvio
Baroni Simona
Stefania Rachele
Rosaria Ruggiero Maria
Lurie David
Broche Lionel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
University of Aberdeen
Degli Studi Di Torino, University of
Universita degli Studi di Torino
Original Assignee
University of Aberdeen
Degli Studi Di Torino, University of
Universita degli Studi di Torino
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Publication of GB202117923D0 publication Critical patent/GB202117923D0/en
Publication of GB2599535A publication Critical patent/GB2599535A/en
Application granted granted Critical
Publication of GB2599535B publication Critical patent/GB2599535B/en
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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
    • A61K49/08—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by the carrier
    • A61K49/10—Organic compounds
    • A61K49/12—Macromolecular compounds
    • A61K49/126—Linear polymers, e.g. dextran, inulin, PEG
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
    • A61K49/18—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes
    • A61K49/1818—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes particles, e.g. uncoated or non-functionalised microparticles or nanoparticles

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  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Radiology & Medical Imaging (AREA)
  • Epidemiology (AREA)
  • Public Health (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Nanotechnology (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Medicinal Preparation (AREA)
  • Magnetic Resonance Imaging Apparatus (AREA)

Abstract

Novel Magnetic Resonance Imaging (MRI) contrast agents including an imidazole-comprising compound,wherein the imidazole-comprising compound comprises at least 5 imidazole moieties, and wherein the imidazole moieties are in an immobilized state so that in use the longitudinal water proton relaxation rate at 1.38±0.3MHz (Proton Larmor Frequency) increases of at least 10%of the pre-contrast value.

Claims (10)

1. A Magnetic Resonance Imaging (MRI) contrast agent including an imidazole-comprising compound, wherein the imidazole-comprising compound comprises at least 5 imidazole moieties, and wherein the imidazole moieties are in an immobilized state, corresponding to a tumbling time in the order of tens of nanoseconds (ns) so that in use the longitudinal water proton relaxation rate at 1.38±0.3 MHz (Proton Larmor Frequency) increases of at least 10% of the pre-contrast value, wherein the MRI contrast agent is free of paramagnetic metal (s) .
2 . The MRI contrast agent according to claim 1, wherein the imidazole-comprising compound has formula (I) : Ri- [S-L- (B) r- (His)t-C] n (I) wherein Ri is selected from polyglycolic acid (PGA) , polylactic acid (PLA) , poly ( lactic-co-glycolic acid) (PLGA) , alginate, hyaluronic acid (HA) and chitosan; S is a spacer selected from a direct bond, -(CH2)2- 0 B is selected from Gly, Phe, Ala or b-Ala; C is selected from b-Ala and none; r is an integer number between 0 and 5; t is an integer number equal to or greater than 5, preferably comprised between 5 and 150, more preferably comprised between 10 and 50; n is an integer number equal to or greater than 1.
3. The MRI contrast agent according to claim 2, wherein Ri is selected from polyglycolic acid (PGA) , polylactic acid (PLA) and poly ( lactic-co-glycolic acid) (PLGA) ; S is selected from- (CH2) 2-0- (CH2) 2-0- and -(CH2)2_ 0- (CH2) 2_0- (CH2) 2_0-; and n is an integer number equal to 1.
4. The MRI contrast agent according to claim 2 or claim 3, wherein Ri is poly ( lactic-co-glycolic acid) (PLGA) ; B is Gly; C is b-Ala; r is equal to 2; t is an integer comprised between 10 and 50. n is equal to 1.
5. The MRI contrast agent according to any one of claims 2 to 3, wherein Ri is poly ( lactic-co-glycolic acid) (PLGA); S is - (CH2) 2-0- (CH2) 2-0-; L is B is Gly; C is b-Ala; r is equal to 2; t is equal to 15; n is equal to 1.
6. The MRI contrast agent according to claim 2, wherein Ri is selected from alginate and hyaluronic acid; S is selected from - (CH2) 2-0- (CH2) 2-0- and- (CH2) 2-0- (CH2) 2- 0-(CH2)2-0-; and n is an integer number greater than 1, preferably comprised 2 and 100.
7. The MRI contrast agent according to claim 2, wherein Ri is chitosan; S is a direct bond; n is an integer number greater than 1, preferably comprised 2 and 200.
8. The MRI contrast agent according to any one of the preceding claims, wherein the imidazole-comprising compound is in form of nanoparticle or scaffold.
9. A pharmaceutical composition comprising a MRI contrast agent according to any one of claims 1 to 8 and a pharmaceutically acceptable vehicle.
10. A pharmaceutical composition according to claim 9 for use as a contrast agent and/or as a pH sensing agent in Fast Field-Cycling (FFC) Magnetic Resonance Imaging (MRI) technique.
GB2117923.9A 2019-05-30 2020-05-27 Novel magnetic resonance imaging contrast agents Active GB2599535B (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT102019000007647A IT201900007647A1 (en) 2019-05-30 2019-05-30 NEW CONTRAST AGENTS FOR MAGNETIC RESONANCE FOR IMAGES
PCT/IB2020/055017 WO2020240431A1 (en) 2019-05-30 2020-05-27 Magnetic resonance imaging contrast agents including an imidazole-comprising compound

Publications (3)

Publication Number Publication Date
GB202117923D0 GB202117923D0 (en) 2022-01-26
GB2599535A true GB2599535A (en) 2022-04-06
GB2599535B GB2599535B (en) 2023-09-20

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Family Applications (1)

Application Number Title Priority Date Filing Date
GB2117923.9A Active GB2599535B (en) 2019-05-30 2020-05-27 Novel magnetic resonance imaging contrast agents

Country Status (3)

Country Link
GB (1) GB2599535B (en)
IT (1) IT201900007647A1 (en)
WO (1) WO2020240431A1 (en)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000016811A2 (en) * 1998-09-17 2000-03-30 Schering Aktiengesellschaft Mri contrast agent

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000016811A2 (en) * 1998-09-17 2000-03-30 Schering Aktiengesellschaft Mri contrast agent

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
DARA Ó HÓGÁIN ET AL, "The use of contrast agents with fast field-cycling magnetic resonance imaging;Use of contrast agents with fast field-cycling magnetic resonance imaging", PHYSICS IN MEDICINE AND BIOLOGY, INSTITUTE OF PHYSICS PUBLISHING, BRISTOL GB, (20101130), vol. 56, no. 1, doi:10.1088/0031-9 *
KIM KYOUNGG SUB ET AL: "A cancer-recognizable MRI contrast agents using pH-responsive polymeric micelle", BIOMATERIALS, ELSEVIER SCIENCE PUBLISHERS BV., BARKING, GB, Vol. 35, no. 1, 15 October 2013, pages 337-343, XPO28762520, ISSN: 0142-9612, DOI: 10.1016/J.BIOMATERIALS.2013.10.004 abstract scheme *
YOSHIKAZU SUZUKI, MITSURU IIDA, IWAO MIURA, TOSHIRO INUBUSHI, SHIGEHIRO MORIKAWA: "A Polymer-Based Magnetic Resonance Tracer for Visualization of Solid Tumors by 13C Spectroscopic Imaging", PLOS ONE, vol. 9, no. 7, pages e102132, XP055720069, DOI: 10.1371/journal.pone.0102132 *

Also Published As

Publication number Publication date
WO2020240431A1 (en) 2020-12-03
GB202117923D0 (en) 2022-01-26
GB2599535B (en) 2023-09-20
IT201900007647A1 (en) 2020-11-30

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