WO2017171685A2 - An agent used in dual fluorescent/ nuclear imaging of pancreatic cancer - Google Patents
An agent used in dual fluorescent/ nuclear imaging of pancreatic cancer Download PDFInfo
- Publication number
- WO2017171685A2 WO2017171685A2 PCT/TR2017/050128 TR2017050128W WO2017171685A2 WO 2017171685 A2 WO2017171685 A2 WO 2017171685A2 TR 2017050128 W TR2017050128 W TR 2017050128W WO 2017171685 A2 WO2017171685 A2 WO 2017171685A2
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- WO
- WIPO (PCT)
- Prior art keywords
- imaging
- fluorescence
- agent
- pancreatic cancer
- phthalocyanine
- Prior art date
Links
- 206010061902 Pancreatic neoplasm Diseases 0.000 title claims abstract description 26
- 238000012633 nuclear imaging Methods 0.000 title claims abstract description 26
- 201000002528 pancreatic cancer Diseases 0.000 title claims abstract description 26
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 title claims abstract description 23
- 208000008443 pancreatic carcinoma Diseases 0.000 title claims abstract description 23
- 230000009977 dual effect Effects 0.000 title description 8
- 238000012632 fluorescent imaging Methods 0.000 title description 4
- 238000000799 fluorescence microscopy Methods 0.000 claims abstract description 29
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims abstract description 26
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 13
- 239000003504 photosensitizing agent Substances 0.000 claims abstract description 6
- 238000003384 imaging method Methods 0.000 claims description 9
- 239000012216 imaging agent Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 210000004881 tumor cell Anatomy 0.000 claims description 2
- 238000001727 in vivo Methods 0.000 claims 1
- 238000011503 in vivo imaging Methods 0.000 claims 1
- 238000002372 labelling Methods 0.000 claims 1
- 210000000496 pancreas Anatomy 0.000 claims 1
- 238000002603 single-photon emission computed tomography Methods 0.000 claims 1
- 210000004027 cell Anatomy 0.000 description 11
- 239000011701 zinc Substances 0.000 description 9
- 206010028980 Neoplasm Diseases 0.000 description 8
- 201000011510 cancer Diseases 0.000 description 5
- 238000003745 diagnosis Methods 0.000 description 4
- 230000003834 intracellular effect Effects 0.000 description 4
- 210000001519 tissue Anatomy 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 239000000412 dendrimer Substances 0.000 description 2
- 229920000736 dendritic polymer Polymers 0.000 description 2
- 210000002288 golgi apparatus Anatomy 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 238000002595 magnetic resonance imaging Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000002428 photodynamic therapy Methods 0.000 description 2
- 238000007626 photothermal therapy Methods 0.000 description 2
- 239000012217 radiopharmaceutical Substances 0.000 description 2
- 229940121896 radiopharmaceutical Drugs 0.000 description 2
- 230000002799 radiopharmaceutical effect Effects 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- FJQZXCPWAGYPSD-UHFFFAOYSA-N 1,3,4,6-tetrachloro-3a,6a-diphenylimidazo[4,5-d]imidazole-2,5-dione Chemical compound ClN1C(=O)N(Cl)C2(C=3C=CC=CC=3)N(Cl)C(=O)N(Cl)C12C1=CC=CC=C1 FJQZXCPWAGYPSD-UHFFFAOYSA-N 0.000 description 1
- FWBHETKCLVMNFS-UHFFFAOYSA-N 4',6-Diamino-2-phenylindol Chemical compound C1=CC(C(=N)N)=CC=C1C1=CC2=CC=C(C(N)=N)C=C2N1 FWBHETKCLVMNFS-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- 102000004895 Lipoproteins Human genes 0.000 description 1
- 108090001030 Lipoproteins Proteins 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 230000005255 beta decay Effects 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 210000003855 cell nucleus Anatomy 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 210000000805 cytoplasm Anatomy 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000013399 early diagnosis Methods 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 208000037828 epithelial carcinoma Diseases 0.000 description 1
- 210000002950 fibroblast Anatomy 0.000 description 1
- 238000002073 fluorescence micrograph Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- XMBWDFGMSWQBCA-RNFDNDRNSA-M iodine-131(1-) Chemical class [131I-] XMBWDFGMSWQBCA-RNFDNDRNSA-M 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000025608 mitochondrion localization Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000002070 nanowire Substances 0.000 description 1
- LKKPNUDVOYAOBB-UHFFFAOYSA-N naphthalocyanine Chemical compound N1C(N=C2C3=CC4=CC=CC=C4C=C3C(N=C3C4=CC5=CC=CC=C5C=C4C(=N4)N3)=N2)=C(C=C2C(C=CC=C2)=C2)C2=C1N=C1C2=CC3=CC=CC=C3C=C2C4=N1 LKKPNUDVOYAOBB-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 150000002990 phenothiazines Chemical class 0.000 description 1
- 238000002600 positron emission tomography Methods 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/06—Zinc compounds
Definitions
- the invention related to an agent that using both fluorescence and nuclear imaging of pancreatic cancer. Particularly, the invention is used for both fluorescence and nuclear imaging of pancreatic cancer at the same time;
- Pancreatic cancer caused by abnormal cell proliferation has become a very common disease in recent years.
- Pancreatic cancer is one of the most aggressive type and difficult to diagnose in early stage.
- Pancreatic cancer is the seventh most common in the world and also difficult to diagnose and therapy. Survival rate after diagnosis is 25% for 1 year and 5% for 5 years. Therefore, early diagnosis of pancreatic cancer is of vital importance.
- MRI magnetic resonance imaging
- PET positron emission tomography
- Fl fluorescence imaging
- MRI has high resolution but low sensitivity.
- nuclear imaging which is radionuclide-based monitoring is quite sensitive and highly quantitative, it has a poor spatial resolution.
- quantitative information is hard to get by using fluorescence imaging (Fl).
- Fl fluorescence imaging
- Fl has wide range application areas due of its low cost, low energy radiation, high sensitivity and allowing non-invasive or minimally invasive applications. The disadvantages of single imaging systems could be eliminated by combined imaging systems.
- phthalocyanine-dendrimer composition prepared by naphthalocyanine could be used as fluorescence imaging agent. Additionally, it was expressed that phthalocyanine-dendrimer compositions could be suitable for photothermal and photodynamic therapy.
- the invention aims to develop an agent suitable for dual imaging systems including fluorescent and nuclear imaging in the diagnosis of pancreatic cancer.
- Zn(ll) phthalocyanine synthesized by us used for fluorescence imaging, and a radionuclide ( 131 l labeled Zn(ll) phthalocyanine) used for nuclear imaging.
- the fluorescence and nuclear imaging potential studies of the agent were performed by MIA PaCa-2 (human pancreatic epithelial carcinoma) and WI-38 (healthy human lung fibroblast) cells. As a result of the studies, It was determined that 131 1 labeled Zn(ll) phthalocyanine is a suitable agent for dual imaging system including fluorescence and nuclear imaging.
- the invention aims to develop an agent suitable for dual imaging systems including fluorescent and nuclear imaging in the diagnosis of pancreatic cancer.
- Zn(ll) phthalocyanine synthesized by us used for fluorescence imaging
- a radionuclide 131 l labeled Zn(ll) phthalocyan
- radiopharmaceuticals prepared in doses that can impact to the target area, and with appropriate encapsulation techniques which doesn't damage healthy tissues has the potential for use in industry in order to nuclear imaging.
- Figure - 1 Chemical structure of synthesized Zn (II) phthalocyanine Figure - 2; (a): Intracellular Uptake (%) of 131 1 in WI-38 cells; (b): Intracellular Uptake (%) of 131 1 in MIA Paca-2 cells; (c): Intracellular Uptake (%) of 131 l-Zn(ll)Pc in WI-38 cells; (d): Intracellular Uptake (%) of 131 l-Zn(ll)Pc in MIA Paca-2 cells.
- Figure - 3 Fluorescence microscope images of Zn(ll)Pc on MIA Paca-2 cells in 10 ⁇ scale, (a) and (b); the images taken by green filter, (c) and (d); the images taken by DAPI filter, (e); ); superimposed image of (a) and (c). (f); superimposed image of (b) and (d).
- the Invention is based on the usage of 131 1 labelled Zn (II) phthalocyanine, which was synthesized by us as a second-generation photosensitizer, in the diagnosis of pancreatic cancer with dual fluorescent / nuclear imaging.
- the inability of fluorescence imaging which comes from penetration into depth tissues can be solved by using near infrared (NIR) fluorescence imaging. Deep tissues and organs can be monitored by an ideal fluorescence probe using NIR fluorescence imaging.
- NIR fluorescence imaging near infrared
- Synthesized Zinc phthalcyanine for using in the invention is very suitable candidate for fluorescence imaging due to its high extinction coeDcient, convenient quantum yield, high photo stability, tumor-localizing property, good biocompatibility and low dark toxicity.
- Synthesized Zn (II) phthalocyanine as shown in Figure 1 can label with iodine isotopes with high efficiency due to its aromatic structure.
- 131 1 radioisotope makes 364 keV gamma emission after ⁇ -decay. Therefore; compounds labelled with this radioiodine isotope is advantageous in terms of using both treatment and imaging when dosing and duration were configured according to the purpose.
- Zn (II) phthalocyanine was labeled with 131 1 with high efficiency (93.4 ⁇ 1 .6 %) via iodogen method. It was determined with in vitro uptake studies that the 131 1 labelled Zn (II) phthalocyanine was uptaken by pancreatic cancer cell line more than healthy cells.
- Tumor-to nontumor (T/NT) ratio of 2 is adequate for imaging of tumor [28].
- T/NT Tumor-to nontumor
- Zn (II) phthalocyanine useful for nuclear imaging of pancreatic cancer.
- Zn (II) phthalocyanine is appropriate probe for NIR fluorescence imaging was determined by fluorescence imaging studies performed with MIA PaCa-2 cell line. Hydrophobic Zn (II) phthalocyanine structures are transported by lipoproteins. Therefore, they are directly taken up with tumor cells and localized in subcellular membrane structures. It's clearly seen in Figure-3, Zn (II) phthalocyanine was not uptaken by cell nucleus, however Zn (II) phthalocyanine was localized in cell cytoplasm.
- Zn (II) phthalocyanines are localized in Golgi apparatus at shorter incubation periods. However, there is still the presence of Zn (II) phthalocyanine in Golgi apparatus and also mitochondrial localization could be observed in the longer incubation periods.
- Zn (II) phthalocyanine labelled with a suitable radioisotope is a imaging agent which can be used in dual fluorescence/nuclear imaging systems.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Abstract
The invention; related to an agent that using both fluorescence and nuclear imaging of pancreatic cancer. Particularly, the invention is used for both fluorescence and nuclear imaging of pancreatic cancer at the same time; related to Zn(II) Phthalocyanine, a photosensitizer that is used both fluorescence and nuclear imaging of pancreatic cancer at the same time, labeled with 131I radionuclide.
Description
AN AGENT USED IN DUAL FLUORESCENT / NUCLEAR IMAGING OF
PANCREATIC CANCER
TECHNICAL FIELD
The invention; related to an agent that using both fluorescence and nuclear imaging of pancreatic cancer. Particularly, the invention is used for both fluorescence and nuclear imaging of pancreatic cancer at the same time;
- related to Zn(ll) Phthalocyanine, a photosensitizer that is used both fluorescence and nuclear imaging of pancreatic cancer at the same time, labeled with 1311 radionuclide. TECHNICAL BACKGROUND
Cancer, caused by abnormal cell proliferation has become a very common disease in recent years. There are many known types of cancer in medicine. Pancreatic cancer is one of the most aggressive type and difficult to diagnose in early stage. Pancreatic cancer is the seventh most common in the world and also difficult to diagnose and therapy. Survival rate after diagnosis is 25% for 1 year and 5% for 5 years. Therefore, early diagnosis of pancreatic cancer is of vital importance.
There are many imaging systems such as magnetic resonance imaging (MRI), positron emission tomography (PET) and fluorescence imaging (Fl), and all these systems have some advantages and disadvantages.
MRI has high resolution but low sensitivity. Although nuclear imaging which is radionuclide-based monitoring is quite sensitive and highly quantitative, it has a poor spatial resolution. However, quantitative information is hard to get by using fluorescence imaging (Fl). However, Fl has wide range application areas due of its
low cost, low energy radiation, high sensitivity and allowing non-invasive or minimally invasive applications. The disadvantages of single imaging systems could be eliminated by combined imaging systems.
The literature review conducted for state-of-the-art; the patent documents numbered as US2014371 192A and WO15026963A3 were found to be similar to the present invention.
When analyzed the content of the application numbered as US2014371192,
It was mentioned the preparation of alpha-form zinc phthalocyanine nanowires / phenothiazines, and dual photothermal and photodynamic therapy potentials of the composite.
When analyzed the content of the application numbered as WO15026963A3,
It was observed that phthalocyanine-dendrimer composition prepared by naphthalocyanine could be used as fluorescence imaging agent. Additionally, it was expressed that phthalocyanine-dendrimer compositions could be suitable for photothermal and photodynamic therapy.
BRIEF DESCRIPTION OF THE INVENTION
The invention; aims to develop an agent suitable for dual imaging systems including fluorescent and nuclear imaging in the diagnosis of pancreatic cancer. Zn(ll) phthalocyanine synthesized by us used for fluorescence imaging, and a radionuclide (131 l labeled Zn(ll) phthalocyanine) used for nuclear imaging. The fluorescence and nuclear imaging potential studies of the agent were performed by MIA PaCa-2 (human pancreatic epithelial carcinoma) and WI-38 (healthy human lung fibroblast) cells. As a result of the studies, It was determined that 1311 labeled Zn(ll) phthalocyanine is a suitable agent for dual imaging system including fluorescence and nuclear imaging.
The invention;
- the development of a new cancer dual imaging radiopharmaceutical,
- in the medical field for fast, reliable and practical diagnosis of different types of cancer,
- radiopharmaceuticals prepared in doses that can impact to the target area, and with appropriate encapsulation techniques which doesn't damage healthy tissues has the potential for use in industry in order to nuclear imaging.
DESCRIPTION OF THE FIGURES
Figure - 1 ; Chemical structure of synthesized Zn (II) phthalocyanine Figure - 2; (a): Intracellular Uptake (%) of 1311 in WI-38 cells; (b): Intracellular Uptake (%) of 1311 in MIA Paca-2 cells; (c): Intracellular Uptake (%) of 131 l-Zn(ll)Pc in WI-38 cells; (d): Intracellular Uptake (%) of 131 l-Zn(ll)Pc in MIA Paca-2 cells.
Figure - 3; Fluorescence microscope images of Zn(ll)Pc on MIA Paca-2 cells in 10 μιη scale, (a) and (b); the images taken by green filter, (c) and (d); the images taken by DAPI filter, (e); ); superimposed image of (a) and (c). (f); superimposed image of (b) and (d).
DETAILED DESCRIPTION OF THE INVENTION
The Invention is based on the usage of 131 1 labelled Zn (II) phthalocyanine, which was synthesized by us as a second-generation photosensitizer, in the diagnosis of pancreatic cancer with dual fluorescent / nuclear imaging. The inability of fluorescence imaging which comes from penetration into depth tissues can be solved by using near infrared (NIR) fluorescence imaging. Deep tissues and organs can be monitored by an ideal fluorescence probe using NIR fluorescence imaging. Synthesized Zinc phthalcyanine for using in the invention is very suitable candidate for fluorescence imaging due to its high extinction coeDcient, convenient quantum yield, high photo stability, tumor-localizing property, good biocompatibility and low dark toxicity.
Synthesized Zn (II) phthalocyanine as shown in Figure 1 can label with iodine isotopes with high efficiency due to its aromatic structure. 1311 radioisotope makes 364 keV gamma emission after β-decay. Therefore; compounds labelled with this radioiodine isotope is advantageous in terms of using both treatment and imaging when dosing and duration were configured according to the purpose.
Zn (II) phthalocyanine was labeled with 1311 with high efficiency (93.4±1 .6 %) via iodogen method. It was determined with in vitro uptake studies that the 1311 labelled Zn (II) phthalocyanine was uptaken by pancreatic cancer cell line more than healthy cells.
As seen in Figure 2, It was determined that the 1311 labelled Zn (II) phthalocyanine was uptaken two times more by cancer cell lines (MIA PaCa-2) than the normal cell line (WI-38).
Tumor-to nontumor (T/NT) ratio of 2 is adequate for imaging of tumor [28]. Thus the 1311 labelled Zn (II) phthalocyanine useful for nuclear imaging of pancreatic cancer. However, Zn (II) phthalocyanine is appropriate probe for NIR fluorescence imaging was determined by fluorescence imaging studies performed with MIA PaCa-2 cell line.
Hydrophobic Zn (II) phthalocyanine structures are transported by lipoproteins. Therefore, they are directly taken up with tumor cells and localized in subcellular membrane structures. It's clearly seen in Figure-3, Zn (II) phthalocyanine was not uptaken by cell nucleus, however Zn (II) phthalocyanine was localized in cell cytoplasm. In the fluorescence imaging studies, Zn (II) phthalocyanines are localized in Golgi apparatus at shorter incubation periods. However, there is still the presence of Zn (II) phthalocyanine in Golgi apparatus and also mitochondrial localization could be observed in the longer incubation periods.
As a result of studies, it was concluded that Zn (II) phthalocyanine labelled with a suitable radioisotope is a imaging agent which can be used in dual fluorescence/nuclear imaging systems.
Claims
1. the invention is related to an agent that is used for both fluorescence and nuclear imaging of pancreatic cancer at the same time, property;
It is characterized with Zn (II) Phthalocyanine, a photosensitizer that is used both fluorescence and nuclear imaging of pancreatic cancer at the same time, labeled with 1311 radionuclide.
2. According to claim 1 , an agent that is used for both fluorescence and nuclear imaging of pancreatic cancer at the same time, property; comprises that Zn (II) Phthalocyanine is labelled by the lodogen method on the contained aromatic ring.
3. According to claim 1 , an agent that is used for both fluorescence and nuclear imaging of pancreatic cancer at the same time, property; contains that 1311 labelled Zn (II) Phthalocyanine, a photosensitizer, is a nuclear imaging agent.
4. According to claim 1 , an agent that is used for both fluorescence and nuclear imaging of pancreatic cancer at the same time, property; contains that 1311 labelled Zn (II) Phthalocyanine is a pancreatic tumor imaging agent which can be uptaken with detected amount by pancreatic tumor cells.
5. According to claim 1 , an agent that is used for both fluorescence and nuclear imaging of pancreatic cancer at the same time, property; contains that preparation of that 1311 labelled Zn (II) Phthalocyanine suitable for in vivo applications and as a result, 1311 labelled Zn (II) Phthalocyanine is especially used as a imaging agent for SPECT imaging of pancreas.
6. According to claim 1 , an agent that is used for both fluorescence and nuclear imaging of pancreatic cancer at the same time, property; contains that Zn (II) Phthalocyanine can be used as a imaging agent for PET in case of labeling with radioisotopes making positron emission such as 124l
7. According to claim 1 , an agent that is used for both fluorescence and nuclear imaging of pancreatic cancer at the same time, property; contains that Zn(ll)
Phthalocyanine, the suitable photosensitizer for fluorescence imaging, is a imaging agent for using in vivo imaging of pancreatic tumor.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| TR2016/04265 | 2016-04-02 | ||
| TR201604265 | 2016-04-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2017171685A2 true WO2017171685A2 (en) | 2017-10-05 |
| WO2017171685A3 WO2017171685A3 (en) | 2017-11-02 |
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| PCT/TR2017/050128 WO2017171685A2 (en) | 2016-04-02 | 2017-03-30 | An agent used in dual fluorescent/ nuclear imaging of pancreatic cancer |
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| Country | Link |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20140371192A1 (en) | 2011-09-26 | 2014-12-18 | Pohang University Of Science And Technology Industryacademy Cooperation Corps | Alpha-form zinc-phthalocyanine nanowires having enhanced water solubility and water dispersibility, composite of an alpha-form zinc-phthalocyanine nanowire/phenothiazine, and method for preparing same |
| WO2015026963A2 (en) | 2013-08-21 | 2015-02-26 | Oregon State University | Phthalocy anine-dendrimer compositions and a method of using |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20100030195A (en) * | 2008-09-09 | 2010-03-18 | 서울대학교산학협력단 | Fluorescent silica nanoparticle with radioactive tag and the detecting method of pet and fluorescent dual imaging using thereof |
| US20160199524A1 (en) * | 2015-01-09 | 2016-07-14 | Immunomedics, Inc. | Radiosensitivity of fluorophores and use of radioprotective agents for dual-modality imaging |
-
2017
- 2017-03-30 WO PCT/TR2017/050128 patent/WO2017171685A2/en active Application Filing
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20140371192A1 (en) | 2011-09-26 | 2014-12-18 | Pohang University Of Science And Technology Industryacademy Cooperation Corps | Alpha-form zinc-phthalocyanine nanowires having enhanced water solubility and water dispersibility, composite of an alpha-form zinc-phthalocyanine nanowire/phenothiazine, and method for preparing same |
| WO2015026963A2 (en) | 2013-08-21 | 2015-02-26 | Oregon State University | Phthalocy anine-dendrimer compositions and a method of using |
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| WO2017171685A3 (en) | 2017-11-02 |
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