Pentamethine cyanine dyes with alkynyl group as perspective structure for conjugation with targeting moiety

[Display omitted] •An asymmetric carbocyanine for the [3+2] cycloaddition reaction was obtained.•A triazole ring does not affect the photophysical properties of the fluorophore.•The conjugation to the vector molecule does not abolish the selective binding. We report a modified carbocyanine-based asy...

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Published inBioorganic & medicinal chemistry letters Vol. 115; pp. 130025 - 130030
Main Authors Uspenskaia, Anastasiia A., Doroshenko, Irina A., Popovicheva, Kseniia A., Shmychkov, Nazar V., Pryakhina, Ekaterina V., Shafikov, Radik R., Skvortsov, Dmitrii A., Beklemishev, Mikhail K., Zaborova, Olga V., Podrugina, Tatiana A., Machulkin, Aleksei E., Beloglazkina, Elena K.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.01.2025
Elsevier
Subjects
Alkynes - chemical synthesis
Alkynes - chemistry
Antigens, Surface - chemistry
Antigens, Surface - metabolism
Asymmetric carbocyanine
Azides - chemistry
Carbocyanines - chemical synthesis
Carbocyanines - chemistry
Chemistry
Chemistry, Medicinal
Chemistry, Organic
Click reaction
Cyanine dyes
Cycloaddition Reaction
Fluorescent Dyes - chemical synthesis
Fluorescent Dyes - chemistry
Glutamate Carboxypeptidase II - antagonists & inhibitors
Glutamate Carboxypeptidase II - metabolism
Humans
Life Sciences & Biomedicine
Ligands
Male
Molecular Structure
Pharmacology & Pharmacy
Photochemistry
Physical Sciences
Prostatic Neoplasms - drug therapy
Science & Technology
Cyanine dyes
PSMA
Click reaction
Asymmetric carbocyanine
DCL
ICG
DMF
Photochemistry
Online AccessGet full text

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Abstract [Display omitted] •An asymmetric carbocyanine for the [3+2] cycloaddition reaction was obtained.•A triazole ring does not affect the photophysical properties of the fluorophore.•The conjugation to the vector molecule does not abolish the selective binding. We report a modified carbocyanine-based asymmetric fluorescent dye, suitable for the azide-alkyne cycloaddition reaction, that possesses promising photochemical properties (Φfl = 0,49). As an example of usage of the new fluorophore, it was conjugated to a ligand targeting prostate-specific membrane antigen (PSMA), one of the widely utilized prostate cancer markers.
AbstractList We report a modified carbocyanine-based asymmetric fluorescent dye, suitable for the azide-alkyne cycloaddition reaction, that possesses promising photochemical properties (Φfl = 0,49). As an example of usage of the new fluorophore, it was conjugated to a ligand targeting prostate-specific membrane antigen (PSMA), one of the widely utilized prostate cancer markers.We report a modified carbocyanine-based asymmetric fluorescent dye, suitable for the azide-alkyne cycloaddition reaction, that possesses promising photochemical properties (Φfl = 0,49). As an example of usage of the new fluorophore, it was conjugated to a ligand targeting prostate-specific membrane antigen (PSMA), one of the widely utilized prostate cancer markers.
We report a modified carbocyanine-based asymmetric fluorescent dye, suitable for the azide-alkyne cycloaddition reaction, that possesses promising photochemical properties (Phi fl= 0,49). As an example of usage of the new fluorophore, it was conjugated to a ligand targeting prostate-specific membrane antigen (PSMA), one of the widely utilized prostate cancer markers.
[Display omitted] •An asymmetric carbocyanine for the [3+2] cycloaddition reaction was obtained.•A triazole ring does not affect the photophysical properties of the fluorophore.•The conjugation to the vector molecule does not abolish the selective binding. We report a modified carbocyanine-based asymmetric fluorescent dye, suitable for the azide-alkyne cycloaddition reaction, that possesses promising photochemical properties (Φfl = 0,49). As an example of usage of the new fluorophore, it was conjugated to a ligand targeting prostate-specific membrane antigen (PSMA), one of the widely utilized prostate cancer markers.
We report a modified carbocyanine-based asymmetric fluorescent dye, suitable for the azide-alkyne cycloaddition reaction, that possesses promising photochemical properties (Φ  = 0,49). As an example of usage of the new fluorophore, it was conjugated to a ligand targeting prostate-specific membrane antigen (PSMA), one of the widely utilized prostate cancer markers.
ArticleNumber 130025
Author Beklemishev, Mikhail K.
Podrugina, Tatiana A.
Machulkin, Aleksei E.
Doroshenko, Irina A.
Uspenskaia, Anastasiia A.
Popovicheva, Kseniia A.
Beloglazkina, Elena K.
Skvortsov, Dmitrii A.
Zaborova, Olga V.
Pryakhina, Ekaterina V.
Shmychkov, Nazar V.
Shafikov, Radik R.
Author_xml – sequence: 1
  givenname: Anastasiia A.
  orcidid: 0000-0002-2451-8336
  surname: Uspenskaia
  fullname: Uspenskaia, Anastasiia A.
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  organization: Lomonosov Moscow State University, Chemistry Dept., Leninskie Gory, Building 1/3, GSP-1, Moscow 119991, Russian Federation
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  givenname: Irina A.
  surname: Doroshenko
  fullname: Doroshenko, Irina A.
  organization: Lomonosov Moscow State University, Chemistry Dept., Leninskie Gory, Building 1/3, GSP-1, Moscow 119991, Russian Federation
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  givenname: Kseniia A.
  surname: Popovicheva
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  organization: Lomonosov Moscow State University, Fundamental Physical and Chemical Engineering Dept., Leninskie Gory, Building 1/3, GSP-1, Moscow 119991, Russian Federation
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  givenname: Nazar V.
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  fullname: Shmychkov, Nazar V.
  organization: Lomonosov Moscow State University, Chemistry Dept., Leninskie Gory, Building 1/3, GSP-1, Moscow 119991, Russian Federation
– sequence: 5
  givenname: Ekaterina V.
  surname: Pryakhina
  fullname: Pryakhina, Ekaterina V.
  organization: National Research University Higher School of Economics, Biology and Biotechnology Dept., Profsoyuznaya St., 33/4, Moscow 117418, Russian Federation
– sequence: 6
  givenname: Radik R.
  surname: Shafikov
  fullname: Shafikov, Radik R.
  organization: Lomonosov Moscow State University, Chemistry Dept., Leninskie Gory, Building 1/3, GSP-1, Moscow 119991, Russian Federation
– sequence: 7
  givenname: Dmitrii A.
  surname: Skvortsov
  fullname: Skvortsov, Dmitrii A.
  organization: Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry Russian Academy of Sciences, GSP-7, Ulitsa Miklukho-Maklaya, 16/10, Moscow 117997, Russian Federation
– sequence: 8
  givenname: Mikhail K.
  surname: Beklemishev
  fullname: Beklemishev, Mikhail K.
  organization: Lomonosov Moscow State University, Chemistry Dept., Leninskie Gory, Building 1/3, GSP-1, Moscow 119991, Russian Federation
– sequence: 9
  givenname: Olga V.
  surname: Zaborova
  fullname: Zaborova, Olga V.
  organization: Lomonosov Moscow State University, Chemistry Dept., Leninskie Gory, Building 1/3, GSP-1, Moscow 119991, Russian Federation
– sequence: 10
  givenname: Tatiana A.
  surname: Podrugina
  fullname: Podrugina, Tatiana A.
  organization: Lomonosov Moscow State University, Chemistry Dept., Leninskie Gory, Building 1/3, GSP-1, Moscow 119991, Russian Federation
– sequence: 11
  givenname: Aleksei E.
  surname: Machulkin
  fullname: Machulkin, Aleksei E.
  organization: Lomonosov Moscow State University, Chemistry Dept., Leninskie Gory, Building 1/3, GSP-1, Moscow 119991, Russian Federation
– sequence: 12
  givenname: Elena K.
  surname: Beloglazkina
  fullname: Beloglazkina, Elena K.
  organization: Lomonosov Moscow State University, Chemistry Dept., Leninskie Gory, Building 1/3, GSP-1, Moscow 119991, Russian Federation
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Cites_doi 10.1016/j.mencom.2023.06.010
10.1039/c4cs00139g
10.1007/s00044-022-03002-w
10.1002/cbin.10055
10.1111/j.1478-4408.2006.00009.x
10.1002/adhm.202001327
10.1002/pros.21383
10.1021/acs.jmedchem.0c01935
10.1016/j.cbpa.2018.03.015
10.3762/bjoc.11.75
10.1038/s41598-020-69394-0
10.1007/s11172-006-0230-2
10.1039/C4CS00139G
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Keywords Cyanine dyes
PSMA
Click reaction
Asymmetric carbocyanine
DCL
ICG
DMF
Photochemistry
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References Uspenskaya, Nimenko, Shafikov (b0040) 2023; 32
Dubey, Singhvi, Tyagi, Agarwal, Krishna (b0055) 2017; 7
Lane, Xue, Nie (b0020) 2018; 45
Tai, Sun, Squires (b0065) 2011; 71
Ciuk, Lindhorst (b0030) 2015; 11
Machulkin, Shafikov, Uspenskaya (b0045) 2021; 64
Ben, Sallami, Céraline, Oueslati (b0060) 2013; 37
Zyk, Petrov, Zavertkina (b0035) 2023; 33
Konno, Matsumoto, Tomono, Okazaki (b0010) 2020; 10
Kiernan (b0005) 2006; 122
Tang, Becker (b0025) 2014; 43
Li, Zhou, Yue, Dai (b0015) 2020; 9
Kvach, Gontarev, Prokhorenko, Stepanova, Shmanai, Korshun (b0050) 2006; 55
Li, Y (WOS:000573863200001) 2020; 9
Konno, A (WOS:000556400100003) 2020; 10
Tang, W (WOS:000342880000008) 2014; 43
Zyk, NY (WOS:001043026900001) 2023; 33
Kiernan, JA (WOS:000236401800002) 2006; 122
Tai, S (WOS:000296261200009) 2011; 71
Uspenskaya, AA (WOS:000900101500001) 2023; 32
Lane, LA (WOS:000441686700013) 2018; 45
Machulkin, AE (WOS:000644437100014) 2021; 64
Ben Jemaa, A (WOS:000317895500010) 2013; 37
Dubey, SK (001360558600001.11) 2017; 7
Kvach, MV (WOS:000238550300023) 2006; 55
Ciuk, AK (WOS:000354083500001) 2015; 11
Kvach (10.1016/j.bmcl.2024.130025_b0050) 2006; 55
Tai (10.1016/j.bmcl.2024.130025_b0065) 2011; 71
Zyk (10.1016/j.bmcl.2024.130025_b0035) 2023; 33
Uspenskaya (10.1016/j.bmcl.2024.130025_b0040) 2023; 32
Li (10.1016/j.bmcl.2024.130025_b0015) 2020; 9
Kiernan (10.1016/j.bmcl.2024.130025_b0005) 2006; 122
Machulkin (10.1016/j.bmcl.2024.130025_b0045) 2021; 64
Ben (10.1016/j.bmcl.2024.130025_b0060) 2013; 37
Dubey (10.1016/j.bmcl.2024.130025_b0055) 2017; 7
Ciuk (10.1016/j.bmcl.2024.130025_b0030) 2015; 11
Tang (10.1016/j.bmcl.2024.130025_b0025) 2014; 43
Lane (10.1016/j.bmcl.2024.130025_b0020) 2018; 45
Konno (10.1016/j.bmcl.2024.130025_b0010) 2020; 10
References_xml – volume: 9
  start-page: 1
  year: 2020
  end-page: 24
  ident: b0015
  article-title: Cyanine conjugate‐based biomedical imaging probes
  publication-title: Adv Healthc Mater
– volume: 71
  start-page: 1668
  year: 2011
  end-page: 1679
  ident: b0065
  article-title: PC3 is a cell line characteristic of prostatic small cell carcinoma
  publication-title: Prostate
– volume: 7
  start-page: 155
  year: 2017
  end-page: 158
  ident: b0055
  article-title: Spectrophotometric determination of pKa and Log P of risperidone
  publication-title: J Appl Pharm Sci
– volume: 64
  start-page: 4532
  year: 2021
  end-page: 4552
  ident: b0045
  article-title: Synthesis and biological evaluation of PSMA ligands with aromatic residues and fluorescent conjugates based on them
  publication-title: J Med Chem
– volume: 11
  start-page: 668
  year: 2015
  end-page: 674
  ident: b0030
  article-title: Synthesis of carbohydrate-scaffolded thymine glycoconjugates to organize multivalency
  publication-title: Beilstein J Org Chem
– volume: 10
  year: 2020
  ident: b0010
  article-title: Pathological application of carbocyanine dye-based multicolour imaging of vasculature and associated structures
  publication-title: Sci Rep
– volume: 122
  start-page: 1
  year: 2006
  end-page: 21
  ident: b0005
  article-title: Dyes and other colorants in microtechnique and biomedical research
  publication-title: Color Technol
– volume: 33
  start-page: 472
  year: 2023
  end-page: 475
  ident: b0035
  article-title: Choice of the optimal synthetic approach for the polypeptide ligands of prostatic specific membrane antigen preparation
  publication-title: Mendeleev Commun
– volume: 32
  start-page: 32
  year: 2023
  end-page: 37
  ident: b0040
  article-title: Optimization of the dipeptide motifs in the PSMA ligands linker structure: synthesis and in vitro evaluation
  publication-title: Med Chem Res
– volume: 43
  start-page: 7013
  year: 2014
  end-page: 7039
  ident: b0025
  article-title: “Click” reactions: a versatile toolbox for the synthesis of peptide-conjugates
  publication-title: Chem Soc Rev
– volume: 45
  start-page: 95
  year: 2018
  end-page: 103
  ident: b0020
  article-title: Emergence of two near-infrared windows for in vivo and intraoperative SERS
  publication-title: Curr Opin Chem Biol
– volume: 55
  start-page: 159
  year: 2006
  end-page: 163
  ident: b0050
  article-title: Simple reagent for the synthesis of oligonucleotides labeled with 3,3,3′,3′-tetramethyl-2,2′-indodicarbocyanine
  publication-title: Russ Chem Bull
– volume: 37
  start-page: 464
  year: 2013
  end-page: 470
  ident: b0060
  article-title: A novel regulation of PSMA and PSA expression by Q640X AR in 22Rv1 and LNCap prostate cancer cells
  publication-title: Cell Biol Int
– volume: 33
  start-page: 472
  year: 2023
  ident: WOS:001043026900001
  article-title: Choice of the optimal synthetic approach for the polypeptide ligands of prostatic specific membrane antigen preparation
  publication-title: MENDELEEV COMMUNICATIONS
  doi: 10.1016/j.mencom.2023.06.010
– volume: 43
  start-page: 7013
  year: 2014
  ident: WOS:000342880000008
  article-title: "Click" reactions: a versatile toolbox for the synthesis of peptide-conjugates
  publication-title: CHEMICAL SOCIETY REVIEWS
  doi: 10.1039/c4cs00139g
– volume: 32
  start-page: 32
  year: 2023
  ident: WOS:000900101500001
  article-title: Optimization of the dipeptide motifs in the PSMA ligands linker structure: synthesis and in vitro evaluation
  publication-title: MEDICINAL CHEMISTRY RESEARCH
  doi: 10.1007/s00044-022-03002-w
– volume: 7
  start-page: 155
  year: 2017
  ident: 001360558600001.11
  article-title: Spectrophotometric determination of pKa and Log P of risperidone
  publication-title: J Appl Pharm Sci
– volume: 37
  start-page: 464
  year: 2013
  ident: WOS:000317895500010
  article-title: A novel regulation of PSMA and PSA expression by Q640X AR in 22Rv1 and LNCaP prostate cancer cells
  publication-title: CELL BIOLOGY INTERNATIONAL
  doi: 10.1002/cbin.10055
– volume: 122
  start-page: 1
  year: 2006
  ident: WOS:000236401800002
  article-title: Dyes and other colorants in microtechnique and biomedical research
  publication-title: COLORATION TECHNOLOGY
  doi: 10.1111/j.1478-4408.2006.00009.x
– volume: 9
  start-page: ARTN 2001327
  year: 2020
  ident: WOS:000573863200001
  article-title: Cyanine Conjugate-Based Biomedical Imaging Probes
  publication-title: ADVANCED HEALTHCARE MATERIALS
  doi: 10.1002/adhm.202001327
– volume: 71
  start-page: 1668
  year: 2011
  ident: WOS:000296261200009
  article-title: PC3 Is a Cell Line Characteristic of Prostatic Small Cell Carcinoma
  publication-title: PROSTATE
  doi: 10.1002/pros.21383
– volume: 64
  start-page: 4532
  year: 2021
  ident: WOS:000644437100014
  article-title: Synthesis and Biological Evaluation of PSMA Ligands with Aromatic Residues and Fluorescent Conjugates Based on Them
  publication-title: JOURNAL OF MEDICINAL CHEMISTRY
  doi: 10.1021/acs.jmedchem.0c01935
– volume: 55
  start-page: 159
  year: 2006
  ident: WOS:000238550300023
  article-title: Simple reagent for the synthesis of oligonucleotides labeled with 3,3,3′,3′-tetramethyl-2,2′-indodicarbocyanine
  publication-title: RUSSIAN CHEMICAL BULLETIN
– volume: 45
  start-page: 95
  year: 2018
  ident: WOS:000441686700013
  article-title: Emergence of two near-infrared windows for in vivo and intraoperative SERS
  publication-title: CURRENT OPINION IN CHEMICAL BIOLOGY
  doi: 10.1016/j.cbpa.2018.03.015
– volume: 11
  start-page: 668
  year: 2015
  ident: WOS:000354083500001
  article-title: Synthesis of carbohydrate-scaffolded thymine glycoconjugates to organize multivalency
  publication-title: BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.3762/bjoc.11.75
– volume: 10
  start-page: ARTN 12613
  year: 2020
  ident: WOS:000556400100003
  article-title: Pathological application of carbocyanine dye-based multicolour imaging of vasculature and associated structures
  publication-title: SCIENTIFIC REPORTS
  doi: 10.1038/s41598-020-69394-0
– volume: 71
  start-page: 1668
  year: 2011
  ident: 10.1016/j.bmcl.2024.130025_b0065
  article-title: PC3 is a cell line characteristic of prostatic small cell carcinoma
  publication-title: Prostate
  doi: 10.1002/pros.21383
– volume: 37
  start-page: 464
  year: 2013
  ident: 10.1016/j.bmcl.2024.130025_b0060
  article-title: A novel regulation of PSMA and PSA expression by Q640X AR in 22Rv1 and LNCap prostate cancer cells
  publication-title: Cell Biol Int
  doi: 10.1002/cbin.10055
– volume: 7
  start-page: 155
  year: 2017
  ident: 10.1016/j.bmcl.2024.130025_b0055
  article-title: Spectrophotometric determination of pKa and Log P of risperidone
  publication-title: J Appl Pharm Sci
– volume: 45
  start-page: 95
  year: 2018
  ident: 10.1016/j.bmcl.2024.130025_b0020
  article-title: Emergence of two near-infrared windows for in vivo and intraoperative SERS
  publication-title: Curr Opin Chem Biol
  doi: 10.1016/j.cbpa.2018.03.015
– volume: 32
  start-page: 32
  year: 2023
  ident: 10.1016/j.bmcl.2024.130025_b0040
  article-title: Optimization of the dipeptide motifs in the PSMA ligands linker structure: synthesis and in vitro evaluation
  publication-title: Med Chem Res
  doi: 10.1007/s00044-022-03002-w
– volume: 64
  start-page: 4532
  year: 2021
  ident: 10.1016/j.bmcl.2024.130025_b0045
  article-title: Synthesis and biological evaluation of PSMA ligands with aromatic residues and fluorescent conjugates based on them
  publication-title: J Med Chem
  doi: 10.1021/acs.jmedchem.0c01935
– volume: 9
  start-page: 1
  year: 2020
  ident: 10.1016/j.bmcl.2024.130025_b0015
  article-title: Cyanine conjugate‐based biomedical imaging probes
  publication-title: Adv Healthc Mater
  doi: 10.1002/adhm.202001327
– volume: 55
  start-page: 159
  year: 2006
  ident: 10.1016/j.bmcl.2024.130025_b0050
  article-title: Simple reagent for the synthesis of oligonucleotides labeled with 3,3,3′,3′-tetramethyl-2,2′-indodicarbocyanine
  publication-title: Russ Chem Bull
  doi: 10.1007/s11172-006-0230-2
– volume: 122
  start-page: 1
  year: 2006
  ident: 10.1016/j.bmcl.2024.130025_b0005
  article-title: Dyes and other colorants in microtechnique and biomedical research
  publication-title: Color Technol
  doi: 10.1111/j.1478-4408.2006.00009.x
– volume: 10
  year: 2020
  ident: 10.1016/j.bmcl.2024.130025_b0010
  article-title: Pathological application of carbocyanine dye-based multicolour imaging of vasculature and associated structures
  publication-title: Sci Rep
  doi: 10.1038/s41598-020-69394-0
– volume: 33
  start-page: 472
  year: 2023
  ident: 10.1016/j.bmcl.2024.130025_b0035
  article-title: Choice of the optimal synthetic approach for the polypeptide ligands of prostatic specific membrane antigen preparation
  publication-title: Mendeleev Commun
  doi: 10.1016/j.mencom.2023.06.010
– volume: 11
  start-page: 668
  year: 2015
  ident: 10.1016/j.bmcl.2024.130025_b0030
  article-title: Synthesis of carbohydrate-scaffolded thymine glycoconjugates to organize multivalency
  publication-title: Beilstein J Org Chem
  doi: 10.3762/bjoc.11.75
– volume: 43
  start-page: 7013
  year: 2014
  ident: 10.1016/j.bmcl.2024.130025_b0025
  article-title: “Click” reactions: a versatile toolbox for the synthesis of peptide-conjugates
  publication-title: Chem Soc Rev
  doi: 10.1039/C4CS00139G
SSID ssj0014044
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Snippet [Display omitted] •An asymmetric carbocyanine for the [3+2] cycloaddition reaction was obtained.•A triazole ring does not affect the photophysical properties...
We report a modified carbocyanine-based asymmetric fluorescent dye, suitable for the azide-alkyne cycloaddition reaction, that possesses promising...
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SubjectTerms Alkynes - chemical synthesis
Alkynes - chemistry
Antigens, Surface - chemistry
Antigens, Surface - metabolism
Asymmetric carbocyanine
Azides - chemistry
Carbocyanines - chemical synthesis
Carbocyanines - chemistry
Chemistry
Chemistry, Medicinal
Chemistry, Organic
Click reaction
Cyanine dyes
Cycloaddition Reaction
Fluorescent Dyes - chemical synthesis
Fluorescent Dyes - chemistry
Glutamate Carboxypeptidase II - antagonists & inhibitors
Glutamate Carboxypeptidase II - metabolism
Humans
Life Sciences & Biomedicine
Ligands
Male
Molecular Structure
Pharmacology & Pharmacy
Photochemistry
Physical Sciences
Prostatic Neoplasms - drug therapy
Science & Technology
Title Pentamethine cyanine dyes with alkynyl group as perspective structure for conjugation with targeting moiety
URI https://dx.doi.org/10.1016/j.bmcl.2024.130025
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https://www.ncbi.nlm.nih.gov/pubmed/39532204
https://www.proquest.com/docview/3128761217
Volume 115
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