Synthesis and initial in vitro evaluation of PSMA-targeting ligands with a modified aromatic moiety at the lysine ε-nitrogen atom

[Display omitted] We report an improved series of ligands targeting prostate specific membrane antigen (PSMA). The new compounds were designed by the introduction of changes in the structure of the aromatic fragment at ε-nitrogen atom of lysine that resulted in improved biological parameters. Some o...

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Published inBioorganic & medicinal chemistry letters Vol. 71; pp. 128840 - 128846
Main Authors Zyk, Nikolai Y., Ber, Anton P., Nimenko, Ekaterina A., Shafikov, Radik R., Evteev, Sergei A., Petrov, Stanislav A., Uspenskaya, Anastasia A., Dashkova, Natalia S., Ivanenkov, Yan A., Skvortsov, Dmitry A., Beloglazkina, Elena K., Majouga, Alexander G., Machulkin, Aleksei E.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.09.2022
Elsevier
Subjects
Chemistry
Chemistry, Medicinal
Chemistry, Organic
Drug delivery
Life Sciences & Biomedicine
Ligands
Pharmacology & Pharmacy
Physical Sciences
Prostate cancer
Prostate-specific membrane antigen
Science & Technology
Sulfo-Cy5
DUPA
PyBOP
DIPEA
Drug delivery
DCL
TFA
DCM
Prostate-specific membrane antigen
2-PMPA
HOBt
Ligands
HBTU
GCPII
DMF
Prostate cancer
NAAG
Sulfo-Cy5
2-MPPA
TIPS
DESIGN
GLUTAMATE CARBOXYPEPTIDASE-II
INHIBITORS
MEMBRANE ANTIGEN PSMA
PRECLINICAL EVALUATION
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Abstract [Display omitted] We report an improved series of ligands targeting prostate specific membrane antigen (PSMA). The new compounds were designed by the introduction of changes in the structure of the aromatic fragment at ε-nitrogen atom of lysine that resulted in improved biological parameters. Some of them demonstrated high selectivity and nanomolar IC50 values. We synthesized and tested two conjugates with a fluorescent label Sulfo-Cy5 as an example of the use of the obtained PSMA inhibitors as a basis for the creation of diagnostic preparations.
AbstractList We report an improved series of ligands targeting prostate specific membrane antigen (PSMA). The new compounds were designed by the introduction of changes in the structure of the aromatic fragment at epsilon-nitrogen atom of lysine that resulted in improved biological parameters. Some of them demonstrated high selectivity and nanomolar IC50 values. We synthesized and tested two conjugates with a fluorescent label Sulfo-Cy5 as an example of the use of the obtained PSMA inhibitors as a basis for the creation of diagnostic preparations.
We report an improved series of ligands targeting prostate specific membrane antigen (PSMA). The new compounds were designed by the introduction of changes in the structure of the aromatic fragment at ε-nitrogen atom of lysine that resulted in improved biological parameters. Some of them demonstrated high selectivity and nanomolar IC values. We synthesized and tested two conjugates with a fluorescent label Sulfo-Cy5 as an example of the use of the obtained PSMA inhibitors as a basis for the creation of diagnostic preparations.
We report an improved series of ligands targeting prostate specific membrane antigen (PSMA). The new compounds were designed by the introduction of changes in the structure of the aromatic fragment at ε-nitrogen atom of lysine that resulted in improved biological parameters. Some of them demonstrated high selectivity and nanomolar IC50 values. We synthesized and tested two conjugates with a fluorescent label Sulfo-Cy5 as an example of the use of the obtained PSMA inhibitors as a basis for the creation of diagnostic preparations.We report an improved series of ligands targeting prostate specific membrane antigen (PSMA). The new compounds were designed by the introduction of changes in the structure of the aromatic fragment at ε-nitrogen atom of lysine that resulted in improved biological parameters. Some of them demonstrated high selectivity and nanomolar IC50 values. We synthesized and tested two conjugates with a fluorescent label Sulfo-Cy5 as an example of the use of the obtained PSMA inhibitors as a basis for the creation of diagnostic preparations.
[Display omitted] We report an improved series of ligands targeting prostate specific membrane antigen (PSMA). The new compounds were designed by the introduction of changes in the structure of the aromatic fragment at ε-nitrogen atom of lysine that resulted in improved biological parameters. Some of them demonstrated high selectivity and nanomolar IC50 values. We synthesized and tested two conjugates with a fluorescent label Sulfo-Cy5 as an example of the use of the obtained PSMA inhibitors as a basis for the creation of diagnostic preparations.
ArticleNumber 128840
Author Machulkin, Aleksei E.
Skvortsov, Dmitry A.
Ber, Anton P.
Evteev, Sergei A.
Majouga, Alexander G.
Nimenko, Ekaterina A.
Ivanenkov, Yan A.
Shafikov, Radik R.
Dashkova, Natalia S.
Zyk, Nikolai Y.
Petrov, Stanislav A.
Uspenskaya, Anastasia A.
Beloglazkina, Elena K.
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  givenname: Stanislav A.
  orcidid: 0000-0002-6000-6100
  surname: Petrov
  fullname: Petrov, Stanislav A.
  organization: Lomonosov Moscow State University, Chemistry Dept., Leninskie Gory, Building 1/3, GSP-1, Moscow 119991, Russian Federation
– sequence: 7
  givenname: Anastasia A.
  surname: Uspenskaya
  fullname: Uspenskaya, Anastasia A.
  organization: Lomonosov Moscow State University, Chemistry Dept., Leninskie Gory, Building 1/3, GSP-1, Moscow 119991, Russian Federation
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  givenname: Natalia S.
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  organization: Lomonosov Moscow State University, Chemistry Dept., Leninskie Gory, Building 1/3, GSP-1, Moscow 119991, Russian Federation
– sequence: 9
  givenname: Yan A.
  surname: Ivanenkov
  fullname: Ivanenkov, Yan A.
  organization: Lomonosov Moscow State University, Chemistry Dept., Leninskie Gory, Building 1/3, GSP-1, Moscow 119991, Russian Federation
– sequence: 10
  givenname: Dmitry A.
  surname: Skvortsov
  fullname: Skvortsov, Dmitry A.
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  givenname: Elena K.
  surname: Beloglazkina
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  givenname: Alexander G.
  surname: Majouga
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  givenname: Aleksei E.
  orcidid: 0000-0001-7975-0346
  surname: Machulkin
  fullname: Machulkin, Aleksei E.
  organization: Lomonosov Moscow State University, Chemistry Dept., Leninskie Gory, Building 1/3, GSP-1, Moscow 119991, Russian Federation
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Keywords DUPA
PyBOP
DIPEA
Drug delivery
DCL
TFA
DCM
Prostate-specific membrane antigen
2-PMPA
HOBt
Ligands
HBTU
GCPII
DMF
Prostate cancer
NAAG
Sulfo-Cy5
2-MPPA
TIPS
DESIGN
GLUTAMATE CARBOXYPEPTIDASE-II
INHIBITORS
MEMBRANE ANTIGEN PSMA
PRECLINICAL EVALUATION
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Snippet [Display omitted] We report an improved series of ligands targeting prostate specific membrane antigen (PSMA). The new compounds were designed by the...
We report an improved series of ligands targeting prostate specific membrane antigen (PSMA). The new compounds were designed by the introduction of changes in...
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SubjectTerms Chemistry
Chemistry, Medicinal
Chemistry, Organic
Drug delivery
Life Sciences & Biomedicine
Ligands
Pharmacology & Pharmacy
Physical Sciences
Prostate cancer
Prostate-specific membrane antigen
Science & Technology
Sulfo-Cy5
Title Synthesis and initial in vitro evaluation of PSMA-targeting ligands with a modified aromatic moiety at the lysine ε-nitrogen atom
URI https://dx.doi.org/10.1016/j.bmcl.2022.128840
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000816032200005
https://www.ncbi.nlm.nih.gov/pubmed/35661685
https://www.proquest.com/docview/2673593046
Volume 71
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