Keywords
1
2
3-triazoles
carboxamides
conjugates
CuAAC click reaction
cyanine dyes
peptide synthesis
photochemistry
prostate-specific membrane antigen.
Abstract
Fluorescent conjugates of carbocyanine dyes with a ligand selective to prostate-specific membrane antigen were accessed by either peptide synthesis or CuAAC methodology, with the latter being more promising. The introduction of a propargylamino moiety at the meso-position of the polymethine chain of the fluorophores afforded the alkyne counterparts for the CuAAC reaction toward the ligand bearing azido group. The photochemical studies showed that the quantum yields of the obtained conjugates exceeded those for the unmodified fluorophores by more than 20 times.
Funders
Russian Science Foundation
23-23-00297
References
.
Doroshenko I.A., Aminulla K.G., Azev V.N., Kulinich T.M., Vasilichin V.A., Shtil A.A., Podrugina T.A.
Mendeleev Communications,
2021
.
Machulkin A.E., Shafikov R.R., Uspenskaya A.A., Petrov S.A., Ber A.P., Skvortsov D.A., Nimenko E.A., Zyk N.U., Smirnova G.B., Pokrovsky V.S., Abakumov M.A., Saltykova I.V., Akhmirov R.T., Garanina A.S., Polshakov V.I., et. al.
Journal of Medicinal Chemistry,
2021
.
Konnert L., Lamaty F., Martinez J., Colacino E.
Chemical Reviews,
2017
.
Kularatne S.A., Zhou Z., Yang J., Post C.B., Low P.S.
Molecular Pharmaceutics,
2009
.
Lane L.A., Xue R., Nie S.
Current Opinion in Chemical Biology,
2018
.
Kele P., Li X., Link M., Nagy K., Herner A., Lőrincz K., Béni S., Wolfbeis O.S.
Organic and Biomolecular Chemistry,
2009
.
Ornelas C., Lodescar R., Durandin A., Canary J.W., Pennell R., Liebes L.F., Weck M.
Chemistry - A European Journal,
2011
.
Elchinger P., Faugeras P., Boëns B., Brouillette F., Montplaisir D., Zerrouki R., Lucas R.
Polymers,
2011
.
Nebra N., García-Álvarez J.
Molecules,
2020
.
Manne S.R., Sharma A., Sazonovas A., El-Faham A., de la Torre B.G., Albericio F.
ACS Omega,
2022
.
Chen H., Dong B., Tang Y., Lin W.
Chemistry - A European Journal,
2015
.
Uspenskaya A.A., Nimenko E.A., Shafikov R.R., Zyk N.Y., Evteev S.A., Dashkova N.S., Ivanenkov Y.A., Majouga A.G., Skvortsov D.A., Garanina A.S., Beloglazkina E.K., Machulkin A.E.
Medicinal Chemistry Research,
2022
.
.
Thomas C.N., Alfahad N., Capewell N., Cowley J., Hickman E., Fernandez A., Harrison N., Qureshi O.S., Bennett N., Barnes N.M., Dick A.D., Chu C.J., Liu X., Denniston A.K., Vendrell M., et. al.
Biosensors and Bioelectronics,
2022
.
Gong L., Zhao H., Liu Y., Wu H., Liu C., Chang S., Chen L., Jin M., Wang Q., Gao Z., Huang W.
Acta Pharmaceutica Sinica B,
2023
.
Zyk N.Y., Petrov S.A., Zavertkina M.V., Uspenskaya A.A., Krasnikov P.A., Dashkova N.S., Beloglazkina E.K., Majouga A.G., Zyk N.V., Machulkin A.E.
Mendeleev Communications,
2023
.
Yu X., Wu Y., Tang W., Duan X.
The Analyst,
2023
.
Machulkin A.E., Petrov S.A., Bodenko V., Larkina M.S., Plotnikov E., Yuldasheva F., Tretyakova M., Bezverkhniaia E., Zyk N.Y., Stasyuk E., Zelchan R., Majouga A.G., Tolmachev V., Orlova A., Beloglazkina E.K., et. al.
ACS Pharmacology & Translational Science,
2024