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Pregled bibliografske jedinice broj: 628317

C-5 Hydroxyethyl and Hydroxypropyl Acyclonucleosides as Substrates for Thymidine Kinase of Herpes Simplex Virus Type 1 (HSV-1 TK): Syntheses and Biological Evaluations


Meščić, Andrijana; Krištafor, Svjetlana; Novaković, Ivana; Osmanović, Amar; Müller, Ursina; Završnik, Davorka; Ametamey, Simon M.; Scapozza, Leonardo; Raić-Malić, Silvana
C-5 Hydroxyethyl and Hydroxypropyl Acyclonucleosides as Substrates for Thymidine Kinase of Herpes Simplex Virus Type 1 (HSV-1 TK): Syntheses and Biological Evaluations // Molecules, 18 (2013), 5; 5104-5124 doi:10.3390/molecules18055104 (međunarodna recenzija, članak, znanstveni)


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Naslov
C-5 Hydroxyethyl and Hydroxypropyl Acyclonucleosides as Substrates for Thymidine Kinase of Herpes Simplex Virus Type 1 (HSV-1 TK): Syntheses and Biological Evaluations

Autori
Meščić, Andrijana ; Krištafor, Svjetlana ; Novaković, Ivana ; Osmanović, Amar ; Müller, Ursina ; Završnik, Davorka ; Ametamey, Simon M. ; Scapozza, Leonardo ; Raić-Malić, Silvana

Izvornik
Molecules (1420-3049) 18 (2013), 5; 5104-5124

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
acyclic nucleoside analogues ; 5-substituted pyrimidines ; herpes simplex virus type 1 thymidine kinase (HSV-1 TK) ; positron emission tomography (PET)

Sažetak
The efficient syntheses of 5-(2-hydroxyethyl)- and 5-(3-hydroxypropyl)-substituted pyrimidine derivatives bearing 2, 3-dihydroxypropyl, acyclovir-, ganciclovir- and penciclovir-like side chains are reported. A synthetic approach that included the alkylation of an N-anionic-5- substituted pyrimidine intermediate (method A) provided the target acyclonucleosides in significantly higher overall yields in comparison to those obtained by method B using sylilation reaction. The phosphorylation assays of novel compounds as potential substrates for thymidine kinase of herpes simplex virus type 1 (HSV-1 TK) showed that solely pyrimidine 5-substituted acyclonucleosides with a penciclovir-like side chain acted as a fraudulent substrates of HSV-1 TK. Moreover, the uracil derivative with penciclovir- like side chain with less bulky 2-hydroxyethyl substituent at C-5 proved to be a better substrate than the corresponding one with a 3-hydroxypropyl substituent. Therefore, this acyclonucleoside was selected as a lead compound for the development of a positron emission tomography HSV-1 TK activity imaging agent.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekti:
125-0982464-2925 - Razvoj i primjena novih molekula u pozitron-emisijskoj tomografiji (PET) (Raić-Malić, Silvana, MZOS ) ( POIROT)

Ustanove:
Fakultet kemijskog inženjerstva i tehnologije, Zagreb

Poveznice na cjeloviti tekst rada:

doi doi.org www.mdpi.com

Citiraj ovu publikaciju:

Meščić, Andrijana; Krištafor, Svjetlana; Novaković, Ivana; Osmanović, Amar; Müller, Ursina; Završnik, Davorka; Ametamey, Simon M.; Scapozza, Leonardo; Raić-Malić, Silvana
C-5 Hydroxyethyl and Hydroxypropyl Acyclonucleosides as Substrates for Thymidine Kinase of Herpes Simplex Virus Type 1 (HSV-1 TK): Syntheses and Biological Evaluations // Molecules, 18 (2013), 5; 5104-5124 doi:10.3390/molecules18055104 (međunarodna recenzija, članak, znanstveni)
Meščić, A., Krištafor, S., Novaković, I., Osmanović, A., Müller, U., Završnik, D., Ametamey, S., Scapozza, L. & Raić-Malić, S. (2013) C-5 Hydroxyethyl and Hydroxypropyl Acyclonucleosides as Substrates for Thymidine Kinase of Herpes Simplex Virus Type 1 (HSV-1 TK): Syntheses and Biological Evaluations. Molecules, 18 (5), 5104-5124 doi:10.3390/molecules18055104.
@article{article, year = {2013}, pages = {5104-5124}, DOI = {10.3390/molecules18055104}, keywords = {acyclic nucleoside analogues, 5-substituted pyrimidines, herpes simplex virus type 1 thymidine kinase (HSV-1 TK), positron emission tomography (PET)}, journal = {Molecules}, doi = {10.3390/molecules18055104}, volume = {18}, number = {5}, issn = {1420-3049}, title = {C-5 Hydroxyethyl and Hydroxypropyl Acyclonucleosides as Substrates for Thymidine Kinase of Herpes Simplex Virus Type 1 (HSV-1 TK): Syntheses and Biological Evaluations}, keyword = {acyclic nucleoside analogues, 5-substituted pyrimidines, herpes simplex virus type 1 thymidine kinase (HSV-1 TK), positron emission tomography (PET)} }
@article{article, year = {2013}, pages = {5104-5124}, DOI = {10.3390/molecules18055104}, keywords = {acyclic nucleoside analogues, 5-substituted pyrimidines, herpes simplex virus type 1 thymidine kinase (HSV-1 TK), positron emission tomography (PET)}, journal = {Molecules}, doi = {10.3390/molecules18055104}, volume = {18}, number = {5}, issn = {1420-3049}, title = {C-5 Hydroxyethyl and Hydroxypropyl Acyclonucleosides as Substrates for Thymidine Kinase of Herpes Simplex Virus Type 1 (HSV-1 TK): Syntheses and Biological Evaluations}, keyword = {acyclic nucleoside analogues, 5-substituted pyrimidines, herpes simplex virus type 1 thymidine kinase (HSV-1 TK), positron emission tomography (PET)} }

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus
  • MEDLINE


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