5-(Sulfamoyl)thien-2-yl 1,3-oxazole inhibitors of carbonic anhydrase II with hydrophilic periphery
Hydrophilic derivatives of an earlier described series of carbonic anhydrase inhibitors have been designed, prepared and profiled against a panel of carbonic anhydrase isoforms, including the glaucoma-related hCA II. For all hydrophilic derivatives, computational prediction of intraocular permeabili...
Saved in:
| Main Authors: | , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Taylor & Francis Group
2022-12-01
|
| Series: | Journal of Enzyme Inhibition and Medicinal Chemistry |
| Subjects: | |
| Online Access: | https://www.tandfonline.com/doi/10.1080/14756366.2022.2056733 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1849421477795856384 |
|---|---|
| author | Stanislav Kalinin Alexander Kovalenko Annika Valtari Alessio Nocentini Maxim Gureev Arto Urtti Mikhail Korsakov Claudiu T. Supuran Mikhail Krasavin |
| author_facet | Stanislav Kalinin Alexander Kovalenko Annika Valtari Alessio Nocentini Maxim Gureev Arto Urtti Mikhail Korsakov Claudiu T. Supuran Mikhail Krasavin |
| author_sort | Stanislav Kalinin |
| collection | DOAJ |
| description | Hydrophilic derivatives of an earlier described series of carbonic anhydrase inhibitors have been designed, prepared and profiled against a panel of carbonic anhydrase isoforms, including the glaucoma-related hCA II. For all hydrophilic derivatives, computational prediction of intraocular permeability routes showed the predominance of conjunctival rather than corneal absorption. The potentially reactive primary or secondary amine periphery of these compounds makes them suitable candidates for bioconjugation to polymeric drug carriers. As was shown previously, the most active hCA II inhibitor is efficacious in alleviating intraocular pressure in normotensive rabbits with efficacy matching that of dorzolamide. |
| format | Article |
| id | doaj-art-4bd8215628fd4666b45c04fefe090d2d |
| institution | Kabale University |
| issn | 1475-6366 1475-6374 |
| language | English |
| publishDate | 2022-12-01 |
| publisher | Taylor & Francis Group |
| record_format | Article |
| series | Journal of Enzyme Inhibition and Medicinal Chemistry |
| spelling | doaj-art-4bd8215628fd4666b45c04fefe090d2d2025-08-20T03:31:27ZengTaylor & Francis GroupJournal of Enzyme Inhibition and Medicinal Chemistry1475-63661475-63742022-12-013711005101110.1080/14756366.2022.20567335-(Sulfamoyl)thien-2-yl 1,3-oxazole inhibitors of carbonic anhydrase II with hydrophilic peripheryStanislav Kalinin0Alexander Kovalenko1Annika Valtari2Alessio Nocentini3Maxim Gureev4Arto Urtti5Mikhail Korsakov6Claudiu T. Supuran7Mikhail Krasavin8Institute of Chemistry, Saint Petersburg State University, St. Petersburg, Russian FederationInstitute of Chemistry, Saint Petersburg State University, St. Petersburg, Russian FederationSchool of Pharmacy, University of Eastern Finland, Kuopio, FinlandDepartment of Neurofarba, Universita degli Studi di Firenze, Florence, ItalyDigital Biodesign and Personalized Healthcare Research Center, Sechenov First Moscow State Medical University, Moscow, Russian FederationInstitute of Chemistry, Saint Petersburg State University, St. Petersburg, Russian FederationPharmaceutical Technology Transfer Center, Ushinsky Yaroslavl State Pedagogical University, Yaroslavl, Russian FederationDepartment of Neurofarba, Universita degli Studi di Firenze, Florence, ItalyInstitute of Chemistry, Saint Petersburg State University, St. Petersburg, Russian FederationHydrophilic derivatives of an earlier described series of carbonic anhydrase inhibitors have been designed, prepared and profiled against a panel of carbonic anhydrase isoforms, including the glaucoma-related hCA II. For all hydrophilic derivatives, computational prediction of intraocular permeability routes showed the predominance of conjunctival rather than corneal absorption. The potentially reactive primary or secondary amine periphery of these compounds makes them suitable candidates for bioconjugation to polymeric drug carriers. As was shown previously, the most active hCA II inhibitor is efficacious in alleviating intraocular pressure in normotensive rabbits with efficacy matching that of dorzolamide.https://www.tandfonline.com/doi/10.1080/14756366.2022.2056733Glaucomaintraocular pressurehydrophilicitybioconjugationintraocular delivery |
| spellingShingle | Stanislav Kalinin Alexander Kovalenko Annika Valtari Alessio Nocentini Maxim Gureev Arto Urtti Mikhail Korsakov Claudiu T. Supuran Mikhail Krasavin 5-(Sulfamoyl)thien-2-yl 1,3-oxazole inhibitors of carbonic anhydrase II with hydrophilic periphery Journal of Enzyme Inhibition and Medicinal Chemistry Glaucoma intraocular pressure hydrophilicity bioconjugation intraocular delivery |
| title | 5-(Sulfamoyl)thien-2-yl 1,3-oxazole inhibitors of carbonic anhydrase II with hydrophilic periphery |
| title_full | 5-(Sulfamoyl)thien-2-yl 1,3-oxazole inhibitors of carbonic anhydrase II with hydrophilic periphery |
| title_fullStr | 5-(Sulfamoyl)thien-2-yl 1,3-oxazole inhibitors of carbonic anhydrase II with hydrophilic periphery |
| title_full_unstemmed | 5-(Sulfamoyl)thien-2-yl 1,3-oxazole inhibitors of carbonic anhydrase II with hydrophilic periphery |
| title_short | 5-(Sulfamoyl)thien-2-yl 1,3-oxazole inhibitors of carbonic anhydrase II with hydrophilic periphery |
| title_sort | 5 sulfamoyl thien 2 yl 1 3 oxazole inhibitors of carbonic anhydrase ii with hydrophilic periphery |
| topic | Glaucoma intraocular pressure hydrophilicity bioconjugation intraocular delivery |
| url | https://www.tandfonline.com/doi/10.1080/14756366.2022.2056733 |
| work_keys_str_mv | AT stanislavkalinin 5sulfamoylthien2yl13oxazoleinhibitorsofcarbonicanhydraseiiwithhydrophilicperiphery AT alexanderkovalenko 5sulfamoylthien2yl13oxazoleinhibitorsofcarbonicanhydraseiiwithhydrophilicperiphery AT annikavaltari 5sulfamoylthien2yl13oxazoleinhibitorsofcarbonicanhydraseiiwithhydrophilicperiphery AT alessionocentini 5sulfamoylthien2yl13oxazoleinhibitorsofcarbonicanhydraseiiwithhydrophilicperiphery AT maximgureev 5sulfamoylthien2yl13oxazoleinhibitorsofcarbonicanhydraseiiwithhydrophilicperiphery AT artourtti 5sulfamoylthien2yl13oxazoleinhibitorsofcarbonicanhydraseiiwithhydrophilicperiphery AT mikhailkorsakov 5sulfamoylthien2yl13oxazoleinhibitorsofcarbonicanhydraseiiwithhydrophilicperiphery AT claudiutsupuran 5sulfamoylthien2yl13oxazoleinhibitorsofcarbonicanhydraseiiwithhydrophilicperiphery AT mikhailkrasavin 5sulfamoylthien2yl13oxazoleinhibitorsofcarbonicanhydraseiiwithhydrophilicperiphery |