Synthesis and characterisation of novel mutual ester prodrug models of acyclovir
Background and Objective: Ocular herpes is a recurrent viral infection caused by the herpes simplex virus-1. Herpes simplex virus type one HSV-1 is one of the most common ocular viruses causing subsequent inflammatory responses and corneal blindness worldwide. This study aimed to synthesize a series...
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| Format: | Article |
| Language: | English |
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Hawler Medical University
2019-08-01
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| Series: | Zanco Journal of Medical Sciences |
| Subjects: | |
| Online Access: | https://zjms.hmu.edu.krd/index.php/zjms/article/view/679/589 |
| _version_ | 1818139047707541504 |
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| author | Dana Ameen Sazan Jameel |
| author_facet | Dana Ameen Sazan Jameel |
| author_sort | Dana Ameen |
| collection | DOAJ |
| description | Background and Objective: Ocular herpes is a recurrent viral infection caused by the herpes simplex virus-1. Herpes simplex virus type one HSV-1 is one of the most common ocular viruses causing subsequent inflammatory responses and corneal blindness worldwide. This study aimed to synthesize a series of novel mutual ester prodrug models to treat viral infection and subsequent inflammation at corneal tissue.
Various formulation strategies have been utilized to improve bioavailability by increasing ocular contact time and improving drug permeation. Chemical approaches, such as prodrug, directed to enhance the ocular bioavailability by improving physicochemical properties of the drug molecule, with the goal of improving drug permeation across cornea.
Methods: Steglich esterification method was to design and synthesis a library of novel mutual prodrugs to increase the bioavailability of acyclovir, owing to enhance the lipophilicity compared with acyclovir. In this study a number of non-steroidal anti-inflammatory drugs (NSAIDs) have been conjugated to acyclovir to improve corneal permeation through enhancing lipophilicity and reduce subsequent inflammation.
Results: The synthesized compounds were characterized through FTIR, 1H-,13C –NMR and Mass spectral data. The partition coefficient (logP) of prodrugs were calculated and showed an increment in lipophilicity and permeability in comparison with acyclovir.
Conclusion: The strategy applied to design the novel compound hypothesized to be a novel mutual prodrug, and it may provide a higher absorption than hydrophilic parent (acyclovir) drug with concurrent anti-inflammatory activity. |
| first_indexed | 2024-12-11T10:21:53Z |
| format | Article |
| id | doaj.art-32990c5ac21e4490acff24bebc48b433 |
| institution | Directory Open Access Journal |
| issn | 1995-5588 1995-5596 |
| language | English |
| last_indexed | 2024-12-11T10:21:53Z |
| publishDate | 2019-08-01 |
| publisher | Hawler Medical University |
| record_format | Article |
| series | Zanco Journal of Medical Sciences |
| spelling | doaj.art-32990c5ac21e4490acff24bebc48b4332022-12-22T01:11:23ZengHawler Medical UniversityZanco Journal of Medical Sciences1995-55881995-55962019-08-0123222623210.15218/zjms.2019.028Synthesis and characterisation of novel mutual ester prodrug models of acyclovirDana Ameen0Sazan Jameel1Hawler Medical UniversityHawler Medical UniversityBackground and Objective: Ocular herpes is a recurrent viral infection caused by the herpes simplex virus-1. Herpes simplex virus type one HSV-1 is one of the most common ocular viruses causing subsequent inflammatory responses and corneal blindness worldwide. This study aimed to synthesize a series of novel mutual ester prodrug models to treat viral infection and subsequent inflammation at corneal tissue. Various formulation strategies have been utilized to improve bioavailability by increasing ocular contact time and improving drug permeation. Chemical approaches, such as prodrug, directed to enhance the ocular bioavailability by improving physicochemical properties of the drug molecule, with the goal of improving drug permeation across cornea. Methods: Steglich esterification method was to design and synthesis a library of novel mutual prodrugs to increase the bioavailability of acyclovir, owing to enhance the lipophilicity compared with acyclovir. In this study a number of non-steroidal anti-inflammatory drugs (NSAIDs) have been conjugated to acyclovir to improve corneal permeation through enhancing lipophilicity and reduce subsequent inflammation. Results: The synthesized compounds were characterized through FTIR, 1H-,13C –NMR and Mass spectral data. The partition coefficient (logP) of prodrugs were calculated and showed an increment in lipophilicity and permeability in comparison with acyclovir. Conclusion: The strategy applied to design the novel compound hypothesized to be a novel mutual prodrug, and it may provide a higher absorption than hydrophilic parent (acyclovir) drug with concurrent anti-inflammatory activity.https://zjms.hmu.edu.krd/index.php/zjms/article/view/679/589ProdrugNovel strategyAcyclovirHerpes simplexOcular deliveryNSAIDs |
| spellingShingle | Dana Ameen Sazan Jameel Synthesis and characterisation of novel mutual ester prodrug models of acyclovir Zanco Journal of Medical Sciences Prodrug Novel strategy Acyclovir Herpes simplex Ocular delivery NSAIDs |
| title | Synthesis and characterisation of novel mutual ester prodrug models of acyclovir |
| title_full | Synthesis and characterisation of novel mutual ester prodrug models of acyclovir |
| title_fullStr | Synthesis and characterisation of novel mutual ester prodrug models of acyclovir |
| title_full_unstemmed | Synthesis and characterisation of novel mutual ester prodrug models of acyclovir |
| title_short | Synthesis and characterisation of novel mutual ester prodrug models of acyclovir |
| title_sort | synthesis and characterisation of novel mutual ester prodrug models of acyclovir |
| topic | Prodrug Novel strategy Acyclovir Herpes simplex Ocular delivery NSAIDs |
| url | https://zjms.hmu.edu.krd/index.php/zjms/article/view/679/589 |
| work_keys_str_mv | AT danaameen synthesisandcharacterisationofnovelmutualesterprodrugmodelsofacyclovir AT sazanjameel synthesisandcharacterisationofnovelmutualesterprodrugmodelsofacyclovir |