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Elucidating the binding affinity of meso porphyrin derivatives with Bcl-2 through synthesis and molecular docking analysis

Reversing multi-drug resistance in a clinical setting remains a formidable issue to date. Porphyrin has high efficiency to conjugate with chemotherapy drugs and effectively deliver within the nucleus of cancer cells which helps in lowering side effect to normal cells. As compared to naturally occurr...

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Main Authors: Ramaiyah, Yasothaa, Bakar, Mohd. Bakri, Abu Bakar, Muntaz
Format: Article
Language:English
Published: Penerbit UKM 2023
Subjects:
QD Chemistry
Online Access:http://eprints.utm.my/106728/1/MohdBakriBakar2023_ElucidatingtheBindingAffinityofMesoPorphyrin.pdf
http://eprints.utm.my/106728/
http://dx.doi.org/10.17576/jsm-2023-5211-22
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spelling my.utm.1067282024-07-28T06:09:27Z http://eprints.utm.my/106728/ Elucidating the binding affinity of meso porphyrin derivatives with Bcl-2 through synthesis and molecular docking analysis Ramaiyah, Yasothaa Bakar, Mohd. Bakri Abu Bakar, Muntaz QD Chemistry Reversing multi-drug resistance in a clinical setting remains a formidable issue to date. Porphyrin has high efficiency to conjugate with chemotherapy drugs and effectively deliver within the nucleus of cancer cells which helps in lowering side effect to normal cells. As compared to naturally occurring beta-substituted porphyrins, synthetic meso-substituted porphyrins have numerous benefits. An extensive variety of substituents have been developed with porphyrins. There are eight new porphyrin derivatives synthesised in this research compounds 14-21 which differ from one size to another using Sonogashira and Suzuki coupling techniques. Sonogashira coupling method undergoes a reaction between alkyne terminal sp hybridized carbon and vinyl halide’s sp2 carbon in the presence of a Palladium catalyst. Furthermore, Suzuki coupling method has been an effective method in conjugation of aryl halides and borylated porphyrins. The synthesized new compounds were characterized by ultra-violet spectroscopy (UV-Vis), high resolution mass spectrometer (HRMS) and nuclear magnetic resonance (NMR) to confirm successful formation of all new compounds. The docking analysis was performed for compound 14-21. Compounds 16 and 18 showed the greater binding mode at the Bcl-2 protein pocket regards free or metal substituted porphyrin with longer linker chain and less bulky compared to compounds 17 and 19. This study could discover the structure of porphyrin that affects accumulation in cancer cells that potentially transmissible to target tumour. Penerbit UKM 2023-11 Article PeerReviewed application/pdf en http://eprints.utm.my/106728/1/MohdBakriBakar2023_ElucidatingtheBindingAffinityofMesoPorphyrin.pdf Ramaiyah, Yasothaa and Bakar, Mohd. Bakri and Abu Bakar, Muntaz (2023) Elucidating the binding affinity of meso porphyrin derivatives with Bcl-2 through synthesis and molecular docking analysis. Sains Malaysiana, 52 (11). pp. 3325-3342. ISSN 0126-6039 http://dx.doi.org/10.17576/jsm-2023-5211-22 DOI:10.17576/jsm-2023-5211-22
institution Universiti Teknologi Malaysia
building UTM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Teknologi Malaysia
content_source UTM Institutional Repository
url_provider http://eprints.utm.my/
language English
topic QD Chemistry
spellingShingle QD Chemistry
Ramaiyah, Yasothaa
Bakar, Mohd. Bakri
Abu Bakar, Muntaz
Elucidating the binding affinity of meso porphyrin derivatives with Bcl-2 through synthesis and molecular docking analysis
description Reversing multi-drug resistance in a clinical setting remains a formidable issue to date. Porphyrin has high efficiency to conjugate with chemotherapy drugs and effectively deliver within the nucleus of cancer cells which helps in lowering side effect to normal cells. As compared to naturally occurring beta-substituted porphyrins, synthetic meso-substituted porphyrins have numerous benefits. An extensive variety of substituents have been developed with porphyrins. There are eight new porphyrin derivatives synthesised in this research compounds 14-21 which differ from one size to another using Sonogashira and Suzuki coupling techniques. Sonogashira coupling method undergoes a reaction between alkyne terminal sp hybridized carbon and vinyl halide’s sp2 carbon in the presence of a Palladium catalyst. Furthermore, Suzuki coupling method has been an effective method in conjugation of aryl halides and borylated porphyrins. The synthesized new compounds were characterized by ultra-violet spectroscopy (UV-Vis), high resolution mass spectrometer (HRMS) and nuclear magnetic resonance (NMR) to confirm successful formation of all new compounds. The docking analysis was performed for compound 14-21. Compounds 16 and 18 showed the greater binding mode at the Bcl-2 protein pocket regards free or metal substituted porphyrin with longer linker chain and less bulky compared to compounds 17 and 19. This study could discover the structure of porphyrin that affects accumulation in cancer cells that potentially transmissible to target tumour.
format Article
author Ramaiyah, Yasothaa
Bakar, Mohd. Bakri
Abu Bakar, Muntaz
author_facet Ramaiyah, Yasothaa
Bakar, Mohd. Bakri
Abu Bakar, Muntaz
author_sort Ramaiyah, Yasothaa
title Elucidating the binding affinity of meso porphyrin derivatives with Bcl-2 through synthesis and molecular docking analysis
title_short Elucidating the binding affinity of meso porphyrin derivatives with Bcl-2 through synthesis and molecular docking analysis
title_full Elucidating the binding affinity of meso porphyrin derivatives with Bcl-2 through synthesis and molecular docking analysis
title_fullStr Elucidating the binding affinity of meso porphyrin derivatives with Bcl-2 through synthesis and molecular docking analysis
title_full_unstemmed Elucidating the binding affinity of meso porphyrin derivatives with Bcl-2 through synthesis and molecular docking analysis
title_sort elucidating the binding affinity of meso porphyrin derivatives with bcl-2 through synthesis and molecular docking analysis
publisher Penerbit UKM
publishDate 2023
url http://eprints.utm.my/106728/1/MohdBakriBakar2023_ElucidatingtheBindingAffinityofMesoPorphyrin.pdf
http://eprints.utm.my/106728/
http://dx.doi.org/10.17576/jsm-2023-5211-22
_version_ 1805880859838906368
score 13.211869

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