Araştırma Makalesi
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Computational Insights in Drug-likeness and ADMT Properties of -dienes Resemble of Geranial

Yıl 2023, Cilt: 13 Sayı: 2, 174 - 192, 31.12.2023
https://doi.org/10.54370/ordubtd.1308195

Öz

This research aims to analyze the drug development potential of geranial, a naturally occurring compound known for its medicinal properties, through in-depth ADMT (Absorption, Distribution, Metabolism, and Toxicity) profiling and Density Functional Theory (DFT) calculations, at B3LYP/6-311G** level and basis set. The optimized and confirmed structures of the data set were used for further computations. The FMO "Frontier Molecular Orbital" energies and MEP "Molecular Electrostatic Potential" were considered to elucidate the possible reactivity features and regions of the molecules, respectively. Concurrently, DFT calculations helped to elucidate the compound's electronic properties and structural stability, further affirming its suitability for drug development. These findings emphasize the potential of compounds structurally related to geranial in the pharmaceutical field and underline the necessity of similar evaluations for novel drug candidates, ensuring safety and efficacy while mitigating potential risks to human health and the environment.

Kaynakça

  • Adorjan, B., & Buchbauer, G. (2010). Biological properties of essential oils: An updated review. Flavour and Fragrance Journal. 25(6), 407-426. 4https://doi.org/10.1002/ffj.2024
  • Ali, J., Camilleri, P., Brown, M. B., Hutt, A. J., & Kirton, S. B. (2012). In silico prediction of aqueous solubility using simple QSPR models: The importance of phenol and phenol-like moieties. Journal of Chemical Information and Modeling, 52, 2950−2957. https://doi.org/10.1021/ci300447c
  • Bailly, C. (2020). Targets and pathways involved in the antitumor activity of citral and its stereo-isomers. European Journal of Pharmacology, 871, 172945. https://doi.org/10.1016/j.ejphar.2020.172945
  • Balusamy, S. R., Perumalsamy, H., Veerappan, K., Huq, M. A., Rajeshkumar, S., Lakshmi, T., & Kim, Y. J. (2020). Citral induced apoptosis through modulation of key genes involved in fatty acid biosynthesis in human prostate cancer cells: In silico and in vitro study. BioMed Research International, 2020, 6040727. https://doi.org/10.1155/2020/6040727
  • Becke, A. D. (1993). A new mixing of Hartree–Fock and local density‐functional theories. Journal of Chemical Physics, 98, 1372-1377. https://doi.org/10.1063/1.464304
  • Bouyahya, A., Guaouguaou, F. E., El Omari, N., El Menyiy, N., Balahbib, A., El-Shazly, M., & Bakri, Y. (2022). Anti-inflammatory and analgesic properties of Moroccan medicinal plants: Phytochemistry, in vitro and in vivo investigations, mechanism insights, clinical evidences and perspectives. Journal of Pharmaceutical Analysis, 12(1), 35-57. https://doi.org/10.1016/j.jpha.2021.07.004
  • Burdock, G. A., & Carabin, I. G. (2009). Safety assessment of coriander (Coriandrum sativum L.) essential oil as a food ingredient. Food and Chemical Toxicology, 47(6), 1202-1209. https://doi.org/10.1016/j.fct.2008.11.006
  • Carpenter, J. F., Pikal, M. J., Chang, B. S., & Randolph, T. W. (1997). Rational design of stable lyophilized protein formulations: Theory and practice. In Pharmaceutical Biotechnology, 9, 189-227. https://doi.org/10.1023/A:1012180707283
  • Cheng, T., Zhao, Y., Li, X., Lin, F., Xu, Y., Zhang, X., Li, Y., & Wang, R. (2007). Computation of octanol−water partition coefficients by guiding an additive model with knowledge. Journal of Chemical Information and Modeling, 47(6), 2140–2148. https://doi.org/10.1021/ci700257y
  • Daina, A., Michielin, O., & Zoete, V. (2014). iLOGP: A simple, robust, and efficient description of n‑octanol/water partition coefficient for drug design using the GB/SA approach. Journal of Chemical Information and Modeling, 54(12), 3284–3301. https://doi.org/10.1021/ci500467k
  • Daina, A., Michielin, O., & Zoete, V. (2017). SwissADME: A free web tool to evaluate pharmacokinetics, druglikeness and medicinal chemistry friendliness of small molecules. Scientific Reports, 7, 42717. https://doi.org/10.1038/srep42717
  • Delaney, J. S. (2004). ESOL: Estimating aqueous solubility directly from molecular structure. Journal of Chemical Information and Computer Sciences, 44, 1000-1005. https://doi.org/10.1021/ci034243x
  • Dennington, R., Keith, T. A., & Millam, J. M. (2016). GaussView, version 6.0.16. Semichem Inc Shawnee Mission KS. Egan, W. J., Merz, K. M., Jr., & Baldwin, J. J. (2000). Prediction of drug absorption using multivariate statistics. Journal of Medicinal Chemistry, 43, 3867-3877. https://doi.org/10.1021/jm000292e
  • Erdogan, M., & Serdaroglu, G. (2021). New Hybrid (E)-4-((pyren-1-ylmethylene)amino)-N-(thiazol-2-yl)benzenesulfonamide as a potential drug candidate: Spectroscopy, TD-DFT, NBO, FMO, and MEP studies. Chemistry Select, 6, 9369–9381. https://doi.org/10.1002/slct.202102602
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  • Gazquez, J. L., Cedillo, A., & Vela, A. (2007). Electrodonatingand Electroaccepting Powers. Journal of Physical Chemistry A, 111(10), 1966-1970. https://doi.org/10.1021/jp065459f
  • Ghose, A. K., Viswanadhan, V. N., & Wendoloski, J. J. (1999). A knowledge-based approach in designing combinatorial or medicinal chemistry libraries for drug discovery. 1. A qualitative and quantitative characterization of known drug databases. Journal of Combinatorial Chemistry, 1, 55-68. https://doi.org/10.1021/cc9800071
  • Gomez, B., Likhanova, N. V., Domínguez-Aguilar, M. A., Martínez-Palou, R., Vela, A., & Gazquez, J. L. (2006). Quantum chemical study of the inhibitive properties of 2-Pyridyl-Azoles. Journal of Physical Chemistry B, 110(18), 8928-8934. https://doi.org/10.1021/jp057143y
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Geranial benzeri -dienlerin İlaç Benzerliği ve ADMT Özelliklerine İlişkin Hesaplamalı Analizler

Yıl 2023, Cilt: 13 Sayı: 2, 174 - 192, 31.12.2023
https://doi.org/10.54370/ordubtd.1308195

Öz

Bu araştırma, tıbbi özellikleriyle bilinen, doğal olarak oluşan bir bileşik olan geranialin (sardunya) ilaç geliştirme potansiyelini, derinlemesine ADMT (Absorbsiyon, Dağıtım, Metabolizma ve Toksisite) profili oluşturma ve B3LYP/6-311G** fonksiyon ve temel setinde, Yoğunluk Fonksiyonel Teorisi (DFT) hesaplamaları yoluyla analiz etmeyi amaçlamaktadır. Veri setinin optimize edilmiş ve onaylanmış yapıları daha sonraki hesaplamalar için kullanıldı. FMO "Frontier Molecular Orbital" enerjileri ve MEP "Moleküler Elektrostatik Potansiyel" sırasıyla moleküllerin olası reaktivite özelliklerini ve bölgelerini aydınlatacak şekilde değerlendirildi. Ayrıca, DFT hesaplamaları bileşiğin elektronik özelliklerinin ve yapısal stabilitesinin aydınlatılmasına yardımcı oldu ve ilaç geliştirmeye uygunluğunu doğruladı. Bu bulgular, farmasötik alanda geranial ile yapısal olarak ilişkili bileşiklerin potansiyelini vurgulamakta ve insan sağlığına ve çevreye yönelik potansiyel riskleri azaltırken güvenlik ve etkinliği sağlayan yeni ilaç adayları için benzer değerlendirmelerin gerekliliğinin altını çizmektedir.

Kaynakça

  • Adorjan, B., & Buchbauer, G. (2010). Biological properties of essential oils: An updated review. Flavour and Fragrance Journal. 25(6), 407-426. 4https://doi.org/10.1002/ffj.2024
  • Ali, J., Camilleri, P., Brown, M. B., Hutt, A. J., & Kirton, S. B. (2012). In silico prediction of aqueous solubility using simple QSPR models: The importance of phenol and phenol-like moieties. Journal of Chemical Information and Modeling, 52, 2950−2957. https://doi.org/10.1021/ci300447c
  • Bailly, C. (2020). Targets and pathways involved in the antitumor activity of citral and its stereo-isomers. European Journal of Pharmacology, 871, 172945. https://doi.org/10.1016/j.ejphar.2020.172945
  • Balusamy, S. R., Perumalsamy, H., Veerappan, K., Huq, M. A., Rajeshkumar, S., Lakshmi, T., & Kim, Y. J. (2020). Citral induced apoptosis through modulation of key genes involved in fatty acid biosynthesis in human prostate cancer cells: In silico and in vitro study. BioMed Research International, 2020, 6040727. https://doi.org/10.1155/2020/6040727
  • Becke, A. D. (1993). A new mixing of Hartree–Fock and local density‐functional theories. Journal of Chemical Physics, 98, 1372-1377. https://doi.org/10.1063/1.464304
  • Bouyahya, A., Guaouguaou, F. E., El Omari, N., El Menyiy, N., Balahbib, A., El-Shazly, M., & Bakri, Y. (2022). Anti-inflammatory and analgesic properties of Moroccan medicinal plants: Phytochemistry, in vitro and in vivo investigations, mechanism insights, clinical evidences and perspectives. Journal of Pharmaceutical Analysis, 12(1), 35-57. https://doi.org/10.1016/j.jpha.2021.07.004
  • Burdock, G. A., & Carabin, I. G. (2009). Safety assessment of coriander (Coriandrum sativum L.) essential oil as a food ingredient. Food and Chemical Toxicology, 47(6), 1202-1209. https://doi.org/10.1016/j.fct.2008.11.006
  • Carpenter, J. F., Pikal, M. J., Chang, B. S., & Randolph, T. W. (1997). Rational design of stable lyophilized protein formulations: Theory and practice. In Pharmaceutical Biotechnology, 9, 189-227. https://doi.org/10.1023/A:1012180707283
  • Cheng, T., Zhao, Y., Li, X., Lin, F., Xu, Y., Zhang, X., Li, Y., & Wang, R. (2007). Computation of octanol−water partition coefficients by guiding an additive model with knowledge. Journal of Chemical Information and Modeling, 47(6), 2140–2148. https://doi.org/10.1021/ci700257y
  • Daina, A., Michielin, O., & Zoete, V. (2014). iLOGP: A simple, robust, and efficient description of n‑octanol/water partition coefficient for drug design using the GB/SA approach. Journal of Chemical Information and Modeling, 54(12), 3284–3301. https://doi.org/10.1021/ci500467k
  • Daina, A., Michielin, O., & Zoete, V. (2017). SwissADME: A free web tool to evaluate pharmacokinetics, druglikeness and medicinal chemistry friendliness of small molecules. Scientific Reports, 7, 42717. https://doi.org/10.1038/srep42717
  • Delaney, J. S. (2004). ESOL: Estimating aqueous solubility directly from molecular structure. Journal of Chemical Information and Computer Sciences, 44, 1000-1005. https://doi.org/10.1021/ci034243x
  • Dennington, R., Keith, T. A., & Millam, J. M. (2016). GaussView, version 6.0.16. Semichem Inc Shawnee Mission KS. Egan, W. J., Merz, K. M., Jr., & Baldwin, J. J. (2000). Prediction of drug absorption using multivariate statistics. Journal of Medicinal Chemistry, 43, 3867-3877. https://doi.org/10.1021/jm000292e
  • Erdogan, M., & Serdaroglu, G. (2021). New Hybrid (E)-4-((pyren-1-ylmethylene)amino)-N-(thiazol-2-yl)benzenesulfonamide as a potential drug candidate: Spectroscopy, TD-DFT, NBO, FMO, and MEP studies. Chemistry Select, 6, 9369–9381. https://doi.org/10.1002/slct.202102602
  • Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G. A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H. P., Izmaylov, A. F., Bloino, J., Zheng, G., Sonnenberg, J. L., Hada, M., Ehara, … Fox, D. J. (2013). Gaussian 09W, Revision D.01. Gaussian Inc.
  • Gaonkar, R., Yallappa, S., Dhananjayac, B. L., & Hegde, G. (2016). Development and validation of reverse phase high-performance liquid chromatography for citral analysis from essential oils. Journal of Chromatography B, 1036–1037, 50–56. https://doi.org/10.1016/j.jchromb.2016.10.001
  • Gazquez, J. L., Cedillo, A., & Vela, A. (2007). Electrodonatingand Electroaccepting Powers. Journal of Physical Chemistry A, 111(10), 1966-1970. https://doi.org/10.1021/jp065459f
  • Ghose, A. K., Viswanadhan, V. N., & Wendoloski, J. J. (1999). A knowledge-based approach in designing combinatorial or medicinal chemistry libraries for drug discovery. 1. A qualitative and quantitative characterization of known drug databases. Journal of Combinatorial Chemistry, 1, 55-68. https://doi.org/10.1021/cc9800071
  • Gomez, B., Likhanova, N. V., Domínguez-Aguilar, M. A., Martínez-Palou, R., Vela, A., & Gazquez, J. L. (2006). Quantum chemical study of the inhibitive properties of 2-Pyridyl-Azoles. Journal of Physical Chemistry B, 110(18), 8928-8934. https://doi.org/10.1021/jp057143y
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Ayrıntılar

Birincil Dil İngilizce
Konular Moleküler İlaç
Bölüm Araştırma Makaleleri
Yazarlar

Goncagül SERDAROĞLU 0000-0001-7649-9168

Erken Görünüm Tarihi 29 Aralık 2023
Yayımlanma Tarihi 31 Aralık 2023
Gönderilme Tarihi 31 Mayıs 2023
Yayımlandığı Sayı Yıl 2023 Cilt: 13 Sayı: 2

Kaynak Göster

APA SERDAROĞLU, G. (2023). Computational Insights in Drug-likeness and ADMT Properties of -dienes Resemble of Geranial. Ordu Üniversitesi Bilim Ve Teknoloji Dergisi, 13(2), 174-192. https://doi.org/10.54370/ordubtd.1308195