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AN IN SILICO PHARMACOKINETIC INVESTIGATION OF ORGANIC LUMINOGENS: UNDERSTANDING THE NIR AIEGENS AND THEIR INTERACTIONS WITH SERUM ALBUMINS

Yıl 2024, Cilt: 48 Sayı: 1, 56 - 74, 20.01.2024
https://doi.org/10.33483/jfpau.1335047

Öz

Objective: Fluorescence imaging (FLI) is accepted as a highly effective method for visualizing bioanalytics directly and gaining insight into complicated biological structures and processes. In this context, newly tailored organic molecules, which have the potential to be used in FLI, especially near-infrared (NIR) regions supported by aggregation-induced emission luminogens (AIEgens), are a rapidly developing area of study. Herein, using ADMET and molecular docking analyses, we examined the pharmacokinetic properties of both model (D2-A2-D2) and newly designed (Dn-An-Dn) organic luminogens to interact with blood proteins, namely bovine serum albumin (BSA) and human serum albumin (HSA), which have emerged as a versatile carrier of several therapeutic agents against preliminary cancer and infectious diseases.
Material and Method: The structural properties of the examined luminogens were computed using the Gaussian 09 software package. The DFT/B3LYP/6-31G(d,p) level was then utilized for geometry optimization and accurately determining electronic structures and molecular properties. Lipinski's rule of five was applied to predict the drugability of the compounds using the SwissADME web tool. Molinspiration was used for further validation of these properties and additional bioactivity parameters. Toxicity parameters were evaluated with OSIRIS Property Explorer (v.4.5.1). Molecular docking simulations of the luminogen-albumin complexes were performed using SAMSON 2022 R2 modeling platform and implemented Autodock-vina extension. The X-ray crystal structures of bovine serum albumin (BSA, PDB ID: 4F5S) and human serum albumin (HSA, PDB ID: 4L9Q) were obtained from the Protein Data Bank. Visualization of the docking interactions was conducted using Discovery Studio Visualizer 2021.
Result and Discussion: The compounds D1-A1-D1 and D1-A4-D1 stood out concerning molecular weight (MW) and ClogPo/w values, making them promising candidates for drug design. An analysis of lipophilicity revealed that these two compounds displayed high miLogP values, indicating a high degree of lipophilicity, which is generally beneficial for drug delivery. They also exhibited moderate bioactivity based on GPCR ligand and protease inhibitor (PI) parameters. On the other hand, D4-A3-D4 showcased paramount interaction with bovine serum albumin (BSA), while D5-A3-D5 demonstrated the highest binding affinity with human serum albumin (HSA).

Kaynakça

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ORGANİK LUMİNOJENLERİN İN SİLİKO FARMAKOKİNETİK İNCELENMESİ: NIR AIEJENLERİ VE SERUM ALBÜMİNLERİ İLE ETKİLEŞİMLERİNİ ANLAMAK

Yıl 2024, Cilt: 48 Sayı: 1, 56 - 74, 20.01.2024
https://doi.org/10.33483/jfpau.1335047

Öz

Amaç: Floresans görüntüleme (FLI), biyoanalitikleri doğrudan görselleştirme ve karmaşık biyolojik yapıları ve süreçleri anlamak için son derece etkili bir yöntem olarak kabul edilir. Bu bağlamda, özellikle agregasyon-indüklü emisyon luminojenleri (AIEjen) tarafından desteklenen ve yakın kızılötesi (NIR) bölgede kullanılma potansiyeli olan yeni özelleştirilmiş organik moleküller, hızla gelişen bir çalışma alanıdır. Bu noktada, ADMET ve moleküler kenetlenme analizlerini kullanarak, hem model (D2-A2-D2) hem de yeni tasarlanmış (Dn-An-Dn) organik luminogenlerin kan proteinleri ile etkileşme özelliklerini farmakokinetik açıdan inceledik. Bu kan proteinleri, özellikle sığır serum albumini (BSA) ve insan serum albumini (HSA), erken kanser ve bulaşıcı hastalıklarla mücadelede çeşitli terapötik ajanların taşıyıcısı olarak öne çıkmıştır.
Gereç ve Yöntem: İncelenen luminojenlerin yapısal özellikleri Gaussian 09 yazılım paketi kullanılarak hesaplandı. Daha sonra DFT/B3LYP/6-31G(d,p) seviyesi, geometri optimizasyonu ve elektronik yapıların ve moleküler özelliklerin doğru bir şekilde belirlenmesi için kullanıldı. Bileşiklerin ilaçlaştırılabilirliğini tahmin etmek için Lipinski'nin beşli kuralı SwissADME web aracı kullanılarak uygulandı. Bu özelliklerin ve ek biyoaktivite parametrelerinin daha fazla doğrulanması için Molinspiration kullanıldı. Toksisite parametreleri OSIRIS Property Explorer (v.4.5.1) ile değerlendirildi. Luminojen-albümin komplekslerinin moleküler kenetlenme simülasyonları SAMSON 2022 R2 modelleme platformu ve Autodock-vina uzantısı kullanılarak gerçekleştirildi. Sığır serum albümininin (BSA, PDB ID: 4F5S) ve insan serum albümininin (HSA, PDB ID: 4L9Q) X-ışını kristal yapıları Protein Data Bank'tan alındı. Bağlanma etkileşimlerinin görselleştirilmesi Discovery Studio Visualizer 2021 kullanılarak gerçekleştirildi.
Sonuç ve Tartışma: D1-A1-D1 ve D1-A4-D1 bileşikleri, moleküler ağırlık (MA) ve ClogPo/w değerleri açısından öne çıkarak onları ilaç tasarımı için umut verici adaylar haline getirdi. Lipofilisite analizi, bu iki bileşiğin yüksek miLogP değerleri gösterdiğini ortaya çıkardı ki bu genellikle ilaç taşınım için istenen yüksek derecede lipofilikliğe işaret etmektedir. Ayrıca bu bileşikler, GPCR ligandı ve proteaz inhibitörü (PI) parametrelerine dayalı olarak da orta düzeyde biyoaktivite sergilediler. Öte yandan D4-A3-D4, sığır serum albümini (BSA) ile olağanüstü etkileşim sergilerken, D5-A3-D5, insan serum albümini (HSA) ile en yüksek bağlanma afinitesini gösterdi.

Kaynakça

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  • 2. Schuster, E., Taftaf, R., Reduzzi, C., Albert, M.K., Romero-Calvo, I., Liu, H. (2021). Better together: Circulating tumor cell clustering in metastatic cancer. Trends in Cancer, 7(11), 1020-1032. [CrossRef]
  • 3. Pucci, C., Martinelli, C., Ciofani, G. (2019). Innovative approaches for cancer treatment: Current perspectives and new challenges. Ecancermedicalscience, 13, 961. [CrossRef]
  • 4. Tokumaru, Y., Joyce, D., Takabe, K. (2020). Current status and limitations of immunotherapy for breast cancer. Surgery, 167(3), 628-630. [CrossRef]
  • 5. Yu, L.Y., Tang, J., Zhang, C.M., Zeng, W.J., Yan, H., Li, M.P., Chen, X.P. (2017). New immunotherapy strategies in breast cancer. International Journal of Environmental Research and Public Health, 14(1), 68. [CrossRef]
  • 6. Chilakamarthi, U., Giribabu, L. (2017). Photodynamic therapy: Past, present and future. Chemical Record, 17(8), 775-802. [CrossRef]
  • 7. Kroschinsky, F., Stölzel, F., von Bonin, S., Beutel, G., Kochanek, M., Kiehl, M., Schellongowski, P. (2017). New drugs, new toxicities: Severe side effects of modern targeted and immunotherapy of cancer and their management. Critical Care, 21(1), 89. [CrossRef]
  • 8. Oun, R., Moussa, Y.E., Wheate, N.J. (2018). The side effects of platinum-based chemotherapy drugs: A review for chemists. Dalton Transactions, 47(19), 6645-6653. [CrossRef]
  • 9. Dos Santos, A.F., De Almeida, D.R.Q., Terra, L.F., Baptista, M.S., Labriola, L. (2019). Photodynamic therapy in cancer treatment - an update review. Journal of Cancer Metastasis and Treatment, 5, 25. [CrossRef]
  • 10. Hamblin, M.R. (2020). Photodynamic therapy for cancer: What's past is prologue. Photochemistry and Photobiology, 96(3), 506-516. [CrossRef]
  • 11. Liu, S., Feng, G., Tang, B.Z., Liu, B. (2021). Recent advances of AIE light-up probes for photodynamic therapy. Chemical Science, 12(19), 6488-6506. [CrossRef]
  • 12. Wang, S., Wu, W., Manghnani, P., Xu, S., Wang, Y., Goh, C.C., Ng, L.G., Liu, B. (2019). Polymerization-enhanced two-photon photosensitization for precise photodynamic therapy. ACS Nano, 13(3), 3095-3105. [CrossRef]
  • 13. Plotino, G., Grande, N.M., Mercade, M. (2019). Photodynamic therapy in endodontics. International Endodontic Journal, 52(6), 760-774. [CrossRef]
  • 14. Gunaydin, G., Gedik, M.E., Ayan, S. (2021). Photodynamic therapy-current limitations and novel approaches. Frontiers in Chemistry, 9, 691697. [CrossRef]
  • 15. Li, X., Wu, J., Wang, L., He, C., Chen, L., Jiao, Y., Duan, C. (2020). Mitochondrial-DNA-targeted IrIII -containing metallohelices with tunable photodynamic therapy efficacy in cancer cells. Angewandte Chemie (International Ed. in English), 59(16), 6420-6427. [CrossRef]
  • 16. Wan, Q., Zhang, R., Zhuang, Z., Li, Y., Huang, Y., Wang, Z., Zhang, W., Hou, J., Tang, B.Z. (2020). Molecular engineering to boost aie-active free radical photogenerators and enable high-performance photodynamic therapy under hypoxia. Advanced Functional Materials, 30(39), 1-12. [CrossRef]
  • 17. Allison, R.R., Moghissi, K. (2013). Photodynamic therapy (PDT): PDT mechanisms. Clinical Endoscopy, 46(1), 24-29. [CrossRef]
  • 18. Filatov, M.A. (2020). Heavy-atom-free BODIPY photosensitizers with intersystem crossing mediated by intramolecular photoinduced electron transfer. Organic and Biomolecular Chemistry, 18(1), 10–27. [CrossRef]
  • 19. Li, X., Lee, D., Huang, J.D., Yoon, J. (2018). Phthalocyanine-assembled nanodots as photosensitizers for highly efficient type I photoreactions in photodynamic therapy. Angewandte Chemie International Edition, 57(31), 9885-9890. [CrossRef]
  • 20. Chinna Ayya Swamy, P., Sivaraman, G., Priyanka, R.N., Raja, S.O., Ponnuvel, K., Shanmugpriya, J., Gulyani, A. (2020). Near Infrared (NIR) absorbing dyes as promising photosensitizer for photo dynamic therapy. Coordination Chemistry Reviews, 411, 213233. [CrossRef]
  • 21. Li, Y., Cai, Z., Liu, S., Zhang, H., Wong, S.T.H., Lam, J.W.Y., Kwok, R.T.K., Qian, J., Tang, B.Z. (2020). Design of AIEgens for near-infrared IIb imaging through structural modulation at molecular and morphological levels. Nature Communications, 11(1), 1255. [CrossRef]
  • 22. Chen, Y., Xue, L., Zhu, Q., Feng, Y., Wu, M. (2021). Recent advances in second near-infrared region (NIR-II) fluorophores and biomedical applications. Frontiers in Chemistry, 9, 750404. [CrossRef]
  • 23. He, B., Situ, B., Zhao, Z., Zheng, L. (2020). Promising applications of AIEgens in animal models. Small Methods, 4(4), 1900583. [CrossRef]
  • 24. He, S., Song, J., Qu, J., Cheng, Z. (2018). Crucial breakthrough of second near-infrared biological window fluorophores: Design and synthesis toward multimodal imaging and theranostics. Chemical Society Reviews, 47(12), 4258-4278. [CrossRef]
  • 25. Anthony, S.P. (2012). Organic solid-state fluorescence: Strategies for generating switchable and tunable fluorescent materials. ChemPlusChem, 77(7), 518-531. [CrossRef]
  • 26. Li, X., Jiang, M., Li, Y., Xue, Z., Zeng, S., Liu, H. (2019). 808 nm laser-triggered NIR-II emissive rare-earth nanoprobes for small tumor detection and blood vessel imaging. Materials Science and Engineering C, 100, 260-268. [CrossRef]
  • 27. Kenry, Duan, Y., Liu, B. (2018). Recent advances of optical imaging in the second near-infrared window. Advanced Materials, 30(47), 1-19. [CrossRef]
  • 28. Hu, C., Guo, T., Li, H., Xu, P., Xiao, Y. (2021). A novel NIR-II probe for improved tumor-targeting NIR-II imaging. RSC Advances, 11(62), 39287-39290. [CrossRef]
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  • 30. Li, Y., Liu, S., Ni, H., Zhang, H., Zhang, H., Chuah, C., Ma, C., Wong, K.S., Lam, J.W.Y., Kwok, R.T.K., Qian, J., Lu, X., Tang, B.Z. (2020). ACQ‐to‐AIE transformation: Tuning molecular packing by regioisomerization for two‐photon NIR bioimaging. Angewandte Chemie, 132(31), 12922-12926. [CrossRef]
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Ayrıntılar

Birincil Dil İngilizce
Konular Farmasotik Kimya
Bölüm Araştırma Makalesi
Yazarlar

Harun NALÇAKAN 0000-0003-3821-8681

Gülbin KURTAY 0000-0003-0920-8409

Dilara Tuğçe ÖZDİL 0009-0005-2845-7402

Züleyha YILMAZ 0000-0003-4459-9206

Erken Görünüm Tarihi 3 Kasım 2023
Yayımlanma Tarihi 20 Ocak 2024
Gönderilme Tarihi 31 Temmuz 2023
Kabul Tarihi 10 Ekim 2023
Yayımlandığı Sayı Yıl 2024 Cilt: 48 Sayı: 1

Kaynak Göster

APA NALÇAKAN, H., KURTAY, G., ÖZDİL, D. T., YILMAZ, Z. (2024). AN IN SILICO PHARMACOKINETIC INVESTIGATION OF ORGANIC LUMINOGENS: UNDERSTANDING THE NIR AIEGENS AND THEIR INTERACTIONS WITH SERUM ALBUMINS. Journal of Faculty of Pharmacy of Ankara University, 48(1), 56-74. https://doi.org/10.33483/jfpau.1335047
AMA NALÇAKAN H, KURTAY G, ÖZDİL DT, YILMAZ Z. AN IN SILICO PHARMACOKINETIC INVESTIGATION OF ORGANIC LUMINOGENS: UNDERSTANDING THE NIR AIEGENS AND THEIR INTERACTIONS WITH SERUM ALBUMINS. Ankara Ecz. Fak. Derg. Ocak 2024;48(1):56-74. doi:10.33483/jfpau.1335047
Chicago NALÇAKAN, Harun, Gülbin KURTAY, Dilara Tuğçe ÖZDİL, ve Züleyha YILMAZ. “AN IN SILICO PHARMACOKINETIC INVESTIGATION OF ORGANIC LUMINOGENS: UNDERSTANDING THE NIR AIEGENS AND THEIR INTERACTIONS WITH SERUM ALBUMINS”. Journal of Faculty of Pharmacy of Ankara University 48, sy. 1 (Ocak 2024): 56-74. https://doi.org/10.33483/jfpau.1335047.
EndNote NALÇAKAN H, KURTAY G, ÖZDİL DT, YILMAZ Z (01 Ocak 2024) AN IN SILICO PHARMACOKINETIC INVESTIGATION OF ORGANIC LUMINOGENS: UNDERSTANDING THE NIR AIEGENS AND THEIR INTERACTIONS WITH SERUM ALBUMINS. Journal of Faculty of Pharmacy of Ankara University 48 1 56–74.
IEEE H. NALÇAKAN, G. KURTAY, D. T. ÖZDİL, ve Z. YILMAZ, “AN IN SILICO PHARMACOKINETIC INVESTIGATION OF ORGANIC LUMINOGENS: UNDERSTANDING THE NIR AIEGENS AND THEIR INTERACTIONS WITH SERUM ALBUMINS”, Ankara Ecz. Fak. Derg., c. 48, sy. 1, ss. 56–74, 2024, doi: 10.33483/jfpau.1335047.
ISNAD NALÇAKAN, Harun vd. “AN IN SILICO PHARMACOKINETIC INVESTIGATION OF ORGANIC LUMINOGENS: UNDERSTANDING THE NIR AIEGENS AND THEIR INTERACTIONS WITH SERUM ALBUMINS”. Journal of Faculty of Pharmacy of Ankara University 48/1 (Ocak 2024), 56-74. https://doi.org/10.33483/jfpau.1335047.
JAMA NALÇAKAN H, KURTAY G, ÖZDİL DT, YILMAZ Z. AN IN SILICO PHARMACOKINETIC INVESTIGATION OF ORGANIC LUMINOGENS: UNDERSTANDING THE NIR AIEGENS AND THEIR INTERACTIONS WITH SERUM ALBUMINS. Ankara Ecz. Fak. Derg. 2024;48:56–74.
MLA NALÇAKAN, Harun vd. “AN IN SILICO PHARMACOKINETIC INVESTIGATION OF ORGANIC LUMINOGENS: UNDERSTANDING THE NIR AIEGENS AND THEIR INTERACTIONS WITH SERUM ALBUMINS”. Journal of Faculty of Pharmacy of Ankara University, c. 48, sy. 1, 2024, ss. 56-74, doi:10.33483/jfpau.1335047.
Vancouver NALÇAKAN H, KURTAY G, ÖZDİL DT, YILMAZ Z. AN IN SILICO PHARMACOKINETIC INVESTIGATION OF ORGANIC LUMINOGENS: UNDERSTANDING THE NIR AIEGENS AND THEIR INTERACTIONS WITH SERUM ALBUMINS. Ankara Ecz. Fak. Derg. 2024;48(1):56-74.

Kapsam ve Amaç

Ankara Üniversitesi Eczacılık Fakültesi Dergisi, açık erişim, hakemli bir dergi olup Türkçe veya İngilizce olarak farmasötik bilimler alanındaki önemli gelişmeleri içeren orijinal araştırmalar, derlemeler ve kısa bildiriler için uluslararası bir yayım ortamıdır. Bilimsel toplantılarda sunulan bildiriler supleman özel sayısı olarak dergide yayımlanabilir. Ayrıca, tüm farmasötik alandaki gelecek ve önceki ulusal ve uluslararası bilimsel toplantılar ile sosyal aktiviteleri içerir.