Pharmacological evaluation and binding behavior of 4,4'-diamino-2,2'-stilbene disulfonic acid with metal ions using spectroscopic techniques

Madeeha Shabnam; Eman A Alabdullkarem; Muhammad Saeed Jan; Saad H Alotaibi; Khairia Mohammed Al-Ahmary; Muhammad Ibrar; Mohamed Hussien; Asmaa E Sherif

doi:10.1016/j.heliyon.2024.e34639

Pharmacological evaluation and binding behavior of 4,4'-diamino-2,2'-stilbene disulfonic acid with metal ions using spectroscopic techniques

Heliyon. 2024 Jul 14;10(14):e34639. doi: 10.1016/j.heliyon.2024.e34639. eCollection 2024 Jul 30.

Authors

Madeeha Shabnam¹, Eman A Alabdullkarem², Muhammad Saeed Jan³, Saad H Alotaibi⁴, Khairia Mohammed Al-Ahmary⁵, Muhammad Ibrar³, Mohamed Hussien⁶, Asmaa E Sherif^{7

8}

Affiliations

¹ Department of Chemistry, Women University, Mardan, KP, Pakistan.
² Chemistry Department, College of Science, King Saud University, Riyadh, 11451, Saudi Arabia.
³ Department of Pharmacy, Bacha Khan University, Charsadda, 24420, KP, Pakistan.
⁴ Department of Chemistry, Turabah University College, Taif University, P.O. box 11099, Taif, 21944, Saudi Arabia.
⁵ Department of Chemistry, College of Science, University of Jeddah, Jeddah, Saudi Arabia.
⁶ Department of Chemistry, Faculty of Science, King Khalid University, P.O. box 9004, Abha, 61413, Saudi Arabia.
⁷ Department of Pharmacognosy, College of Pharmacy, Prince Sattam Bin Abdul Aziz University, Al-Kharj, 11942, Saudi Arabia.
⁸ Department of Pharmacognosy, Faculty of Pharmacy, Mansoura University, Mansoura, 35516, Egypt.

Abstract

Industrial and human activities contribute significantly to the environmental contamination of heavy metal ions (HMIs), which have detrimental effects on aquatic life, plants, and animals, causing major toxicological problems. The commercially available 4,4'-diamino-2,2'-stilbenedisulfonic acid (DSD) has been playing a vital role in the detection of heavy metal ions and has significantly inhibited a variety of cancer cells in numerous field of modern science. The current investigation aimed to ensure the detection of heavy metals ions from the environment and fluorescence imaging of DSD in the treatment of cancer cells. Fluorescence and UV-Visible spectroscopic analysis was performed to sense the selective behavior of the probe DSD with several heavy metal ions, including Fe²⁺, K¹⁺, Co²⁺, Ni²⁺, Zn²⁺, Cd²⁺, Pb²⁺, Mn²⁺, Sn²⁺, and Cr³⁺. Furthermore, DSD was subjected to examine enzyme inhibition such as anti-Alzheimer, anti-inflammatory, antioxidant, anticancer, and antimicrobial activities in search of multifaceted drugs. Test compounds have demonstrated dose-dependent responses in the in-vitro enzyme inhibition assays for acetylcholinesterase (AChE), butyrylcholinesterase (BChE), cyclooxygenase (COX), and lipoxygenase (LOX), as well as antioxidant [DPPH = 2,2-diphenyl-1-picrylhydrazyl and ABTS = 2,2'-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid]. The DSD were shown to be more effective than the conventional medication galantamine in inhibiting acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), with an IC₅₀ value of 12.18 and 20.87 μM, which is equivalent to the standard drug. The results obtained has revealed that DSD has the potential to become an effective sensor for the detection of Sn²⁺ ions over competing metal ions due to the inhibition of photo-induced electron transfer pathway (PET). The MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazoliumbromide tetrazolium) test, demonstrated that DSD had strong anticancer effects against the brain cancer cell line NIH/3T3, HeLa and MCF-7 with an IC₅₀ value of 32.59, 15.31 and 96.46 μM respectively. The antimicrobial testing has shown that DSD outperforms the standard drug cefixime against Candida albicans and Pseudomonas aeruginosa, respectively. This study makes a substantial contribution to the ongoing search for efficient treatments for breast cancer.

Keywords: ABTS; AChE; BChE; COX; DPPH; LOX; MTT assay.