Exploring the anticancer potential of sulfate-hydroxy-butanone derivatives: insights from experimental and quantum chemical investigations

Abstract Urinary incontinence and erectile dysfunction represent enduring adverse outcomes resulting from prostate cancer, a leading cause of global mortality. Given this critical context, there exists an imperative to explore efficacious therapeutic interventions. In this context, a comprehensive investigation of the potential roles of 4-(3ʹ-O-sulfate-4ʹ-hydroxyphenyl)-2-butanone (CDR1), 4-(3ʹ-O-sulfate-4ʹ-hydroxyphenyl)-2(R)-butanol (CDR2), and dihydrodehydrodiconiferyl alcohol 9-O-sulfate (CDR3) as agents for prostate cancer is of paramount importance. These compounds, extracted from the mangrove plant Acrostichum aureum , have been meticulously characterized through GC-MS, FT-IR, and NMR analyses. Detailed insights into the molecular structures, reactivity, bonding nature, and vibrational behaviors of these studied compounds were gleaned via rigorous examination at the DFT/B3LYP-GD3BJ/6-311+G (d,p) level of theory. Moreover, in-depth in-silico molecular docking investigations were conducted, delineating their potential as agents against castration-resistant prostate cancer. Electronic assessments underscored the reactivity of the studied compounds, while analysis of natural bond orbitals affirmed their stability, thus signifying their prospective utility as potent anticancer agents. The bioactivity and compatibility profiles of the investigated compounds in relation to cancer proteins were meticulously evaluated through molecular docking analyses, and the results were meticulously benchmarked against recommended drugs. Among the discernible outcomes, compound CDR3 emerged as a standout candidate, boasting binding affinities of −6.7, −8.6, and −6.4 kcal/mol, predicated on pivotal hydrogen bonding interactions, which inherently dictate the potency of a potential therapeutic agent. Importantly, CDR3 exhibits promising characteristics as an anticancer agent, surpassing its counterparts, and even the recommended drug dorlutamide, thus positioning it favorably for further consideration in prostate cancer treatment modalities.