Contents lists available at ScienceDirect Inorganica Chimica Acta journal homepage: www.elsevier.com/locate/ica Organotin(IV) derivatives of amide-based carboxylates: Synthesis, spectroscopic characterization, single crystal studies and antimicrobial, antioxidant, cytotoxic, anti-leishmanial, hemolytic, noncancerous, anticancer activities Iftikhar Ahmad a , Zia-ur-Rehman a, ⁎ , Amir Waseem a , Muhammad Tariq b , Cora MacBeth c , John Bacsa c , Deepak Venkataraman d , Augustine Rajakumar d , Nazif Ullah e , Saira Tabassum f a Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan b Institute of Chemical Sciences, Bahauddin Zakariya University Multan, 60000, Pakistan c Department of Chemistry, Emory University Atlanta, GA, United States d Department of Gynecology and Obstetrics, Emory University Atlanta, GA, United States e Department of Biotechnology, Faculty of Chemical and Life Sciences, Abdul Wali Khan University Mardan-23200, Pakistan f School of Applied Sciences and Humanities, National University of Technology Islamabad, Pakistan ARTICLE INFO Keywords: Polymeric Organotin(IV) carboxylates Intramolecular hydrogen bond Antileishmanial activity Anticancer activity ABSTRACT Four new triorganotin(IV) amide based carboxylates of general formula R 3 SnL 1 and R 3 SnL 2 , where R = Me(1,3) and n-butyl (2,4), and L 1 = (Z)-4-(p-methoxyphenylamino)-4-oxo-2-butenoic acid (HL 1 )L 2 = (Z)-4-(3,5-bis (trifluoromethyl)phenylamino)-4-oxo-2-butenoic acid (HL 2 ) have been synthesized by refluxing methanolic solution of organtin(IV) chloride and ligand (1:1 M ratio). The synthesized compounds were characterized by FT- IR, elemental analysis, NMR ( 1 H, 13 C, 119 Sn & 19 F) and single crystal X-ray crystallography. The ligands co- ordinate to tin atom through oxygens (carboxylate and amide) showing distorted trigonal bipyramidal geometry with polymeric bridging behavior in solid state. However, the geometry is switched over from trigonal bipyr- amidal to tetrahedral upon dissolution as confirmed by multinuclear ( 1 H, 13 C, 19 F and 119 Sn) NMR. The prepared ligands and compounds 1–4 were screened for antimicrobial, antioxidant, cytotoxicity, hemolysis, antil- eishmanial and anticancer and noncancerous activities. The results showed significant antimicrobial activities, antioxidant, good cytotoxic LD 50 values, percent hemolytic values, antileishmanial and anti-cancer activities. Compound 2 and 4 were found the most active antileishmanial and anticancer agent, respectively. 1. Introduction Cancer, recognized by uncontrolled cell growth, is a reason for million deaths worldwide [1]. It is the leading cause of mortality after the heart disease. In USA every 5th mortality is due to cancer [2]. In year 2005, cancer surpassed the heart diseases in USA. Chemotherapy is one of the strategies used to cure cancer. In this context, the use of metallodrugs as anticancer agents is track back to the fortunate dis- covery of cisplatin, which has shown the ability of halting cell division and since then metallo-anticancer drugs remain the focus of intensive investigations. Cisplatin has been approved as anticancer drug for - testicular and ovarian malignancies in 1971 [3]. Several other analo- gues including oxaliplatin, carboplatin, lobaplatin and nedaplatin have got clinical status. Being similar in structure to cisplatin, the mechanism of action of the aforesaid variants is almost the same – they form adduct with DNA [4–6]. However, resistance and damaging side effects, due to their interaction with sulfur containing off-target biomolecules [7], diverted the attention of bioinorganic chemists to find alternate metal- based drugs. Among the known anticancer metallodrugs, organotin(IV) based drugs have received more attention due to their better anticancer activity [8,9]. In this context, organotin(IV) carboxylates have been evaluated and some of them were found more active anticancer agents than other compounds. Furthermore, organotin(IV) carboxylates un- veiled a non-cross resistance and might have better activities as com- pared to platinum complexes [10]. The anticancer activity depends on the alkyl/aryl group and ligands attached to Sn atom. The better bio- logical activities of triorganotin(IV) than the di- and mono-organotin (IV) analogues are because of their higher lipophilic characteristics https://doi.org/10.1016/j.ica.2020.119433 Received 1 October 2019; Received in revised form 8 January 2020; Accepted 10 January 2020 ⁎ Corresponding author. E-mail address: zrehman@qau.edu.pk (Zia-ur-Rehman). Inorganica Chimica Acta 505 (2020) 119433 Available online 11 January 2020 0020-1693/ © 2020 Elsevier B.V. All rights reserved. T