Citation: Lifang HE, Yaoze LUO, Qiying SHI, Jianxin TANG, Fuxing ZHANG, Xiaoming ZHU. Synthesis, structure, and properties of hydrated tricyclohexyltin theophylline-7-acetic acid complex[J]. Chinese Journal of Inorganic Chemistry, ;2026, 42(3): 632-640. doi: 10.11862/CJIC.20250244 shu

Synthesis, structure, and properties of hydrated tricyclohexyltin theophylline-7-acetic acid complex

Lifang HE ^{1, 2} ,
Yaoze LUO ³ ,
Qiying SHI ³ ,
Jianxin TANG ³ ,
Fuxing ZHANG ^{2, 3, 4,,} ,
Xiaoming ZHU ^{2, 3, 4}

1.
Department of Life Sciences, Hengyang Normal University, Hengyang, Hunan 421008, China
2.
Key Laboratory of Functional Metal-Organic Compounds of Hunan Province, Hengyang Normal University, Hengyang, Hunan 421008, China
3.
Department of Chemistry and Material Science, Hengyang Normal University, Hengyang, Hunan 421008, China
4.
Key Laboratory of Organometallic New Materials of University of Hunan Province, Hengyang Normal University, Hengyang, Hunan 421008, China

Corresponding author: Fuxing ZHANG, zfx8056@163.com
Received Date: 29 July 2025
Revised Date: 14 December 2025

Figures(6)

The hydrated tricyclohexyltin theophylline-7-acetic acid (tpH) complex [Sn(C₆H₁₁)₃(tp)(H₂O)] was synthesized via an ethanol solvothermal method using tricyclohexyltin hydroxide and tpH in a 1∶1 molar ratio. The complex was characterized by IR, ¹H (¹³C) NMR, elemental analysis, and powder X-ray diffraction, and the crystal structure was determined by single-crystal X-ray diffraction. The crystal belongs to the orthorhombic system with space group Iba2, and the central tin atom is in a five-coordinated trigonal bipyramidal configuration. Quantum chemistry ab initio calculations were performed to investigate the stability, molecular orbital energy, and frontier molecular orbital characteristics of the complex. Additionally, its thermal stability, electrochemical properties, and in vitro anticancer activity were evaluated.
- hydrated tricyclohexyltin theophylline-7-acetic acid complex,
- synthesis,
- crystal structure,
- in vitro antitumor activity
1. [1]
  YADAV V K, NATH M. Diorganotin (Ⅳ) derivatives of quinoline-2-carboxaldehyde 4-phenylthio-semicarbazone: Synthesis, spectroscopic characterization, the crystal structure of [Bu₂Sn(QCP)Cl], DFT studies, CT-DNA binding, and plasmid-DNA cleavage studies[J]. J. Mol. Struct., 2025, 1319: 139594 doi: 10.1016/j.molstruc.2024.139594
2. [2]
  PANDEY P, WALAWALKAR M G, MURUGAVEL R. Luminescent 8-hydroxyquinoline derived tin(Ⅳ) complexes[J]. J. Org. Chem., 2024, 1007: 123023 doi: 10.1016/j.jorganchem.2024.123023
3. [3]
  TAN Y X, QIN Q Q, LI A D, FU W W, JIANG W J. Synthesis, characterization, and biological activity of six di-p-chlorobenzyltin complexes derived from ONO tridentate ligands[J]. J. Org. Chem., 2023, 1002: 122905 doi: 10.1016/j.jorganchem.2023.122905
4. [4]
  PARVEEN B, SHAHZADI S, ALI S, FEIZI-DEHNAYEBI M, MUNAWAR K S, ASHFAQ M, TAHIR M N. Synthesis, spectral characterizations, computational studies and biological investigation of 4-(4-(2-hydroxyethyl)phenylamino)-4-oxobutanoic acid and its trimethyltin(Ⅳ) complex[J]. J. Mol. Struct., 2024, 1315: 138851 doi: 10.1016/j.molstruc.2024.138851
5. [5]
  SU H Q, ZHANG R F, GUO Q, WANG J, LI Q L, DU X M, RU J, ZHANG Q F, MA C L. Five organotin complexes derived from hydroxycinnamic acid ligands: Synthesis, structure, in vitro cytostatic activity and binding interaction with BSA[J]. J. Mol. Struct., 2022, 247: 131290-131301
6. [6]
  RUAN B F, TIAN Y P, ZHOU H P, WU J Y, HU R T, ZHU C H, YANG J X, ZHU H. Synthesis, characterization and in vitro antitumor activity of three organotin(Ⅳ) complexes with carbazole ligand[J]. Inorg. Chim. Acta, 2011, 365(1): 302-308 doi: 10.1016/j.ica.2010.09.024
7. [7]
  FENG Y L, KUANG D Z, ZHANG F X, YU J X, JIANG W J, ZHU X M. Two di-n-butyltin carboxylates with a Sn₄O₄ladder-like framework: Microwave solvothermal syntheses, structures and in vitro antitumor activities[J]. Chinese J. Inorg. Chem., 2017, 33(5): 830-836
8. [8]
  KUANG D Z, YU J X, FENG Y L, ZHU X M, JIANG W J, ZHANG F X. Syntheses, structures and in vitro antitumor activity of bis(tricyclohexyltin) pyridinedicarboxylate with macrocyclic supramolecular structure[J]. Chinese J. Inorg. Chem., 2018, 34(6): 1035-1042
9. [9]
  JIANG W J, FAN S J, ZHU Z H, HUANG H F, TAN Y X, ENG Y Y. Design, synthesis and mechanistic studies of novel arylformylhydrazone butylphenyltin complexes as potential anticancer agents[J]. Bioorg. Chem., 2024, 149: 107502 doi: 10.1016/j.bioorg.2024.107502
10. [10]
  TAN Y X, ZHANG Z J, LIU J Z, TAN Y J, JIANG W J. Syntheses, crystal structures, and anticancer activities of organotin carboxylates based on Alrestatin[J]. J. Mol. Struct., 2025, 1322: 140697 doi: 10.1016/j.molstruc.2024.140697
11. [11]
  QING Q Q, HE F, LIU Z H, HOU S P, LIU Y, JIANG Y F, TAN M T, HE L F, ZHANG F X, ZHU X M. Synthesis, structure, and anticancer activity of two complexes of dimethylglyoximeorganotin[J]. Chinese J. Inorg. Chem., 2024, 40(7): 1301-1308
12. [12]
  VIEIRA F T, LIMA G M, MAIA J R S, SPEZIALI N L, ARDISSON J D, RODRIGUES L, JUNIOR A C, ROMERO O B. Synthesis, characterization and biocidal activity of new organotin complexes of 2-(3-oxocyclohex-1-enyl)benzoic acid[J]. Eur. J. Med. Chem., 2010, 45: 883-889 doi: 10.1016/j.ejmech.2009.11.026
13. [13]
  XIAO X, LIANG J W, XIE J Y, LIU X, ZHU D S, DONG Y. Organotin(Ⅳ) carboxylates based on 2-(1, 3-dioxo-1H-benzo[de]-isoquinolin-2(3H)-yl)acetic acid: Syntheses, crystal structures, luminescent properties and antitumor activities[J]. J. Mol. Struct., 2017, 1146: 233-241 doi: 10.1016/j.molstruc.2017.05.141
14. [14]
  YUSOF E N M, LATIF M A M, TAHIR, M I M, SAKOFF J A, VEERAKUMARASIVAM A, PAGE A J, TIEKINK E R T, RAVOOF T B S A. Homoleptic tin(Ⅳ) compounds containing tridentate ONS dithiocarbazate Schiff bases: Synthesis, X-ray crystallography, DFT and cytotoxicity studies[J]. J. Mol. Struct., 2020, 1205: 127635-127643 doi: 10.1016/j.molstruc.2019.127635
15. [15]
  DENG X, ZHANG F X, QING J J, YANG G, HE F, HE L F, LIU Z H, HOU S P. Synthesis, structure and anticancer activity of two benzohydroxamic acid organotin complexes[J]. Chinese J. Inorg. Chem., 2023, 39(11): 2083-2090
16. [16]
  TAN Y X, HUANG H F, ZANG C W, YUAN S T, JIANG W J. Molecular structure regulation and herbicidal activity of dibutyltin aryloxyacetate complexes[J]. J. Mol. Struct., 2025, 1320: 139476 doi: 10.1016/j.molstruc.2024.139476
17. [17]
  JIANG W J, LUO Q, HUANG W, TAN Y X, PENG Y Y. Synthesis, anticancer activity, and mechanistic investigations of aryl-alkyl diorganotin arylformylhydrazone complexes[J]. J. Inorg. Biochem., 2025, 262: 112756 doi: 10.1016/j.jinorgbio.2024.112756
18. [18]
  SHU S, ZHANG F X, TANG R H, YAN S Y, ZHU X M, SHENG L B, KUANG D Z, FENG Y L, YU J X, JIANG W J. Syntheses, structures and antitumor activities of tri(o-bromobenzyl)tin diethyldithiocarbamate and tri(m-fluorobenzyl)tin pyrrolidine dithiocarbamate[J]. Chin. J. Struct. Chem., 2020, 39(3): 459-466
19. [19]
  LIU J, LIN Y C, LIU M, WANG S Q, LI Y X, LIU X C, TIAN L J. Synthesis, structural characterization and cytotoxic activity of triorganotin 5-(salicylideneamino)salicylates[J]. Appl. Organomet. Chem., 2019, 33(3): e4715 doi: 10.1002/aoc.4715
20. [20]
  PAUL A, KHAN R A, SHAIK G M, SHAIK J P, RAI A K, DA SILVA M F C G, POMBEIRO A J L. Anthracene appended organotin(Ⅳ) compounds: Synthesis, structure elucidation and their cytotoxicity against A549 and RBL cancer cell lines[J]. Appl. Organomet. Chem., 2023, 37(3): e7232
21. [21]
  GUL R, MUHAMMAD N, SIRAJUDDIN M, NOOR A, TUMANOV N, WOUTERS J, CHAFIK A, SOLAK K, MAVI A, SHUJAH S, ALI S, KHAN G S, QAYYUM S. Design, physicochemical confirmation, single crystal structures as well as exploration of antibacterial and anticancer potential of organotin(Ⅳ) carboxylates[J]. J. Mol. Struct., 2024, 1300: 137306 doi: 10.1016/j.molstruc.2023.137306
22. [22]
  SHI H L, MA J W, LI Q L, DU X M, MENG Z X, RU J, MA C L. Four organotin(Ⅳ) complexes derived from 2, 6-difluoro-3-(propylsulfona-mido)benzoic acid: Synthesis, structure, in vitro cytostatic activity and antifungal activity evaluation[J]. Inorg. Chim. Acta, 2023, 551: 121485 doi: 10.1016/j.ica.2023.121485
23. [23]
  ZHANG F X, KUANG D Z, WANG J Q, FENG Y L, XU Z F, CHEN Z M, ZENG R Y. Synthesis, crystal structure and quantum chemistry of the ring-form dimer tris(o-methylbenzyl)tin hydroxide[J]. Chin. J. Org. Chem., 2008, 28(8): 1457-1461
24. [24]
  CHANDRASEKHAR V, THIRUMOORTHI R. Facile, ambient temperature, double Sn—C bond cleavage: Synthesis, structure, and electrochemistry of organotin and organotellurium ferrocene carboxylates[J]. Eur. J. Inorg. Chem., 2008(29): 4578-4585
25. [25]
  ZHANG J H, ZHANG R F, MA C L, WANG D Q, WANG H Z. New organotin carboxylates derived from 6-chloro-3-pyridineacetic acid exhibiting discrete molecular, drum-like, linear polymeric and ladder structures constructed from dimeric tetraorganodistannoxane units[J]. Polyhedron, 2011, 30: 624-631 doi: 10.1016/j.poly.2010.11.035
26. [26]
  AIRAPETYAN D V, PETROSYAN V S, GRUENER S V, ZAITSEV K V, ARKHIPOV D E, KORLYUKOV A A. Disproportionation reactions within the series of coordinated monoorganostannanes[J]. J. Organomet. Chem., 2013, 747: 241-248 doi: 10.1016/j.jorganchem.2013.07.005
27. [27]
  IQBAL M, ALI S, MUHAMMAD N, PARVEZ M, LANGER P, VILLINGER A. Synthesis, characterization, crystal structures and electrochemical studies of organotin(Ⅳ) carboxylates[J]. J. Organomet. Chem., 2013, 723: 214-223 doi: 10.1016/j.jorganchem.2012.10.006
28. [28]
  HE L F, TANG W J, LUO Y Z, LIANG M S, TANG J X, WU Y X, ZHANG F X, ZHU X M. Synthesis, structure, and anticancer activity of two dialkyltin complexes constructed based on 2,2′-bipyridin-6,6′-dicarboxylic acid[J]. Chinese J. Inorg. Chem., 2025, 41(8): 1601-1609
29. [29]
  SALAS J M, QUIRÓS M, ROMERO M A, SÁNCHEZ M P, SALAS M A. Metal complexes of theophylline-7-acetic acid. Crystal structure of a nickel(Ⅱ) compound containing noncoordinated theophylline-7-acetate ion[J]. Polyhedron, 1995, 14(5): 611-616 doi: 10.1016/0277-5387(94)00279-N
30. [30]
  VIJAYANTHIMALA R, UDUPA M R. Complexes of palladium(Ⅱ) with theophylline-7-acetic acid[J]. Inorg. Chim. Acta, 1990, 175: 163-170 doi: 10.1016/S0020-1693(00)84823-9
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