Stealth Liposomes (PEGylated) Containing an Anticancer Drug Camptothecin: In Vitro Characterization and In Vivo Pharmacokinetic and Tissue Distribution Study

Numerous attempts to overcome the poor water solubility of cam ptothecin (CPT) by various nano drug delivery systems are described in various sources in the literature. However, the results of these approaches may be hampered by the incomplete separation of free CPT from the formulations, and this issue has not been investigated in detail. This study aimed to promote the solubility and continuous delivery of CPT by developing long-lasting liposomes using various weights (M.W. 2000 and 5000 Daltons) of the hydrophilic polymer polyethylene glycol (PEG). Conventional and PEGylated liposomes containing CPT were formulated via the lipid film hydration method (solvent evaporation) using a rotary flash evaporator after optimising various formulation parameters. The following physicochemical characteristics were investigated: surface morphology, particle size, encapsulation efficiency, in vitro release, and formulation stability. Different molecular weights of PEG were used to improve the encapsulation efficiency and particle size. The stealth liposomes prepared with PEG₅₀₀₀ were discrete in shape and with a higher encapsulation efficiency (83 ± 0.4%) and a prolonged rate of drug release (32.2% in 9 h) compared with conventional liposomes (64.8 ± 0.8% and 52.4%, respectively) and stealth liposomes containing PEG₂₀₀₀ (79.00 ± 0.4% and 45.3%, respectively). Furthermore, the stealth liposomes prepared with PEG₅₀₀₀ were highly stable at refrigeration temperature. Significant changes were observed using various pharmacokinetic parameters (mean residence time (MRT), half-life, elimination rate, volume of distribution, clearance, and area under the curve) of stealth liposomes containing PEG₂₀₀₀ and PEG₅₀₀₀ compared with conventional liposomes. The stealth liposomes prepared with PEG₅₀₀₀ showed promising results with a slow rate of release over a long period compared with conventional liposomes and liposomes prepared with PEG₂₀₀₀, with altered tissue distribution and pharmacokinetic parameters.     

Copper nanoparticles supported on polyethylene glycol-modified magnetic Fe3O4 nanoparticles: Its anti-human gastric cancer investigation

In that work, we have described the synthesis of novel Cu NPs decorated polyethylene glycol (PEG₂₀₀₀) coated magnetic nanoparticles (Fe₃O₄/PEG2000/Cu NPs) in an eco-friendly pathway applying Green Tea extract as reducing/stabilizing agent. The morphological and physicochemical features of the prepared nanocomposite were determined using several advanced techniques like ICP-OES, FE-SEM, EDX, atomic mapping, TEM, VSM, and XRD studies. In the antioxidant test, the IC50 of Fe₃O₄/PEG₂₀₀₀/Cu nanocomposite and BHT against DPPH free radicals were 198 and 85 µg/mL, respectively. In the cellular and molecular part of the recent study, the treated cells with Fe₃O₄/PEG₂₀₀₀/Cu nanocomposite were assessed by MTT assay for 48 h about the cytotoxicity and anti-human gastric cancer properties on normal (HUVEC) and gastric cancer cell lines i.e. NCI-N87 and MKN45. The IC50 of Fe₃O₄/PEG₂₀₀₀/Cu nanocomposite were 316 and 131 µg/mL against NCI-N87 and MKN45 cell lines, respectively. The viability of malignant gastric cell line reduced dose-dependently in the presence of Fe₃O₄/PEG₂₀₀₀/Cu nanocomposite. It seems that the anti-human gastric cancer effect of recent nanoparticles is due to their antioxidant effects.     

Vapor Pressure Osmometry and Its Applications in the Osmotic Coefficients Determination of the Aqueous Monomer Glycol and Polymer Polyethylene Glycol Solutions at Various Temperature

Based on the principle and calibration of vapor pressure osmometer and its application in the thermodynamics of the aqueous solutions, the results on aqueous solution of monomer glycol,PEG200,PEG400,PEG1500 and PEG2000 over the different concentration range at various temperatures were reported.Using a linear least-square fitting routing,the osmotic coefficients were fitted by a simple polynomial equation.It was found that the relationship between the molar osmotic coefficients (Φ） and the molar concentration(c) of the solutions are in a quite good agreement with the fitted polynomial equation at various temperatures over the different concentration range.The experimental results also show that over the studied concentration range and at various temperatures,the concentration dependence of the molar osmotic coefficients of the aqueous solution systems with the solutes of PEG200,PEG400,PEG1500 and PEG2000 are totally presented in a rising tend,and their temperature dependence of the osmotic coefficients of the aqueous solution systems of the molar concentration exhibits their own regularities,respectively.The aqueous glycol solution system exhibits the properties of the dilute solution.     

Structural Analysis and Properties of Organic-Inorganic Hybrid Ionic Conductor Prepared by Sol-Gel Process

Organic-inorganic hybrid lithium ion conductors were prepared by the sol-gel process. The hybrid ion conductor will be used as the electrolyte for Li based high-energy density batteries. The hybrid ion conductor was prepared from a mixture of tetramethyl orthosilicate (TMOS), polyethylene glycol 200 (PEG₂₀₀), lithium perchlorate (LiClO₄) and water. A wet gel was prepared at room temperature. The gels dried at 80°C under vacuum did not contain water. The dried hybrid ion conductor gel had homogeneity and high transparency. Ionic conductivity of the hybrid sample was measured by the complex impedance method and it increased with increasing PEG₂₀₀ content. The dried hybrid gel that contained no LiClO₄ did not show ion conduction. Conductivity on the order of 10^–5 S·cm^–1 at room temperature was obtained. Structural characterization was done by Fourier Transform Infrared Spectra (FTIR) and NMR measurement of ¹³C and ¹H, and the thermal stability and glass transition properties were studied by DSC. Glass transition temperature decreased with increasing PEG₂₀₀ content and increased with increasing [Li]/[O] ratio (the oxygen considered is from the polyethylene glycol). Existence of the Si–O–(C₂H₄O) _n –bond and the C–OH bond in the framework of the organic and inorganic phases was confirmed. TMOS and PEG₂₀₀ were hydrolyzed and condensed. The organic and inorganic phases were chemically bonded and the microstructure of the hybrid matrix was shaped as comb. The comb shape leads to high ionic conduction.     

Visible‐Light‐Induced Annihilation of Tumor Cells with Platinum–Porphyrin Conjugates

Despite the extensive use of porphyrins in photodynamic therapy (PDT), tetraplatinated porphyrins have so far not been studied for their anticancer properties. Herein, we report the synthesis of such novel platinum–porphyrin conjugates as well as their photophysical characterization and in vitro light‐induced anticancer properties. These conjugates showed only minor cytotoxicity in the dark, but IC₅₀ values down to 19 nM upon irradiation with light at 420 nm.These values correspond to an excellent phototoxic index (PI=IC₅₀ in the dark/IC₅₀ in light), which reached 5000 in a cisplatin‐resistant cell line. After incubation with HeLa cells, nuclear Pt concentrations were 30 times higher than with cisplatin. All of these favorable characteristics imply that tetraplatinated porphyrin complexes are worthy of exploration as novel PDT anticancer agents in vivo.     

Synthesis,characterization and cytotoxicity of Pt(II), Pd(II), Cu(II) and Zn(II) complexes with 4’‐substituted terpyridine

Eight novel Pt(II), Pd(II), Cu(II) and Zn(II) complexes with 4’‐substituted terpyridine were synthesized and characterized by elemental analysis, UV, IR, NMR, electron paramagnetic resonance, high‐resolution mass spectrometry and molar conductivity measurements. The cytotoxicity of these complexes against HL‐60, BGC‐823, KB and Bel‐7402 cell lines was evaluated by MTT assay. All the complexes displayed cytotoxicity with low IC₅₀ values (<20 μm ) and showed selectivity. Complexes 3 , 5 , 7 and 8 exerted 9‐, 5‐, 12‐ and 7‐fold higher cytotoxicity than cisplatin against Bel‐7402 cell line. The cytotoxicity of complexes 3 , 5 , 6 , 7 and 8 was higher than that of cisplatin against BGC‐823 cell line. Complexes 3 , 7 and 8 showed similar cytotoxicity to cisplatin against KB cell line. Complex 7 exhibited higher cytotoxicity than cisplatin against HL‐60 cell line. Among these complexes, complex 7 demonstrated the highest in vitro cytotoxicity, with IC₅₀ values of 1.62, 3.59, 2.28 and 0.63 μm against HL‐60, BGC‐823, Bel‐7402 and KB cells lines, respectively. The results suggest that the cytotoxicity of these complexes is related to the nature of the terminal group of the ligand, the metal center and the leaving groups. Copyright © 2013 John Wiley & Sons, Ltd.     

Thermotropic copolyamides from polyethyleneglycol bis(4-carboxyphenyl)ethers with different oxyethylene units

Copolymerizations of polyethyleneglycol bis(4-carboxyphenyl)ethers (PEG_n) with different n values were found to significantly lower the anisotropic transition temperature (T_m) of the copolymers produced, and the thermotropic copolyamides of thermally more stable nematic phases were obtained. The effect was investigated in terms of PEG_m/PEG_n molar ratios, the number of oxyethylene units, and the even—odd character of the flexible segment. Several modes of copolymerization were carried out to investigate the effect of monomer (PEG_n sequence on T_m. By these copolymerizations thermally stable copolyamides even from p-phenylenic diamines such as methyl-p-phenylenediamine and p-phenylenediamine were obtained. © 1993 John Wiley & Sons, Inc.     

Modulated Differential Scanning Calorimetry

The reproducibility and reliability of the TA Instruments Modulated Differential Scanning Calorimeter (MDSC) was tested over a range of conditions. The equipment base line was found to be fairly constant with a very small fluctuation (10 W), which means a 0.1 % fluctuation on the scale of a normal polymer MDSC curve. The excellent stability of the base line and the reasonable reproducibility of the curves (5%) suggest that frequent calibration is not required.The heat capacities calculated from the modulated response to the variable temperature depend on the frequency for a given cell constant. The heat capacity cell constant is a unique function of the modulation frequency:k _c =K _c ^o p/(p–6.3) wherep is the time of the periodicity expressed in seconds and K _c ^o is the heat capacity cell constant measured on a standard material and reduced to zero frequency. The cell constants depend on the flow rate of the helium according to:K(He)=K ^o(1.298–0.004424He+1.438·10^–5 He ²) whereHe is the flow rate of helium in ml min^–1 andK ^o represents a constant at 100 cm³ min^–1. There is a strong dependence of cell constant on the flow rate ranges from 10 to 80 cm³ min^–1, while above this rate (up to 135 ml min^–1) the cell constant approaches a plateau.     

Novel organotin antibacterial and anticancer drugs

From the reaction of 6-(p-methoxyphenyl) fulvene (1a), 6-(p-N,N-dimethylaminophenyl) fulvene (1b) and 6-(3,4-dimethoxyphenyl) fulvene (1c) with LiBEt₃H, lithiated cyclopentadienide intermediates (2a–c) were synthesised. These intermediates were then transmetallated to tin with SnCl₄ to yield tetra-substituted bis(cyclopentadienyl)tin dichloride complexes (3a–c). Further reaction with tin tetrachloride yielded the benzyl-substituted derivatives bis-[(p-methoxybenzyl)cyclopentadienyl] tin(IV) dichloride (4a), bis-[(p-N,N-dimethylaminobenzyl)cyclopentadienyl] tin(IV) dichloride (4b), and bis-[(3,4-dimethoxyphenyl)cyclopentadienyl] tin(IV) dichloride (4c). Preliminary antibacterial tests were carried out using the Kirby–Bauer disk-diffusion method, in which 4a–c showed little to no activity against the Gram-negative bacterium Escherichia coli, but medium activity against Gram-positive bacteria (MRSA, MSSA). In addition, the organotin complexes had their cytotoxicity investigated through preliminary in vitro testing on the LLC-PK (pig kidney epithelial) cell line in order to determine their IC50 values. Compound 4c showed no cytotoxic activity, while 4a and 4b were found to have IC50 values of 15 and 205 μM, respectively.     

Synthesis and Cytotoxicity of Derivatives of Di(3-indolyl) Selenide

A method has been developed for the synthesis of di(3-indolyl) selenides. From indole and SeO₂. N-Alkyl derivatives of di(3-indolyl) selenide have been obtained in the two-phase system alkyl halide–solid K₂CO₃ (or KOH)–18-crown-6–toluene. It was discovered that N-unsubstituted di(3-indolyl) selenides possess high cytotoxicity on HT-1080 and MG-22A tumor cell lines.     

Synthesis of Novel Porphyrin Derivatives and Their Cytotoxic Activities against A431 Cells

Three novel porphyrins, including two Schiff‐bases porphyrins, 5,10,15‐triphenyl‐20‐[4‐(2‐(4‐formyl)phenoxy)ethoxy]phenyl porphyrin ( H₂Pp ( 1 )), 5,10,15‐triphenyl‐20‐[4‐(2‐(4‐hydroxyimino)phenoxy)ethoxy]phenyl porphyrin ( H₂Pp ( 2 )) and 5,10,15‐triphenyl‐20‐[4‐(2‐(4‐m‐hydroxyanilinodeneformyl)phenoxy)ethoxy]phenyl porphyrin ( H₂Pp ( 3 )), as well as three metalloporphyrins ( CuPp ( 1a ), ZnPp ( 1b ), and CoPp ( 1c )) of porphyrin H₂Pp ( 1 ) were synthesized. Their molecular structures were characterized by ¹H‐NMR, MS, UV/VIS, and FT‐IR spectra. Furthermore, they were evaluated by their cytotoxicities against human epidermal squamous cell carcinoma cell (A431) and normal human horn cells (HaCaT) in vitro with MTT assay. Interestingly, these porphyrins and metalloporphyrins, which had a negligible cytotoxicity to HaCaT cells, showed highly cytotoxicity against A431 cells with IC₅₀ values in the range of 6.6–9.8 μM , and metalloporphyrins exhibited higher cytotoxicity than that of metal‐free porphyrins.     

Synthesis,characterization and biological evaluation of some novel sulfonylthiosemicarbazides

Abstract

A series of thiosemicarbazides were synthesized and structurally characterized by spectroscopic techniques (NMR, FT-IR) besides elemental analysis. These compounds were evaluated for their cytotoxicity against human breast cancer cell line MCF7 and prostate cancer cell line PC3 and nonmalignant fibroblast L929 cell line by MTT assay. Among the compounds, N-[2-(4-chlorophenyl)ethyl]-2-[(4-methylphenyl)sulfonyl]hydrazinecarbothioamide (3d) and 2-[(4-methylphenyl)sulfonyl]-N-[4-(trifluoromethoxy)phenyl]hydrazinecarbothioamide (3f) were found to display significant cytotoxicity with IC₅₀ of 13.87?μM (against PC3 cell line) and 1.47?μM (against MCF7 cell line), respectively. These compounds were non-cytotoxic to normal cell line with IC₅₀>100?μM. Western blotting studies demonstrated that compound 3f induced apoptosis and caused cell death in the MCF7 and PC3 cell lines via an increase in Bax protein expression and a slight decrease in Bcl-2 protein expression. The gene expression ratio Bax/Bcl-2 showed the induction of mitochondrial apoptosis in cancer cell lines. All of synthesized compounds have also been tested for antioxidant activity and all compounds achieved strong inhibition of the DPPH radical. These findings showed that compound 3f, displays potential to be further explored in the development of new anticancer agents.     

Synthesis and in vitro cytotoxicity of platinum(II) complexes with chiral N-monosubstituted 1,2-cyclohexyldiamine derivatives as the carrier groups

Eight platinum(II) complexes with the new chiral ligands, (1R,2R)-N ¹-(pyridine-2-ylmethyl) cyclohexane-1,2-diamine (R) or (1S,2S)-N ¹-(pyridine-2-ylmethyl) cyclohexane-1,2-diamine (S) as the carrier groups were designed, synthesized, and spectrally characterized. All platinum(II) complexes showed much better aqueous solubility than cisplatin and oxaliplatin. In vitro cytotoxicity of the compounds against human HepG-2, MCF-7, A549, and HCT-116 cell lines was evaluated. Results indicate that all compounds with R as the carrier group showed cytotoxicity against HCT-116, A549, and MCF-7 cell lines; however, all compounds with S as carrier group exhibited disappointing cytotoxicity against tested cell lines. Compound R2, bearing ClCH₂COO^- as leaving group, exhibited better cytotoxicity than that of carboplatin against A549 and MCF-7 cell lines and also showed close activity to oxaliplatin against HCT-116 cell line.     

Development and qualification of an LC–MS/MS method for investigating the biological implications of micelle entrapped paclitaxel in cell culture and rats

Paclitaxel is a front‐line antineoplastic drug used in chemotherapeutic modalities for treatment of various types of malignancies. However, its efficacy is limited by dose‐related toxicities. In this study, we have explored two important biological aspects of entrapping paclitaxel in PEG₂₀₀₀‐DSPE micelles. First, we evaluated the impact of this micellar delivery system on P‐glycoprotein (P‐gp)–paclitaxel interaction, and we investigated differences in plasma pharmacokinetics of free and micelle‐entrapped paclitaxel. For quantification of paclitaxel, an LC–MS/MS method was developed. Paclitaxel was extracted from samples using a simple one‐step protein precipitation. Chromatographic conditions included a C₁₈ column with a mobile phase consisting of 0.1% formic acid in acetonitrile–water (60:40, v /v) pumped at 1 mL/min. The lower limit of quantitation in both plasma and cell lysate was 1.0 ng/mL. The quantitative linear range was 1–1000 ng/mL. In addition, P‐gp efflux studies on free and micellar paclitaxel showed the proficiency of PEG₂₀₀₀‐DSPE micelles in evading P‐gp‐mediated efflux, thus increasing paclitaxel uptake. Furthermore, the micellar paclitaxel levels were maintained in the body for longer time as compared with taxol, which is desirable for increasing the efficacy of paclitaxel in cancer treatment.     

A novel fluorescein-porphyrinatozinc(II) hybrid: synthesis and its supramolecular self-assembly with imidazolyl-linked porphyrinatomanganese(III) by coordinative bonding

A novel fluorescein–porphyrinatozinc(II) hybrid, Zn(Fl–PPTPP), was synthesized and characterized by u.v.–vis., i.r., ¹H-n.m.r, ESMS and elemental analyses. The supramolecular self-assembly of Zn(Fl–PPTPP) with an imidazolyl-linked porphyrinatomanganese(III), Mn^(III)(p-ImBPTPP)Cl, complex has been studied by fluorescence spectroscopic titration, VPO measurements and ESMS, which indicates that the formation of the Zn(Fl–PPTPP)–Mn^(III)(p-ImBPTPP)Cl. supramolecular complex is driven by coordinative bonding formed by the coordination of imidazolyl group in Mn^(III)(p-ImBPTPP)Cl to Zn(II) in Zn(Fl–PPTPP). The association constant of the supramolecular complex was calculated from the fluorescence spectroscopic titration data. It was found that the conformation of the Zn(Fl–PPTPP)–Mn^(III)(p-ImBPTPP)Cl supramolecular complex, the steric hindrance and the electronic effect of the fluorescein group linked to porphyrin through a flexible long alkoxy chain are all acting on the association constant of the Zn(Fl–PPTPP)–Mn^(III)(p-ImBPTPP)Cl supramolecular complex. It seems that the steric hindrance and the electronic effect of the fluorescein group are the primary factors effecting the association constant of Zn(Fl–PPTPP)–Mn^(III)(p-ImBPTPP)Cl supramolecular complex, especially the electronic effect of the fluorescein group, which is the reason for the association constant of Zn(Fl–PPTPP)–Mn^(III)(p-ImBPTPP)Cl being smaller than that of ZnTPP–Mn^(III)(p-ImBPTPP)Cl.     

The synthesis and photoactivated cytotoxicity of 2-methyl-4-oxo-3-prop-2-yn-1-ylcyclopent-2-en-1-yl-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate conjugated with α-terthienyl derivatives

The synthesis of one pyrethroid insecticide [2-methyl-4-oxo-3-prop-2-yn-1-ylcyclopent-2-en-1-yl-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate (Abbrev. JZ) (Fig. 1)] conjugated with a series of α-terthienyl derivatives (2–8) (Fig. 1) by palladium/copper-catalyzed cross-coupling reaction is presented here for evaluating the photoactivated cytotoxicity. The photoactivated cytotoxicity on Spodoptera litura (SL) cell line was detected by MTT assay. The inhibitory activity of all the conjugates was enhanced in the irradiation condition, compared with that of JZ. The IC₅₀ values of the most effective compound 9 (Fig. 1) treated with irradiation were 11.60 μg mL⁻¹ at 24 h and 8.93 μg mL⁻¹ at 48 h, respectively. Generation of intracellular reactive oxygen species (ROS) and change of mitochondrial transmembrane potential (MMP) on SL cells treated with compound 9 were used for the further photoactivated study. A summary of these experiments on compound 9 demonstrated the notable ROS generation and dramatic MMP decrease when irradiated with UVA light. The results also represented statistically significant difference between dark and irradiation treatment of compound 9. However, in control and JZ groups, the effects were not statistically different. It was proved that our prepared compounds were ideal candidates for new photoactivated pyrethroid insecticides.     

Formulation of Piperine–Chitosan-Coated Liposomes: Characterization and In Vitro Cytotoxic Evaluation

The present research work is designed to prepare and evaluate piperine liposomes and piperine–chitosan-coated liposomes for oral delivery. Piperine (PPN) is a water-insoluble bioactive compound used for different diseases. The prepared formulations were evaluated for physicochemical study, mucoadhesive study, permeation study and in vitro cytotoxic study using the MCF7 breast cancer cell line. Piperine-loaded liposomes (PLF) were prepared by the thin-film evaporation method. The selected liposomes were coated with chitosan (PLFC) by electrostatic deposition to enhance the mucoadhesive property and in vitro therapeutic efficacy. Based on the findings of the study, the prepared PPN liposomes (PLF3) and chitosan coated PPN liposomes (PLF3C1) showed a nanometric size range of 165.7 ± 7.4 to 243.4 ± 7.5, a narrow polydispersity index (>0.3) and zeta potential (−7.1 to 29.8 mV). The average encapsulation efficiency was found to be between 60 and 80% for all prepared formulations. The drug release and permeation study profile showed biphasic release behavior and enhanced PPN permeation. The in vitro antioxidant study results showed a comparable antioxidant activity with pure PPN. The anticancer study depicted that the cell viability assay of tested PLF3C2 has significantly (p < 0.001)) reduced the IC₅₀ when compared with pure PPN. The study revealed that oral chitosan-coated liposomes are a promising delivery system for the PPN and can increase the therapeutic efficacy against the breast cancer cell line.     

pH‐sensitive liposome retaining Fe‐porphyrin as SOD mimic for novel anticancer drug delivery system

In this article the novel design of an anticancer drug delivery system is reported based on a pH‐sensitive liposome retaining the Fe‐porphyrin as a superoxide dismutase(SOD) mimic. The liposomes contained cationic/anionic lipid combinations and were composed of Fe‐porphyrin, L ‐α‐phosphatidylcholine (DMPC), dimethylditetradecylammonium bromide (DTDAB), sodispdum oleate (OA_Na), and Tween‐80. The size of the liposome was approximately 30 nm. The EC₅₀ value (the effective concentration of compound required to produce a 50% lethal dose against cells) of the liposome was found to be significantly smaller than that of cisplatin as the control drug, suggesting that the liposome showed a high cytotoxicity toward the cancer cells. This is due to the fact that the pH‐sensitive liposome rapidly corresponds to the acidic environments of the endosomes and is unstable, and the Fe‐porphyrin is delivered into the cytosol. This result suggests that O may be useful as a target molecule to induce the selective death of cancer cells and that a pH‐sensitive liposome retaining Fe‐porphyrin as an SOD mimic is a new class of anticancer agent. Copyright © 2006 John Wiley & Sons, Ltd.     

Synthesis of novel chlorophyll a derivatives bearing glucose moieties and estimation of their photocytotoxic activity

A series of chlorophyll a derivatives bearing glucose moieties linked to the porphyrin macrocycle via ester bonds were synthesized. The dark cytotoxicity and photocytotoxicity of new chlorin-glucose conjugates were competitively evaluated in comparison with those of structurally similar chlorin-galactose derivatives synthesized previously. It was revealed that the introduction of the glucose moiety into the molecule of chlorophyll a derivative facilitates a decrease in the dark cytotoxicity relative to chlorin-galactose conjugates.

     

Exploring Supramolecular Self‐Assembly of Tetraarylporphyrins by Halogen Bonding: Crystal Engineering with Diversely Functionalized Six‐Coordinate Tin(L)2–Porphyrin Tectons

This study targets the construction of porphyrin assemblies directed by halogen bonds, by utilizing a series of purposely synthesized Sn(axial ligand)₂–(5,10,15,20‐tetraarylporphyrin) [Sn(L)₂‐TArP] complexes as building units. The porphyrin moiety and the axial ligands in these compounds contain different combinations of complimentary molecular recognition functions. The former bears p‐iodophenyl, p‐bromophenyl, 4′‐pyridyl, or 3′‐pyridyl substituents at the meso positions of the porphyrin ring. The latter comprises either a carboxylate or hydroxy anchor for attachment to the porphyrin‐inserted tin ion and a pyridyl‐, benzotriazole‐, or halophenyl‐type aromatic residue as the potential binding site. The various complexes were structurally analyzed by single‐crystal X‐ray diffraction, accompanied by computational modeling evaluations. Halogen‐bonding interactions between the lateral aryl substituents of one unit of the porphyrin complex and the axial ligands of neighboring moieties was successfully expressed in several of the resulting samples. Their occurrence is affected by structural (for example, specific geometry of the six‐coordinate complexes) and electronic effects (for example, charge densities and electrostatic potentials). The shortest intermolecular I???N halogen‐bonding distance of 2.991 Å was observed between iodophenyl (porphyrin) and benzotriazole (axial ligand) moieties. Manifestation of halogen bonds in these relatively bulky compounds without further activation of the halophenyl donor groups by electron‐withdrawing substituents is particularly remarkable.