Novel benzoylthiourea derivatives had differential anti-inflammatory photodynamic therapy potentials on in vitro stimulated mammalian macrophages

Abstract

Novel benzoylthioureas, N-((5-chloropyridin-2yl)carbamothioyl)benzamide, (HL¹), N-((2-chloropyridin-3yl)carbamothioyl)benzamide, (HL²), N-((5-bromopyridin-2yl)carbamothioyl)benzamide, (HL³) and N-(Naphthalene-1-yl(phenyl)carbamothioyl)benzamide, (HL⁴), were synthesized. Their characterizations were made by FT-IR,¹H NMR and ¹³C NMR spectrophotometric analysis. Single crystal X-ray diffraction measurements were conducted to determine the crystal structure of HL¹ and HL⁴. The HL¹ crystallization conditions are: in the monoclinic crystal system with P2₁/c space group, Z = 2, a = 8.118(2) Å, b = 12.056(3) Å, c = 13.753(4) Å. HL⁴crystallization conditions are: in the orthorhombic crystal system with Pbca space group, Z = 8, a = 19.597(9) Å, b = 8.270(4) Å, c = 24.299(11) Å. Investigation of photodynamic and antiinflamatory effects of these compounds revealed that they are potent adducts. Using these derivatives, mammalian macrophages were stimulated with LPS to test their anti-inflammatory activity. Based on pro-inflammatory cytokine production levels, the photodynamic anti-inflammatory activity of these adducts were found to differ. Our results showedthat benzoylthioureas can be used as potential photodynamic therapy agents to suppress the excessive inflammatory reactions encountered in autoimmune and inflammatory disorders.

Keywords: Anti-inflammatory compounds; Aroylthiouurea; Benzoylthiourea; Inflammation; Macrophages; Photodynamic therapy.