Review Article

Polymorphic Nucleic Acid Binding of Bioactive Isoquinoline Alkaloids and Their Role in Cancer

Table 1

Some physicochemical properties of isoquinoline alkaloids [15, 16, 27, 28].

PropertiesBerberinePalmatineCoralyneSanguinarine (iminium form)

Empirical formulaeC20H18O4N+C21H22O4N+C22H22O4N+
Chemical name7,8,13,13a-tetradehydro-9,10-dimethoxy-2,3-methylenedioxy berberinium7,8,13,13a-tetradehydro- 2,3,9,10-tetramethoxy- berberinium5,6,7,8,13,13a-hexadehydro-8-methyl-2,3,10,11-tetramethoxy berberiniumC20H14O4N+(13-methyl [ 1 , 3 ] benzodioxolo [5,6-c]-1,3-dioxolo[4,5-i]-phenanthridium(1+)

Crystal colourYellowCanary yellowDark yellowChloride salts are orange red

SolubilityWaterWaterEthanolSalts are soluble in water

Molecular weight (ion)336.36352.50364.42332.33

Melting point (°C)210 (chloride salt)221 (chloride salt)250–252 (chloride salt)277–280°C

Peak position of absorption spectrum (nm)230, 267, 344 and 420 (in aqueous buffer)232, 268, 344.5 and 420 (in aqueous buffer)219, 231, 300, 311 326, 360, 405, and 424 (in 30% ethanol) 219, 231, 300, 311 326, 360, 405, and 420 (in aqueous buffer)273, 327, 400 and 475 nm (in aqueous buffer of pH 5.5)

Molar extinction coefficient ( 𝜀 ) (M−1 cm−1)22,500 at 344 nm25,000 at 344 nm14,500 at 420 nm (in aqueous buffer) and 17,500 at 424 nm (30% alcohol)30,700 M−1 cm−1 at 327 nm in 0.1 N HCl

Peak position of fluorescence emission spectrumVery weak, at 530 nm ( 𝜆 e x 350 nm)Very weak, at 530 nm ( 𝜆 e x 350 nm)Strong, at 470 nm (both in aqueous and alcoholic media) ( 𝜆 e x at 424 nm)at 580 nm ( 𝜆 e x 327 or 475 nm)

Optical rotation [ 𝛼 ] D (solvent)0°(H2O)0°(H2O)0°(in H2O and 30% ethanol)0°(zero degree)

IC50 value (in mice)27.5 mg/Kg65 mg/Kg40 mg/Kg19.4 mg/Kg