Spectral studies on inclusion complexation between 3-hydroxyflavone and 2-Hydroxypropyl-β-cyclodextrin

Rajamohan Rajaram 2, Arumugam Praveena 1, Samikannu Prabu 3


3-hydroxy-2-phenylchromen-4-one (HF) is a flavonols that is formed when hypoxanthine is attached to a ribose ring (also known as a ribofuranose) via a β-N9-glycosidic bond. Cyclodextrins are able to form host-guest complexes with hydrophobic molecules given the unique nature imparted by their structure.As a result, these molecules have found a number of applications in a wide range of fields. The inclusion complex of HF with 2HP-β-CD is prepared by various synthetic method such as physical method (PM), kneading method (KM) and co-precipitation method (CP). The solid inclusion complex is characterized by UV, luminescence spectra, Fourier transform infrared (FT-IR) spectroscopy, scanning electron microscopy (SEM) and powder X-ray diffraction (XRD). The anticancer activity of the solid complex is performed against breast cancer cell line and it is noticed that there is no much better activity than the HF alone. Both the HF and its solid complex showed the poor anticancer activity against MDA MB 231 cell line. 


3-Hydroxyflavone; 2-Hydroxypropyl-β-Cyclodextrin; Inclusion Complex; XRD; Cytotoxicity

Full Text:



Wu Feng, Lin Lie, Li Xiang-Ping, et al. All-optical switchings of 3-hydroxyflavone in different solvents [J]. Chin. Phys. B, 17: 1461-1466.

Jayanti Guharay, Rupali Chaudhuri, Abhijit Chakrabarti, et al. Excited state proton transfer fluorescence of 3-hydroxyflavone in model membranes [J]. Spectrochim Acta Part A. 1997; 53 (3): 457-462.

Sudip Chaudhuri, Anwesha Banerjee, Kaushik Basu, et al. Interaction of flavonoids with red blood cell membrane lipids and proteins: Antioxidant and antihemolytic effects [J]. I.J.Biolog.Macromolec, 2007; 41 (1): 42-48.

Biswapathik Pahari, Sandipan Chakraborty, Pradeep K. Sengupta. Encapsulation of 3-hydroxyflavone in γ-cyclodextrin nanocavities: Excited state proton transfer fluorescence and molecular docking studies [J]. J.Molec.Struct, 2011; 1006 (1–3): 483–488.

Saenger W. Angew [J].Chem, Int. Ed. Engl. 1980; 19, 344.

Tabushi I, Acc Chem. Res. 1982; 15, 66.

Szejtli J, In Cyclodextrins, Szejtli J, et al. Elsevier Science Ltd.: New York, 1996;

: 5.

Jicsinszky L, Fenyvesi E, Hashimoto H, et al. Elsevier Science Ltd.: New York, 1996; 3: p 57.

Li S, Purdy, Chem WC. Rev. 1992; 92, 1457.

Eftink M R, Harrison JC, Bioorg Chem. 1981; 10: 388.

Huroda Y, Hiroshige T, Takashi S, et al. Soc. 1989; 111: 1912.

Manka JS, Lawrence DSJ, Am. Chem. Soc. 1990; 112: 2441.

Harada A, Li J, Kamachi M. Nature, 1994; 370: 126.

MacEdo OFL, Andrade GRS, Conegero LS, et al. Physicochemical study and characterization of the trimethoprim/2- hydroxypropyl- γ-cyclodextrin inclusion complex [J]. Spectrochim. Acta Part A, 2012; 86: 101–106.

Misiuk W, Jasiuk E. Study of the inclusion interaction of HP-γ-cyclodextrin with bupropion and its analytical application [J]. J. Mol. Struct, 2014; 1060: 272–279.

Muankaew C, Jansook P, Sigurcrossed HH, et al. Cyclodextrin-based telmisartan ophthalmic suspension: Formulation development for water-insoluble drugs [J]. Int. J. Pharm, 2016; 507: 21–31.

Wei Y, Zhang J, Zhou Y, et al. Characterization of and enhanced bioactivity [J]. Carbohydr. Polym, 2017; 159: 152–160.

Prado AR, Yokaichiya F, Franco MKKD, et al. Complexation of oxethazaine with 2-hydroxypropyl-β-cyclodextrin: increased drug solubility, decreased cytotoxicity and analgesia at inflamed tissues [J]. J. Pharm. Pharmacol, 2017; 69: 652–662.

Yan HH, Zhang JQ, Ren SH, et al. Experimental and computational studies of naringin/cyclodextrin inclusion complexation [J]. J. Incl. Phenom. Macrocycl. Chem, 2017; 88: 15–26.

Shityakov S, Salmas RE, Durdagi S, et al. Solubility profiles, hydration and desolvation of curcumin complexed with γ- cyclodextrin and hydroxypropyl- γ –cyclodextrin [J]. J. Mol. Struct, 2017; 1134: 91–98.

do Carmo CS, Maia C, Poejo J, et al. Microencapsulation of α-tocopherol with zein and β- cyclodextrin using spray drying for colour stability and shelf-life improvement of fruit beverages [J]. RSC Adv, 2017; 7: 32065–32075.

Mangolima CS, Moriwakib C, Satoc F, et al. Curcumin–β-cyclodextrin inclusion complex: Stability, solubility, characterization by FT-IR, FT-Raman, X-ray diffraction and photoacoustic spectroscopy, and food application [J]. Food Chem, 2014;153 (15): 361–370.

Wang X, Luo Z, Xiao Z. Preparation, characterization, and thermal stability of β- cyclodextrin/soybean lecithin inclusion complex [J]. Carbohydr. Polym, 2014; 101: 1027–1032.

Wei Y, Zhang J, Memon AH, et al. Molecular model and in vitro antioxidant activity of a water-soluble and stable phloretin/hydroxypropyl-β- cyclodextrin inclusion complex [J]. J. Mol. Liq, 2017; 236: 68–75.

Zhang CL, Liu JC, Yang WB, et al. Experimental and molecular docking investigations on the inclusion mechanism of the complex of phloridzin and hydroxypropyl-β-cyclodextrin [J]. Food Chem, 2017; 215: 124–128.

Cetin H, Ali B, Necla B, et al. Encapsulation of clove essential oil in hydroxypropyl beta-cyclodextrin for characterization, controlled release, and antioxidant activity [J]. J Ournal Food Process Preserv, 2017: 1–8.

Alonso ECP, Riccomini K, Silva LAD, et al. Development of carvedilol-cyclodextrin inclusion complexes using fluid-bed granulation: a novel solid-state complexation alternative with technological advantages [J]. J. Pharm. Pharmacol, 2016; 68: 1299–1309.

Li W, Liu X, Yang Q, et al. Preparation and characterization of inclusion complex of benzyl isothiocyanate extracted from papaya seed with β- cyclodextrin [J]. Food Chem, 2015; 184: 99–104.

Sambasevam KP, Mohamad S, Sarih NM, et al. Int. J. Mol. Sci, 2013; 14: 3671-3682.

Rajamohan R, Kothai Nayaki S, Swaminathan M, et al. 2011; 40: 803–817.

Rajamohan R, Kothai Nayaki S, Swaminathan M, et al. 2011; 21: 521–529.

Rajamohan R, Kothai Nayaki S, Swaminathan M. Spectrochim Acta Part A, 2008; 69: 371–377.

Zornoza A, Mart´ın C, anchez MS´, et al. 1998; 169: 239.

Mura P, Bettinetti GP, Manderioli A, et al. 1998; 166: 189.

DOI: http://dx.doi.org/10.24294/jacs.v1i3.980


  • There are currently no refbacks.

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.

Creative Commons License

This site is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.