Effect of proton ion concentration on the supramolecular interaction between phenoxazine and ?-cyclodextrin

被引:1
|
作者
Rajamohan, Rajaram [1 ]
Lee, Yong Rok [1 ]
Nayaki, Sundarrajulu Kothai [2 ]
Swaminathan, Meenakshisundaram [3 ]
Prabu, Samikannu [4 ]
Murugavel, Kuppusamy [5 ]
机构
[1] Yeungnam Univ, Sch Chem Engn, Organ Mat Synth Lab, Gyongsan 38541, South Korea
[2] Annamalai Univ, Dept Chem, Annamalainagar 608002, India
[3] Kalasalingam Acad Res & Educ, Int Res Ctr, Dept Chem, Nanomat Lab, Krishnankoil 626126, India
[4] Ariel Univ, Dept Chem Sci, IL-40700 Ariel, Israel
[5] Govt Arts Coll, PG & Res Dept Chem, Chidambaram 608102, India
关键词
Phenoxazine; -Cyclodextrin; Inclusion complex; Effect of pH; Molecular docking; BETA-CYCLODEXTRIN; INCLUSION COMPLEX; DISSOLUTION;
D O I
10.1016/j.cjac.2023.100229
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
In aqueous and /3-cyclodextrin ( /3-CD) media, the spectral characteristics of phenoxazine (POZ) have been in-vestigated by means of absorption, steady-state, and time-resolved fluorescence techniques. The stoichiometric ratio of the mono-cationic and neutral forms of POZ in the /3-CD medium is found to be 1:1. Inclusion complexes of POZ with /3-CD has been confirmed in the solid state by the analysis of characterization techniques, such as Fourier transfer infrared spectroscopy (FT-IR), and proton nuclear magnetic resonance spectroscopy, POZ has a significant difference in the ground and excited-state pKa values in aqueous and /3-CD media. As a result, the amino group of the molecule, POZ is affected by the complexation process, i.e., it lies within the cavity of /3-CD. It is clear from the shape and dimensions of /3-CD that the POZ molecule cannot fit completely inside the cavity. As a result, 2POZ's overall height is 10.6 angstrom, while /3-CD's is just 7.8 angstrom. As per the discussion, the structure of the 1:1 complex has also been proposed.
引用
收藏
页数:12
相关论文
共 28 条
  • [1] Characterization of beta-cyclodextrin inclusion complexes containing an essential oil component
    Abarca, Romina L.
    Rodriguez, Francisco J.
    Guarda, Abel
    Galotto, Maria J.
    Bruna, Julio E.
    [J]. FOOD CHEMISTRY, 2016, 196 : 968 - 975
  • [2] Ariga K., 2006, Supramolecular Chemistry-Fundamentals and Applications
  • [3] Atwood J. L., 1996, Comprehensive Supramolecular Chemistry, P11
  • [4] Naftopidil-fumaric acid interaction in a solid dispersion system: Improving the dissolution rate and oral absorption of naftopidil in rats
    Choi, Jin-Seok
    Byeon, Jong Chan
    Park, Jeong-Sook
    [J]. MATERIALS SCIENCE & ENGINEERING C-MATERIALS FOR BIOLOGICAL APPLICATIONS, 2019, 95 : 264 - 274
  • [5] ANALYTICAL MOLECULAR-SURFACE CALCULATION
    CONNOLLY, ML
    [J]. JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1983, 16 (OCT) : 548 - 558
  • [6] SOLVENT-ACCESSIBLE SURFACES OF PROTEINS AND NUCLEIC-ACIDS
    CONNOLLY, ML
    [J]. SCIENCE, 1983, 221 (4612) : 709 - 713
  • [7] Cyclodextrins and their uses: a review
    Del Valle, EMM
    [J]. PROCESS BIOCHEMISTRY, 2004, 39 (09) : 1033 - 1046
  • [8] Duhovny D, 2002, EFFICIENT UNBOUND DO, V185, P2452
  • [9] Enhancement of ibuprofen dissolution via wet granulation with β-cyclodextrin
    Ghorab, MK
    Adeyeye, MC
    [J]. PHARMACEUTICAL DEVELOPMENT AND TECHNOLOGY, 2001, 6 (03) : 305 - 314
  • [10] Heather EG, 2013, J INCL PHENOM MACRO, V77, P269