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Interfacial and spectroscopic behavior of phenothiazine drug/bile salt mixture in urea solution

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Abstract

Bile salts are bio-surfactant molecules, anionic in nature, and show an energetic character in cholesterol and lipid solubilization. These amphiphiles are also used as a drug carrier. Being anionic they can interact strongly with other cationic amphiphiles. Keeping in mind this fact, we have investigated the interfacial and spectroscopic performance of cationic phenothiazine drug with bile salt in the nonattendance and attendance 250 mM urea. Surface tension and absorbance (UV-visible spectroscopy) experiments have been performed to elucidate the nature of interactions. The composition and interaction parameters at the interface or surface were computed by using the Rosen theory of mixed monolayer. The other surface parameters were computed by adopting Gibbs adsorption isotherm. Benesi-Hildebrand (B–H) model was utilized to evaluate the binding constant.

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References

  • Armstrong MJ, Carey MC (1982) The Hydrophobic-hydrophilic balance of bile salts. inverse correlation between reverse-phase high performance liquid chromatographic mobilities and micellar cholesterol-solubilizing capacities. J Lipid Res 23(1):70–80

    Article  CAS  PubMed  Google Scholar 

  • Attwood D, Florence AT (1983) Surfactant systems. Springer, Netherlands, Dordrecht

    Book  Google Scholar 

  • Attwood David, Waigh Roger, Blundell Ross, Bloor Debra, Thévand André, Boitard Elizabeth, Dubès Jean-Paul, Tachoire Henri (1994) 1H And13C NMR Studies of the Self-association of chlorpromazine hydrochloride in aqueous solution. Magn Reson Chem 32(8):468–72

    Article  CAS  Google Scholar 

  • Azum Naved, Rub Malik Abdul, Asiri Abdullah M (2017) Interaction of Triblock-copolymer with cationic gemini and conventional surfactants: a physicochemical study. J Dispers Sci Technol 38(12):1785–91

    Article  CAS  Google Scholar 

  • Azum Naved, Rub Malik Abdul, Asiri Abdullah M (2018) Interaction of antipsychotic drug with novel surfactants: micellization and binding studies. Chinese J Chem Eng 26(3):566–73

    Article  CAS  Google Scholar 

  • Azum Naved, Rub Malik Abdul, Asiri Abdullah M (2019) Bile Salt-bile salt interaction in mixed monolayer and mixed micelle formation. J Chem Thermodynam 128:406–14

    Article  CAS  Google Scholar 

  • Azum Naved, Rub Malik Abdul, Asiri Abdullah M (2020) Aggregation behavior of antipsychotic drug under the influence of bile salt in aqueous/urea solution. J Oleo Sci 69(4):327–35

    Article  CAS  PubMed  Google Scholar 

  • Benesi HA, Hildebrand JH (1949) A Spectrophotometric Investigation of the Interaction of Iodine with Aromatic Hydrocarbons. Journal of the American Chemical Society 71(8):2703–7

    Article  CAS  Google Scholar 

  • Camille, Wermuth, Aldous David, Rabiosson Pierre, and Rognan Didier. 2015. The Practice of Medicinal Chemistry. 4th ed. Academic press.

  • Cheng Chuan-Jie, Bai Xiong-Xiong, Fan Wu-Qin, Hai-Ming Wu, Shen Liang, Huang Qing-Hua, Yuan-Ming Tu (2014) Synthesis of a photoactive gemini surfactant and its use in aget atrp miniemulsion polymerisation and UV curing. Chem Papers 68(1):1791–98

    Article  Google Scholar 

  • de Castro Baltazar, Gameiro Paula, Guimarães Carla, Lima José L. F, Reis Salette (2001) Study of partition of nitrazepam in bile salt micelles and the role of lecithin. J Pharma Biomed Anal 24(4):595–602

    Article  Google Scholar 

  • du Noüy P, Lecomte. (1925) An interfacial tensiometer for universal USE. J General Physiol 7(5):625–31

    Article  Google Scholar 

  • Dudley, Katharine, Xiaomeng Liu, and Saskia De Haan. 2017. “Chlorpromazine Dose for People with Schizophrenia.” Cochrane Database of Systematic Reviews.

  • Garidel Patrick, Hildebrand Annegret, Knauf Katja, Blume Alfred (2007) Membranolytic activity of bile salts: influence of biological membrane properties and composition. Molecules 12(10):2292–2326

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Ghosh Soumen, Chakraborty Tanushree (2007) Mixed micelle formation among anionic gemini surfactant (212) and its monomer (SDMA) with conventional surfactants (C 12 E 5 and C 12 E 8) in brine solution at PH 11. J Phys Chem B 111(28):8080–88

    Article  CAS  PubMed  Google Scholar 

  • Gupta Saurabh Kumar, Sharma Ashima, Tapadia Kavita (2020) A convenient nanodrop spectrophotometric approach to determine cationic surfactant tetraoctylammonium bromide (toab) in environmental and biological samples. Chem Papers 74(6):1791–98

    Article  CAS  Google Scholar 

  • Hofmann AF (1999) Bile acids in hepatobiliary disease. Kluwer Academic Publishers, Boston

    Google Scholar 

  • Israelachvili Jacob (2011) Intermolecular and surface forces. Elsevier

    Google Scholar 

  • Israelachvili Jacob N, John Mitchell D, Ninham Barry W (1976) Theory of self-assembly of hydrocarbon amphiphiles into micelles and bilayers. J Chem Soc, Faraday Trans 2(72):1525

    Article  Google Scholar 

  • Kronberg Bengt, Holmberg Krister, Lindman Björn (2014) Surface chemistry of surfactants and polymers. John Wiley & Sons Ltd, Chichester, UK

    Book  Google Scholar 

  • Kumar Dileep, Rub Malik Abdul (2019) Kinetic and mechanistic investigations of [Zn(II)-Trp]+ and ninhydrin in aqueous and cationic CTAB surfactant. J Phys Org Chem 32(11):e3997

    Article  CAS  Google Scholar 

  • Kumar Dileep, Rub Malik Abdul (2019) Kinetic study of ninhydrin with chromium (III)-glycylleucine in aqueous–alkanediyl-α, ω-bis (Dimethylcetylammonium Bromide) gemini surfactants. J Phys Org Chem 32(7):e3946

    Article  Google Scholar 

  • Kumar Dileep, Azum Naved, Rub Malik Abdul, Asiri Abdullah M (2018) Aggregation behavior of sodium salt of ibuprofen with conventional and gemini surfactant. J Mol Liquids 262:86–96

    Article  CAS  Google Scholar 

  • Kumar Dileep, Rub Malik Abdul, Azum Naved, Asiri Abdullah M (2018) Mixed micellization study of ibuprofen (Sodium Salt) and cationic surfactant (Conventional as well as Gemini). J Phys Org Chem 31(1):e3730

    Article  Google Scholar 

  • Liu Jianfei, Wang Yuru, Li Huifang (2020) Synergistic solubilization of phenanthrene by mixed micelles composed of biosurfactants and a conventional non-ionic surfactant. Molecules 25(18):4327

    Article  CAS  PubMed Central  Google Scholar 

  • Malik Nisar Ahmad (2016) Solubilization and interaction studies of bile salts with surfactants and drugs: a review. Appl Biochem Biotechnol 179(2):179–201

    Article  CAS  PubMed  Google Scholar 

  • Mestri Rohan S, Pratap Amit P, Panchal Khushboo H, Gamot Komal, Datir Kirti A (2020) Synthesis of cleavable silicone surfactant for water-repellent application. Chem Papers 74(5):1407–16

    Article  CAS  Google Scholar 

  • Nair Padmanabhan P, Kritchevsky David (eds) (1971) The bile acids chemistry, physiology, and metabolism. Springer, US, Boston, MA

    Google Scholar 

  • Ninomiya, Ryoko, Keisuke Matsuoka, and Yoshikiyo Moroi. 2003. “Micelle Formation of Sodium Chenodeoxycholate and Solubilization into the Micelles: Comparison with Other Unconjugated Bile Salts.” Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids 1634(3):116–25.

  • Rakowska Joanna, Prochaska Krystyna, Twardochleb Bożena, Rojewska Monika, Porycka Bożenna, Jaszkiewicz Anna (2014) Selection of surfactants as main components of ecological wetting agent for effective extinguishing of forest and peat-bog fires. Chem0 Papers 68(6):3389–97

    Google Scholar 

  • Reshetnyak Vasiliy Ivanovich (2013) Physiological and molecular biochemical mechanisms of bile formation. World J Gastroenterol 19(42):7341

    Article  PubMed  PubMed Central  Google Scholar 

  • Roda A, Hofmann AF, Mysels KJ (1983) The Influence of bile salt structure on self-association in aqueous solutions. J Biol Chem 258(10):6362–70

    Article  CAS  PubMed  Google Scholar 

  • Rosen Milton J (2004) Surfactants and interfacial phenomena. John Wiley & Sons Inc, Hoboken, NJ, USA

    Book  Google Scholar 

  • Rosen Milton J, Aronson Seymour (1981) Standard free energies of adsorption of surfactants at the aqueous solution/air interface from surface tension data in the vicinity of the critical micelle concentration. Coll Surf 3(3):201–8

    Article  CAS  Google Scholar 

  • Rub Malik Abdul, Azum Naved, Khan Farah, Asiri Abdullah M (2017) Surface, micellar, and thermodynamic properties of antidepressant drug nortriptyline hydrochloride with TX-114 in aqueous/Urea solutions. J Phys Org Chem 30(10):e3676

    Article  Google Scholar 

  • Rub Abdul, Malik Naved Azum, Asiri Abdullah M (2017) Binary mixtures of sodium salt of ibuprofen and selected bile salts: interface, micellar, thermodynamic, and spectroscopic study. J Chem Eng Data 62(10):3216–28

    Article  Google Scholar 

  • Rub Malik Abdul, Azum Naved, Khan Farah, Asiri Abdullah M (2018) Aggregation of sodium salt of ibuprofen and sodium taurocholate mixture in different media: a tensiometry and fluorometry study. J Chem Thermodynam 121:199–210

    Article  Google Scholar 

  • Schwenke KD (1976) Charles tanford: the hydrophobic effect: formation of micelles and biological membranes. 200 seiten, zahlreiche Abb. Und Tab., John Wiley & Sons, New York, London, Sydney, Toronto 1973. Preis: 7,90 £. Food / Nahrung 20(4):449–449

    Article  Google Scholar 

  • Sharma VK, Yadav OP, Singh J (1996) Physicochemical studies of aqueous sodium dodecyl sulphate solutions in pyridine and isomeric picolines. Coll Surf A: Physicochem Eng Aspect 110(1):23–35

    Article  CAS  Google Scholar 

  • Shi Zhentian, Chen Jiajun, Yin Xue (2013) Effect of Anionic–nonionic-mixed surfactant micelles on solubilization of PAHs. J Air Waste Manag Assoc 63(6):694–701

    Article  CAS  PubMed  Google Scholar 

  • Sugihara, Gohsuke, Ayaki Miyazono, Shigemi Nagadome, Tatsuo Oida, Yoshiyuki Hayashi, and Jeong-Soo ko. 2003. “Adsorption and Micelle Formation of Mixed Surfactant Systems in Water II: A Combination of Cationic Gemini-Type Surfactant with MEGA-10.” Journal of Oleo Science 52(9):449–61

  • Vashishat Rajni, Sanan Reshu, Mahajan Rakesh Kumar (2015) Bile Salt-surface active ionic liquid mixtures: mixed micellization and solubilization of phenothiazine. RSC Adv 5(88):72132–41

    Article  CAS  Google Scholar 

  • Wiedmann Timothy Scott, Kamel Lamya (2002) Examination of the solubilization of drugs by bile salt micelles. J Pharm Sci 91(8):1743–64

    Article  CAS  PubMed  Google Scholar 

  • Zhang Rong-Xian, Gong Jin-Song, Dou Wen-Fang, Zhang Dan-Dan, Zhang Yu-Xia, Li Heng, Zhen-Ming Lu, Shi Jin-Song, Zheng-Hong Xu (2016) Production and characterization of surfactant-stable fungal keratinase from gibberella intermedia ca3-1 with application potential in detergent industry. Chem Papers 70(11):3376–88

    Article  Google Scholar 

  • Zhou Qiong, Rosen Milton J (2003) Molecular interactions of surfactants in mixed monolayers at the air/aqueous solution interface and in mixed micelles in aqueous media: the regular solution approach. Langmuir 19(11):4555–62

    Article  CAS  Google Scholar 

  • Zhu Guo-Quan (2009) Study on polymeric micelles of poly(γ-Benzyl l-Glutamate)-Graft-Poly(Ethylene Glycol) copolymer and its mixtures with poly(γ-Benzyl l-Glutamate) homopolymer in ethanol. Chem Papers 63(6):2022–31

    Article  Google Scholar 

  • Zhu Guo-Quan, Wang Fa-Gang, Liu Yu-Ying, Gao Qiao-Chun (2010) Factors influencing aggregation behavior of poly(γ-Benzyl l-Glutamate)-Graft-Poly(Ethylene Glycol) copolymer in mixed solvents. Chem Papers 64(5):3376–88

    Article  Google Scholar 

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Authors and Affiliations

  1. Division of Computational Physics, Institute for Computational Science, Ton Duc Thang University, Ho Chi Minh City, Vietnam

    Dileep Kumar

  2. Faculty of Applied Sciences, Ton Duc Thang University, Ho Chi Minh City, Vietnam

    Dileep Kumar

  3. Center of Excellence for Advanced Materials Research, King Abdulaziz University, Jeddah, 21589, Saudi Arabia

    Naved Azum, Malik Abdul Rub & Abdullah M. Asiri

  4. Chemistry Department, Faculty of Science, King Abdulaziz University, Jeddah, 21589, Saudi Arabia

    Abdullah M. Asiri

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  1. Dileep Kumar
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  2. Naved Azum
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  3. Malik Abdul Rub
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  4. Abdullah M. Asiri
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Correspondence to Naved Azum.

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Kumar, D., Azum, N., Rub, M.A. et al. Interfacial and spectroscopic behavior of phenothiazine drug/bile salt mixture in urea solution. Chem. Pap. 75, 3949–3956 (2021). https://doi.org/10.1007/s11696-021-01634-7

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  • DOI: https://doi.org/10.1007/s11696-021-01634-7

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