Home Physical Sciences Synthesis of Nitrogen Containing Biocompatible Non-ionic Surfactants and Investigation for Their Self-Assembly Based Nano-Scale Vesicles
Article
Licensed
Unlicensed Requires Authentication

Synthesis of Nitrogen Containing Biocompatible Non-ionic Surfactants and Investigation for Their Self-Assembly Based Nano-Scale Vesicles

  • Imdad Ali , Hiba Manzoor , Muhamad Imran , Shafiulah and Muhammad Raza Shah
Published/Copyright: January 24, 2019
Become an author with De Gruyter Brill
Submit Manuscript Author Information
Tenside Surfactants Detergents
From the journal Tenside Surfactants Detergents Volume 56 Issue 1

Abstract

Nonionic surfactants are increasingly interesting because of the solubility and release of drugs. Here, a synthesis of four nonionic nitrogen-containing surfactants is reported. In the synthesis, sulfonamide was reacted with alkyl halides of different lipophilicity. The synthesized nonionic surfactants were characterized by 1H NMR and mass spectroscopy. Their critical micelle concentration (CMC) was determined with a UV spectrophotometer. The self-assembly of surfactants to form drug-loaded, niosomal vesicles with Simvastatin as model drug was investigated. The resulting niosoaml vesicles were characterized by atomic force microscope (AFM), zeta-sizer, and UV spectrophotometer for shape, size, polydispersity index, zeta potential, and drug inclusion efficiency. Their biocompatibility has been determined by blood hemolysis and cell toxicity tests. The synthesized surfactants showed low CMC values and were able to form nano-sized round niosomal vesicles with a homogeneous population and surface negativity. Depending on the lipophilicity, they absorbed an increased amount of drug. The biocompatibility studies show that the surfactants are hemocompatible and non-toxic. The results of the study confirm that the synthesized nonionic surfactants are suitable for the solubilization and release of hydrophobic drugs as efficient novel biocompatible carriers.

Kurzfassung

Nichtionische Tenside sind zunehmend wegen der Löslichkeit und Freisetzung von Arzneiwirkstoffen interessant. Hier wird über eine Synthese von vier nichtionischen stickstoffhaltigen Tensiden berichtet. Bei der Synthese wurde Sulfonamid mit Alkylhalogeniden unterschiedlicher Lipophilie umgesetzt. Die synthetisierten nichtionischen Tenside wurden mittels 1H NMR und Massenspektroskopie charakterisiert. Ihre kritische Mizellenbildungskonzentration (CMC) wurde mit einem UV-Spektrophotometer bestimmt. Es wurde die Selbstorganisation der Tenside zur Bildung von wirkstoffbeladenen niosomaler Vesikel mit Simvastatin als Modellwirkstoff erforscht. Die resultierenden Niosomal-Vesikel wurden mit Hilfe eines Atomkraftmikroskops (AFM), eines Zetasizers und eines UV-Spektrophotometer hinsichtlich Form, Größe, Polydispersitätsindex, Zetapotential und der Wirksamkeit des Wirkstoffeinschlusses charakterisiert. Ihre Biokompatibilität wurde anhand von Bluthämolyse- und Zelltoxizitätstests bestimmt. Die synthetisierten Tenside zeigten niedrige CMC-Werte und waren in der Lage, im Nanobereich runde niosomale Vesikel mit homogener Population und Oberflächennegativität zu bilden. In Abhängigkeit von der Lipophilie nahmen sie eine erhöhte Wirkstoffmenge auf. Die Untersuchungen der Biokompatibilität zeigen, dass die Tenside hämokompatibel und nicht toxisch sind. Die Ergebnisse der Studie bestätigen, dass die synthetisierten nichtionischen Tenside für die Solubilisierung und Freisetzung hydrophober Arzneiwirkstoffe als effiziente neuartige biokompatible Träger geeignet sind.

Key words: Non-ionic surfactants; biocompatibility; niosomal vesicles; drug entrapment
Stichwörter: Nichtionische Tenside; Biokompatibilität; niosomale Vesikel; Wirkstoffeinschluss
*Correspondence address, Prof. Dr. Muhammad Raza Shah, H.E.J. Research Institute of Chemistry International Center for Chemical and Biological Sciences, Karachi University, Karachi, 74200, Pakistan, Tel.: + 92 21 99 26 17 01-2, 34 82 49 30, 34, 36, 4 82 49 01-02., Fax: + 92 21 34 81 90 18-9, 99 26 17 13-4, E-Mail:

Imdad Ali is PhD scholar based at HEJ Research Institute of Chemistry, International Center of Chemical and Biological Sciences, Karachi University, Pakistan. His research focuses the synthesis of non-ionic surfactants for various applications. He has published more than five research papers in peer reviewed journals.

Hiba Manzoor is M.Phil scholar at Department of Chemistry and Chemical Engineering, SBA School of Engineering. Her research interests include nano systems fabrications.

Muhammad Imran obtained his PhD degree from Department of Pharmacy, University of Malakand, KPK, Pakistan. His research interests include synthesis of self-assembling amphiphiles for nano drug delivery applications. He has published more than twenty papers in prestigious journals.

Shafiullah obtained his PhD degree from Department of Pharmacy, University of Malakand, KPK, Pakistan. He focuses synthesis of amphiphilic biomaterials for drug delivery applications. He has published more than twenty papers in prestigious journals.

Muhammad Raza Shah is a Full Professor at the International Center for Chemical and Biological Sciences, H.E.J. Research Institute of Chemistry University of Karachi, Pakistan. He is also the Head of the Center for Bioequivalence Studies and Clinical Research (CBSCR) and the recipient of numerous awards, including the civil award Tamgha-i-Imtiaz from President of Pakistan, and the Dr. M. Raziuddin Siddiqi Prize (2015) for Scientists under 40 in the Field of Chemistry by Pakistan Academy of Sciences. He has written over 200 peer-reviewed journal papers.

References

1. Raffa, P., BroekhuisA. A. and Picchioni, F.: Polymeric surfactants for enhanced oil recovery: A review, J Petrol Sci Eng.145 (2016) 723–733. 10.1016/j.petrol.2016.07.007Search in Google Scholar

2. Anwar, M. and Wahyuningsih, T.: Synthesis and characterization of dialkanolamides from castor oil (Ricinus communis) as nonionic surfactant, In: IOP Conf. Ser: Earth Environ. Sci. (2017) 012037. 10.1088/1755-1315/101/1/012037Search in Google Scholar

3. Ullah, I., Shah, A., Khan, M., Khan, S. Z., ur-Rehman, Z. and Badshah, A.: Synthesis and Spectrophotometric Study of Toxic Metals Extraction by Novel Thio-Based Non-Ionic Surfactant, Tenside Surf. Det.52 (2015) 406–413. 10.3139/113.110392Search in Google Scholar

4. Munir, A., Ullah, I., Shah, A, Rana, U. A., Khan, S. U-D., Adhikari, B., Shah, S. M., Khan, S. B., Kraatz, H-B. and Badshah, A.: Synthesis, spectroscopic characterization and pH dependent electrochemical fate of two non-ionic surfactants, J. Electrochem. Soc.161 (2014) 885–890. 10.1149/2.0391414jesSearch in Google Scholar

5. Chen, M., Hu, X. and Fu, M.: Novel synthesis of a new surfactant 4-((4-bromophenyl)(dodecyl) amino)-4-oxobutanoic acid containing a benzene ring using a copper catalyst cross-coupling reaction and its properties, J Surfactants Deterg.16 (2013) 581–585. 10.1007/s11743-012-1423-3Search in Google Scholar

6. Beneito-Cambra, M., Herrero-Martinez, J. and Ramis-Ramos, G.: Analytical methods for the characterization and determination of nonionic surfactants in cosmetics and environmental matrices, Anal Methods.5 (2013) 341–354. 10.1039/C2AY25847ASearch in Google Scholar

7. Yang, Y., Leser, ME., Sher, A. A. and McClements, D. J.: Formation and stability of emulsions using a natural small molecule surfactant: Quillaja saponin (Q-Naturale®), Food Hydrocoll30 (2013) 589–596. 10.1016/j.foodhyd.2012.08.008Search in Google Scholar

8. Ullah, S., Shah, M. R., Shoaib, M., Imran, M., Elhissi, A. M., Ahmad, F., Ali, I. and Shah, SWA.: Development of a biocompatible creatinine-based niosomal delivery system for enhanced oral bioavailability of clarithromycin, Drug delive23 (2016) 3480–3491. 10.1080/10717544.2016.1196768Search in Google Scholar PubMed

9. Imran, M., Shah, M. R., Ullah, F., Ullah, S., Elhissi, A. M, Nawaz, W., Ahmad, F., Sadiq, A. and Ali, I.: Glycoside-based niosomal nanocarrier for enhanced in-vivo performance of Cefixime, Int J Pharm.505 (2016) 122–132. PMid:27050867; 10.1016/j.ijpharm.2016.03.042Search in Google Scholar PubMed

10. Kumar, G. P. and Rajeshwarrao, P.: Nonionic surfactant vesicular systems for effective drug delivery – an overview, Acta Pharm Sin B.1 (2011) 208–219. 10.1016/j.apsb.2011.09.002Search in Google Scholar

11. Ullah, S., Shah, M. R., Shoaib, M., Imran, M., Shah, S. W. A., Ali, I. and Ahmed, F.: Creatinine-based non-phospholipid vesicular carrier for improved oral bioavailability of Azithromycin, Drug Dev. Ind. Pharm.43 (2017) 1011–1022. PMid:28157445; 10.1080/03639045.2017.1291667Search in Google Scholar PubMed

12. Imran, M., Shah, M. R., Ullah, F., Ullah, S., Elhissi, A. M., Nawaz, W., Ahmad, F., Sadiq, A and Ali, I.: Sugar-based novel niosomal nanocarrier system for enhanced oral bioavailability of levofloxacin, Drug deliv23 (2016) 3653–3664. PMid:27886514; 10.1080/10717544.2016.1214991Search in Google Scholar PubMed

13. Ali, I., Shah, M. R., Imran, M. and Ullah, S.: Synthesis of Sulfur-Based Biocompatible Nonionic Surfactants and Their Nano-Vesicle Drug Delivery, J Surfactants Deterg20 (2017) 1367–1375. 10.1007/s11743-017-2023-zSearch in Google Scholar

14. Söderlind, E., Wollbratt, M. and von Corswant, C.: The usefulness of sugar surfactants as solubilizing agents in parenteral formulations, Int J Pharm252 (2003), 61–71. 10.1016/S0378-5173(02)00599-9Search in Google Scholar PubMed

15. Cosco, D., Paolino, D., Muzzalupo, R., Celia, C., Citraro, R., Caponio, D., Picci, N. and Fresta, M.: Novel PEG-coated niosomes based on bola-surfactant as drug carriers for 5-fluorouracil, Biomed. microdevices.11 (2009) 1115. PMid:19507033; 10.1007/s10544-009-9328-2Search in Google Scholar PubMed

16. Ullah, I., Shah, A., Badshah, A., Shah, N. A. and Tabor, R.: Surface, aggregation properties and antimicrobial activity of four novel thiourea-based non-ionic surfactants, Colloids Surf A Physicochem Eng Asp.464 (2015) 104–109. 10.1016/j.colsurfa.2014.10.002Search in Google Scholar

17. Goth, L.: A simple method for determination of serum catalase activity and revision of reference range, Clin. Chim. Acta.196 (1991) 143–151. 10.1016/0009-8981(91)90067-MSearch in Google Scholar

18. Keiser, K., Johnson, C. C. and Tipton, DA: Cytotoxicity of mineral trioxide aggregate using human periodontal ligament fibroblasts, J Endod.26 (2000) 288–291. PMid:11199738; 10.1097/00004770-200005000-00010Search in Google Scholar PubMed

19. Ullah, I., Ahmad, K., Shah, A., Badshah, A., Rana, U. A., Shakir, I. and Khan, S. Z.: Synthesis, characterization and effect of a solvent mixture on the CMC of a thio-based novel cationic surfactant using a UV–visible spectroscopic technique, J Surfactants Deterg17 (2014) 501–507. 10.1007/s11743-013-1554-ss1Search in Google Scholar

20. Ullah, I., Shah, A., Badshah, A., Rana, U. A., Shakir, I., Khan, A. M. and Khan, S. Z: Synthesis, characterization and investigation of different properties of three novel thiourea-based non-ionic surfactants, J Surfactants Deterg.17 (2014) 1013–1019. 10.1007/s11743-014-1575-4Search in Google Scholar

21. Rao, K., Aziz, S., Roome, T., Razzak, A., Sikandar, B., Jamali, K. S., Imran, M., Jabri, T. and Shah, M. R.: Gum acacia stabilized silver nanoparticles based nano-cargo for enhanced anti-arthritic potentials of hesperidin in adjuvant induced arthritic rats, Artif Cells Nanomed Biotechnol. (2018) 1–11. 10.1080/21691401.2018.1431653Search in Google Scholar PubMed

22. Essa, E.: Effect of formulation and processing variables on the particle size of sorbitan monopalmitate niosomes, Asian J Pharm.4 (2010) 227. 10.4103/0973-8398.76752Search in Google Scholar

23. Kazi, K. M., Mandal, A. S., Biswas, N., Guha, A., Chatterjee, S., Behera, M. and Kuotsu, K.: Niosome: a future of targeted drug delivery systems, J Adv Pharm Technol Res.1 (2010) 374. PMid:22247876; 10.4103/0110-5558.76435Search in Google Scholar PubMed PubMed Central

24. Abdelkader, H., Alani, A. W. and Alany, R. G.: Recent advances in non-ionic surfactant vesicles (niosomes): self-assembly, fabrication, characterization, drug delivery applications and limitations, Drug Deliv.21 (2014) 87–100. PMid:24156390; 10.3109/10717544.2013.838077Search in Google Scholar PubMed

25. Aramaki, K., Yamada, J., Tsukijima, Y., Maehara, T., Aburano, D., Sakanishi, Y. and Kitao, K.: Formation of bilayer membrane and niosomes by double-tailed polyglyceryl-type nonionic surfactant, Langmuir31 (2015) 10664–10671. PMid:26355349; 10.1021/acs.langmuir.5b02454Search in Google Scholar PubMed

26. Manconi, M., Sinico, C., Valenti, D., Lai, F. and Fadda, A. M.: Niosomes as carriers for tretinoin: III. A study into the in vitro cutaneous delivery of vesicle-incorporated tretinoin, Int J Pharm311 (2006) 11–19. PMid:16439071; 10.1016/j.ijpharm.2005.11.045Search in Google Scholar PubMed

27. Tao, L. and Uhrich, K. E.: Novel amphiphilic macromolecules and their in vitro characterization as stabilized micellar drug delivery systems, J. Colloid Interface Sci.298 (2006) 102–110. PMid:16403508; 10.1016/j.jcis.2005.12.018Search in Google Scholar PubMed

28. Imran, M., Shah, M. R., Ullah, F., Ullah, S., Elhissi, A. M., Nawaz, W., Ahmad, F., SadiqA. and AliI.: Glycoside-based niosomal nanocarrier for enhanced in-vivo performance of Cefixime, Int J Pharm505 (2016) 122–132. PMid:27050867; 10.1016/j.ijpharm.2016.03.042Search in Google Scholar PubMed

Received: 2018-03-08
Accepted: 2018-07-17
Published Online: 2019-01-24
Published in Print: 2019-01-21

© 2019, Carl Hanser Publisher, Munich

Articles in the same Issue

  1. Contents/Inhalt
  2. Contents
  3. Editorial
  4. Review of the Year 2018
  5. Short Communication
  6. How Can Online Tools Help One Learn About and Improve Consumer Behaviour: Exemplarily, Laundry and Dishwashing Treatments?
  7. Review Article
  8. Novel Methods for Efficacy Testing of Disinfectants – Part I
  9. Detergent Analysis
  10. Simultaneous Determination of Two Alcohols and One Anionic Surfactant in Commercial Liquid Cleaners Using Partial Least Square Regression by Fourier Transform Infrared Spectrometry
  11. Novel Surfactants
  12. Synthesis of Nitrogen Containing Biocompatible Non-ionic Surfactants and Investigation for Their Self-Assembly Based Nano-Scale Vesicles
  13. Synthesis and Properties of Sodium Salts of Sulfonated Cardanol Polyethoxylates
  14. Synthesis of Mesoporous ZSM-5 Zeolite Crystals by a New Organosilane Template with Double-carbamate Carbon Chains
  15. Physical Chemistry
  16. Micellization and Counterion Binding Behavior of Cetylpyridinium Chloride in Aqueous Solutions of Sodium Bromide and Tetrabutylammonium Bromide
  17. Synergistic Properties of a Mixed Micelle System Consisting of a Nonionic Fluorinated Surfactant and a Cationic Surfactant
  18. Synthesis
  19. Optimization of Formation Reaction Conversions of Fatty Acid Amidopropyl Dimethylamines
https://doi.org/10.3139/113.110605
Keywords for this article
Non-ionic surfactants; biocompatibility; niosomal vesicles; drug entrapment

Articles in the same Issue

  1. Contents/Inhalt
  2. Contents
  3. Editorial
  4. Review of the Year 2018
  5. Short Communication
  6. How Can Online Tools Help One Learn About and Improve Consumer Behaviour: Exemplarily, Laundry and Dishwashing Treatments?
  7. Review Article
  8. Novel Methods for Efficacy Testing of Disinfectants – Part I
  9. Detergent Analysis
  10. Simultaneous Determination of Two Alcohols and One Anionic Surfactant in Commercial Liquid Cleaners Using Partial Least Square Regression by Fourier Transform Infrared Spectrometry
  11. Novel Surfactants
  12. Synthesis of Nitrogen Containing Biocompatible Non-ionic Surfactants and Investigation for Their Self-Assembly Based Nano-Scale Vesicles
  13. Synthesis and Properties of Sodium Salts of Sulfonated Cardanol Polyethoxylates
  14. Synthesis of Mesoporous ZSM-5 Zeolite Crystals by a New Organosilane Template with Double-carbamate Carbon Chains
  15. Physical Chemistry
  16. Micellization and Counterion Binding Behavior of Cetylpyridinium Chloride in Aqueous Solutions of Sodium Bromide and Tetrabutylammonium Bromide
  17. Synergistic Properties of a Mixed Micelle System Consisting of a Nonionic Fluorinated Surfactant and a Cationic Surfactant
  18. Synthesis
  19. Optimization of Formation Reaction Conversions of Fatty Acid Amidopropyl Dimethylamines
Sign up now to receive a 20% welcome discount
Institutional Access
How does access work?
Have an idea on how to improve our website?
Please write us.
© 2026 De Gruyter Brill
Downloaded on 20.2.2026 from https://www.degruyterbrill.com/document/doi/10.3139/113.110605/html
Scroll to top button