Abstract
In this manuscript, we discussed the synthesis of non-ionic (C18) and (C18-cis) amphiphiles from [PG]-dendron-based biocompatible starting materials. The physicochemical studies of amphiphiles show some significant results. The presence of an amide as a linker group has affected the hydrophilicity of the amphiphiles to respond to a low critical micelle concentration. The graph of surface tension versus concentration shows that the CMC of non-ionic amphiphiles falls in the range of 18.10 µmol L−1–00.61 µmol L−1. The dynamic light scattering study of the synthesized compounds confirmed that the G.n-amide amphiphiles with the unsaturation 6, 8 and 10 have an average aggregated particle size range of 93.0 nm–13.0 nm, while the average aggregated particle size of saturated amphiphiles 13, 15 and 17 showed a range from 28.0 nm to 7.5 nm. The morphological study of self-aggregated particles of amphiphiles using transmission electron microscopy studies in an aqueous medium showed the worm-like shape for G.1 amphiphiles and circular shape for G.2 and G.3 amphiphiles.
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References
D. Shi, D. Nguyen, M. Maaloum, J. Gallani, D. Felder-Flesch, M.P. Krafft, Molecules 24, 4114–4127 (2019)
D.A. Tomalia, L.S. Nixon, D.M. Hedstrand, Biomolecules 10, 642–698 (2020)
E. Fedeli, A. Lancelot, J.M. Dominguez, J.L. Serrano, P. Calvo, T. Sierra, Nanomaterials 9, 161–175 (2019)
J. Shi, A.R. Votruba, O.C. Farokhzad, R. Langer, J. Shi, A.R. Votruba, O.C. Farokhzad, Nano Lett. 10, 3223–3230 (2010)
H. Zhu, L. Shangguan, B. Shi, G. Yu, F. Haung, Mat. Chem. Front. 2, 2152–2174 (2018)
N. Zacharopoulos, I.G. Economou, Macromolecules 35, 1814–1821 (2002)
S. Senapati, A.K. Mahanta, S. Kumar, P. Maiti, Signal Transduction and Targeted. Therapy 3, 7 (2018)
A. Kumar, S. Tyagi, R. Singh, Y.K. Tyagi, New J. Chem. 43(2), 1025–1031 (2019)
Y. Ohta, Y. Abe, K. Hoka, E. Baba, Y.-P. Lee, C.-A. Dai, T. Yokozawa, Polym. Chem. 10, 4246–4251 (2019)
P.K. Vuram, U. Subuddhi, S.T. Krishnaji, A. Chadha, A.K. Mishra, Eur. J. Org. Chem. 26, 5030–5040 (2010)
Xi. Liu, I. Gitsov, Macromolecules. 52, 5563–5573 (2019)
S. Tripathy, M.K. Das, JAPS. 3(09), 142–149 (2013)
M. Gupta, V. Sharma, Res. J. Chem. Sci. 1(2), 135 (2011)
S. Mirsharghi, K. D. Knudsen, S. Bagherifam, B. Nystro¨m, U. Boas, New. J. Chem. 40, 3597–3611 (2016)
A. Popielec, E. Fenyvesi, K. Yannakopoulou, T. Loftsson, Pharmazie. 71, 68–75 (2016)
B. Yoo, J.K. Shah, Y. Zhu, E.J. Maginn, Soft Matter 10, 8641–8651 (2014)
N. Kalra, G. Jeyabalan, G. Singh, S. Choudhary, JIPBS. 3(2), 193 (2016)
P. Degen, D.C.F. Wieland, C. Strötges, Langmuir 31(43), 11851–11857 (2015)
Xi. Zhang, H. Xing, Y. Zhao, Z. Ma, Pharmaceutics. 10, 74 (2018)
S. Kalepu, V. Nekkanti, Acta Pharm. Sin. B. 5(5), 442–453 (2015)
I.O. Lebedeva, E.B. Zhulina, O.V. Borisov, Macromolecules 52, 3655–3667 (2019)
Xi Zhang, and C. Wang, Chem. Soc. Rev. 40, 94–101 (2011)
A. Banerjee, A. Tam, M. Dutt, Nanoscale Adv. 3, 725–737 (2021)
M.S. Bakshi, A. Kaura, R.K. Mahajan, T. Yoshimura, K. Esumi, Colloids and Surfaces A: Physicochem. Eng. Aspects. 246, 39–48 (2004)
B. Lin, A.V. McCormick, H.T. Davis, R. Strey, J. Colloid Interface Sci. 291, 543–549 (2005)
B.M. Rosen, C.J. Wilson, D.A. Wilson, M. Peterca, M.R. Imam, V. Percec, Chem. Rev. 109, 6275–6540 (2009)
A.P. Singh, A. Biswas, A. Shukla, P. Maiti, Sig Transduct Target Ther. 4(33), 1–21 (2019)
F. Bahadori, A. Dag, H. Durmaz, N. Cakir, H. Onyuksel, U. Tunca, G. Topcu, G. Hizal, Polymers 6, 214–242 (2014)
K.A. Kosakowska, B.K. Casey, S.L. Kurtz, L.B. Lawson, S.M. Grayson, Biomacromol 19(8), 3163–3189 (2018)
Y. Muraji, T. Fujita, H. Itoh, D. Fujita, Microsc. Res. 1, 24–28 (2013)
A. Kumar, Y.K. Tyagi, Materials Today: Proceedings. 43, 250–255 (2021)
V. Brega, F. Scaletti, X. Zhang, Li-S. Wang, P. Li, Q. Xu, V. M. Rotello, S. W. Thomas, ACS Appl. Mater. Interfaces. 11, 2814–2820 (2019)
H.-Y. Li, Y.-H. Chu, Molecules 25, 104–115 (2020)
N. Dayyani, S. Khoee, A. Ramazani, Eur. J. Med. Chem. 98(15), 190–202 (2015)
L. H. Urner, Y. B. Maier, R. Haag, K. J. Pagel, Am. Soc. Mass Spectrom. 30:174Y180 (2018)
M. Wyszogrodzka, R. Haag, Biomacromol 10, 1043–1054 (2009)
N. Dayyani, A. Ramazani, A. Khoee, SILICON 10, 595–601 (2018)
C. Durukan, B. Kiskan, Y. Yagci, Polymers 11, 679–690 (2019)
D. Lombardo, M. A. Kiselev, S. Magazù, P. Calandra, Advances in Condensed Matter Physics Volume 2015, Article ID 151683 (2015)
Y. Wang, Y. Zhang, Xi. Liu, J. Wang, Li. Wei, Y. Feng, J Surfact Deterg. 17, 295–301 (2014)
B. Lin, A.V. McCormick, H.T. Davis, R. Strey, J. Colloid Interface Sci. 291(2), 543–549 (2005)
N. Bagalkot, A.A. Hamouda, O.M. Isdahl, MethodsX. 5, 676–683 (2018)
Y. Gohon, J.D. Vindigni, A. Pallier, F. Wien, H. Celia, A. Giuliani, C. Tribet, T. Chardot, P. Briozzo, Biophysica Acta. 1808, 706–716 (2011)
T. Yoshimura, A. Ebihara, H. Iwase, Colloids Surf. A 533, 197–203 (2017)
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Kumar, A., Singh, R. & Tyagi, Y.K. Design, synthesis and self-assembly of amide-linked dendron-based non-ionic amphiphiles. J IRAN CHEM SOC 19, 1167–1177 (2022). https://doi.org/10.1007/s13738-021-02370-1
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DOI: https://doi.org/10.1007/s13738-021-02370-1