ACS Publications. Most Trusted. Most Cited. Most Read
My Activity
CONTENT TYPES

Cationic Lipid-Mediated Gene Delivery to Murine Lung:  Correlation of Lipid Hydration with in Vivo Transfection Activity

View Author Information
Departments of Chemistry and Medical Pathology, University of California, Davis, California 95616
Cite this: J. Med. Chem. 1997, 40, 25, 4069–4078
Publication Date (Web):December 5, 1997
https://doi.org/10.1021/jm970155q
Copyright © 1997 American Chemical Society

    Article Views

    798

    Altmetric

    -

    Citations

    LEARN ABOUT THESE METRICS
    Read OnlinePDF (652 KB)

    Abstract

    A panel of lipidic tetraalkylammonium chlorides has been prepared and screened in studies of both lipid hydration and in vivo mouse transfection. The effect of cationic lipid structure on liposome surface hydration was determined using differential scanning calorimetry. Increases in headgroup steric bulk and the inclusion of cis-unsaturation in the hydrophobic domain led to greater lipid hydration, indicative of a decrease in lipid polar domain associations. Cationic lipids containing hydrogen-bonding functionality in the polar domain exhibited a corresponding decrease in observed lipid hydration, indicative of an increase in lipid polar domain associations. To explore a potential correlation of the hydration data with transfection activity, we examined the in vivo transfection activity of the lipid panel by direct intratracheal instillation of cationic liposome−DNA complexes into BALB/c mice. The more active transfection agents were the lipids that featured headgroup structures promoting close polar domain association in combination with fatty acyl cis-unsaturation. The hydration data suggest that the more effective transfection lipids for mouse lung delivery are those possessing the greatest imbalance between the cross-sectional areas occupied by the polar and hydrophobic domains.

     Department of Chemistry.

     Department of Medical Pathology.

    *

    In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

    §

     Current address:  Department of Pathology, University of Maryland at Baltimore, Baltimore, MD 21201-1192.

     Abstract published in Advance ACS Abstracts, November 15, 1997.

    Cited By

    This article is cited by 90 publications.

    1. Grayson Tilstra, Julien Couture-Senécal, Yan Ming Anson Lau, Alanna M. Manning, Daniel S. M. Wong, Wanda W. Janaeska, Titobioluwa A. Wuraola, Janice Pang, Omar F. Khan. Iterative Design of Ionizable Lipids for Intramuscular mRNA Delivery. Journal of the American Chemical Society 2023, 145 (4) , 2294-2304. https://doi.org/10.1021/jacs.2c10670
    2. Yuebao Zhang, Changzhen Sun, Chang Wang, Katarina E. Jankovic, Yizhou Dong. Lipids and Lipid Derivatives for RNA Delivery. Chemical Reviews 2021, 121 (20) , 12181-12277. https://doi.org/10.1021/acs.chemrev.1c00244
    3. Mange R. Yadav, Mukesh Kumar, Prashant R. Murumkar, Puja P. Hazari, Anil K. Mishra. Gemini Amphiphile-Based Lipoplexes for Efficient Gene Delivery: Synthesis, Formulation Development, Characterization, Gene Transfection, and Biodistribution Studies. ACS Omega 2018, 3 (9) , 11802-11816. https://doi.org/10.1021/acsomega.8b01014
    4. Mathieu Berchel, Tony Le Gall, Jean-Pierre Haelters, Pierre Lehn, Tristan Montier, and Paul-Alain Jaffrès . Cationic Lipophosphoramidates Containing a Hydroxylated Polar Headgroup for Improving Gene Delivery. Molecular Pharmaceutics 2015, 12 (6) , 1902-1910. https://doi.org/10.1021/mp500807k
    5. Charles H. Jones, Chih-Kuang Chen, Anitha Ravikrishnan, Snehal Rane, and Blaine A. Pfeifer . Overcoming Nonviral Gene Delivery Barriers: Perspective and Future. Molecular Pharmaceutics 2013, 10 (11) , 4082-4098. https://doi.org/10.1021/mp400467x
    6. Defu Zhi, Shubiao Zhang, Shaohui Cui, Yinan Zhao, Yinhuan Wang, and Defeng Zhao . The Headgroup Evolution of Cationic Lipids for Gene Delivery. Bioconjugate Chemistry 2013, 24 (4) , 487-519. https://doi.org/10.1021/bc300381s
    7. Animesh Ghosh, Koushik Mukherjee, Xinpeng Jiang, Ying Zhou, Joshua McCarroll, James Qu, Pamela M. Swain, Huricha Baigude, and Tariq M. Rana . Design and Assembly of New Nonviral RNAi Delivery Agents by Microwave-Assisted Quaternization (MAQ) of Tertiary Amines. Bioconjugate Chemistry 2010, 21 (9) , 1581-1587. https://doi.org/10.1021/bc900482r
    8. Michael H. Nantz, Christopher W. Dicus, Brendan Hilliard, Sri Yellayi, Shaomin Zou and James G. Hecker . The Benefit of Hydrophobic Domain Asymmetry on the Efficacy of Transfection as Measured by in Vivo Imaging. Molecular Pharmaceutics 2010, 7 (3) , 786-794. https://doi.org/10.1021/mp900298f
    9. DeFu Zhi, ShuBiao Zhang, Bing Wang, YiNan Zhao, BaoLing Yang and ShiJun Yu. Transfection Efficiency of Cationic Lipids with Different Hydrophobic Domains in Gene Delivery. Bioconjugate Chemistry 2010, 21 (4) , 563-577. https://doi.org/10.1021/bc900393r
    10. Meredith A. Mintzer and Eric E. Simanek. Nonviral Vectors for Gene Delivery. Chemical Reviews 2009, 109 (2) , 259-302. https://doi.org/10.1021/cr800409e
    11. Shuang Wu, Meiyan Liu, Xiang Hu, Chengxi He, Chunyan Zhao, Shuanglin Xiang, Youlin Zeng. Evaluation of pentaerythritol-based and trimethylolpropane-based cationic lipidic materials for gene delivery. Bioorganic & Medicinal Chemistry Letters 2022, 62 , 128635. https://doi.org/10.1016/j.bmcl.2022.128635
    12. Mi So Lee, Ju Won Lee, Su Ji Kim, Oanh‐Vu Pham‐Nguyen, Jongmin Park, Ju Hyun Park, Young Mee Jung, Jun Bae Lee, Hyuk Sang Yoo. Comparison Study of the Effects of Cationic Liposomes on Delivery across 3D Skin Tissue and Whitening Effects in Pigmented 3D Skin. Macromolecular Bioscience 2021, 21 (5) https://doi.org/10.1002/mabi.202000413
    13. A. Gigante, M. Li, S. Junghänel, C. Hirschhäuser, S. Knauer, C. Schmuck. Non-viral transfection vectors: are hybrid materials the way forward?. MedChemComm 2019, 10 (10) , 1692-1718. https://doi.org/10.1039/C9MD00275H
    14. Defu Zhi, Yuchao Bai, Jian Yang, Shaohui Cui, Yinan Zhao, Huiying Chen, Shubiao Zhang. A review on cationic lipids with different linkers for gene delivery. Advances in Colloid and Interface Science 2018, 253 , 117-140. https://doi.org/10.1016/j.cis.2017.12.006
    15. Shaohui Cui, Yueying Wang, Yan Gong, Xiao Lin, Yinan Zhao, Defu Zhi, Quan Zhou, Shubiao Zhang. Correlation of the cytotoxic effects of cationic lipids with their headgroups. Toxicology Research 2018, 7 (3) , 473-479. https://doi.org/10.1039/C8TX00005K
    16. Yushin Yazaki, Ayako Oyane, Yu Sogo, Atsuo Ito, Atsushi Yamazaki, Hideo Tsurushima. Area-Specific Cell Stimulation via Surface-Mediated Gene Transfer Using Apatite-Based Composite Layers. International Journal of Molecular Sciences 2015, 16 (12) , 8294-8309. https://doi.org/10.3390/ijms16048294
    17. Emile Jubeli, Amanda B. Maginty, Nada Abdul Khalique, Liji Raju, Mohamad Abdulhai, David G. Nicholson, Helge Larsen, Michael D. Pungente, William P.D. Goldring. Next generation macrocyclic and acyclic cationic lipids for gene transfer: Synthesis and in vitro evaluation. Bioorganic & Medicinal Chemistry 2015, 23 (19) , 6364-6378. https://doi.org/10.1016/j.bmc.2015.08.032
    18. Ling Li, Zhi-Yao He, Xia-Wei Wei, Guang-Ping Gao, Yu-Quan Wei. Challenges in CRISPR/CAS9 Delivery: Potential Roles of Nonviral Vectors. Human Gene Therapy 2015, 26 (7) , 452-462. https://doi.org/10.1089/hum.2015.069
    19. Ahmad Aljaberi, Suhair Saleh, Khalid M. Abu Khadra, Molinda Kearns, Michalakis Savva. Physicochemical and biological characterization of 1,2-dialkoylamidopropane-based lipoplexes for gene delivery. Biophysical Chemistry 2015, 199 , 9-16. https://doi.org/10.1016/j.bpc.2015.02.004
    20. E. Ojeda, G. Puras, M. Agirre, J. Zárate, S. Grijalvo, R. Pons, R. Eritja, G. Martinez-Navarrete, C. Soto-Sanchez, E. Fernández, J. L. Pedraz. Niosomes based on synthetic cationic lipids for gene delivery: the influence of polar head-groups on the transfection efficiency in HEK-293, ARPE-19 and MSC-D1 cells. Organic & Biomolecular Chemistry 2015, 13 (4) , 1068-1081. https://doi.org/10.1039/C4OB02087A
    21. Kshitij Gupta, Stephanie J Mattingly, Ralph J Knipp, Kirill A Afonin, Mathias Viard, Joseph T Bergman, Marissa Stepler, Michael H Nantz, Anu Puri, Bruce A Shapiro. . Nanomedicine 2015, 2805. https://doi.org/10.2217/nnm.15.105
    22. Yushin Yazaki, Ayako Oyane, Hideo Tsurushima, Hiroko Araki, Yu Sogo, Atsuo Ito, Atsushi Yamazaki. Improved gene transfer efficiency of a DNA-lipid-apatite composite layer by controlling the layer molecular composition. Colloids and Surfaces B: Biointerfaces 2014, 122 , 465-471. https://doi.org/10.1016/j.colsurfb.2014.07.001
    23. Yushin Yazaki, Ayako Oyane, Hideo Tsurushima, Hiroko Araki, Yu Sogo, Atsuo Ito, Atsushi Yamazaki. Coprecipitation of DNA-lipid complexes with apatite and comparison with superficial adsorption for gene transfer applications. Journal of Biomaterials Applications 2014, 28 (6) , 937-945. https://doi.org/10.1177/0885328213486706
    24. Paria Parvizi, Emile Jubeli, Liji Raju, Nada Abdul Khalique, Ahmed Almeer, Hebatalla Allam, Maryem Al Manaa, Helge Larsen, David Nicholson, Michael D. Pungente, Thomas M. Fyles. Aspects of nonviral gene therapy: Correlation of molecular parameters with lipoplex structure and transfection efficacy in pyridinium-based cationic lipids. International Journal of Pharmaceutics 2014, 461 (1-2) , 145-156. https://doi.org/10.1016/j.ijpharm.2013.11.045
    25. Weihong Qiao, Min Zhou. Hydroxyl‐modified cationic lipids with a carbamate linkage as gene delivery vehicles. European Journal of Lipid Science and Technology 2013, 115 (5) , 483-489. https://doi.org/10.1002/ejlt.201200265
    26. Albert Kwok. The Challenges and Current Advances in Delivering RNAi as Therapeutics. 2013, 189-224. https://doi.org/10.1007/978-3-662-45775-7_8
    27. Xiao-Xiang Zhang, Caroline M. LaManna, Richie E. Kohman, Thomas J. McIntosh, Xue Han, Mark W. Grinstaff. Lipid-mediated DNA and siRNA transfection efficiency depends on peptide headgroup. Soft Matter 2013, 9 (17) , 4472. https://doi.org/10.1039/c3sm27633c
    28. Albert Kwok. The Challenges and Current Advances in Delivering RNAi as Therapeutics. 2013, 189-224. https://doi.org/10.1007/978-3-642-36853-0_8
    29. Yushin Yazaki, Ayako Oyane, Hiroko Araki, Yu Sogo, Atsuo Ito, Atsushi Yamazaki, Hideo Tsurushima. Fabrication of DNA-antibody–apatite composite layers for cell-targeted gene transfer. Science and Technology of Advanced Materials 2012, 13 (6) , 064204. https://doi.org/10.1088/1468-6996/13/6/064204
    30. Weihong Qiao, Zhibo Zheng, Wenhui Qu, Shumin Zhang. Synthesis and Characterization of Carbamate‐Linked Cationic Lipids with Hydroxyethyl Group. Journal of the American Oil Chemists' Society 2012, 89 (12) , 2121-2125. https://doi.org/10.1007/s11746-012-2115-x
    31. Ayako Oyane, Yushin Yazaki, Hiroko Araki, Yu Sogo, Atsuo Ito, Atsushi Yamazaki, Hideo Tsurushima. Fabrication of a DNA-lipid-apatite composite layer for efficient and area-specific gene transfer. Journal of Materials Science: Materials in Medicine 2012, 23 (4) , 1011-1019. https://doi.org/10.1007/s10856-012-4581-y
    32. Yushin Yazaki, Ayako Oyane, Yu Sogo, Atsuo Ito, Atsushi Yamazaki, Hideo Tsurushima. Control of gene transfer on a DNA–fibronectin–apatite composite layer by the incorporation of carbonate and fluoride ions. Biomaterials 2011, 32 (21) , 4896-4902. https://doi.org/10.1016/j.biomaterials.2011.03.021
    33. Yoshiyuki HATTORI. Development of Non-viral Vector for Cancer Gene Therapy. YAKUGAKU ZASSHI 2010, 130 (7) , 917-923. https://doi.org/10.1248/yakushi.130.917
    34. Souvik Biswas, Xuan Huang, Wesley R. Badger, Michael H. Nantz. Nucleophilic cationization reagents. Tetrahedron Letters 2010, 51 (13) , 1727-1729. https://doi.org/10.1016/j.tetlet.2010.01.094
    35. Ayako Oyane, Hideo Tsurushima, Atsuo Ito. Highly efficient gene transfer system using a laminin-DNA-apatite composite layer. The Journal of Gene Medicine 2010, 52 , n/a-n/a. https://doi.org/10.1002/jgm.1425
    36. Sarantis Giatrellis, George Nikolopoulos, Zili Sideratou, George Nounesis. Calorimetric study of the interaction of binary DMTAP/DOTAP cationic liposomes with plasmid DNA. Journal of Liposome Research 2009, 19 (3) , 220-230. https://doi.org/10.1080/08982100902746596
    37. R.A.S. Randazzo, R. Bucki, P.A. Janmey, S.L. Diamond. A series of cationic sterol lipids with gene transfer and bactericidal activity. Bioorganic & Medicinal Chemistry 2009, 17 (9) , 3257-3265. https://doi.org/10.1016/j.bmc.2009.03.049
    38. Ayako Oyane, Masami Murayama, Atsushi Yamazaki, Yu Sogo, Atsuo Ito, Hideo Tsurushima. Fibronectin-DNA-apatite composite layer for highly efficient and area-specific gene transfer. Journal of Biomedical Materials Research Part A 2009, 9999A , NA-NA. https://doi.org/10.1002/jbm.a.32449
    39. N. S. Chiaramoni, L. C. Baccarini, M. C. Taira, S. del V. Alonso. Liposome/DNA Systems: Correlation Between Hydrophobicity and DNA Conformational Changes. Journal of Biological Physics 2008, 34 (1-2) , 179-188. https://doi.org/10.1007/s10867-008-9103-2
    40. Armandodoriano Bianco, Raffaella Napolitano, Francesco Bonadies, Diana Celona, Giancarlo Ortaggi, Cesare Cametti. Liposomes from a new chiral cationic lipid based on iridoidic template. Natural Product Research 2007, 21 (14) , 1221-1227. https://doi.org/10.1080/14786410500162526
    41. A Oyane, H Tsurushima, A Ito. Novel gene-transferring scaffolds having a cell adhesion molecule–DNA–apatite nanocomposite surface. Gene Therapy 2007, 14 (24) , 1750-1753. https://doi.org/10.1038/sj.gt.3303041
    42. Baichao Ma, Shubiao Zhang, Huiming Jiang, Budiao Zhao, Hongtao Lv. Lipoplex morphologies and their influences on transfection efficiency in gene delivery. Journal of Controlled Release 2007, 123 (3) , 184-194. https://doi.org/10.1016/j.jconrel.2007.08.022
    43. Yoshiyuki Hattori, Wu-xiao Ding, Yoshie Maitani. Highly efficient cationic hydroxyethylated cholesterol-based nanoparticle-mediated gene transfer in vivo and in vitro in prostate carcinoma PC-3 cells. Journal of Controlled Release 2007, 120 (1-2) , 122-130. https://doi.org/10.1016/j.jconrel.2007.04.012
    44. N. Madhusudhana Rao, Vijaya Gopal. Cell Biological and Biophysical Aspects of Lipid-mediated Gene Delivery. Bioscience Reports 2006, 26 (4) , 301-324. https://doi.org/10.1007/s10540-006-9026-8
    45. Rajkumar Banerjee, Leaf Huang. Vector System: Plasmid DNA. 2006https://doi.org/10.1002/3527600906.mcb.200500030
    46. N Madhusudhana Rao, Vijaya Gopal. Cationic lipids for gene delivery in vitro and in vivo. Expert Opinion on Therapeutic Patents 2006, 16 (6) , 825-844. https://doi.org/10.1517/13543776.16.6.825
    47. An Cao, Dominique Briane, Robert Coudert. Chapter 5: Cationic Liposomes as Transmembrane Carriers of Nucleic Acids. 2006, 135-190. https://doi.org/10.1016/S1554-4516(06)04005-1
    48. Michalakis Savva, Pensung Chen, Ahmad Aljaberi, Bilge Selvi, Michael Spelios. In Vitro Lipofection with Novel Asymmetric Series of 1,2-Dialkoylamidopropane-Based Cytofectins Containing Single Symmetric Bis-(2-dimethylaminoethane) Polar Headgroups. Bioconjugate Chemistry 2005, 16 (6) , 1411-1422. https://doi.org/10.1021/bc050138c
    49. Marco Scarzello, Anno Wagenaar, Marc C. A. Stuart, Dick Hoekstra, Jan B. F. N. Engberts, Ron Hulst. Sunfish Cationic Amphiphiles:  Toward an Adaptative Lipoplex Morphology. Journal of the American Chemical Society 2005, 127 (29) , 10420-10429. https://doi.org/10.1021/ja0515147
    50. Michalakis Savva, Ahmad Aljaberi, Jennifer Feig, Donna Beer Stolz. Correlation of the physicochemical properties of symmetric 1,3-dialkoylamidopropane-based cationic lipids containing single primary and tertiary amine polar head groups with in vitro transfection activity. Colloids and Surfaces B: Biointerfaces 2005, 43 (1) , 43-56. https://doi.org/10.1016/j.colsurfb.2005.03.008
    51. Ahmad Aljaberi, Pensung Chen, Michalakis Savva. Synthesis, in vitro transfection activity and physicochemical characterization of novel N,N′-diacyl-1,2-diaminopropyl-3-carbamoyl-(dimethylaminoethane) amphiphilic derivatives. Chemistry and Physics of Lipids 2005, 133 (2) , 135-149. https://doi.org/10.1016/j.chemphyslip.2004.09.017
    52. Ajit S. Narang, Laura Thoma, Duane D. Miller, Ram I. Mahato. Cationic Lipids with Increased DNA Binding Affinity for Nonviral Gene Transfer in Dividing and Nondividing Cells. Bioconjugate Chemistry 2005, 16 (1) , 156-168. https://doi.org/10.1021/bc049818q
    53. Rita Cortesi, Claudio Nastruzzi, Elisabetta Esposito. Cationic Lipospheres as Delivery Systems for Nucleic Acid Molecules. 2004, 143-159. https://doi.org/10.1201/9780203505281.ch8
    54. Hong Shen, Jian Tan, W. Mark Saltzman. Surface-mediated gene transfer from nanocomposites of controlled texture. Nature Materials 2004, 3 (8) , 569-574. https://doi.org/10.1038/nmat1179
    55. A Percot, D Briane, R Coudert, P Reynier, N Bouchemal, N Lièvre, E Hantz, J.L Salzmann, A Cao. A hydroxyethylated cholesterol-based cationic lipid for DNA delivery: effect of conditioning. International Journal of Pharmaceutics 2004, 278 (1) , 143-163. https://doi.org/10.1016/j.ijpharm.2004.03.003
    56. Ron Hulst, Inouk Muizebelt, Peter Oosting, Cornelia van der Pol, Anno Wagenaar, Jarmila Šmisterová, Erna Bulten, Cecile Driessen, Dick Hoekstra, Jan B. F. N. Engberts. Sunfish Amphiphiles: Conceptually New Carriers for DNA Delivery. European Journal of Organic Chemistry 2004, 2004 (4) , 835-849. https://doi.org/10.1002/ejoc.200300524
    57. Dirk Pijper, Erna Bulten, Jarmila Šmisterová, Anno Wagenaar, Dick Hoekstra, Jan B. F. N. Engberts, Ron Hulst. Novel Biodegradable Pyridinium Amphiphiles for Gene Delivery. European Journal of Organic Chemistry 2003, 2003 (22) , 4406-4412. https://doi.org/10.1002/ejoc.200300361
    58. Rajkumar Banerjee, Leaf Huang. Plasmid DNA–Mediated Gene Therapy. 2003, 641-667. https://doi.org/10.1002/0471266949.bmc073
    59. Dua M. Anderson, Leon L. Hall, Anitha R. Ayyalapu, Van R. Irion, Michael H. Nantz, James G. Hecker. Stability of mRNA/Cationic Lipid Lipoplexes in Human and Rat Cerebrospinal Fluid: Methods and Evidence for Nonviral mRNA Gene Delivery to the Central Nervous System. Human Gene Therapy 2003, 14 (3) , 191-202. https://doi.org/10.1089/10430340360535751
    60. Man-Zhou Zhu, Qi-Hua Wu, Guisheng Zhang, Tan Ren, Dexi Liu, Qing-Xiang Guo. Synthesis and Evaluation of Cationic Lipids Bearing Cholesteryl Groups for Gene Delivery In Vitro. Bulletin of the Chemical Society of Japan 2002, 75 (10) , 2207-2213. https://doi.org/10.1246/bcsj.75.2207
    61. Edmund J Niedzinski, Scott K Fujii, Mike E Lizarzaburu, James G Hecker, Michael H Nantz. A Versatile Linker for Nontoxic Polyamine-Mediated DNA Transfection. Molecular Therapy 2002, 6 (2) , 279-286. https://doi.org/10.1006/mthe.2002.0645
    62. Crispin R Dass. Biochemical and biophysical characteristics of lipoplexes pertinent to solid tumour gene therapy. International Journal of Pharmaceutics 2002, 241 (1) , 1-25. https://doi.org/10.1016/S0378-5173(02)00194-1
    63. Astrid Roosjen, Jarmila Šmisterová, Cecile Driessen, Joachim T. Anders, Anno Wagenaar, Dick Hoekstra, Ron Hulst, Jan B. F. N. Engberts. Synthesis and Characteristics of Biodegradable Pyridinium Amphiphiles Used for in vitro DNA Delivery. European Journal of Organic Chemistry 2002, 2002 (7) , 1271-1277. https://doi.org/10.1002/1099-0690(200204)2002:7<1271::AID-EJOC1271>3.0.CO;2-G
    64. Rajkumar Sunil Singh, Koushik Mukherjee, Rajkumar Banerjee, Arabinda Chaudhuri, Samik Kumar Hait, Satya Priya Moulik, Yerramsetti Ramadas, Amash Vijayalakshmi, Nalam Madhusudhana Rao. Anchor Dependency for Non-Glycerol Based Cationic Lipofectins: Mixed Bag of Regular and Anomalous Transfection Profiles. Chemistry - A European Journal 2002, 8 (4) , 900-909. https://doi.org/10.1002/1521-3765(20020215)8:4<900::AID-CHEM900>3.0.CO;2-X
    65. Gollapudi Venkata Srilakshmi, Joyeeta Sen, Arabinda Chaudhuri, Yerramsetti Ramadas, Nalam Madhusudhana Rao. Anchor-dependent lipofection with non-glycerol based cytofectins containing single 2-hydroxyethyl head groups11IICT Communication No. 4813.. Biochimica et Biophysica Acta (BBA) - Biomembranes 2002, 1559 (2) , 87-95. https://doi.org/10.1016/S0005-2736(01)00442-4
    66. Jill Glasspool-Malone, Robert W. Malone. [4] Enhancing direct in vivo transfection with nuclease inhibitors and pulsed electrical fields. 2002, 72-91. https://doi.org/10.1016/S0076-6879(02)46049-1
    67. Ayyagari Ananta Laxmi, Penumarthy Vijayalakshmi, Thengumpillil Narayana Balagopala Kaimal, Arabinda Chaudhuri, Yerramsetti Ramadas, Nalam Madhusudhana Rao. Novel Non-Glycerol-Based Cytofectins with Lactic Acid-Derived Head Groups. Biochemical and Biophysical Research Communications 2001, 289 (5) , 1057-1062. https://doi.org/10.1006/bbrc.2001.6065
    68. Jarmila S̆misterová, Anno Wagenaar, Marc C.A. Stuart, Evgeny Polushkin, Gerrit ten Brinke, Ron Hulst, Jan B. F.N. Engberts, Dick Hoekstra. Molecular Shape of the Cationic Lipid Controls the Structure of Cationic Lipid/Dioleylphosphatidylethanolamine-DNA Complexes and the Efficiency of Gene Delivery. Journal of Biological Chemistry 2001, 276 (50) , 47615-47622. https://doi.org/10.1074/jbc.M106199200
    69. Alexandru T Balaban, Marc Antoniu Ilies. Recent developments in cationic lipid-mediated gene delivery and gene therapy. Expert Opinion on Therapeutic Patents 2001, 11 (11) , 1729-1752. https://doi.org/10.1517/13543776.11.11.1729
    70. Rajkumar Banerjee, Yenugonda Venkata Mahidhar, Arabinda Chaudhuri, Vijaya Gopal, Nalam Madhusudhana Rao. Design, Synthesis, and Transfection Biology of Novel Cationic Glycolipids for Use in Liposomal Gene Delivery. Journal of Medicinal Chemistry 2001, 44 (24) , 4176-4185. https://doi.org/10.1021/jm000466s
    71. KK Goncz, A Colosimo, B Dallapiccola, L Gagné, K Hong, G Novelli, D Papahadjopoulos, T Sawa, H Schreier, J Wiener-Kronish, Z Xu, DC Gruenert. Expression of ΔF508 CFTR in normal mouse lung after site-specific modification of CFTR sequences by SFHR. Gene Therapy 2001, 8 (12) , 961-965. https://doi.org/10.1038/sj.gt.3301476
    72. Ruthven N.A.H. Lewis, Stephanie Tristram-Nagle, John F. Nagle, Ronald N. McElhaney. The thermotropic phase behavior of cationic lipids: calorimetric, infrared spectroscopic and X-ray diffraction studies of lipid bilayer membranes composed of 1,2-di- O -myristoyl-3- N,N,N -trimethylaminopropane (DM-TAP). Biochimica et Biophysica Acta (BBA) - Biomembranes 2001, 1510 (1-2) , 70-82. https://doi.org/10.1016/S0005-2736(00)00336-9
    73. Séverine Loisel, Virginie Floch, Christelle Le Gall, Claude Férec. FACTORS INFLUENCING THE EFFICIENCY OF LIPOPLEXES MEDIATED GENE TRANSFER IN LUNG AFTER INTRAVENOUS ADMINISTRATION*. Journal of Liposome Research 2001, 11 (2-3) , 127-138. https://doi.org/10.1081/LPR-100108457
    74. Edmund J. Niedzinski, Michael J. Bennett, David C. Olson, Michael H. Nantz. Gastroprotection of DNA with a synthetic cholic acid analog. Lipids 2000, 35 (7) , 721-727. https://doi.org/10.1007/s11745-000-0578-y
    75. Michel Bessodes, Catherine Dubertret, Gabrielle Jaslin, Daniel Scherman. Synthesis and biological properties of new glycosidic cationic lipids for DNA delivery. Bioorganic & Medicinal Chemistry Letters 2000, 10 (12) , 1393-1395. https://doi.org/10.1016/S0960-894X(00)00251-1
    76. P. Delépine, C. Guillaume, V. Floch, S. Loisel, J.‐J. Yaouanc, J.‐C. Clément, H. Des Abbayes, C. Férec. Cationic Phosphonolipids as Nonviral Vectors: In Vitro and in Vivo Applications. Journal of Pharmaceutical Sciences 2000, 89 (5) , 629-638. https://doi.org/10.1002/(SICI)1520-6017(200005)89:5<629::AID-JPS8>3.0.CO;2-P
    77. T Ren, Y K Song, G Zhang, D Liu. Structural basis of DOTMA for its high intravenous transfection activity in mouse. Gene Therapy 2000, 7 (9) , 764-768. https://doi.org/10.1038/sj.gt.3301153
    78. Ulrich Massing, Jörg T. Kley, Laura Gürtesch, Stefan Fankhaenel. A simple approach to DOTAP and its analogs bearing different fatty acids. Chemistry and Physics of Lipids 2000, 105 (2) , 189-191. https://doi.org/10.1016/S0009-3084(00)00121-3
    79. M. A. Maslov, E. V. Syicheva, N. G. Morozova, G. A. Serebrennikova. Cationic amphiphiles of both lipid and nonlipid nature in gene therapy. Russian Chemical Bulletin 2000, 49 (3) , 385-401. https://doi.org/10.1007/BF02494765
    80. Mike E. Lizarzaburu, Mark J. Kurth, Michael H. Nantz. A versatile synthesis of tetraester polyamine lipids for gene transfection. Tetrahedron Letters 1999, 40 (51) , 8985-8988. https://doi.org/10.1016/S0040-4039(99)01934-6
    81. Danielle Hirsch-Lerner, Yechezkel Barenholz. Hydration of lipoplexes commonly used in gene delivery: follow-up by laurdan fluorescence changes and quantification by differential scanning calorimetry. Biochimica et Biophysica Acta (BBA) - Biomembranes 1999, 1461 (1) , 47-57. https://doi.org/10.1016/S0005-2736(99)00145-5
    82. Patrick C Ross, Sek Wen Hui. Polyethylene glycol enhances lipoplex-cell association and lipofection. Biochimica et Biophysica Acta (BBA) - Biomembranes 1999, 1421 (2) , 273-283. https://doi.org/10.1016/S0005-2736(99)00132-7
    83. M. A. Maslov, E. V. Sycheva, N. G. Morozova, G. A. Serebrennikova. Synthesis of alkyl glycerolipids with various cationic groups linked directly to the glycerol backbone. Russian Chemical Bulletin 1999, 48 (7) , 1369-1372. https://doi.org/10.1007/BF02495307
    84. Tan Ren, Dexi Liu. Synthesis of diether-linked cationic lipids for gene delivery. Bioorganic & Medicinal Chemistry Letters 1999, 9 (9) , 1247-1250. https://doi.org/10.1016/S0960-894X(99)00187-0
    85. Tan Ren, Dexi Liu. Synthesis of cationic lipids from 1,2,4-butanetriol. Tetrahedron Letters 1999, 40 (2) , 209-212. https://doi.org/10.1016/S0040-4039(98)02381-8
    86. Tan Ren, Guisheng Zhang, Young K. Song, Dexi Liu. Synthesis and Characterization of Aromatic Ring-Based Cationic Lipids for Gene Delivery In Vitro and In Vivo. Journal of Drug Targeting 1999, 7 (4) , 285-292. https://doi.org/10.3109/10611869909085511
    87. Michael H. Nantz, Ling Li, Ji Zhu, Kim L. Aho-Sharon, Debora Lim, Kent L. Erickson. Inductive electron-withdrawal from ammonium ion headgroups of cationic lipids and the influence on DNA transfection. Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism 1998, 1394 (2-3) , 219-223. https://doi.org/10.1016/S0005-2760(98)00114-3
    88. Rajkumar Banerjee, Prasanta Kumar Das, Arabinda Chaudhuri. Interfacial indazolization: novel chemical evidence for remarkably high exo-surface pH of cationic liposomes used in gene transfection. Biochimica et Biophysica Acta (BBA) - Biomembranes 1998, 1373 (2) , 299-308. https://doi.org/10.1016/S0005-2736(98)00113-8
    89. Alfred M. Aberle, Fern Tablin, Ji Zhu, Naomi J. Walker, Dieter C. Gruenert, Michael H. Nantz. A Novel Tetraester Construct That Reduces Cationic Lipid-Associated Cytotoxicity. Implications for the Onset of Cytotoxicity. Biochemistry 1998, 37 (18) , 6533-6540. https://doi.org/10.1021/bi9801154
    90. Erik R. Wisner, Kimberly L. Aho-Sharon, Michael J. Bennett, Sharron G. Penn, Carlito B. Lebrilla, Michael H. Nantz. A Modular Lymphographic Magnetic Resonance Imaging Contrast Agent:  Contrast Enhancement with DNA Transfection Potential. Journal of Medicinal Chemistry 1997, 40 (25) , 3992-3996. https://doi.org/10.1021/jm970665k

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    MENDELEY PAIRING EXPIRED
    Your Mendeley pairing has expired. Please reconnect