Antiviral mechanism of polyanionic carbosilane dendrimers against HIV-I

International Journal of Nanomedicine

Volumn 11, Issue , 2016, Pages 1281-1294

  Vacas Córdoba, Enrique ^a,b,c,d   Maly, Marek ^e,f   De la mata, Francisco J ^d,g   Gómez, Rafael ^d,g   Pion, Marjorie ^a,b,c,d   Muñoz Fernández, Ma Ángeles ^a,b,c,d  

^a HOSPITAL GENERAL UNIVERSITARIO GREGORIO MARAÑÓN   (Spain)

^b HOSPITAL GENERAL UNIVERSITARIO GREGORIO MARAÑÓN   (Spain)

^c Spanish HIV HG M BioBanK ^*  (Spain)

^d BIOMATERIALES Y NANOMEDICINA CIBER BBN   (Spain)

^e J E PURKINJE UNIVERSITY   (Czech Republic)

^f UNIVERSITY OF APPLIED SCIENCES AND ARTS OF SOUTHERN SWITZERLAND   (Switzerland)

^g UNIVERSITY OF ALCALÁ   (Spain)

Author keywords

Carbosilane dendrimer; HIV; Mechanism; Microbicide; Nanotechnology

Indexed keywords

ANTIVIRUS AGENT; CARBOSILANE; CD4 ANTIGEN; CHEMOKINE RECEPTOR CXCR4; DENDRIMER; GLYCOPROTEIN GP 120; TRANSACTIVATOR PROTEIN; UNCLASSIFIED DRUG; POLYANIONS; POLYMER; SILANE DERIVATIVE;

ANTIVIRAL ACTIVITY; ARTICLE; BINDING SITE; CD4+ T LYMPHOCYTE; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOPLASM; DISEASE TRANSMISSION; DRUG EFFICACY; DRUG MECHANISM; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; PROTEIN INTERACTION; PROTEIN LOCALIZATION; PROTEIN PROTEIN INTERACTION; PROTEIN TARGETING; SYNAPSE; TARGET CELL; VIRUS ATTACHMENT; VIRUS ENTRY; VIRUS ENVELOPE; VIRUS PARTICLE; VIRUS REPLICATION; ANTAGONISTS AND INHIBITORS; CHEMISTRY; DRUG EFFECTS; HIV INFECTIONS; MEMBRANE FUSION; METABOLISM; MOLECULAR MODEL; VIROLOGY;

ANTIVIRAL AGENTS; DENDRIMERS; HIV ENVELOPE PROTEIN GP120; HIV INFECTIONS; HIV-1; HUMANS; MEMBRANE FUSION; MODELS, MOLECULAR; POLYMERS; SILANES; VIRUS REPLICATION;

EID: 84962773840     PISSN: 11769114     EISSN: 11782013     Source Type: Journal    
DOI: 10.2147/IJN.S96352     Document Type: Article

References (54)

1. (UNAIDS) JUNPoHA. UNAIDS Report on the Global AIDS Epidemic. (UNAIDS) JUNPoHA; 2014. Available from: http://www. unaids. org/sites/default/files/media_asset/GARPR_2014_guidelines_en_0. pdf. Accessed January 21, 2016.
2. (UNAIDS) JUNPoHA. UNAIDS 2011-2015 STRATEGY: Getting to Zero. (UNAIDS) JUNPoHA; 2010. Available from: http://www. unaids. org/sites/default/files/sub_landing/files/JC2034_UNAIDS_Strategy_en.pdf.
3. Abdool Karim SS, Baxter C. Microbicides & their implications in HIV prevention. Indian J Med Res. 2010; 132(6): 656-659.
4. Anton PA. Future prospects and perspectives on microbicides. Curr HIV Res. 2012; 10(1): 113-115.
5. Buckheit RW Jr, Watson KM, Morrow KM, Ham AS. Development of topical microbicides to prevent the sexual transmission of HIV. Antiviral Res. 2010; 85(1): 142-158.
6. Quinones-Mateu ME, Vanham G. HIV microbicides: where are we now? Curr HIV Res. 2012; 10(1): 1-2.
7. Abdool Karim Q, Abdool Karim SS, Frohlich JA, et al. Effectiveness and safety of tenofovir gel, an antiretroviral microbicide, for the prevention of HIV infection in women. Science. 2010; 329(5996): 1168-1174.
8. Gibson RM, Arts EJ. Past, present, and future of entry inhibitors as HIV microbicides. Curr HIV Res. 2012; 10(1): 19-26.
9. Pirrone V, Wigdahl B, Krebs FC. The rise and fall of polyanionic inhibitors of the human immunodeficiency virus type 1. Antiviral Res. 2011; 90(3): 168-182.
10. Van Damme L, Govinden R, Mirembe FM, et al. Lack of effectiveness of cellulose sulfate gel for the prevention of vaginal HIV transmission. N Engl J Med. 2008; 359(5): 463-472.
11. Bourne N, Stanberry LR, Kern ER, Holan G, Matthews B, Bernstein DI. Dendrimers, a new class of candidate topical microbicides with activity against herpes simplex virus infection. Antimicrob Agents Chemother. 2000; 44(9): 2471-2474.
12. Chonco L, Pion M, Vacas E, et al. Carbosilane dendrimer nanotechnology outlines of the broad HIV blocker profile. J Control Release. 2012; 161(3): 949-958.
13. Jimenez J, Pion M, De la Mata FJ, et al. Dendrimers as topical microbicides with activity against HIV. New J Chem. 2012; 36: 299-309.
14. Kim BY, Rutka JT, Chan WC. Nanomedicine. N Engl J Med. 2010; 363(25): 2434-2443.
15. Klajnert B, Bryszewska M. Dendrimers: properties and applications. Acta Biochim Pol. 2001; 48(1): 199-208.
16. Mallipeddi R, Rohan LC. Progress in antiretroviral drug delivery using nanotechnology. Int J Nanomedicine. 2010; 5: 533-547.
17. Weber N, Ortega P, Clemente MI, et al. Characterization of carbosilane dendrimers as effective carriers of siRNA to HIV-infected lymphocytes. J Control Release. 2008; 132(1): 55-64.
18. Tyssen D, Henderson SA, Johnson A, et al. Structure activity relationship of dendrimer microbicides with dual action antiviral activity. PLoS One. 2010; 5(8): e12309.
19. Telwatte S, Moore K, Johnson A, et al. Virucidal activity of the dendrimer microbicide SPL7013 against HIV-1. Antiviral Res. 2011; 90(3): 195-199.
20. Asaftei S, Huskens D, Schols D. HIV-1 X4 activities of polycationic "viologen" based dendrimers by interaction with the chemokine receptor CXCR4: study of structure-activity relationship. J Med Chem. 2012; 55(23): 10405-10413.
21. Witvrouw M, Fikkert V, Pluymers W, et al. Polyanionic (ie, polysulfonate) dendrimers can inhibit the replication of human immunodeficiency virus by interfering with both virus adsorption and later steps (reverse transcriptase/integrase) in the virus replicative cycle. Mol Pharmacol. 2000; 58(5): 1100-1108.
22. Rosa Borges A, Wieczorek L, Johnson B, et al. Multivalent dendrimeric compounds containing carbohydrates expressed on immune cells inhibit infection by primary isolates of HIV-1. Virology. 2010; 408(1): 80-88.
23. Garcia-Vallejo JJ, Koning N, Ambrosini M, et al. Glycodendrimers prevent HIV transmission via DC-SIGN on dendritic cells. Int Immunol. 2013; 25(4): 221-233.
24. Cordoba EV, Arnaiz E, Relloso M, et al. Development of sulphated and naphthylsulfonated carbosilane dendrimers as topical microbicides to prevent HIV-1 sexual transmission. AIDS. 2013; 27(8): 1219-1229.
25. Galan M, Sanchez-Rodriguez J, Cangiotti M, et al. Antiviral properties against HIV of water soluble copper carbosilane dendrimers and their EPR characterization. Curr Med Chem. 2012; 19(29): 4984-4994.
26. Ortega P, Copa-Patino JL, Munoz-Fernandez MA, Soliveri J, Gomez R, de la Mata FJ. Amine and ammonium functionalization of chloromethylsilane-ended dendrimers. Antimicrobial activity studies. Org Biomol Chem. 2008; 6(18): 3264-3269.
27. Ortega P, Macarena Cobaleda B, Hernandez-Ros JM, et al. Hyperbranched polymers versus dendrimers containing a carbosilane framework and terminal ammonium groups as antimicrobial agents. Org Biomol Chem. 2011; 9(14): 5238-5248.
28. Rasines B, Sanchez-Nieves J, Maiolo M, et al. Synthesis, structure and molecular modelling of anionic carbosilane dendrimers. Dalton Trans. 2012; 41(41): 12733-12748.
29. Sepulveda-Crespo D, Lorente R, Leal M, et al. Synergistic activity profile of carbosilane dendrimer G2-STE16 in combination with other dendrimers and antiretrovirals as topical anti-HIV-1 microbicide. Nanomedicine. 2014; 10(3): 609-618.
30. Garcia-Merino I, de Las Cuevas N, Jimenez JL, et al. The Spanish HIV BioBank: a model of cooperative HIV research. Retrovirology. 2009; 6: 27.
31. Wu L, Martin TD, Carrington M, KewalRamani VN. Raji B cells, misidentified as THP-1 cells, stimulate DC-SIGN-mediated HIV transmission. Virology. 2004; 318(1): 17-23.
32. Folks TM, Powell D, Lightfoote M, et al. Biological and biochemical characterization of a cloned Leu-3-cell surviving infection with the acquired immune deficiency syndrome retrovirus. J Exp Med. 1986; 164(1): 280-290.
33. Pion M, Stalder R, Correa R, Mangeat B, Towers GJ, Piguet V. Identification of an arsenic-sensitive block to primate lentiviral infection of human dendritic cells. J Virol. 2007; 81(21): 12086-12090.
34. Arnáiz E, Vacas-Córdoba E, Galán M, et al. Synthesis of anionic carbosilane dendrimers via "click chemistry" and their antiviral properties against HIV. J Polym Sci A Polym Chem. 2014; 52: 1099-1112.
35. Furukawa H, Momota K, Agatsuma T, Yamamoto I, Kimura S, Shimada K. Mechanism of inhibition of HIV-1 infection in vitro by guanine-rich oligonucleotides modified at the 5′ terminal by dimethoxytrityl residue. Nucleic Acids Res. 1994; 22(25): 5621-5627.
36. Bayly CI, Cieplak P, Cornell W, Kollman PA. A well-behaved electrostatic potential based method using charge restraints for deriving atomic charges: the RESP model. J Phys Chem. 1993; 97(40): 10269-10280.
37. Gordon MS, Schmidt MW, editors. Advances in Electronic Structure Theory: GAMESS a Decade Later in Theory and Applications of Computational Chemistry: The First Forty Years. Amsterdam: Elsevier; 2005.
38. Wang J, Wolf RM, Caldwell JW, Kollman PA, Case DA. Development and testing of a general amber force field. J Comput Chem. 2004; 25(9): 1157-1174.
39. Case DA, Darden TA, Cheatham TE, et al, editors. AMBER 12. San Francisco, CA: University of California; 2012.
40. Jenn-Huei Lii A, Norman A, Allinger L. The MM3 force field for amides, polypeptides and proteins. J Comput Chem. 1991; 12(2): 186-199.
41. Huang CC, Tang M, Zhang MY, et al. Structure of a V3-containing HIV-1 gp120 core. Science. 2005; 310(5750): 1025-1028.
42. Anandakrishnan R, Aguilar B, Onufriev AV. H++ 3. 0: automating pK prediction and the preparation of biomolecular structures for atomistic molecular modeling and simulations. Nucleic Acids Res. 2012; 40(Web Server issue): W537-W541.
43. Pettersen EF, Goddard TD, Huang CC, et al. UCSF chimera-a visualization system for exploratory research and analysis. J Comput Chem. 2004; 25(13): 1605-1612.
44. Gotz AW, Williamson MJ, Xu D, Poole D, Le Grand S, Walker RC. Routine microsecond molecular dynamics simulations with AMBER on GPUs. 1. generalized born. J Chem Theory Comput. 2012; 8(5): 1542-1555.
45. Miller BR, McGee TD, Swails JM, Homeyer N, Gohlke H, Roitberg AE. MMPBSA. py: an efficient program for end-state free energy calculations. J Chem Theory Comput. 2012; 8(9): 3314-3321.
46. Baker NA, Sept D, Joseph S, Holst MJ, McCammon JA. Electrostatics of nanosystems: application to microtubules and the ribosome. Proc Natl Acad Sci U S A. 2001; 98(18): 10037-10041.
47. Garcia E, Pion M, Pelchen-Matthews A, et al. HIV-1 trafficking to the dendritic cell-T-cell infectious synapse uses a pathway of tetraspanin sorting to the immunological synapse. Traffic. 2005; 6(6): 488-501.
48. Yu HJ, Reuter MA, McDonald D. HIV traffics through a specialized, surface-accessible intracellular compartment during trans-infection of T cells by mature dendritic cells. PLoS Pathog. 2008; 4(8): e1000134.
49. Massanella M, Puigdomenech I, Cabrera C, et al. Antigp41 antibodies fail to block early events of virological synapses but inhibit HIV spread between T cells. AIDS. 2009; 23(2): 183-188.
50. Rodriguez-Plata MT, Puigdomenech I, Izquierdo-Useros N, et al. The infectious synapse formed between mature dendritic cells and CD4+ T cells is independent of the presence of the HIV-1 envelope glycoprotein. Retrovirology. 2013; 10: 42.
51. Izquierdo-Useros N, Lorizate M, Puertas MC, et al. Siglec-1 is a novel dendritic cell receptor that mediates HIV-1 trans-infection through recognition of viral membrane gangliosides. PLoS Biol. 2012; 10(12): e1001448.
52. Coleman CM, Gelais CS, Wu L. Cellular and viral mechanisms of HIV-1 transmission mediated by dendritic cells. Adv Exp Med Biol. 2013; 762: 109-130.
53. Belec L, Jenabian MA, Charpentier C, Saidi H. Combinatorial prevention of HIV transmission in women: the case for a vaginal microbicide. Future Microbiol. 2011; 6(7): 731-737.
54. Cordoba EV, Arnaiz E, De La Mata FJ, et al. Synergistic activity of carbosilane dendrimers in combination with maraviroc against HIV in vitro. AIDS. 2013; 27(13): 2053-2058.