journal article·2018-03

Engineering CNDP’s of dendrimers containing phosphorous interior compositions to produce new emerging properties

Anne-Marie Caminade, Jean-Pierre Majoral

Journal of Nanoparticle Research· Volume 20· Issue 3
Publisher page

Abstract

Phosphorus-containing dendrimers are defined as dendrimers having at least one phosphorus atom at each branching point. In this review, we will show how phosphorhydrazone dendrimers can be modified at will at the level of the core and of the branches, to afford specific properties, such as fluorescence to image biological events. Accelerated methods of synthesis of phosphorus (one step for one generation) will be also displayed, as well as the specific reactivity of P=N–P=S linkages obtained in most of these accelerated method of synthesis, which has led to particularly original dendritic architectures, such as dendrons included in dendrimers. Finally, we will display how modifications of the internal structure of a series of dendrimers having the same type and number of terminal functions can deeply modify their biological anti-inflammatory properties. Among the six critical nanoscale design parameters (CNDP), we will show how two of them, i.e., architecture and elemental composition, have been particularly engineered to modify phosphorus-containing dendrimers, in order to fulfill the desired properties.
Source: openaire · Quality: candidate unverified · Source record ↗

Research context

OpenAlex topics: Dendrimers and Hyperbranched Polymers · Advanced biosensing and bioanalysis techniques · RNA Interference and Gene Delivery

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

References (100+)

Show source-provided references
1. Aharoni SM, Crosby CR, Walsh EK (1982) Size and solution properties of globular tert-butyloxycarbonyl-poly(alpha,XI-L-lysine). Macromolecules 15:1093–1098. https://doi.org/10.1021/ma00232a02610.1021/ma00232a026 ↗
2. Brauge L, Caminade AM, Majoral JP, Slomkowski S, Wolszczak M (2001a) Segmental mobility in phosphorus-containing dendrimers. Studies by fluorescent spectroscopy. Macromolecules 34:5599–5606. https://doi.org/10.1021/ma002007710.1021/ma0020077 ↗
3. Brauge L, Magro G, Caminade AM, Majoral JP (2001b) First divergent strategy using two AB(2) unprotected monomers for the rapid synthesis of dendrimers. J Am Chem Soc 123:6698–6699. https://doi.org/10.1021/ja002922810.1021/ja0029228 ↗
4. Brauge L, Magro G, Caminade AM, Majoral JP (2001c) First divergent strategy using two AB(2) unprotected monomers for the rapid synthesis of dendrimers (vol 123, pg 6698, 2001). J Am Chem Soc 123:8446–8446. https://doi.org/10.1021/ja015159610.1021/ja0151596 ↗
5. Cadierno V, Igau A, Donnadieu B, Caminade AM, Majoral JP (1999) Dendrimers containing zwitterionic phosphonium anionic zirconocene(IV) complexes. Organometallics 18:1580–1582. https://doi.org/10.1021/om980880e10.1021/om980880e ↗
6. Caminade AM, Laurent R, Chaudret B, Majoral JP (1998) Phosphine-terminated dendrimers—synthesis and complexation properties. Coord Chem Rev 178:793–821. https://doi.org/10.1016/s0010-8545(98)00057-510.1016/S0010-8545(98)00057-5 ↗
7. Caminade AM, Servin P, Laurent R, Majoral JP (2008) Dendrimeric phosphines in asymmetric catalysis. Chem Soc Rev 37(1):56–67. https://doi.org/10.1039/b606569b10.1039/B606569B ↗
8. Caminade AM, Hameau A, Majoral JP (2009) Multicharged and/or water-soluble fluorescent dendrimers: properties and uses. Chem Eur J 15:9270–9285. https://doi.org/10.1002/chem.20090159710.1002/chem.200901597 ↗
9. Caminade AM, Laurent R, Delavaux-Nicot B, Majoral JP (2012) “Janus” dendrimers: syntheses and properties. New J Chem 36(2):217–226. https://doi.org/10.1039/c1nj20458k10.1039/C1NJ20458K ↗
10. Caminade AM, Fruchon S, Turrin CO, Poupot M, Ouali A, Maraval A, Garzoni M, Maly M, Furer V, Kovalenko V, Majoral JP, Pavan GM, Poupot R (2015) The key role of the scaffold on the efficiency of dendrimer nanodrugs. Nature Comm 6:7722. https://doi.org/10.1038/ncomms872210.1038/ncomms8722 ↗
11. Caminade AM, Hameau A, Majoral JP (2016a) The specific functionalization of cyclotriphosphazene for the synthesis of smart dendrimers. Dalton Trans 45:1810–1822. https://doi.org/10.1039/c5dt03047a10.1039/C5DT03047A ↗
12. Caminade AM, Ouali A, Laurent R, Turrin CO, Majoral JP (2016b) Coordination chemistry with phosphorus dendrimers. Applications as catalysts, for materials, and in biology. Coord Chem Rev 308:478–497. https://doi.org/10.1016/j.ccr.2015.06.00710.1016/j.ccr.2015.06.007 ↗
13. Ciepluch K, Katir N, El Kadib A, Felczak A, Zawadzka K, Weber M, Klajnert B, Lisowska K, Caminade AM, Bousmina M, Bryszewska M, Majoral JP (2012a) Biological properties of new Viologen-phosphorus dendrimers. Mol Pharm 9(3):448–457. https://doi.org/10.1021/mp200549c10.1021/mp200549c ↗
14. Ciepluch K, Katir N, El Kadib A, Weber M, Caminade AM, Bousmina M, Majoral JP, Bryszewska M (2012b) Photo-physical and structural interactions between viologen phosphorus-based dendrimers and human serum albumin. J Lumin 132(6):1553–1563. https://doi.org/10.1016/j.jlumin.2012.01.04410.1016/j.jlumin.2012.01.044 ↗
15. Ciepluch K, Weber M, Katir N, Caminade AM, El Kadib A, Klajnert B, Majoral JP, Bryszewska M (2013) Effect of viologen-phosphorus dendrimers on acetylcholinesterase and butyrylcholinesterase activities. Int J Biol Macromol 54:119–124. https://doi.org/10.1016/j.ijbiomac.2012.12.00210.1016/j.ijbiomac.2012.12.002 ↗
16. de Brabander van den Berg EMM, Meijer EW (1993) Poly(propylene imine) dendrimers—large-scale synthesis by hetereogeneously catalyzed hydrogenations. Angew Chem Int Ed Engl 32:1308–1311. https://doi.org/10.1002/anie.19931308110.1002/anie.199313081 ↗
17. de Jong ER, Manoury E, Daran JC, Turrin CO, Chiffre J, Sournia-Saquet A, Knoll W, Majoral JP, Caminade AM (2012) Synthesis and characterization of water-soluble ferrocene-dendrimers. J Organomet Chem 718:22–30. https://doi.org/10.1016/j.jorganchem.2012.07.04810.1016/j.jorganchem.2012.07.048 ↗
18. de Jong ER, Deloch N, Knoll W, Turrin CO, Majoral JP, Caminade AM, Koper I (2015) Synthesis and characterization of bifunctional dendrimers: preliminary use for the coating of gold surfaces and the proliferation of human osteoblasts (HOB). New J Chem 39:7194–7205. https://doi.org/10.1039/c5nj00620a10.1039/C5NJ00620A ↗
19. Deloncle R, Coppel Y, Rebout C, Majoral JP, Caminade AM (2008) Characterization of two series of nitrogen-containing dendrimers by natural abundance N-15 NMR. Magn Reson Chem 46:493–496. https://doi.org/10.1002/mrc.220310.1002/mrc.2203 ↗
20. Dib H, Rebout C, Laurent R, Mallet-Ladeira S, Sournia-Saquet A, Sarosi MB, Hey-Hawkins E, Majoral JP, Delavaux-Nicot B, Caminade AM (2016) Ordered layered dendrimers constructed from two known dendrimer families: inheritance and emergence of properties. Chem Eur J 22:10736–10742. https://doi.org/10.1002/chem.20160135410.1002/chem.201601354 ↗
21. El Brahmi N, El Kazzouli S, Mignani SM, Essassi E, Aubert G, Laurent R, Caminade AM, Bousmina MM, Cresteil T, Majoral JP (2013) Original multivalent copper(II)-conjugated phosphorus dendrimers and corresponding mononuclear copper(II) complexes with antitumoral activities. Mol Pharm 10:1459–1464. https://doi.org/10.1021/mp400018410.1021/mp4000184 ↗
22. Feng CL, Zhong XH, Steinhart M, Caminade AM, Majoral JP, Knoll W (2008) Functional quantum-dot/dendrimer nanotubes for sensitive detection of DNA hybridization. Small 4(5):566–571. https://doi.org/10.1002/smll.20070045310.1002/smll.200700453 ↗
23. Franc G, Mazeres S, Turrin CO, Vendier L, Duhayon C, Caminade AM, Majoral JP (2007) Synthesis and properties of dendrimers possessing the same fluorophore(s) located either peripherally or off-center. J Org Chem 72:8707–8715. https://doi.org/10.1021/jo701462f10.1021/jo701462f ↗
24. Fruchon S, Poupot M, Martinet L, Turrin CO, Majoral JP, Fournie JJ, Caminade AM, Poupot R (2009) Anti-inflammatory and immunosuppressive activation of human monocytes by a bioactive dendrimer. J Leukoc Biol 85:553–562. https://doi.org/10.1189/jlb.060837110.1189/jlb.0608371 ↗
25. Fruchon S, Mouriot S, Thiollier T, Grandin C, Caminade AM, Turrin CO, Contamin H, Poupot R (2015) Repeated intravenous injections in non-human primates demonstrate preclinical safety of an anti-inflammatory phosphorus-based dendrimer. Nanotoxicology 9:433–441. https://doi.org/10.3109/17435390.2014.94040610.3109/17435390.2014.940406 ↗
26. Fuchs S, Pla-Quintana A, Mazeres S, Caminade AM, Majoral JP (2008) Cationic and fluorescent “Janus” dendrimers. Org Lett 10(21):4751–4754. https://doi.org/10.1021/ol801698k10.1021/ol801698k ↗
27. Furer VL, Vandyukov AE, Majoral JP, Caminade AM, Gottis S, Laurent R, Kovalenko VI (2015a) DFT study of structure, IR and Raman spectra of dendrimer with P=N-P=S linkages and its complexation with gold. J Mol Struct 1084:103–113. https://doi.org/10.1016/j.molstruc.2014.12.02610.1016/j.molstruc.2014.12.026 ↗
28. Furer VL, Vandyukov AE, Majoral JP, Caminade AM, Gottis S, Laurent R, Kovalenko VI (2015b) Comparative DFT study of structure, reactivity and IR spectra of phosphorus-containing dendrons with P=N-P=S linkages, vinyl and azide functional groups. J Mol Struct 1091:6–15. https://doi.org/10.1016/j.molstruc.2015.02.06710.1016/j.molstruc.2015.02.067 ↗
29. Galliot C, Caminade AM, Dahan F, Majoral JP (1993) Synthesis, structure, and reactivity of stable PN heterocycles with 2 and 6 methyleneamine units: H2C=N-N(Me)2P(S)(Ph) and H2C=N-N(Me)6P3N3. Angew Chem Int Ed Engl 32(10):1477–1479. https://doi.org/10.1002/anie.19931477110.1002/anie.199314771 ↗
30. Galliot C, Prevote D, Caminade AM, Majoral JP (1995) Polyaminophosphines containing dendrimers—syntheses and characterizations. J Am Chem Soc 117(20):5470–5476. https://doi.org/10.1021/ja00125a00610.1021/ja00125a006 ↗
31. Galliot C, Larre C, Caminade AM, Majoral JP (1997) Regioselective stepwise growth of dendrimer units in the internal voids of a main dendrimer. Science 277(5334):1981–1984. https://doi.org/10.1126/science.277.5334.198110.1126/science.277.5334.1981 ↗
32. Griffe L, Poupot M, Marchand P, Maraval A, Turrin CO, Rolland O, Metivier P, Bacquet G, Fournie JJ, Caminade AM, Poupot R, Majoral JP (2007) Multiplication of human natural killer cells by nanosized phosphonate-capped dendrimers. Angew Chem Int Ed 46:2523–2526. https://doi.org/10.1002/anie.20060465110.1002/anie.200604651 ↗
33. Hameau A, Fuchs S, Laurent R, Majoral JP, Caminade AM (2011) Synthesis of dye/fluorescent functionalized dendrons based on cyclotriphosphazene. Beilstein J Org Chem 7:1577–1583. https://doi.org/10.3762/bjoc.7.18610.3762/bjoc.7.186 ↗
34. Hayder M, Poupot M, Baron M, Nigon D, Turrin CO, Caminade AM, Majoral JP, Eisenberg RA, Fournie JJ, Cantagrel A, Poupot R, Davignon JL (2011) A phosphorus-based dendrimer targets inflammation and osteoclastogenesis in experimental arthritis. Science Transl Med 3:11. https://doi.org/10.1126/scitranslmed.300221210.1126/scitranslmed.3002212 ↗
35. Hayder M, Varilh M, Turrin CO, Saoudi A, Caminade AM, Poupot R, Liblau RS (2015) Phosphorus-based dendrimer ABP treats neuroinflammation by promoting IL-10-producing CD4(+) T cells. Biomacromolecules 16:3425–3433. https://doi.org/10.1021/acs.biomac.5b0064310.1021/acs.biomac.5b00643 ↗
36. Ielasi F, Ledall J, Anes AP, Fruchon S, Caminade AM, Poupot R, Turrin CO, Blanzat M (2016) Influence of PPH dendrimers’ surface functions on the activation of human monocytes: a study of their interactions with pure lipid model systems. Phys Chem Chem Phys 18:21871–21880. https://doi.org/10.1039/c6cp03536a10.1039/C6CP03536A ↗
37. Kannan RM, Nance E, Kannan S, Tomalia DA (2014) Emerging concepts in dendrimer-based nanomedicine: from design principles to clinical applications. J Intern Med 276:579–617. https://doi.org/10.1111/joim.1228010.1111/joim.12280 ↗
38. Katir N, Majoral JP, El Kadib A, Caminade AM, Bousmina M (2012) Molecular and macromolecular engineering with viologens as building blocks: rational design of phosphorus-viologen dendritic structures. Eur J Org Chem 2:269–273. https://doi.org/10.1002/ejoc.20110137610.1002/ejoc.201101376 ↗
39. Katir N, El Brahmi N, El Kadib A, Mignani S, Caminade AM, Bousmina M, Majoral JP (2015) Synthesis of onion-peel nanodendritic structures with sequential functional phosphorus diversity. Chem-Eur J 21(17):6400–6408. https://doi.org/10.1002/chem.20150013810.1002/chem.201500138 ↗
40. Kazmierczak-Baranska J, Pietkiewicz A, Janicka M, Wei YQ, Turrin CO, Majoral JP, Nawrot B, Caminade AM (2010) Synthesis of a fluorescent cationic phosphorus dendrimer and preliminary biological studies of its interaction with DNA. Nucleosides Nucleotides Nucleic Acids 29:155–167. https://doi.org/10.1080/1525777100370846210.1080/15257771003708462 ↗
41. Keller M, Colliere V, Reiser O, Caminade AM, Majoral JP, Ouali A (2013) Pyrene-tagged dendritic catalysts noncovalently grafted onto magnetic co/C nanoparticles: an efficient and recyclable system for drug synthesis. Angew Chem Int Ed 52:3626–3629. https://doi.org/10.1002/anie.20120996910.1002/anie.201209969 ↗
42. Kim DH, Karan P, Goring P, Leclaire J, Caminade AM, Majoral JP, Gosele U, Steinhart M, Knoll W (2005) Formation of dendrimer nanotubes by layer-by-layer deposition. Small 1(1):99–102. https://doi.org/10.1002/smll.20040002410.1002/smll.200400024 ↗
43. Knoll W, Caminade AM, Char K, Duran H, Feng CL, Gitsas A, Kim DH, Lau A, Lazzara TD, Majoral JP, Steinhart M, Yameen B, Zhong XH (2011) Nanostructuring polymeric materials by templating strategies. Small 7(10):1384–1391. https://doi.org/10.1002/smll.20110002610.1002/smll.201100026 ↗
44. Krishna TR, Parent M, Werts MHV, Moreaux L, Gmouh S, Charpak S, Caminade AM, Majoral JP, Blanchard-Desce M (2006) Water-soluble dendrimeric two-photon tracers for in vivo imaging. Angew Chem Int Ed 45:4645–4648. https://doi.org/10.1002/anie.20060124610.1002/anie.200601246 ↗
45. Larpent C, Genies C, Delgado APD, Caminade AM, Majoral JP, Sassi JF, Leising F (2004) Giant dendrimer-like particles from nanolatexes. Chem Commun 16:1816–1817. https://doi.org/10.1039/b406686c10.1039/B406686C ↗
46. Larre C, Caminade AM, Majoral JP (1997) Chemoselective polyalkylations of phosphorus-containing dendrimers. Angew Chem Int Ed Engl 36:596–599. https://doi.org/10.1002/anie.19970596110.1002/anie.199705961 ↗
47. Larre C, Bressolles D, Turrin C, Donnadieu B, Caminade AM, Majoral JP (1998a) Chemistry within megamolecules: Regiospecific functionalization after construction of phosphorus dendrimers. J Am Chem Soc 120:13070–13082. https://doi.org/10.1021/ja982778e10.1021/ja982778e ↗
48. Larre C, Donnadieu B, Caminade AM, Majoral JP (1998b) Phosphorus-containing dendrimers: chemoselective functionalization of internal layers. J Am Chem Soc 120(16):4029–4030. https://doi.org/10.1021/ja973994a10.1021/ja973994a ↗
49. Larre C, Donnadieu B, Caminade AM, Majoral JP (1998c) Regioselective gold complexation within the cascade structure of phosphorus-containing dendrimers. Chem Eur J 4:2031–2036. https://doi.org/10.1002/(sici)1521-3765(19981002)4:10<2031::aid-chem2031>3.0.co;2-j10.1002/(SICI)1521-3765(19981002)4:10<2031::AID-CHEM2031>3.0.CO;2-J ↗
50. Lartigue ML, Donnadieu B, Galliot C, Caminade AM, Majoral JP, Fayet JP (1997) Large dipole moments of phosphorus-containing dendrimers. Macromolecules 30:7335–7337. https://doi.org/10.1021/ma970570s10.1021/ma970570s ↗
51. Launay N, Caminade AM, Lahana R, Majoral JP (1994) A general synthetic strategy for neutral phosphorus-containing dendrimers. Angew Chem Int Ed Engl 33:1589–1592. https://doi.org/10.1002/anie.19941589110.1002/anie.199415891 ↗
52. Launay N, Caminade AM, Majoral JP (1995) Synthesis and reactivity of unusual phosphorus dendrimers—a useful divergent growth approach up to the 7th generation. J Am Chem Soc 117:3282–3283. https://doi.org/10.1021/ja00116a03710.1021/ja00116a037 ↗
53. Launay N, Caminade AM, Majoral JP (1997) Synthesis of bowl-shaped dendrimers from generation 1 to generation 8. J Organomet Chem 529:51–58. https://doi.org/10.1016/s0022-328x(96)06293-610.1016/S0022-328X(96)06293-6 ↗
54. Lazniewska J, Janaszewska A, Milowska K, Caminade AM, Mignani S, Katir N, El Kadib A, Bryszewska M, Majoral JP, Gabryelak T, Klajnert-Maculewicz B (2013) Promising low-toxicity of viologen-phosphorus dendrimers against embryonic mouse hippocampal cells. Molecules 18(10):12222–12240. https://doi.org/10.3390/molecules18101222210.3390/molecules181012222 ↗
55. Lazzara TD, Lau KHA, Abou-Kandil AI, Caminade AM, Majoral JP, Knoll W (2010) Polyelectrolyte layer-by-layer deposition in cylindrical nanopores. ACS Nano 4(7):3909–3920. https://doi.org/10.1021/nn100759410.1021/nn1007594 ↗
56. Leclaire J, Coppel Y, Caminade AM, Majoral JP (2004) Nanometric sponges made of water-soluble hydrophobic dendrimers. J Am Chem Soc 126:2304–2305. https://doi.org/10.1021/ja039684b10.1021/ja039684b ↗
57. Leclaire J, Dagiral R, Fery-Forgues S, Coppel Y, Donnadieu B, Caminade AM, Majoral JP (2005) Octasubstituted metal-free phthalocyanine as core of phosphorus dendrimers: a probe for the properties of the internal structure. J Am Chem Soc 127:15762–15770. https://doi.org/10.1021/ja054797b10.1021/ja054797b ↗
58. Ledall J, Fruchon S, Garzoni M, Pavan GM, Caminade AM, Turrin CO, Blanzat M, Poupot R (2015) Interaction studies reveal specific recognition of an anti-inflammatory polyphosphorhydrazone dendrimer by human monocytes. Nano 7:17672–17684. https://doi.org/10.1039/c5nr03884g10.1039/c5nr03884g ↗
59. Lee OJ, Maraval V, Caminade AM, Chung K, Lau KHA, Shin K, Majoral JP, Knoll W, Kim DH (2016) Layer-by-layer self-assembly of bisdendrons: an unprecedented route to multilayer thin films. Macromol Res 24(10):851–855. https://doi.org/10.1007/s13233-016-4128-z10.1007/s13233-016-4128-z ↗
60. Lim J, Kostiainen M, Maly J, da Costa VCP, Annunziata O, Pavan GM, Simanek EE (2013) Synthesis of large dendrimers with the dimensions of small viruses. J Am Chem Soc 135:4660–4663. https://doi.org/10.1021/ja400432e10.1021/ja400432e ↗
61. Maraval V, Laurent R, Donnadieu B, Mauzac M, Caminade AM, Majoral JP (2000a) Rapid synthesis of phosphorus-containing dendrimers with controlled molecular architectures: first example of surface-block, layer-block, and segment-block dendrimers issued from the same dendron. J Am Chem Soc 122(11):2499–2511. https://doi.org/10.1021/ja992099j10.1021/ja992099j ↗
62. Maraval V, Laurent R, Merino S, Caminade AM, Majoral JP (2000b) Michael-type addition of amines to the vinyl core of dendrons—application to the synthesis of multidendritic systems. Eur J Org Chem 3555–3568. doi: https://doi.org/10.1002/1099-0690(200011)2000:21<3555::AID-EJOC3555>3.0.CO;2-V10.1002/1099-0690(200011)2000:21<3555::AID-EJOC3555>3.0.CO;2-V ↗
63. Maraval V, Caminade AM, Majoral JP, Blais JC (2003a) Dendrimer design: how to circumvent the dilemma of a reduction of steps or an increase of function multiplicity? Angew Chem Int Ed 42:1822–1826. https://doi.org/10.1002/anie.20025082710.1002/anie.200250827 ↗
64. Maraval V, Pyzowski J, Caminade AM, Majoral JP (2003b) “Lego” chemistry for the straightforward synthesis of dendrimers. J Org Chem 68:6043–6046. https://doi.org/10.1021/jo034443810.1021/jo0344438 ↗
65. Maraval V, Maraval A, Spataro G, Caminade AM, Majoral JP, Kim DH, Knoll W (2006) Design of tailored multi-charged phosphorus surface-block dendrimers. New J Chem 30(12):1731–1736. https://doi.org/10.1039/b610632n10.1039/b610632n ↗
66. Marmillon C, Gauffre F, Gulik-Krzywicki T, Loup C, Caminade AM, Majoral JP, Vors JP, Rump E (2001) Organophosphorus dendrimers as new gelators for hydrogels. Angew Chem Int Ed 40(14):2626–2629. https://doi.org/10.1002/1521-3773(20010716)40:14<2626::aid-anie2626>3.0.co;2-f10.1002/1521-3773(20010716)40:14<2626::AID-ANIE2626>3.0.CO;2-F ↗
67. Martinez-Ferrero E, Franc G, Mazeres S, Turrin CO, Boissiere U, Caminade AM, Majoral JP, Sanchez C (2008) Optical properties of hybrid dendritic-mesoporous titania nanocomposite films. Chem Eur J 14(25):7658–7669. https://doi.org/10.1002/chem.20080060610.1002/chem.200800606 ↗
68. Maszewska M, Leclaire J, Cieslak M, Nawrot B, Okruszek A, Caminade AM, Majoral JP (2003) Water-soluble polycationic dendrimers with a phosphoramidothioate backbone: preliminary studies of cytotoxicity and oligonucleotide/plasmid delivery in human cell culture. Oligonucleotides 13:193–205. https://doi.org/10.1089/15454570332246058610.1089/154545703322460586 ↗
69. Merino S, Brauge L, Caminade AM, Majoral JP, Taton D, Gnanou Y (2001) Synthesis and characterization of linear, hyperbranched, and dendrimer-like polymers constituted of the same repeating unit. Chem Eur J 7:3095–3105. https://doi.org/10.1002/1521-3765(20010716)7:14<3095::aid-chem3095>3.0.co;2-s10.1002/1521-3765(20010716)7:14<3095::AID-CHEM3095>3.0.CO;2-S ↗
70. Mignani S, El Brahmi N, Eloy L, Poupon J, Nicolas V, Steinmetz A, El Kazzouli S, Bousmina MM, Blanchard-Desce M, Caminade AM, Majoral JP, Cresteil T (2017) Anticancer copper(II) phosphorus dendrimers are potent proapoptotic Bax activators. Eur J Med Chem 132:142–156. https://doi.org/10.1016/j.ejmech.2017.03.03510.1016/j.ejmech.2017.03.035 ↗
71. Milowska K, Grochowina J, Katir N, El Kadib A, Majoral JP, Bryszewska M, Gabryelak T (2013) Viologen-phosphorus dendrimers inhibit alpha-synuclein fibrillation. Mol Pharm 10(3):1131–1137. https://doi.org/10.1021/mp300636h10.1021/mp300636h ↗
72. Milowska K, Szwed A, Zablocka M, Caminade AM, Majoral JP, Mignani S, Gabryelak T, Bryszewska M (2014) In vitro PAMAM, phosphorus and viologen-phosphorus dendrimers prevent rotenone-induced cell damage. Int J Pharm 474(1–2):42–49. https://doi.org/10.1016/j.ijpharm.2014.08.01010.1016/j.ijpharm.2014.08.010 ↗
73. Mitjaville J, Caminade AM, Mathieu R, Majoral JP (1994) New synthetic strategies for phosphorus-containing cryptands and the first phosphorus spherant type compound. J Am Chem Soc 116(11):5007–5008. https://doi.org/10.1021/ja00090a06410.1021/ja00090a064 ↗
74. Mongin O, Pla-Quintana A, Terenziani F, Drouin D, Le Droumaguet C, Caminade AM, Majoral JP, Blanchard-Desce M (2007) Organic nanodots for multiphotonics: synthesis and photophysical studies. New J Chem 31:1354–1367. https://doi.org/10.1039/b702452p10.1039/b702452p ↗
75. Mongin O, Rouxel C, Robin AC, Pla-Quintana A, Krishna TR, Recher G, Tiaho F, Caminade AM, Majoral JP, Blanchard-Desce M (2008) Brilliant organic nanodots: novel nano-objects for bionanophotonics. In: Heckman EM, Singh TB, Yoshida J (eds) Nanobiosystems: processing, characterization, and applications, Spie-Int Soc Optical Engineering, Bellingham, Vol. 704010.1117/12.797873 ↗
76. Mongin O, Rouxel C, Vabre JM, Mir Y, Pla-Quintana A, Wei YQ, Caminade AM, Majoral JP, Blanchard-Desce M (2009) Customized multiphotonics nanotools for bioapplications: soft organic nanodots as an eco-friendly alternative to quantum dots. In: Kobayashi N, Ouchen F, Rau I (eds) Nanobiosystems: processing, characterization, and applications Ii. Proceedings of SPIE-The International Society for Optical Engineering, vol 7403. Spie-Int Soc Optical Engineering, Bellingham10.1117/12.826699 ↗
77. Moreno S, Szwed A, El Brahmi N, Milowska K, Kurowska J, Fuentes-Paniagua E, Pedziwiatr-Werbicka E, Gabryelak T, Katir N, de la Mata FJ, Munoz-Fernandez MA, Gomez-Ramirez R, Caminade AM, Majoral JP, Bryszewska M (2015) Synthesis, characterization and biological properties of new hybrid carbosilane-viologen-phosphorus dendrimers. RSC Adv 5(33):25942–25958. https://doi.org/10.1039/c5ra00960j10.1039/C5RA00960J ↗
78. Neumann P, Dib H, Caminade AM, Hey-Hawkins E (2015a) Redox control of a dendritic ferrocenyl-based homogeneous catalyst. Angew Chem Int Ed 54:311–314. https://doi.org/10.1002/anie.20140831410.1002/anie.201408314 ↗
79. Neumann P, Dib H, Sournia-Saquet A, Grell T, Handke M, Caminade AM, Hey-Hawkins E (2015b) Ruthenium complexes with dendritic ferrocenyl phosphanes: synthesis, characterization, and application in the catalytic redox isomerization of allylic alcohols. Chem Eur J 21:6590–6604. https://doi.org/10.1002/chem.20140648910.1002/chem.201406489 ↗
80. Portevin D, Poupot M, Rolland O, Turrin CO, Fournie JJ, Majoral JP, Caminade AM, Poupot R (2009) Regulatory activity of azabisphosphonate-capped dendrimers on human CD4(+) T cell proliferation enhances ex-vivo expansion of NK cells from PBMCs for immunotherapy. J Transl Med 7:13. https://doi.org/10.1186/1479-5876-7-8210.1186/1479-5876-7-82 ↗
81. Poupot M, Griffe L, Marchand P, Maraval A, Rolland O, Martinet L, L'Faqihi-Olive FE, Turrin CO, Caminade AM, Fournie JJ, Majoral JP, Poupot R (2006) Design of phosphorylated dendritic architectures to promote human monocyte activation. FASEB J 20:2339–2351. https://doi.org/10.1096/fj.06-5742com10.1096/fj.06-5742com ↗
82. Poupot M, Turrin CO, Caminade AM, Fournie JJ, Attal M, Poupot R, Fruchon S (2016) Poly(phosphorhydrazone) dendrimers: yin and yang of monocyte activation for human NK cell amplification applied to immunotherapy against multiple myeloma. Nanomedicine Nanotech Biol Med 12:2321–2330. https://doi.org/10.1016/j.nano.2016.07.00910.1016/j.nano.2016.07.009 ↗
83. Riegert D, Pla-Quintana A, Fuchs S, Laurent R, Turrin CO, Duhayon C, Majoral JP, Chaumonnot A, Caminade AM (2013) Diversified strategies for the synthesis of bifunctional dendrimeric structures. Eur J Org Chem 2013:5414–5422. https://doi.org/10.1002/ejoc.20130045610.1002/ejoc.201300456 ↗
84. Riegert D, Bareille L, Laurent R, Majoral JP, Caminade AM, Chaumonnot A (2016) Silica functionalized by bifunctional dendrimers: hybrid nanomaterials for trapping CO2. Eur J Inorg Chem 19:3103–3110. https://doi.org/10.1002/ejic.20160042610.1002/ejic.201600426 ↗
85. Rolland O, Griffe L, Poupot M, Maraval A, Ouali A, Coppel Y, Fournie JJ, Bacquet G, Turrin CO, Caminade AM, Majoral JP, Poupot R (2008) Tailored control and optimisation of the number of phosphonic acid termini on phosphorus-containing dendrimers for the ex-vivo activation of human monocytes. Chem Eur J 14:4836–4850. https://doi.org/10.1002/chem.20070106310.1002/chem.200701063 ↗
86. Rouxel C, Charlot M, Mongin O, Krishna TR, Caminade AM, Majoral JP, Blanchard-Desce M (2012) From graftable biphotonic chromophores to water-soluble organic nanodots for biophotonics: the importance of environmental effects. Chem Eur J 18:16450–16462. https://doi.org/10.1002/chem.20120283210.1002/chem.201202832 ↗
87. Salamonczyk GM, Kuznikowski M, Skowronska A (2000) A divergent synthesis of thiophosphate-based dendrimers. Tetrahedron Lett 41:1643–1645. https://doi.org/10.1016/S0040-4039(00)00005-810.1016/S0040-4039(00)00005-8 ↗
88. Sebastian RM, Magro G, Caminade AM, Majoral JP (2000) Dendrimers with N,N-disubstituted hydrazines as end groups, useful precursors for the synthesis of water-soluble dendrimers capped with carbohydrate, carboxylic or boronic acid derivatives. Tetrahedron 56(34):6269–6277. https://doi.org/10.1016/s0040-4020(00)00576-710.1016/S0040-4020(00)00576-7 ↗
89. Sebastian RM, Blais JC, Caminade AM, Majoral JP (2002) Synthesis and photochemical behavior of phosphorus dendrimers containing azobenzene units within the branches and/or on the surface. Chem Eur J 8:2172–2183. https://doi.org/10.1002/1521-3765(20020503)8:9<2172::aid-chem2172>3.0.co;2-g10.1002/1521-3765(20020503)8:9<2172::AID-CHEM2172>3.0.CO;2-G ↗
90. Servin P, Rebout C, Laurent R, Peruzzini M, Caminade AM, Majoral JP (2007) Reduced number of steps for the synthesis of dense and highly functionalized dendrimers. Tetrahedron Lett 48:579–583. https://doi.org/10.1016/j.tetlet.2006.11.11210.1016/j.tetlet.2006.11.112 ↗
91. Shakhbazau A, Mishra M, Chu TH, Brideau C, Cummins K, Tsutsui S, Shcharbin D, Majoral JP, Mignani S, Blanchard-Desce M, Bryszewska M, Yong VW, Stys PK, van Minnen J (2015) Fluorescent phosphorus dendrimer as a spectral nanosensor for macrophage polarization and fate tracking in spinal cord injury. Macromol Biosci 15:1523–1534. https://doi.org/10.1002/mabi.20150015010.1002/mabi.201500150 ↗
92. Slany M, Bardaji M, Casanove MJ, Caminade AM, Majoral JP, Chaudret B (1995) Dendrimer surface-chemistry—facile route to polyphosphines and their gold complexes. J Am Chem Soc 117:9764–9765. https://doi.org/10.1021/ja00143a02310.1021/ja00143a023 ↗
93. Slany M, Bardaji M, Caminade AM, Chaudret B, Majoral JP (1997) Versatile complexation ability of very large phosphino-terminated dendrimers. Inorg Chem 36(9):1939–1945. https://doi.org/10.1021/ic961258m10.1021/ic961258m ↗
94. Szwed A, Milowska K, Ionov M, Shcharbin D, Moreno S, Gomez-Ramirez R, de la Mata FJ, Majoral JP, Bryszewska M, Gabryelak T (2016) Interaction between dendrimers and regulatory proteins. Comparison of effects of carbosilane and carbosilane-viologen-phosphorus dendrimers. RSC Adv 6(100):97546–97554. https://doi.org/10.1039/c6ra16558c10.1039/C6RA16558C ↗
95. Tomalia DA (2009) In quest of a systematic framework for unifying and defining nanoscience. J Nanoparticle Research 11:1251–1310. https://doi.org/10.1007/s11051-009-9632-z10.1007/s11051-009-9632-z ↗
96. Tomalia DA (2010) Dendrons/dendrimers: quantized, nano-element like building blocks for soft-soft and soft-hard nano-compound synthesis. Soft Matter 6(3):456–474. https://doi.org/10.1039/b917370f10.1039/B917370F ↗
97. Tomalia DA (2012) Dendritic effects: dependency of dendritic nano-periodic property patterns on critical nanoscale design parameters (CNDPs). New J Chem 36:264–281. https://doi.org/10.1039/c1nj20501c10.1039/C1NJ20501C ↗
98. Tomalia DA, Khanna SN (2016) A systematic framework and nanoperiodic concept for unifying nanoscience: hard/soft nanoelements, superatoms, meta-atoms, new emerging properties, periodic property patterns, and predictive Mendeleev-like nanoperiodic tables. Chem Rev 116:2705–2774. https://doi.org/10.1021/acs.chemrev.5b0036710.1021/acs.chemrev.5b00367 ↗
99. Tomalia DA, Baker H, Dewald J, Hall M, Kallos G, Martin S, Roeck J, Ryder J, Smith P (1985) A new class of polymers—starburst-dendritic macromolecules. Polymer J 17:117–132. https://doi.org/10.1295/polymj.17.11710.1295/polymj.17.117 ↗
100. Tomalia DA, Baker H, Dewald J, Hall M, Kallos G, Martin S, Roeck J, Ryder J, Smith P (1986) Dendritic macromolecules. Synthesis of starburst dendrimers. Macromolecules 19:2466–2468. https://doi.org/10.1021/ma00163a02910.1021/ma00163a029 ↗