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1 Supporting Information Water-Stable Ammonium-Terminated Carbosilane Dendrimers as Efficient Antibacterial Agents Beatriz Rasines, [a] José Manuel Hernández-Ros, [a] Natividad de las Cuevas, [b] José Luis Copa-Patiño, [c] Juan Soliveri, [c] Mª Angeles Muñoz-Fernández, [b] Rafael Gómez, [a] and F. Javier de la Mata. [a] [a] Beatriz Rasines, Dr. J. M. Hernández-Ros, Dr. R. Gómez, Dr. F. J. De la Mata Departamento de Química Inorgánica, Universidad de Alcalá, E Alcalá de Henares (Spain). Networking Research Center on Bioengineering, Biomaterials and Nanomedicine (CIBER-BBN), Spain. FAX: (+34) [b] [c] Dr. Natividad de las Cuevas, Dr. M. A. Muñoz-Fernández Laboratorio de Inmunobiología Molecular, Hospital General Universitario Gregorio Marañón, Madrid (Spain). Networking Research Center on Bioengineering, Biomaterials and Nanomedicine (CIBER-BBN), Spain. Dr. J. L. Copa-Patiño, Dr. J. Soliveri Departamento de Microbiología y Parasitología, Universidad de Alcalá, E Alcalá de Henares (Spain). josel.copa@uah.es 1
2 Figure S1. Molecular representation of amine-terminated carbosilane dendrimers
3 A) [(CH 2 =CHCH 2 )N(Et)(CH 2 CH 2 NMe 2 )] (1) Figure S2. 1 H NMR spectrum of [(CH 2 =CHCH 2 )N(Et)(CH 2 CH 2 NMe 2 )] (1) in CDCl 3. Figure S3. 13 C NMR spectrum of [(CH 2 =CHCH 2 )N(Et)(CH 2 CH 2 NMe 2 )] (1) in CDCl 3. 3
4 Adduct [(CH 2 =CHCH 2 )N(Et)(CH 2 CH 2 NMe 2 )] (1) LiBr Figure S4. 1 H NMR spectrum of adduct [(CH 2 =CHCH 2 )N(Et)(CH 2 CH 2 NMe 2 )] (1) LiBr in CDCl 3. Figure S5. 13 C NMR spectrum of adduct [(CH 2 =CHCH 2 )N(Et)(CH 2 CH 2 NMe 2 )] (1) LiBr in CDCl 3. 4
5 B) [(Et 3 SiCH 2 CH 2 CH 2 )N(Et)(CH 2 CH 2 NMe 2 )] (2) Figure S6. 1 H NMR spectrum of [(Et 3 SiCH 2 CH 2 CH 2 )N(Et)(CH 2 CH 2 NMe 2 )] (2) in CDCl 3. Figure S7. 13 C NMR spectrum of [(Et 3 SiCH 2 CH 2 CH 2 )N(Et)(CH 2 CH 2 NMe 2 )] (2) in CDCl 3. 5
6 C) G 1 -[Si(CH 2 CH 2 CH 2 )N(Et)(CH 2 CH 2 NMe 2 )] 4 (3) Figure S8. 1 H NMR spectrum of G 1 -[Si(CH 2 CH 2 CH 2 )N(Et)(CH 2 CH 2 NMe 2 )] 4 (3) in CDCl 3. Figure S9. 13 C NMR spectrum of G 1 -[Si(CH 2 CH 2 CH 2 )N(Et)(CH 2 CH 2 NMe 2 )] 4 (3) in CDCl 3. 6
7 Figure S10. MALDI-TOF spectrum of G 1 -[Si(CH 2 CH 2 CH 2 )N(Et) (CH 2 CH 2 NMe 2 )] 4 (3) in dithranol. D) G 2 -[Si(CH 2 CH 2 CH 2 )N(Et)(CH 2 CH 2 NMe 2 )] 8 (4) Figure S11. 1 H NMR spectrum of G 2 -[Si(CH 2 CH 2 CH 2 )N(Et)(CH 2 CH 2 NMe 2 )] 8 (4) in CDCl 3. 7
8 Figure S C NMR spectrum of G 2 -[Si(CH 2 CH 2 CH 2 )N(Et)(CH 2 CH 2 NMe 2 )] 8 (4) in CDCl 3. Figure S13. HMBC { 1 H- 15 N} spectrum of G 2 -[Si(CH 2 CH 2 CH 2 )N(Et) (CH 2 CH 2 NMe 2 )] 8 (4) in CDCl 3. 8
9 Figure S14. HMBC { 1 H- 29 Si} spectrum of G 2 -[Si(CH 2 CH 2 CH 2 )N(Et) (CH 2 CH 2 NMe 2 )] 8 (4) in CDCl 3. Figure S15. MALDI-TOF spectrum of G 2 -[Si(CH 2 CH 2 CH 2 )N(Et) (CH 2 CH 2 NMe 2 )] 8 (4) in dithranol. 9
10 E) G 3 -[Si(CH 2 CH 2 CH 2 )N(Et)(CH 2 CH 2 NMe 2 )] 16 (5) Figure S16. 1 H NMR spectrum of G 3 -[Si(CH 2 CH 2 CH 2 )N(Et)(CH 2 CH 2 NMe 2 )] 16 (5) in CDCl 3. Figure S C NMR spectrum of G 3 -[Si(CH 2 CH 2 CH 2 )N(Et)(CH 2 CH 2 NMe 2 )] 16 (5) in CDCl 3. 10
11 Figure S18. HMQC-{ 1 H- 13 C} spectrum of G 3 -[Si(CH 2 CH 2 CH 2 )N(Et) (CH 2 CH 2 NMe 2 )] 16 (5) in CDCl 3. Figure S19. HMBC { 1 H- 15 N} spectrum of G 3 -[Si(CH 2 CH 2 CH 2 )N(Et) (CH 2 CH 2 NMe 2 )] 16 (5) in CDCl 3. 11
12 Figure S20. HMBC { 1 H- 29 Si} spectrum of G 3 -[Si(CH 2 CH 2 CH 2 )N(Et) (CH 2 CH 2 NMe 2 )] 16 (5) in CDCl 3. F) {[Et 3 Si(CH 2 CH 2 CH 2 )N + H(Et)(CH 2 CH 2 N + HMe 2 )] 2Cl - } (6) Figure S21. 1 H NMR spectrum of {[Et 3 Si(CH 2 CH 2 CH 2 )N + H(Et) (CH 2 CH 2 N + HMe 2 )] 2Cl - } (6) in DMSO. 12
13 Figure S C NMR spectrum of {[Et 3 Si(CH 2 CH 2 CH 2 )N + H(Et) (CH 2 CH 2 N + HMe 2 )] 2Cl - } (6) in DMSO. G)G) G 1 -{[Si(CH 2 CH 2 CH 2 )N + H(Et)(CH 2 CH 2 N + HMe 2 )] 4 8Cl - } (7) Figure S23. 1 H NMR spectrum of G 1 -{[Si(CH 2 CH 2 CH 2 )N + H(Et) (CH 2 CH 2 N + HMe 2 )] 4 8Cl - } (7) in DMSO. 13
14 Figure S C NMR spectrum of G 1 -{[Si(CH 2 CH 2 CH 2 )N + H(Et) (CH 2 CH 2 N + HMe 2 )] 4 8Cl - } (7) in DMSO. Figure S25. HMBC { 1 H- 29 Si} spectrum (CH 2 CH 2 N + HMe 2 )] 4 8Cl - } (7) in DMSO. of G 1 -{[Si(CH 2 CH 2 CH 2 )N + H(Et) 14
15 H) G 2 -{[Si(CH 2 CH 2 CH 2 )N + H(Et)(CH 2 CH 2 N + HMe 2 )] 8 16Cl - } (8) Figure S26. 1 H NMR spectrum of G 2 -{[Si(CH 2 CH 2 CH 2 )N + H(Et) (CH 2 CH 2 N + HMe 2 )] 8 16Cl - } (8) in DMSO. Figure S C NMR spectrum of G 2 -{[Si(CH 2 CH 2 CH 2 )N + H(Et) (CH 2 CH 2 N + HMe 2 )] 8 16Cl - } (8) in DMSO. 15
16 Figure S28. HMQC-{ 1 H- 13 C} spectrum of G 2 -{[Si(CH 2 CH 2 CH 2 )N + H(Et) (CH 2 CH 2 N + HMe 2 )] 8 16Cl - } (8) in DMSO. Figure S29. HMBC { 1 H- 29 Si} spectrum (CH 2 CH 2 N + HMe 2 )] 8 16Cl - } (8) in DMSO. of G 2 -{[Si(CH 2 CH 2 CH 2 )N + H(Et) 16
17 I) G 3 -{[Si(CH 2 CH 2 CH 2 )N + H(Et)(CH 2 CH 2 N + HMe 2 )] 16 32Cl - } (9) Figure S30. 1 H spectrum of G 3 -{[Si(CH 2 CH 2 CH 2 )N + H(Et)(CH 2 CH 2 N + HMe 2 )] 16 32Cl - } (9) in DMSO. Figure S C spectrum of G 3 -{[Si(CH 2 CH 2 CH 2 )N + H(Et)(CH 2 CH 2 N + HMe 2 )] 16 32Cl - } (9) in DMSO. 17
18 Figure S32. HMBC { 1 H- 29 Si} spectrum of G 3 -{[Si(CH 2 CH 2 CH 2 )N + H(Et) (CH 2 CH 2 N + HMe 2 )] 16 32Cl - } (9) in DMSO. J) {[Et 3 Si(CH 2 CH 2 CH 2 )N + Me(Et)(CH 2 CH 2 N + Me 3 )] 2I - } (10) Figure S33. 1 H spectrum of {[Et 3 Si(CH 2 CH 2 CH 2 )N + Me(Et)(CH 2 CH 2 N + Me 3 )] 2I - } (10) in DMSO. 18
19 Figure S C spectrum of {[Et 3 Si(CH 2 CH 2 CH 2 )N + Me(Et)(CH 2 CH 2 N + Me 3 )] 2I - } (10) in DMSO. K) G 1 -{[Si(CH 2 CH 2 CH 2 )N + (Me)(Et)(CH 2 CH 2 NMe + 3)] 4 8I - } (11) Figure S35. 1 H spectrum of G 1 -{[Si(CH 2 CH 2 CH 2 )N + (Me)(Et)(CH 2 CH 2 NMe + 3)] 4 8I - } (11) in DMSO. 19
20 Figure S C spectrum of G 1 -{[Si(CH 2 CH 2 CH 2 )N + (Me)(Et)(CH 2 CH 2 NMe + 3)] 4 8I - } (11) in DMSO. Figure S37. HMBC { 1 H- 15 N} of G 1 -{[Si(CH 2 CH 2 CH 2 )N + (Me)(Et) (CH 2 CH 2 NMe + 3)] 4 8I - } (11) in DMSO. 20
21 Figure S38. HMBC { 1 H- 29 Si} spectrum of G 1 -{[Si(CH 2 CH 2 CH 2 )N + (Me)(Et) (CH 2 CH 2 NMe + 3)] 4 8I - } (11) in DMSO. L) G 2 -{[Si(CH 2 CH 2 CH 2 )N + (Me)(Et)(CH 2 CH 2 NMe + 3)] 8 16I - } (12) Figure S39. 1 H NMR spectrum of G 2 -{[Si(CH 2 CH 2 CH 2 )N + (Me)(Et) (CH 2 CH 2 NMe + 3)] 4 16I - } (12) in DMSO. 21
22 Figure S C NMR spectrum of G 2 -{[Si(CH 2 CH 2 CH 2 )N + (Me)(Et) (CH 2 CH 2 NMe + 3)] 4 16I - } (12) in DMSO. Figure S41. HMQC-{ 1 H- 13 C} spectrum of G 2 -{[Si(CH 2 CH 2 CH 2 )N + (Me)(Et) (CH 2 CH 2 NMe + 3)] 4 16I - } (12) in DMSO. 22
23 Figure S42. HMBC { 1 H- 15 N} spectrum of G 2 -{[Si(CH 2 CH 2 CH 2 )N + (Me)(Et) (CH 2 CH 2 NMe + 3)] 4 16I - } (12) in DMSO. Figure S43. HMBC { 1 H- 29 Si} spectrum of G 2 -{[Si(CH 2 CH 2 CH 2 )N + (Me)(Et) (CH 2 CH 2 NMe + 3)] 4 16I - } (12) in DMSO. 23
24 M) G 3 -{[Si(CH 2 CH 2 CH 2 )N + (Me)(Et)(CH 2 CH 2 NMe + 3)] 16 32I - } (13) Figure S44. 1 H NMR spectrum of G 3 -{[Si(CH 2 CH 2 CH 2 )N + (Me)(Et) (CH 2 CH 2 NMe + 3)] 16 32I - } (13) in DMSO. Figure S C spectrum of G 3 -{[Si(CH 2 CH 2 CH 2 )N + (Me)(Et) (CH 2 CH 2 NMe + 3)] 16 32I - } (13) in DMSO. 24
25 Figure S46. HMBC { 1 H- 15 N} spectrum of G 3 -{[Si(CH 2 CH 2 CH 2 )N + (Me)(Et) (CH 2 CH 2 NMe + 3)] 16 32I - } (13) in DMSO. Figure S47. HMBC { 1 H- 29 Si} spectrum of G 3 -{[Si(CH 2 CH 2 CH 2 )N + (Me)(Et) (CH 2 CH 2 NMe + 3)] 16 32I - } (13) in DMSO. 25
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