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Bioinspired computational design of lankacidin derivatives for improvement in antitumor activity - supplement information

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posted on 2022-09-08, 08:43 authored by Ahmed Taha Ayoub, Natsumi Nishiura, Aiko Teshima, Mohamed Ali Elrefaiy, Rukman Muslimin, Kiep Minh Do, Takeshi Kodama, Cody Wayne Lewis, Gordon Chan, Hiroyuki Morita, Kenji Arakawa

Table S1. 1H- and 13C-NMR data of lankacidin C (1), 7-O-acetyl-lankacidin C (2), 13-Oacetyl-

lankacidin C (3), and 7,13-di-O-acetyl-lankacidin C (4)

Table S2. 1H- and 13C-NMR data of lankacidin C (1), 7-O-cinnamoyl-lankacidin C (5), 13-

O-cinnamoyl-lankacidin C (6), 7,13-di-O-cinnamoyl-lankacidin C (7), 7-Ohydrocinnamoyl-

lankacidin C (8), 13-O-hydrocinnamoyl-lankacidin C (9), and

7,13-di-O-hydrocinnamoyl-lankacidin C (10)

Figure S1. 1H-NMR spectrum of lankacidin C (1)

Figure S2. 13C-NMR spectrum of lankacidin C (1)

Figure S3. DEPT spectrum of lankacidin C (1)

Figure S4. DQF-COSY spectrum of lankacidin C (1)

Figure S5. HMQC spectrum of lankacidin C (1)

Figure S6. HMBC spectrum of lankacidin C (1)

Figure S7. 1H-NMR spectrum of 7-O-Ac-lankacidin C (2)

Figure S8. 13C-NMR spectrum of 7-O-Ac-lankacidin C (2)

Figure S9. DEPT spectrum of 7-O-Ac-lankacidin C (2)

Figure S10. DQF-COSY spectrum of 7-O-Ac-lankacidin C (2)

Figure S11. HMQC spectrum of 7-O-Ac-lankacidin C (2)

Figure S12. HMBC spectrum of 7-O-Ac-lankacidin C (2)

Figure S13. 1H-NMR spectrum of 13-O-Ac-lankacidin C (3)

Figure S14. 13C-NMR spectrum of 13-O-Ac-lankacidin C (3)

Figure S15. DEPT spectrum of 13-O-Ac-lankacidin C (3)

Figure S16. DQF-COSY spectrum of 13-O-Ac-lankacidin C (3)

Figure S17. HMQC spectrum of 13-O-Ac-lankacidin C (3)

Figure S18. HMBC spectrum of 13-O-Ac-lankacidin C (3)

Figure S19. 1H-NMR spectrum of 7,13-di-O-Ac-lankacidin C (4)

Figure S20. 13C-NMR spectrum of 7,13-di-O-Ac-lankacidin C (4)

Figure S21. DEPT spectrum of 7,13-di-O-Ac-lankacidin C (4)

Figure S22. DQF-COSY spectrum of 7,13-di-O-Ac-lankacidin C (4)

Figure S23. HMQC spectrum of 7,13-di-O-Ac-lankacidin C (4)

Figure S24. HMBC spectrum of 7,13-di-O-Ac-lankacidin C (4)

Figure S25. 1H-NMR spectrum of 7-O-cinnamoyl-lankacidin C (5)

Figure S26. 13C-NMR spectrum of 7-O-cinnamoyl-lankacidin C (5)

Figure S27. DEPT spectrum of 7-O-cinnamoyl-lankacidin C (5)

Figure S28. DQF-COSY spectrum of 7-O-cinnamoyl-lankacidin C (5)

Figure S29. HMQC spectrum of 7-O-cinnamoyl-lankacidin C (5)

Figure S30. HMBC spectrum of 7-O-cinnamoyl-lankacidin C (5)

Figure S31. 1H-NMR spectrum of 13-O-cinnamoyl-lankacidin C (6)

Figure S32. 13C-NMR spectrum of 13-O-cinnamoyl-lankacidin C (6)

Figure S33. DEPT spectrum of 13-O-cinnamoyl-lankacidin C (6)

Figure S34. DQF-COSY spectrum of 13-O-cinnamoyl-lankacidin C (6)

Figure S35. HMQC spectrum of 13-O-cinnamoyl-lankacidin C (6)

Figure S36. HMBC spectrum of 13-O-cinnamoyl-lankacidin C (6)

Figure S37. 1H-NMR spectrum of 7,13-di-O-cinnamoyl-lankacidin C (7)

Figure S38. 13C-NMR spectrum of 7,13-di-O-cinnamoyl-lankacidin C (7)

Figure S39. DEPT spectrum of 7,13-di-O-cinnamoyl-lankacidin C (7)

Figure S40. DQF-COSY spectrum of 7,13-di-O-cinnamoyl-lankacidin C (7)

Figure S41. HMQC spectrum of 7,13-di-O-cinnamoyl-lankacidin C (7)

Figure S42. HMBC spectrum of 7,13-di-O-cinnamoyl-lankacidin C (7)

Figure S43. 1H-NMR spectrum of 7-O-hydrocinnamoyl-lankacidin C (8)

Figure S44. 13C-NMR spectrum of 7-O-hydrocinnamoyl-lankacidin C (8)

Figure S45. DEPT spectrum of 7-O-hydrocinnamoyl-lankacidin C (8)

Figure S46. DQF-COSY spectrum of 7-O-hydrocinnamoyl-lankacidin C (8)

Figure S47. HMQC spectrum of 7-O-hydrocinnamoyl-lankacidin C (8)

Figure S48. HMBC spectrum of 7-O-hydrocinnamoyl-lankacidin C (8)

Figure S49. 1H-NMR spectrum of 13-O-hydrocinnamoyl-lankacidin C (9)

Figure S50. 13C-NMR spectrum of 13-O-hydrocinnamoyl-lankacidin C (9)

Figure S51. DEPT spectrum of 13-O-hydrocinnamoyl-lankacidin C (9)

Figure S52. DQF-COSY spectrum of 13-O-hydrocinnamoyl-lankacidin C (9)

Figure S53. HMQC spectrum of 13-O-hydrocinnamoyl-lankacidin C (9)

Figure S54. HMBC spectrum of 13-O-hydrocinnamoyl-lankacidin C (9)

Figure S55. 1H-NMR spectrum of 7,13-di-O-hydrocinnamoyl-lankacidin C (10)

Figure S56. 13C-NMR spectrum of 7,13-di-O-hydrocinnamoyl-lankacidin C (10)

Figure S57. DEPT spectrum of 7,13-di-O-hydrocinnamoyl-lankacidin C (10)

Figure S58. DQF-COSY spectrum of 7,13-di-O-hydrocinnamoyl-lankacidin C (10)

Figure S59. HMQC spectrum of 7,13-di-O-hydrocinnamoyl-lankacidin C (10)

Figure S60. HMBC spectrum of 7,13-di-O-hydrocinnamoyl-lankacidin C (10)

Figure S61. HPLC chromatogram of compounds 1–10

Figure S62. TLC analysis of compounds 1–10

Figure S63. The 2D-interaction between the 10 different ligands to the paclitaxel-binding

site

Figure S64. Dose-response curves and IC50 values for compounds 1-10 and positive controls,

5-fluorouracil and paclitaxel, in three human cancer cells, HeLa, MCF-7, and A549 cells

Funding

Ministry of Education, Culture, Sports, Science and Technology, (Grant / Award Number:: '17H05446','19H04659','23108515','25108718')

History

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