Amino acid appended supramolecular self-associating amphiphiles demonstrate dual activity against both MRSA and ovarian cancer
Popoola, Precious I. A.; Allam, Thomas L.; Lilley, Rebecca J.; Manwani, Chandni; Keers, Olivia B.; Tan, Junyang; Yang, Kylie; Long, Yifan; Clark, Ewan R.; White, Lisa J.; Hilton, Kira L. F.; Rankin, Jennifer; Baker, Jennifer; Bennett, Charlotte; Wilson, Hollie B.; Morton, Evelyn R.; Keskküla, Alvaro; Martin, Bethany; O'Connor, Christopher; Sutton, J. Mark; Hind, Charlotte K.; Garrett, Michelle D.; Haynes, Cally J. E.; Hiscock, Jennifer R.; Chemical Science  (2026) –; doi:10.1039/D5SC03376D

data_1576838
_publ_section_title
;
 Amino acid appended supramolecular self-associating amphiphiles
 demonstrate dual activity against both MRSA and ovarian cancer.
;
_journal_issue                   17
_journal_name_full               'Chemical science'
_journal_page_first              8567
_journal_page_last               8579
_journal_paper_doi               10.1039/d5sc03376d
_journal_volume                  17
_journal_year                    2026
_chemical_formula_moiety         'C21 H23 F3 N2 O3'
_chemical_formula_sum            'C21 H23 F3 N2 O3'
_chemical_formula_weight         408.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-17
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-09-07 deposited with the CCDC.	2026-01-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.7353(4)
_cell_length_b                   18.3597(18)
_cell_length_c                   19.4042(15)
_cell_measurement_reflns_used    3348
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      71.2340
_cell_measurement_theta_min      4.8090
_cell_volume                     2043.2(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2887
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -114.00 -19.00   1.00    7.50    --  -42.16 -38.00 -60.00   95
  2  \w    -36.00  -8.00   1.00    7.50    --  -42.16 125.00   0.00   28
  3  \w   -115.00 -25.00   1.00    7.50    --  -42.16 -38.00-150.00   90
  4  \w     68.00 103.00   1.00    7.50    --   42.16-143.00 -89.00   35
  5  \w     24.00  65.00   1.00    7.50    --   42.16-125.00 120.00   41
  6  \w      1.00  43.00   1.00    7.50    --   42.16 -99.00-180.00   42
  7  \w    110.00 172.00   1.00   20.00    --  103.72 125.00 120.00   62
  8  \w     54.00 112.00   1.00   20.00    --  103.72 -30.00 -30.00   58
  9  \w     35.00 106.00   1.00   20.00    --  103.72 -94.00 -90.00   71
 10  \w     33.00 108.00   1.00   20.00    --  103.72 -94.00  60.00   75
 11  \w    101.00 178.00   1.00   20.00    --  103.72  30.00-180.00   77
 12  \w     70.00 102.00   1.00   20.00    --  103.72-125.00-150.00   32
 13  \w     36.00 122.00   1.00   20.00    --  103.72 -45.00  60.00   86
 14  \w     60.00 176.00   1.00   20.00    --  103.72  15.00 -60.00  116
 15  \w     67.00 130.00   1.00   20.00    --  103.72 -45.00-150.00   63
 16  \w     33.00 122.00   1.00   20.00    --  103.72-143.00 -89.00   89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0477859000
_diffrn_orient_matrix_UB_12      0.0728346000
_diffrn_orient_matrix_UB_13      0.0368622000
_diffrn_orient_matrix_UB_21      -0.0417076000
_diffrn_orient_matrix_UB_22      0.0371202000
_diffrn_orient_matrix_UB_23      -0.0701808000
_diffrn_orient_matrix_UB_31      -0.2607192000
_diffrn_orient_matrix_UB_32      -0.0193639000
_diffrn_orient_matrix_UB_33      0.0043396000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0790
_diffrn_reflns_av_unetI/netI     0.0731
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13037
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.417
_diffrn_reflns_theta_min         4.557
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.911
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.033
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       needle
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.779
_exptl_crystal_size_mid          0.047
_exptl_crystal_size_min          0.022
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 905 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3930
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0717
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0832P)^2^+0.8093P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1733
_refine_ls_wR_factor_ref         0.1927
_reflns_Friedel_coverage         0.707
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                2932
_reflns_number_total             3930
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc03376d2.cif
_cod_data_source_block           jrh20220102_res
_cod_depositor_comments
'Adding full bibliography for 1576838--1576842.cif.'
_cod_database_code               1576838
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20N2O2SF3
_chemical_oxdiff_usercomment     '100 K 56p'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C7(H7), C4(H4), C6(H6), C3(H3), C12(H12), C16(H16), C13(H13),
 C15(H15), C14(H14)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              8951
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.387
_oxdiff_exptl_absorpt_empirical_full_min 0.445