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_1576839
_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         'C14 H16 F3 N2 O3, C16 H36 N'
_chemical_formula_sum            'C30 H52 F3 N3 O3'
_chemical_formula_weight         559.74
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-11-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-11-10 deposited with the CCDC.	2026-01-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.99(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.470(4)
_cell_length_b                   18.843(6)
_cell_length_c                   10.856(3)
_cell_measurement_reflns_used    1544
_cell_measurement_temperature    100.0(10)
_cell_measurement_theta_max      69.0010
_cell_measurement_theta_min      4.6750
_cell_volume                     3164.1(16)
_computing_cell_refinement       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2887
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 1.000
_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    -48.00   8.00   1.00   15.00    --  -41.91  38.00 150.00   56
  2  \w   -129.00  39.00   1.00   15.00    --  -41.91   0.00 120.00  168
  3  \w     31.00  69.00   1.00   15.00    --   41.91-125.00-150.00   38
  4  \w     31.00  94.00   1.00   15.00    --   41.91-125.00  30.00   63
  5  \w     18.00  45.00   1.00   15.00    --   41.91 -99.00 -90.00   27
  6  \w     22.00 105.00   1.00   20.00    --  103.72 -94.00  60.00   83
  7  \w     32.00 110.00   1.00   20.00    --  103.72 -61.00 150.00   78
  8  \w     30.00 135.00   1.00   20.00    --  103.72 -77.00 -90.00  105
  9  \w     35.00 121.00   1.00   20.00    --  103.72 -45.00  30.00   86
 10  \w     96.00 152.00   1.00   20.00    --  103.72  45.00 120.00   56
 11  \w     40.00  66.00   1.00   20.00    --  103.72-125.00 -60.00   26
 12  \w     29.00 119.00   1.00   20.00    --  103.72 -30.00-120.00   90
 13  \w     31.00  59.00   1.00   20.00    --  103.72-125.00  60.00   28
 14  \w    124.00 150.00   1.00   20.00    --  103.72  77.00  60.00   26
 15  \w     33.00  60.00   1.00   20.00    --  103.72-125.00 -90.00   27
 16  \w     51.00 178.00   1.00   20.00    --  103.72  15.00-120.00  127
 17  \w     86.00 113.00   1.00   20.00    --  103.72-125.00 -90.00   27
 18  \w     65.00 113.00   1.00   20.00    --  103.72-125.00  30.00   48
 19  \w     64.00 108.00   1.00   20.00    --  103.72-105.00 151.91   44
;
_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      0.0023301000
_diffrn_orient_matrix_UB_12      -0.0506178000
_diffrn_orient_matrix_UB_13      -0.1113870000
_diffrn_orient_matrix_UB_21      0.0975542000
_diffrn_orient_matrix_UB_22      0.0140939000
_diffrn_orient_matrix_UB_23      -0.0123199000
_diffrn_orient_matrix_UB_31      0.0195967000
_diffrn_orient_matrix_UB_32      -0.0626138000
_diffrn_orient_matrix_UB_33      0.0872829000
_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  0.2749
_diffrn_reflns_av_unetI/netI     0.1847
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            21210
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.598
_diffrn_reflns_theta_min         3.697
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.715
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.522
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.57a (Rigaku Oxford Diffraction, 2022)
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    1.175
_exptl_crystal_description       plate
_exptl_crystal_F_000             1216
_exptl_crystal_preparation       'slow evaporation from methanol'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         5590
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_all          0.3219
_refine_ls_R_factor_gt           0.1757
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3783
_refine_ls_wR_factor_ref         0.4984
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1247
_reflns_number_total             5590
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc03376d2.cif
_cod_data_source_block           exp_1609_auto_res
_cod_depositor_comments
'Adding full bibliography for 1576838--1576842.cif.'
_cod_original_cell_volume        3164.2(15)
_cod_database_code               1576839
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         C20H20N2O2F3
_chemical_oxdiff_usercomment     'ssa 72 jrh20220207'
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.836
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C5(H5), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C20(H20A,H20B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,
 H25B), C15(H15A,H15B), C28(H28A,H28B), C29(H29A,H29B), C27(H27A,H27B),
 C16(H16A,H16B), C21(H21A,H21B), C17(H17A,H17B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C9(H9), C13(H13), C14(H14), C10(H10)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C2(H2A,H2B,H2C), C26(H26A,H26B,H26C), C30(H30A,H30B,
 H30C), C18(H18A,H18B,H18C), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              92216
_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 1.952
_oxdiff_exptl_absorpt_empirical_full_min 0.311