Targeting lysosomes by design: novel <i>N</i>-acridine thiosemicarbazones that enable direct detection of intracellular drug localization and overcome P-glycoprotein (Pgp)-mediated resistance.
Kaya, Busra; Smith, Henry; Chen, Yanbing; Azad, Mahan Gholam; M Russell, Tiffany; Richardson, Vera; Bernhardt, Paul V.; Dharmasivam, Mahendiran; Richardson, Des R.; Chemical science 15 (2024) 15109–15124; doi:10.1039/d4sc04339a

data_1572360
_publ_section_title
;
 Targeting lysosomes by design: novel <i>N</i>-acridine thiosemicarbazones
 that enable direct detection of intracellular drug localization and
 overcome P-glycoprotein (Pgp)-mediated resistance.
;
_journal_issue                   37
_journal_name_full               'Chemical science'
_journal_page_first              15109
_journal_page_last               15124
_journal_paper_doi               10.1039/d4sc04339a
_journal_volume                  15
_journal_year                    2024
_chemical_formula_sum            'C26 H19 N5 S'
_chemical_formula_weight         433.52
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_creation_date             2022-07-17T19:19:31-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2024-05-14 deposited with the CCDC.	2024-07-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.829(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0272(12)
_cell_length_b                   12.4547(8)
_cell_length_c                   14.7177(13)
_cell_measurement_reflns_used    2429
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      28.98
_cell_measurement_theta_min      4.15
_cell_measurement_wavelength     0.71073
_cell_volume                     2167.2(4)
_computing_cell_refinement       'CrysalisPro (Agilent Technologies,     )'
_computing_data_collection       'CrysalisPro (Agilent Technologies,     )'
_computing_data_reduction        'CrysalisPro (Agilent Technologies,     )'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_diffrn_ambient_temperature      190(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.02
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type
'Agilent Technologies Xcalibur, EosS2, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.053121
_diffrn_orient_matrix_UB_12      0.023303
_diffrn_orient_matrix_UB_13      -0.009262
_diffrn_orient_matrix_UB_21      -0.017742
_diffrn_orient_matrix_UB_22      -0.049055
_diffrn_orient_matrix_UB_23      0.01343
_diffrn_orient_matrix_UB_31      0.021503
_diffrn_orient_matrix_UB_32      0.01723
_diffrn_orient_matrix_UB_33      0.050534
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9220
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_reduction_process
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         3.271
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3812
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.02
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0477
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0406P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1086
_reflns_Friedel_coverage         0
_reflns_number_gt                2830
_reflns_number_total             3812
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc04339a2.cif
_cod_data_source_block           2247aobp2ga
_cod_depositor_comments
'Adding full bibliography for 1572360--1572364.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1572360
_shelx_estimated_absorpt_t_min   0.934
_shelx_estimated_absorpt_t_max   0.983
_shelx_shelxl_version_number     2018/1