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_1572364
_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_moiety         'C40 H30 N12 S2 Zn, C H4 O, C2 H6 O'
_chemical_formula_sum            'C43 H40 N12 O2 S2 Zn'
_chemical_formula_weight         886.36
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_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             2024-05-31T11:16:20-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2024-05-31 deposited with the CCDC.	2024-07-31 downloaded from the CCDC.
;
_cell_angle_alpha                100.070(2)
_cell_angle_beta                 99.897(2)
_cell_angle_gamma                103.258(2)
_cell_formula_units_Z            2
_cell_length_a                   12.7994(5)
_cell_length_b                   13.0450(5)
_cell_length_c                   13.6798(6)
_cell_measurement_reflns_used    9934
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      68.38
_cell_measurement_theta_min      3.36
_cell_measurement_wavelength     1.54184
_cell_volume                     2134.75(15)
_computing_cell_refinement       'SAINT V8.40B integration software'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_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      150(2)
_diffrn_detector                 'PHOTON III CPAD'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_UB_11      -0.014388
_diffrn_orient_matrix_UB_12      0.012779
_diffrn_orient_matrix_UB_13      -0.070459
_diffrn_orient_matrix_UB_21      0.021673
_diffrn_orient_matrix_UB_22      -0.066775
_diffrn_orient_matrix_UB_23      -0.026199
_diffrn_orient_matrix_UB_31      -0.078087
_diffrn_orient_matrix_UB_32      -0.043663
_diffrn_orient_matrix_UB_33      -0.012038
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            34059
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_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        65
_diffrn_reflns_theta_max         65
_diffrn_reflns_theta_min         3.365
_diffrn_source_type              'INCOATEC I\mS DIAMONDII'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.137
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.635
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        SADABS-2016/2 - Bruker AXS area detector scaling and absorption correcti
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             920
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: MeOH and EtOH'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.282
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     554
_refine_ls_number_reflns         7221
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0462
_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^)+(0.0629P)^2^+4.2011P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1319
_reflns_Friedel_coverage         0
_reflns_number_gt                6629
_reflns_number_total             7221
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc04339a2.cif
_cod_data_source_block           2409ZnAOAPz
_cod_depositor_comments
'Adding full bibliography for 1572360--1572364.cif.'
_cod_database_code               1572364
_shelx_estimated_absorpt_t_min   0.567
_shelx_estimated_absorpt_t_max   0.939
_shelx_shelxl_version_number     2018/1
_shelx_res_checksum              60487