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Sulfo-PDBA-DM4

  CAS No.: 1461704-01-7   Cat No.: BADC-00600 4.5  

Sulfo-PDBA-DM4 is a drug-linker conjugate composed of a potent a tubulin inhibitor DM4 and a linker Sulfo-PDBA to make antibody drug conjugate (ADC). Sulfo-PDBA is a gluthatione cleavable linker.

Sulfo-PDBA-DM4

Structure of 1461704-01-7

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Category
ADC Cytotoxin
Molecular Formula
C42H60ClN3O15S3
Molecular Weight
978.58
Shipping
Room temperature

* For research and manufacturing use only. We do not sell to patients.

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Popular Publications Citing BOC Sciences Products
Synonyms
Soravtansine; DM4-Sulfo-TBA; 4-[[5-[[(2S)-1-[[(1S,2R,3S,5S,6S,16E,18E,20R,21S)-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10,12,14(26),16,18-pentaen-6-yl]oxy]-1-oxopropan-2-yl]-methylamino]-2-methyl-5-oxopentan-2-yl]disulfanyl]-2-sulfobutanoic acid
IUPAC Name
4-[[5-[[(2S)-1-[[(1S,2R,3S,5S,6S,16E,18E,20R,21S)-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10,12,14(26),16,18-pentaen-6-yl]oxy]-1-oxopropan-2-yl]-methylamino]-2-methyl-5-oxopentan-2-yl]disulfanyl]-2-sulfobutanoic acid
Canonical SMILES
CC1C2CC(C(C=CC=C(CC3=CC(=C(C(=C3)OC)Cl)N(C(=O)CC(C4(C1O4)C)OC(=O)C(C)N(C)C(=O)CCC(C)(C)SSCCC(C(=O)O)S(=O)(=O)O)C)C)OC)(NC(=O)O2)O
InChI
InChI=1S/C42H60ClN3O15S3/c1-23-12-11-13-31(58-10)42(53)22-29(59-39(52)44-42)24(2)36-41(6,61-36)32(21-34(48)46(8)27-19-26(18-23)20-28(57-9)35(27)43)60-38(51)25(3)45(7)33(47)14-16-40(4,5)63-62-17-15-30(37(49)50)64(54,55)56/h11-13,19-20,24-25,29-32,36,53H,14-18,21-22H2,1-10H3,(H,44,52)(H,49,50)(H,54,55,56)/b13-11+,23-12+/t24-,25+,29+,30?,31-,32+,36+,41+,42+/m1/s1
InChIKey
GQSPYHXXAXFCRB-DSIKUUPMSA-N
Shipping
Room temperature
1.Effects of Drug-Antibody Ratio on Pharmacokinetics, Biodistribution, Efficacy, and Tolerability of Antibody-Maytansinoid Conjugates
Sun X, Ponte JF, Yoder NC, Laleau R, Coccia J, Lanieri L, Qiu Q, Wu R, Hong E, Bogalhas M, Wang L, Dong L, Setiady Y, Maloney EK, Ab O, Zhang X, Pinkas J, Keating TA, Chari R, Erickson HK, Lambert JM.
Antibody-drug conjugates (ADCs) are being actively pursued as a treatment option for cancer following the regulatory approval of brentuximab vedotin (Adcetris) and ado-trastuzumab emtansine (Kadcyla). ADCs consist of a cytotoxic agent conjugated to a targeting antibody through a linker. The two approved ADCs (and most ADCs now in the clinic that use a microtubule disrupting agent as the payload) are heterogeneous conjugates with an average drug-to-antibody ratio (DAR) of 3-4 (potentially ranging from 0 to 8 for individual species). Ado-trastuzumab emtansine employs DM1, a semisynthetic cytotoxic payload of the maytansinoid class, which is conjugated via lysine residues of the antibody to an average DAR of 3.5. To understand the effect of DAR on the preclinical properties of ADCs using maytansinoid cytotoxic agents, we prepared a series of conjugates with a cleavable linker (M9346A-sulfo-SPDB-DM4 targeting folate receptor α (FRα)) or an uncleavable linker (J2898A-SMCC-DM1 targeting the epidermal growth factor receptor (EGFR)) with varying DAR and evaluated their biochemical characteristics, in vivo stability, efficacy, and tolerability. For both formats, a series of ADCs with DARs ranging from low (average of ∼2 and range of 0-4) to very high (average of 10 and range of 7-14) were prepared in good yield with high monomer content and low levels of free cytotoxic agent. The in vitro potency consistently increased with increasing DAR at a constant antibody concentration. We then characterized the in vivo disposition of these ADCs. Pharmacokinetic analysis showed that conjugates with an average DAR below ∼6 had comparable clearance rates, but for those with an average DAR of ∼9-10, rapid clearance was observed. Biodistribution studies in mice showed that these 9-10 DAR ADCs rapidly accumulate in the liver, with maximum localization for this organ at 24-28% percentage injected dose per gram (%ID/g) compared with 7-10% for lower-DAR conjugates (all at 2-6 h post-injection). Our preclinical findings on tolerability and efficacy suggest that maytansinoid conjugates with DAR ranging from 2 to 6 have a better therapeutic index than conjugates with very high DAR (∼9-10). These very high DAR ADCs suffer from decreased efficacy, likely due to faster clearance. These results support the use of DAR 3-4 for maytansinoid ADCs but suggest that the exploration of lower or higher DAR may be warranted depending on the biology of the target antigen.

The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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