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CL2-SN-38

  CAS No.: 1036969-20-6   Cat No.: BADC-00847   Purity: >98% 4.5  

CL2-SN-38 is a cleavable linker-based antibody-drug conjugate (ADC) containing the topoisomerase I inhibitor SN-38 and a maleimidocaproyl linker.

CL2-SN-38

Structure of 1036969-20-6

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Category
ADC Cytotoxin
Molecular Formula
C82H106N12O23
Molecular Weight
1627.79
Shipping
-20°C (International: -20°C)
Shipping
-20°C

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

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Synonyms
Tert-Butyl N,N-bis(2-hydroxyethyl)carbamate
IUPAC Name
[4-[[(2S)-6-amino-2-[[(2S)-2-[[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[4-[[[4-[(2,5-dioxopyrrol-1-yl)methyl]cyclohexanecarbonyl]amino]methyl]triazol-1-yl]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethylamino]-2-oxoethoxy]acetyl]amino]-3-phenylpropanoyl]amino]hexanoyl]amino]phenyl]methyl [(19S)-10,19-diethyl-7-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaen-19-yl] carbonate
Canonical SMILES
CCC1=C2CN3C(=CC4=C(C3=O)COC(=O)C4(CC)OC(=O)OCC5=CC=C(C=C5)NC(=O)C(CCCCN)NC(=O)C(CC6=CC=CC=C6)NC(=O)COCC(=O)NCCOCCOCCOCCOCCOCCOCCOCCOCCN7C=C(N=N7)CNC(=O)C8CCC(CC8)CN9C(=O)C=CC9=O)C2=NC2=C1C=C(C=C2)O
InChI
InChI=1S/C82H106N12O23/c1-3-62-63-45-61(95)21-22-67(63)88-75-64(62)50-93-70(75)46-66-65(79(93)103)52-115-80(104)82(66,4-2)117-81(105)116-51-57-15-19-59(20-16-57)86-77(101)68(12-8-9-25-83)89-78(102)69(44-55-10-6-5-7-11-55)87-72(97)54-114-53-71(96)84-26-28-106-30-32-108-34-36-110-38-40-112-42-43-113-41-39-111-37-35-109-33-31-107-29-27-92-49-60(90-91-92)47-85-76(100)58-17-13-56(14-18-58)48-94-73(98)23-24-74(94)99/h5-7,10-11,15-16,19-24,45-46,49,56,58,68-69,95H,3-4,8-9,12-14,17-18,25-44,47-48,50-54,83H2,1-2H3,(H,84,96)(H,85,100)(H,86,101)(H,87,97)(H,89,102)/t56?,58?,68-,69-,82-/m0/s1
InChIKey
SSDFVXUQLUAHIC-DPMVZHECSA-N
Solubility
10 mm in DMSO
Shelf Life
2 years -20°C Powder, 2 weeks 4°C in DMSO, 6 months -80°C in DMSO
Shipping
-20°C (International: -20°C)
Storage
-20°C
In Vitro
Two SN-38 derivatives, CL2-SN-38 and CL2A-SN-38, were conjugated to the anti-Trop-2-humanized antibody, hRS7. The immunoconjugates were characterized in vitro for stability, binding, and cytotoxicity. The hRS7 conjugates of the two SN-38 derivatives were equivalent in drug substitution (~ 6), cell binding (K(d) ~ 1.2 nmol/L), cytotoxicity (IC(50) ~ 2.2 nmol/L), and serum stability in vitro (t/(½) ~ 20 hours). Exposure of cells to the ADC demonstrated signaling pathways leading to PARP cleavage, but differences versus free SN-38 in p53 and p21 upregulation were noted. Significant antitumor effects were produced by hRS7-SN-38 at nontoxic doses in mice bearing Calu-3 (P ≤0.05), Capan-1 (P <0.018), BxPC-3 (P < 0.005), and COLO 205 tumors (P < 0.033) when compared to nontargeting control ADCs. Mice tolerated a dose of 2 × 12 mg/kg (SN-38 equivalents) with only short-lived elevations in ALT and AST liver enzyme levels. Cynomolgus monkeys infused with 2 × 0.96 mg/kg exhibited only transient decreases in blood counts, although, importantly, the values did not fall below normal ranges.
Biological Activity
CL2-SN-38 is a part of the antibody drug conjugate (ADC), can conjugate with the anti-Trop-2-humanized antibody hRS7. SN-38 is a DNA topoisomerase I inhibitor. The anti-Trop-2 hRS7-CL2A-SN-38 ADC provides significant and specific antitumor effects against a range of human solid tumor types[1]

CL2-SN-38, a prodrug yielding the potent topoisomerase I inhibitor SN-38, finds diverse applications. Here are four key uses:

Anticancer Therapy: Utilized in treating various cancers, especially metastatic colorectal cancer, CL2-SN-38 undergoes conversion to SN-38 within the tumor microenvironment. This transformation enables selective targeting of cancer cells while sparing normal tissues, resulting in heightened antitumor efficacy coupled with diminished systemic toxicity.

Targeted Drug Delivery: Through conjugation with antibodies or nanoparticles, CL2-SN-38 achieves precise delivery to specific tumor sites, minimizing off-target effects and elevating the drug’s therapeutic index. Such targeted strategies not only enhance patient outcomes but also mitigate adverse side effects, revolutionizing the landscape of drug delivery systems.

Research Tool: Serving as a pivotal research tool in preclinical studies, CL2-SN-38 aids in deciphering the mechanisms of topoisomerase I inhibitors. Researchers leverage it to investigate drug resistance mechanisms and screen for potential combination therapies, offering critical insights for the advancement of more potent cancer treatments.

Pharmacokinetics Studies: Integral to drug development endeavors, CL2-SN-38 plays a crucial role in elucidating the pharmacokinetics and biodistribution of prodrugs. Through the examination of SN-38 release and activation, researchers can fine-tune dosing regimens and delivery methods, essential for optimizing therapeutic efficacy and minimizing toxicity in clinical settings.

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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Historical Records: MAC glucuronide phenol-linked SN-38 | MAC glucuronide α-hydroxy lactone-linked SN-38 | NH2-PEG4-VC-PAB-DMEA-SN38 | Cantuzumab mertansine | SC-VC-PAB-DM1 | SPDB-DM1 | DM1-SPP | Lys-SMCC-DM1 | Daunorubicin hydrochloride | MC-DM1 | CL2-SN-38
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