MC-GGFG-DX8951 - CAS 1600418-29-8

MC-GGFG-DX8951 - CAS 1600418-29-8 Catalog number: BADC-00608

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MC-GGFG-DX8951 is a DX8951 derivative with MC-GGFG linker, in which DX8951 was covalently connected via a peptidyl spacer (Gly-Gly-Phe-Gly), which is assumed to be stable in circulation, and were cleaved by lysosomal enzymes following ADC internalization into tumor tissue. MC-GGFG-DX8951 is very useful to prepare DX8951 antibody conjugate (ADC).

Category
ADCs Cytotoxin with Linkers
Product Name
MC-GGFG-DX8951
CAS
1600418-29-8
Catalog Number
BADC-00608
Molecular Formula
C49H51FN8O11
Molecular Weight
946.97
MC-GGFG-DX8951

Ordering Information

Catalog Number Size Price Quantity
BADC-00608 -- $-- Inquiry
Description
MC-GGFG-DX8951 is a DX8951 derivative with MC-GGFG linker, in which DX8951 was covalently connected via a peptidyl spacer (Gly-Gly-Phe-Gly), which is assumed to be stable in circulation, and were cleaved by lysosomal enzymes following ADC internalization into tumor tissue. MC-GGFG-DX8951 is very useful to prepare DX8951 antibody conjugate (ADC).
Synonyms
6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-N-(2-((2-(((S)-1-((2-(((1R,9S)-9-ethyl-5-fluoro-9-hydroxy-4-methyl-10,13-dioxo-2,3,9,10,13,15-hexahydro-1H,12H-benzo[de]pyrano[3',4':6,7]indolizino[1,2-b]quinolin-1-yl)amino)-2-oxoethyl)amino)-1-oxo-3-phenylpropan-2-yl)amino)-2-oxoethyl)amino)-2-oxoethyl)hexanamide; MC-GGFG-DX8951; MC-GGFG-DX-8951; MC-GGFG-DX 8951; MC-GGFG-DX.
IUPAC Name
6-(2,5-dioxopyrrol-1-yl)-N-[2-[[2-[[(2S)-1-[[2-[[(10S,23S)-10-ethyl-18-fluoro-10-hydroxy-19-methyl-5,9-dioxo-8-oxa-4,15-diazahexacyclo[14.7.1.02,14.04,13.06,11.020,24]tetracosa-1,6(11),12,14,16,18,20(24)-heptaen-23-yl]amino]-2-oxoethyl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-2-oxoethyl]amino]-2-oxoethyl]hexanamide
Canonical SMILES
O=C1[C@](O)(CC)C2=C(CO1)C(N3CC4=C5C6=C(CC[C@@H]5NC(CNC([C@H](CC7=CC=CC=C7)NC(CNC(CNC(CCCCCN8C(C=CC8=O)=O)=O)=O)=O)=O)=O)C(C)=C(F)C=C6N=C4C3=C2)=O
InChI
InChI=1S/C49H51FN8O11/c1-3-49(68)31-19-36-45-29(24-58(36)47(66)30(31)25-69-48(49)67)44-33(14-13-28-26(2)32(50)20-34(56-45)43(28)44)54-40(62)23-53-46(65)35(18-27-10-6-4-7-11-27)55-39(61)22-52-38(60)21-51-37(59)12-8-5-9-17-57-41(63)15-16-42(57)64/h4,6-7,10-11,15-16,19-20,33,35,68H,3,5,8-9,12-14,17-18,21-25H2,1-2H3,(H,51,59)(H,52,60)(H,53,65)(H,54,62)(H,55,61)/t33-,35+,49+/m1/s1
InChIKey
XEKFDUNPKACYAY-UAVZYSABSA-N
Shipping
Room temperature, or blue ice upon request.

MC-GGFG-DX8951 represents a novel advancement in the field of targeted cancer therapeutics, serving as a pivotal compound for the development of DX8951-based antibody-drug conjugates (ADCs). These conjugates are designed to selectively deliver the potent anticancer agent DX8951 directly to tumor cells. The use of a peptidyl spacer, specifically Gly-Gly-Phe-Gly, connects DX8951 covalently, ensuring that the drug remains stable during circulation, significantly reducing systemic toxicity. This stability is crucial for minimizing side-effects often associated with chemotherapy and improving patient quality of life

The mechanism of action for MC-GGFG-DX8951 begins with its incorporation into an ADC, which involves linking the drug to a monoclonal antibody that specifically targets antigens expressed on cancer cells. Once the ADC binds to the tumor cell surface, it undergoes internalization primarily through receptor-mediated endocytosis. Inside the tumor cells, the MC-GGFG linker is cleaved by lysosomal enzymes. This enzymatic cleavage is a critical step, releasing DX8951 in its active form directly within the lysosome, thereby achieving a more effective and targeted cytotoxic effect. This approach not only enhances the drug concentration at the tumor site but also mitigates adverse effects on healthy tissues

MC-GGFG-DX8951 is particularly valuable in the context of solid tumors where conventional therapies have limited efficacy. Its application in ADC technology allows for the personalization of cancer treatment, enabling therapies to be tailored based on the specific molecular profiles of tumors. This approach can lead to improved response rates and outcomes in patients who are resistant to standard chemotherapeutic agents. Furthermore, by leveraging the antigen-specific targeting capabilities of monoclonal antibodies, MC-GGFG-DX8951-based ADCs exhibit a higher specificity, reducing off-target effects and enhancing the therapeutic index

1.Novel antibody drug conjugates containing exatecan derivative-based cytotoxic payloads
Nakada T, Masuda T, Naito H, Yoshida M, Ashida S, Morita K, Miyazaki H, Kasuya Y, Ogitani Y, Yamaguchi J, Abe Y, Honda T
Trastuzumab conjugates consisting of exatecan derivatives were prepared and their biological activities and physicochemical properties were evaluated. The ADCs showed strong efficacy and a low aggregation rate. The exatecan derivatives were covalently connected via a peptidyl spacer (Gly-Gly-Phe-Gly), which is assumed to be stable in circulation, and were cleaved by lysosomal enzymes following ADC internalization into tumor tissue. These anti-HER2 ADCs exhibited a high potency, specifically against HER2-positive cancer cell lines in vitro. The ADCs, bearing exatecan derivatives which have more than two methylene chains, exhibited superior cytotoxicity. It was speculated that steric hindrance of the cleavable amide moiety could be involved in the drug release. The adequate alkyl lengths of exatecan derivatives (13, 14, 15) were from two to four in terms of aggregation rate. The ADC having a hydrophilic moiety showed good efficacy in a HER2-positive and Trastuzumab-resistant breast carcinoma cell model in mice.
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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