Name: DBCO-(PEG2-Val-Cit-PAB)2
Brand: BOC Sciences
Rating: 5 (1 reviews)

IUPAC Name

Canonical SMILES

CC(C)C(C(=O)NC(CCCNC(=O)N)C(=O)NC1=CC=C(C=C1)CO)NC(=O)CCOCCOCCN(CCOCCOCCC(=O)NC(C(C)C)C(=O)NC(CCCNC(=O)N)C(=O)NC2=CC=C(C=C2)CO)C(=O)CCC(=O)N3CC4=CC=CC=C4C#CC5=CC=CC=C53

InChI

InChI=1S/C69H94N12O16/c1-46(2)62(66(90)76-55(14-9-31-72-68(70)92)64(88)74-53-23-17-48(44-82)18-24-53)78-58(84)29-35-94-39-41-96-37-33-80(60(86)27-28-61(87)81-43-52-13-6-5-11-50(52)21-22-51-12-7-8-16-57(51)81)34-38-97-42-40-95-36-30-59(85)79-63(47(3)4)67(91)77-56(15-10-32-73-69(71)93)65(89)75-54-25-19-49(45-83)20-26-54/h5-8,11-13,16-20,23-26,46-47,55-56,62-63,82-83H,9-10,14-15,27-45H2,1-4H3,(H,74,88)(H,75,89)(H,76,90)(H,77,91)(H,78,84)(H,79,85)(H3,70,72,92)(H3,71,73,93)/t55-,56-,62-,63-/m0/s1

InChIKey

OJIQRDAILYOKEI-MBSGQPJDSA-N

Solubility

10 mm in DMSO

Shelf Life

-20°C 3 years powder; -80°C 2 years in solvent

Shipping

-20°C (International: -20°C)

Storage

-20°C

DBCO-(PEG2-Val-Cit-PAB)2, a specialized chemical linker, plays a pivotal role in bioconjugation and drug delivery systems, particularly in the advancement of antibody-drug conjugates (ADCs). Here are four key applications of DBCO-(PEG2-Val-Cit-PAB)2:

Antibody-Drug Conjugates (ADCs): Positioned at the forefront of cancer therapy, this compound is indispensable for constructing ADCs that link potent cytotoxic drugs to specific antibodies targeting cancer cells. The PEG2 spacer adds bioavailability and flexibility, while the Val-Cit dipeptide responds to tumor-associated proteases to ensure drug release at the precise site. This meticulous delivery strategy heightens therapeutic efficacy and minimizes unintended impacts with surgical precision.

Bioconjugation: A cornerstone of bioconjugation endeavors, DBCO-(PEG2-Val-Cit-PAB)2 excels at labeling biomolecules such as proteins, peptides, and nucleic acids. The DBCO group interacts with azide-containing molecules through strain-promoted azide-alkyne cycloaddition (SPAAC), enabling efficient and enduring conjugation. This capability is crucial for crafting versatile bioconjugates utilized in diagnostics, imaging, and therapeutics across a diverse array of applications, pushing the boundaries of biotechnology.

Targeted Drug Delivery: Serving as a linchpin in the evolution of targeted drug delivery systems, this linker ensures the controlled release of therapeutic agents in response to specific triggers found in the tumor microenvironment. The PEG2-Val-Cit component guarantees stability during circulation and triggers drug release following enzymatic cleavage. Such precision drastically reduces systemic toxicity and amplifies the therapeutic potential of anticancer treatments.

Pharmaceutical Research: Within the intricate landscape of drug discovery and development, DBCO-(PEG2-Val-Cit-PAB)2 assumes a pivotal role in formulating dual-targeted or multifunctional drugs. Researchers leverage its capabilities to fuse disparate bioactive molecules, amalgamating therapeutic and diagnostic functionalities seamlessly. This adaptability cultivates the creation of cutting-edge therapies capable of diagnosing and treating diseases simultaneously, particularly within the dynamic realm of oncology.

1. Discovery of new ferroelectrics: [H2dbco]2 x [Cl3] x [CuCl3(H2O)2] x H2O (dbco = 1,4-Diaza-bicyclo[2.2.2]octane)

Wen Zhang, Heng-Yun Ye, Hong-Ling Cai, Jia-Zhen Ge, Ren-Gen Xiong, Songping D Huang J Am Chem Soc. 2010 Jun 2;132(21):7300-2.doi: 10.1021/ja102573h.

Compound [H(2)dbco](2) x [Cl(3)] x [CuCl(3)(H(2)O)(2)] x H(2)O undergoes a sharp dielectric anomaly and a paraelectric-to-ferroelectric phase transition at approximately -23 degrees C with a spontaneous polarization of 1.04 microC cm(-2), being the first molecular metal coordination compound ferroelectrics with a large dielectric response involving a 2 orders of magnitude enhancement and distinct Curie phase transition point. This work has proved an effective way for exploration of new ferroelectrics based on a five-coordinated divalent metal through the combination of crystal engineering and Landau phase transition theory.

2. Multi-antitumor therapy and synchronous imaging monitoring based on exosome

Ruijie Qian, Boping Jing, Dawei Jiang, Yongkang Gai, Ziyang Zhu, Xiaojuan Huang, Yu Gao, Xiaoli Lan, Rui An Eur J Nucl Med Mol Imaging. 2022 Jul;49(8):2668-2681.doi: 10.1007/s00259-022-05696-x.Epub 2022 Jan 29.

Background:Tumor-derived exosomes (TEX) have shown great potential for drug delivery and tumor targeting. Here, we developed a novel multi-drug loaded exosomes nanoprobe for combined antitumor chemotherapy and photodynamic therapy, and monitoring the drug delivery capabilities with pre-targeting technique.

3. Engineered DBCO+PD-1 Nanovesicles Carrying 1-MT for Cancer-Targeted Immunotherapy

Xichao Xu, Liang Liu, Huan Wang, Wenwen Li, Yigui Zou, Yinzhen Zeng, Qinghua Yang, Daming Bai, Dongling Dai ACS Biomater Sci Eng. 2022 Nov 14;8(11):4819-4826.doi: 10.1021/acsbiomaterials.2c00639.Epub 2022 Oct 7.

Liver cancer cells evade immune surveillance and anticancer response through various pathways, including the programmed death-ligand 1 (PD-L1)/programmed death-1 (PD-1) immune checkpoint axis that exhausts CD8+ T cells. Inhibitors or antibodies of the PD-L1/PD-1 signaling axis are considered promising drugs for cancer immunotherapy and exhibit favorable clinical responses. However, adverse effects, immune tolerance, and delivery barriers of most patients limit the clinical application of PD-L1/PD-1 antibodies. Thus, it is critical to develop a novel delivery strategy to enhance anticancer immunotherapy. In this study, we bioengineered cell membrane-derived nanovesicles (NVs) presenting PD-1 proteins and dibenzocyclooctyne (DBCO) to encapsulate 1-methyltryptophan (1-MT) (DBCO+PD-1@1-MT NVs). DBCO can specifically interact with N-azidoacetylmannosamine-tetraacetylate (Ac4ManN3) labeled onto metabolic cells for targeted killing of cancers. We next explored the effects of DBCO+PD-1@1-MT NVs on anticancer Hepa1-6 cells in vitro and in vivo. Results showed that PD-1@1-MT NVs dramatically inhibited Hepa1-6 proliferation, promoted peripheral blood mononuclear cell (PBMC) expansion, and strengthened anticancer therapy via blockading the PD-1/PD-L1 immune checkpoint axis, owing to the 1-methyltryptophan (1-MT) enhancement of anticancer immunotherapy efficacy through suppressing the activity of indoleamine 2,3-dioxygenase (IDO). Thus, 1-MT was encapsulated into PD-1 NVs to synergistically enhance cancer immunotherapy. Results have shown that PD-1@1-MT NVs obviously attenuated tumor growth, promoting IFN-γ production, increasing the T cells infiltration in tumors and spleens, and improving the survival period of tumor-bearing mice compared to monotherapy. Therefore, we propose a promising delivery strategy of the combination of DBCO+PD-1 NVs and 1-MT for specific and effective cancer-targeted immunotherapy.

Catalog	Product Name	CAS
BADC-01679	Mal-PEG2-Val-Cit-PABA-PNP	1345681-52-8
BADC-00929	Fmoc-D-Val-Cit-PAB	1350456-65-3
BADC-01448	mDPR-Val-Cit-PAB-MMAE	1491152-26-1
BADC-00968	MC-Val-Cit-PAB	159857-80-4
BADC-00501	Mc-Val-Cit-PABC-PNP	159857-81-5
BADC-00364	Fmoc-Val-Cit-PAB	159858-22-7
BADC-01745	MC-Val-Cit-PAB-NH-C2-NH-Boc	1616727-22-0
BADC-00610	Mc-Val-Cit-PAB-Cl	1639351-92-0
BADC-01470	MC-Val-Cit-PAB-dimethylDNA31	1639352-06-9
BADC-00611	MC-Val-Cit-PAB-clindamycin	1639793-13-7