| Field | Specification |
|---|---|
| CAS no. | |
| Applications | |
| Molecular weight | |
| Molecular formula | C114H165ClN20O26 |
| Purity | |
| Activity | |
| SMILES | |
| Form | Solid |
| Storage | |
| Shipping | |
| Catalog no. (Mfr.) | |
| Main SKU |
Compound Overview
PSMA-Val-Cit-PAB-MMAE is a small-molecule conjugate that targets PSMA and carries monomethyl auristatin E (MMAE) as its cytotoxic payload. After binding PSMA, it is taken up into PSMA-expressing prostate cancer cells, where cathepsin B cleaves the Val-Cit linker to release active MMAE. The conjugate inhibits CYP3A4 activity (IC50 = 11.2 μM), generates intracellular ROS and oxidative stress, destabilizes microtubules to disrupt the cytoskeleton, and drives prostate cancer cell death, and it can be used in research related to prostate cancer[1]. It is supplied as a white to off-white solid (C114H165ClN20O26, MW 2267.10) at 99.52% purity.
Physical & Chemical Properties
| CAS Number | 2748039-79-2 |
|---|---|
| Molecular Formula | C114H165ClN20O26 |
| Molecular Weight | 2267.10 g/mol |
| Purity | 99.52% |
| Appearance | Solid |
| Color | White to off-white |
| SMILES | OC(CC[C@@H](C(O)=O)NC(N[C@@H](CCCCN(CC1=CC(Cl)=CC=C1)C(CCCCCNC(CCC(N[C@H](C(N[C@H](C(NCCCN2N=NC(CCCC(N[C@H](C(N[C@H](C(NC3=CC=C(C=C3)COC(N([C@H](C(N[C@@H](C(C)C)C(N([C@H]([C@@H](CC(N4CCC[C@]4([C@@H]([C@@H](C)C(N[C@@H]([C@H](C5=CC=CC=C5)O)C)=O)OC)[H])=O)OC)[C@@H](C)CC)C)=O)=O)C(C)C)C)=O)=O)CCCNC(N)=O)=O)C(C)C)=O)=C2)=O)CC6=CC=C(C=C6)O)=O)CC7=CC=CC=C7)=O)=O)=O)C(O)=O)=O)=O |
| Signaling Pathway | Cell Cycle/DNA Damage; Cytoskeleton; Metabolic Enzyme/Protease; Immunology/Inflammation; NF-κB |
| Bioactivity Class | Auristatin |
| Solubility | In Vitro: DMSO: 100 mg/mL (44.11 mM; Requires sonication; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO) |
| Storage | Powder: -20°C, 3 years; 4°C, 2 years. In solvent: -80°C, 6 months; -20°C, 1 month. |
| Shipping | Room temperature in continental US; may vary elsewhere. |
Literature Cited
Sources cited in this description and in the In Vitro & In Vivo Data tab. Peer-reviewed publications that used this product are listed under References.
Safety
For Research Use Only. Not for use in diagnostic or therapeutic procedures, and not for human or veterinary use. Handle in accordance with the Safety Data Sheet and your institution's chemical hygiene plan.
In Vitro
| Solvent | Solubility | Notes |
|---|---|---|
| DMSO | 100 mg/mL (44.11 mM) | requires sonication; use freshly opened DMSO (absorbed moisture lowers solubility) |
Aliquot the stock solution and store it at -80°C (up to 6 months) or -20°C (up to 1 month); avoid repeated freeze-thaw cycles.
Data provided by the manufacturer.
In Vitro
PSMA-Val-Cit-PAB-MMAE is cytotoxic at nanomolar levels in the human prostate cancer cell lines PSMA-expressing 22Rv1 and PSMA-null PC-3, giving CC50 values of 29 nM and 27 nM, in that order[1]. At its CC50 concentration (27-29 nM; 1 h), PSMA-Val-Cit-PAB-MMAE causes marked oxidative stress in 22Rv1 and PC-3 human prostate cancer cells, with intracellular hydrogen peroxide rising to twice and three times the control levels, in that order, after 1 h of incubation[1]. At its CC50 concentration (27-29 nM; up to 40 min), PSMA-Val-Cit-PAB-MMAE significantly lowers the stiffness of 22Rv1 human prostate cancer cells, whereas the stiffness of PC-3 human prostate cancer cells is unchanged over 40 minutes[1]. Recombinant cathepsin B efficiently cleaves PSMA-Val-Cit-PAB-MMAE (40 μM; up to 8 h) in a pH-dependent manner; hydrolysis is fastest at pH 3.6, while free MMAE release is highest at pH 5.6[1]. PSMA-Val-Cit-PAB-MMAE (1-10000 μg/mL) causes no gene mutations in Salmonella typhimurium strains TA98, TA97, or TA100, with or without metabolic activation, at concentrations reaching 10000 μg/mL[1].
In Vivo
In nude mice bearing PSMA-positive 22Rv1 prostate cancer xenografts, PSMA-Val-Cit-PAB-MMAE (0.3 mg/kg; i.v.; three times at five-day intervals) displays strong antitumor effects, achieving 77.4−84.5% tumor growth inhibition[1]. In nude mice bearing low-PSMA PC-3 prostate cancer xenografts, the same regimen of PSMA-Val-Cit-PAB-MMAE (0.3 mg/kg; i.v.; three times at five-day intervals) shows only weak antitumor activity, with a maximum of 37.7% tumor growth inhibition[1]. PSMA-Val-Cit-PAB-MMAE (0.3 mg/kg; i.p.; daily; 5 days) shows potent antitumor activity in nude mice carrying PSMA-positive 22Rv1 prostate cancer xenografts, with 70−85% tumor growth inhibition and 100% survival[1]. Tumor growth in DU145 prostate cancer xenografts in nude mice is inhibited by PSMA-Val-Cit-PAB-MMAE (0.2-0.4 mg/kg; i.p.; daily; 5 days)[1]. In healthy male ICR mice given a single intravenous injection, the median lethal dose of PSMA-Val-Cit-PAB-MMAE (2-60 mg/kg; i.v.; single dose) is 6.3 mg/kg, which gives a therapeutic index of 21[1]. In healthy male Wistar rats given a single intravenous injection, the median lethal dose of PSMA-Val-Cit-PAB-MMAE (1-30 mg/kg; i.v.; single dose) is 4.9 mg/kg[1]. In healthy male Wistar rats, PSMA-Val-Cit-PAB-MMAE (150-225 μg/kg; i.v.; once every three weeks; three months) produces moderate chronic toxicity, with testicular pathology that depends on dose, plus transient gastrointestinal effects at 225 μg/kg (the top dose tested); no animals die[1]. In healthy male Soviet Chinchilla rabbits, PSMA-Val-Cit-PAB-MMAE (81-122 μg/kg; i.v.; once every three weeks; three months) produces moderate chronic toxicity, with one death in the top dose group, effects on the immune system and pancreas, and testicular pathology in some animals[1]. With daily repeated intravenous injections in healthy male Wistar rats, PSMA-Val-Cit-PAB-MMAE (up to 14 mg/kg cumulative; i.v.; daily) shows no significant cumulative toxicity (cumulation index of 1.45), although mortality rises at higher cumulative doses[1].
| Animal Model | BALB/c nu/nu (male, 8−10 weeks old, 21−25 g, subcutaneous xenograft of 22Rv1 PSMA-positive human prostate carcinoma cells)[1] |
|---|---|
| Dosage | 0.3 mg/kg |
| Administration | i.v.; three times at five-day intervals |
| Result | Achieved tumor growth inhibition (TGI) ranging from 77.4−84.5% relative to the control group. Had no effect on the general condition or body weight of the mice. |
| Animal Model | BALB/c nu/nu (male, 8−10 weeks old, 21−25 g, subcutaneous xenograft of PC-3 low-PSMA human prostate adenocarcinoma cells)[1] |
|---|---|
| Dosage | 0.3 mg/kg |
| Administration | i.v.; three times at five-day intervals |
| Result | Achieved tumor growth inhibition (TGI) not exceeding 37.7% relative to the control group. Had no effect on the general condition or body weight of the mice. |
| Animal Model | Nude mice (male, subcutaneous xenograft of 22Rv1 PSMA-positive human prostate carcinoma cells)[1] |
|---|---|
| Dosage | 0.3 mg/kg |
| Administration | i.p.; daily; 5 days |
| Result | Maintained 100% mice survival during the experiment. Achieved tumor growth inhibition (TGI) ranging from 70−85% relative to the control group. |
| Animal Model | Nude mice (male, subcutaneous xenograft of DU145 human prostate cancer cells)[1] |
|---|---|
| Dosage | 0.2 mg/kg; 0.4 mg/kg |
| Administration | i.p.; daily; 5 days |
| Result | Reduced average tumor volume relative to the control group at both 0.2 mg/kg and 0.4 mg/kg. Inhibited tumor growth to levels comparable to low-dose docetaxel groups. |
| Animal Model | ICR (male, ~2 months old, 19−21 g)[1] |
|---|---|
| Dosage | 2 mg/kg; 3 mg/kg; 5 mg/kg; 6 mg/kg; 7 mg/kg; 8 mg/kg; 9 mg/kg; 30 mg/kg; 45 mg/kg; 60 mg/kg |
| Administration | i.v.; single dose |
| Result | Resulted in a median lethal dose (LD50) of 6.3 mg/kg. Produced a therapeutic index of 21, calculated as LD50/ED50. |
| Animal Model | Wistar (male, ~2 months old, 190−210 g)[1] |
|---|---|
| Dosage | 1 mg/kg; 2 mg/kg; 3 mg/kg; 4 mg/kg; 4.5 mg/kg; 5 mg/kg; 5.1 mg/kg; 5.4 mg/kg; 6 mg/kg; 8 mg/kg; 9 mg/kg; 15 mg/kg; 23 mg/kg; 30 mg/kg |
| Administration | i.v.; single dose |
| Result | Resulted in a median lethal dose (LD50) of 4.9 mg/kg. |
| Animal Model | Wistar (male, ~2 months old, 190−210 g)[1] |
|---|---|
| Dosage | 150 μg/kg; 188 μg/kg; 225 μg/kg |
| Administration | i.v.; once every three weeks; three months |
| Result | Ensured all rats survived to the end of the experiment. Caused externally visible signs of intoxication (diarrhea resolving within seven days post-injection) only in the 225 μg/kg group. Induced dose-dependent hypo- and aplasia of spermatogenesis in the testes. Resulted in body weight changes significantly different from controls only at the highest dose, with changes not constant. |
| Animal Model | Soviet Chinchilla (male, ~2 months old, 2.0−2.2 kg)[1] |
|---|---|
| Dosage | 81 μg/kg; 102 μg/kg; 122 μg/kg |
| Administration | i.v.; once every three weeks; three months |
| Result | Caused one death in the 122 μg/kg group after the second injection; all other rabbits survived. Induced decreased blood lymphocyte counts and increased glucose levels. Caused hypo- and aplasia of spermatogenesis in some animals, with no clear dose-dependence. Resulted in body weight changes significantly different from controls only at the highest dose, with changes not constant. |
Data provided by the manufacturer. Numbered citations refer to the Literature Cited list in the product description.
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