Paclitaxel-SMCC
new
featured

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 407803

CAS#: Paclitaxel-SMCC

Description: Paclitaxel-SMCC is a paclitaxel derivative with a SMCC linker. (Succinimidyl-4-( N -maleimidomethyl)cyclohexane-1-carboxylate). Maleimide in Paclitaxel-SMCC can react with sulfhydryl groups at pH 6.5-7.5 to form a stable thioether bond. Paclitaxel-SMCC can be used to synthesize Paclitaxel bioconjugates with proteins, enzymes; antobodies, antigens, and other biopolymers. Paclitaxel-SMCC is often used for drug delivery research.

Chemical Structure

img
Paclitaxel-SMCC
CAS# Paclitaxel-SMCC
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 407803
Name: Paclitaxel-SMCC
CAS#: Paclitaxel-SMCC
Chemical Formula: C59H64N2O17
Exact Mass: 1,072.42
Molecular Weight: 1,073.158
Elemental Analysis: C, 66.03; H, 6.01; N, 2.61; O, 25.34

Price and Availability

Size Price Availability Quantity
1mg USD 90 Ready to ship
5mg USD 350 Ready to ship
10mg USD 550 Ready to ship
25mg USD 1250 Ready to ship
50mg USD 2250 Ready to ship
Bulk inquiry

Related CAS #: 186040-50-6 (ceribate)   33069-62-4 (free base)   263351-82-2 (Poliglumex)   Paclitaxel-SMCC   117527-50-1 (Paclitaxel-Succinic acid)   Paclitaxel-MVCP  

Synonym: Paclitaxel-SMCC; Paclitaxel with SMCC linker; Paclitaxel ADC conjugate.; SMCC-Taxol; SMCC taxol, Taxol-SMCC, Taxol SMCC;

IUPAC/Chemical Name: (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-9-(((2R,3S)-3-benzamido-2-((4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexane-1-carbonyl)oxy)-3-phenylpropanoyl)oxy)-12-(benzoyloxy)-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-3,4,4a,5,6,9,10,11,12,12a-decahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b(2aH)-diyl diacetate

InChi Key: INJXTVZVAWCWGH-YIDBHEPESA-N

InChi Code: InChI=1S/C59H64N2O17/c1-32-40(75-55(71)48(46(36-16-10-7-11-17-36)60-52(68)37-18-12-8-13-19-37)76-53(69)39-24-22-35(23-25-39)30-61-43(65)26-27-44(61)66)29-59(72)51(77-54(70)38-20-14-9-15-21-38)49-57(6,41(64)28-42-58(49,31-73-42)78-34(3)63)50(67)47(74-33(2)62)45(32)56(59,4)5/h7-21,26-27,35,39-42,46-49,51,64,72H,22-25,28-31H2,1-6H3,(H,60,68)/t35?,39?,40-,41-,42+,46-,47+,48+,49-,51-,57+,58-,59+/m0/s1

SMILES Code: CC1=C2[C@@H](OC(C)=O)C([C@]3(C)[C@@H](O)C[C@@H]4[C@](CO4)(OC(C)=O)[C@H]3[C@H](OC(C5=CC=CC=C5)=O)[C@@](C[C@@H]1OC([C@H](OC(C6CCC(CC6)CN7C(C=CC7=O)=O)=O)[C@@H](NC(C8=CC=CC=C8)=O)C9=CC=CC=C9)=O)(O)C2(C)C)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 1,073.16 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Zhai Q, Chen Y, Xu J, Huang Y, Sun J, Liu Y, Zhang X, Li S, Tang S. Lymphoma immunochemotherapy: targeted delivery of doxorubicin via a dual functional nanocarrier. Mol Pharm. 2017 Aug 29. doi: 10.1021/acs.molpharmaceut.7b00606. [Epub ahead of print] PubMed PMID: 28850241.

2: Eldar-Boock A, Blau R, Ryppa C, Baabur-Cohen H, Many A, Vicent MJ, Kratz F, Sanchis J, Satchi-Fainaro R. Integrin-targeted nano-sized polymeric systems for paclitaxel conjugation: a comparative study. J Drug Target. 2017 Aug 8:1-16. doi: 10.1080/1061186X.2017.1358727. [Epub ahead of print] PubMed PMID: 28737432.

3: Markovsky E, Vax E, Ben-Shushan D, Eldar-Boock A, Shukrun R, Yeini E, Barshack I, Caspi R, Harari-Steinberg O, Pode-Shakked N, Dekel B, Satchi-Fainaro R. WILMS TUMOR NCAM-EXPRESSING CANCER STEM CELLS AS POTENTIAL THERAPEUTIC TARGET FOR POLYMERIC NANOMEDICINE. Mol Cancer Ther. 2017 Jul 20. pii: molcanther.0184.2017. doi: 10.1158/1535-7163.MCT-17-0184. [Epub ahead of print] PubMed PMID: 28729402.

4: Weiss C, Figueras E, Borbely AN, Sewald N. Cryptophycins: cytotoxic cyclodepsipeptides with potential for tumor targeting. J Pept Sci. 2017 Jul;23(7-8):514-531. doi: 10.1002/psc.3015. Epub 2017 Jun 29. PubMed PMID: 28661555.

5: Han X, Dong X, Li J, Wang M, Luo L, Li Z, Lu X, He R, Xu R, Gong M. Free paclitaxel-loaded E-selectin binding peptide modified micelle self-assembled from hyaluronic acid-paclitaxel conjugate inhibit breast cancer metastasis in a murine model. Int J Pharm. 2017 Aug 7;528(1-2):33-46. doi: 10.1016/j.ijpharm.2017.05.063. Epub 2017 May 31. PubMed PMID: 28576551.

6: Dichwalkar T, Patel S, Bapat S, Pancholi P, Jasani N, Desai B, Yellepeddi VK, Sehdev V. Omega-3 Fatty Acid Grafted PAMAM-Paclitaxel Conjugate Exhibits Enhanced Anticancer Activity in Upper Gastrointestinal Cancer Cells. Macromol Biosci. 2017 Aug;17(8). doi: 10.1002/mabi.201600457. Epub 2017 May 9. PubMed PMID: 28485094.

7: Duan Z, Chen C, Qin J, Liu Q, Wang Q, Xu X, Wang J. Cell-penetrating peptide conjugates to enhance the antitumor effect of paclitaxel on drug-resistant lung cancer. Drug Deliv. 2017 Nov;24(1):752-764. doi: 10.1080/10717544.2017.1321060. PubMed PMID: 28468542.

8: Yasunaga M, Manabe S, Tsuji A, Furuta M, Ogata K, Koga Y, Fujiwara Y, Saga T, Matsumura Y. Development of ADCs Using Molecular Imaging. Yakugaku Zasshi. 2017;137(5):535-544. doi: 10.1248/yakushi.16-00255-3. Review. PubMed PMID: 28458285.

9: Zanella S, Angerani S, Pina A, López Rivas P, Giannini C, Panzeri S, Arosio D, Caruso M, Gasparri F, Fraietta I, Albanese C, Marsiglio A, Pignataro L, Belvisi L, Piarulli U, Gennari C. Tumor Targeting with an isoDGR-Drug Conjugate. Chemistry. 2017 Jun 12;23(33):7910-7914. doi: 10.1002/chem.201701844. Epub 2017 May 26. PubMed PMID: 28449309; PubMed Central PMCID: PMC5488297.

10: Alhalili Z, Shapter J, Auliya NH, Sandersonb B. Investigation of the pH Dependent Cytotoxicity of Paclitaxel Conjugated Gold Nanoparticles. Pharm Nanotechnol. 2017;5(2):111-118. doi: 10.2174/2211738505666170424121637. PubMed PMID: 28440201.

11: Makwana H, Mastrotto F, Magnusson JP, Sleep D, Hay J, Nicholls KJ, Allen S, Alexander C. Engineered Polymer-Transferrin Conjugates as Self-Assembling Targeted Drug Delivery Systems. Biomacromolecules. 2017 May 8;18(5):1532-1543. doi: 10.1021/acs.biomac.7b00101. Epub 2017 Apr 11. PubMed PMID: 28350442.

12: Willuda J, Linden L, Lerchen HG, Kopitz C, Stelte-Ludwig B, Pena C, Lange C, Golfier S, Kneip C, Carrigan PE, Mclean K, Schuhmacher J, von Ahsen O, Müller J, Dittmer F, Beier R, El Sheikh S, Tebbe J, Leder G, Apeler H, Jautelat R, Ziegelbauer K, Kreft B. Preclinical Antitumor Efficacy of BAY 1129980-a Novel Auristatin-Based Anti-C4.4A (LYPD3) Antibody-Drug Conjugate for the Treatment of Non-Small Cell Lung Cancer. Mol Cancer Ther. 2017 May;16(5):893-904. doi: 10.1158/1535-7163.MCT-16-0474. Epub 2017 Mar 14. PubMed PMID: 28292941.

13: Liang Y, Tian B, Zhang J, Li K, Wang L, Han J, Wu Z. Tumor-targeted polymeric nanostructured lipid carriers with precise ratiometric control over dual-drug loading for combination therapy in non-small-cell lung cancer. Int J Nanomedicine. 2017 Mar 2;12:1699-1715. doi: 10.2147/IJN.S121262. eCollection 2017. PubMed PMID: 28280336; PubMed Central PMCID: PMC5340246.

14: Gawde KA, Kesharwani P, Sau S, Sarkar FH, Padhye S, Kashaw SK, Iyer AK. Synthesis and characterization of folate decorated albumin bio-conjugate nanoparticles loaded with a synthetic curcumin difluorinated analogue. J Colloid Interface Sci. 2017 Jun 15;496:290-299. doi: 10.1016/j.jcis.2017.01.092. Epub 2017 Feb 14. PubMed PMID: 28236692.

15: Edelman R, Assaraf YG, Levitzky I, Shahar T, Livney YD. Hyaluronic acid-serum albumin conjugate-based nanoparticles for targeted cancer therapy. Oncotarget. 2017 Apr 11;8(15):24337-24353. doi: 10.18632/oncotarget.15363. PubMed PMID: 28212584; PubMed Central PMCID: PMC5421851.

16: He R, Yin C. Trimethyl chitosan based conjugates for oral and intravenous delivery of paclitaxel. Acta Biomater. 2017 Apr 15;53:355-366. doi: 10.1016/j.actbio.2017.02.012. Epub 2017 Feb 9. PubMed PMID: 28189812.

17: Markovsky E, Eldar-Boock A, Ben-Shushan D, Baabur-Cohen H, Yeini E, Pisarevsky E, Many A, Aviel-Ronen S, Barshack I, Satchi-Fainaro R. Targeting NCAM-expressing neuroblastoma with polymeric precision nanomedicine. J Control Release. 2017 Mar 10;249:162-172. doi: 10.1016/j.jconrel.2017.01.044. Epub 2017 Feb 1. PubMed PMID: 28159518.

18: Yang J, Zhang R, Pan H, Li Y, Fang Y, Zhang L, Kopeček J. Backbone Degradable N-(2-Hydroxypropyl)methacrylamide Copolymer Conjugates with Gemcitabine and Paclitaxel: Impact of Molecular Weight on Activity toward Human Ovarian Carcinoma Xenografts. Mol Pharm. 2017 May 1;14(5):1384-1394. doi: 10.1021/acs.molpharmaceut.6b01005. Epub 2017 Feb 3. PubMed PMID: 28094954.

19: Dong Y, Wang S, Wang C, Li Z, Ma Y, Liu G. Antagonizing NOD2 Signaling with Conjugates of Paclitaxel and Muramyl Dipeptide Derivatives Sensitizes Paclitaxel Therapy and Significantly Prevents Tumor Metastasis. J Med Chem. 2017 Feb 9;60(3):1219-1224. doi: 10.1021/acs.jmedchem.6b01704. Epub 2017 Jan 24. PubMed PMID: 28075581.

20: Ruttala HB, Ramasamy T, Shin BS, Choi HG, Yong CS, Kim JO. Layer-by-layer assembly of hierarchical nanoarchitectures to enhance the systemic performance of nanoparticle albumin-bound paclitaxel. Int J Pharm. 2017 Mar 15;519(1-2):11-21. doi: 10.1016/j.ijpharm.2017.01.011. Epub 2017 Jan 6. PubMed PMID: 28069389.