Aroplatin

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

MedKoo CAT#: 200280

CAS#: 114488-24-3

Description: Aroplatin is a synthetic liposomal formulation of bis-neodecanoate diaminocyclohexane platinum (NDDP), a third-generation platinum complex analogue of cisplatin, with potential antineoplastic activity. After displacement of the 2 long-chain aliphatic leaving groups (neodecanoic acid), platinum diaminocyclohexane (DACH) complexes become highly reactive and alkylate macromolecules, forming both inter- and intra-strand DNA crosslinks and inhibiting DNA synthesis, which results in tumor cell cytotoxicity. Because DNA mismatch-repair (MMR) complexes do not recognize DACH–platinum adducts, DNA repair mechanisms are inhibited, overcoming limitations observed with other platinum-based agents. In addition, the liposomal encapsulation improves the bioavailability of NDDP and reduces its toxicity profile.


Chemical Structure

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Aroplatin
CAS# 114488-24-3

Theoretical Analysis

MedKoo Cat#: 200280
Name: Aroplatin
CAS#: 114488-24-3
Chemical Formula: C26H52N2O4Pt
Exact Mass: 651.35748
Molecular Weight: 651.8
Elemental Analysis: C, 47.91; H, 8.04; N, 4.30; O, 9.82; Pt, 29.93

Size Price Shipping out time Quantity
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Pricing updated 2021-02-25. Prices are subject to change without notice.

Aroplatin, purity > 98%, is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.

Synonym: Aroplatin

IUPAC/Chemical Name: cyclohexane-1,2-diamine; 7,7-dimethyloctanoate; platinum(+2)

InChi Key: PZAQDVNYNJBUTM-UHFFFAOYSA-L

InChi Code: InChI=1S/2C10H20O2.C6H14N2.Pt/c2*1-10(2,3)8-6-4-5-7-9(11)12;7-5-3-1-2-4-6(5)8;/h2*4-8H2,1-3H3,(H,11,12);5-6H,1-4,7-8H2;/q;;;+2/p-2

SMILES Code: CC(C)(C)CCCCCC(O[Pt-2]1(OC(CCCCCC(C)(C)C)=O)[NH2+]C2C([NH2+]1)CCCC2)=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, not in water

Shelf Life:
>5 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

Handling Instructions:

Preparing Stock Solutions

The following data is based on the product molecular weight 651.8 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.

Select a batch to recalculate based on the batch molecular weight:
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

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2: Dragovich T, Mendelson D, Kurtin S, Richardson K, Von Hoff D, Hoos A. A Phase 2 trial of the liposomal DACH platinum L-NDDP in patients with therapy-refractory advanced colorectal cancer. Cancer Chemother Pharmacol. 2006 Dec;58(6):759-64. Epub 2006 May 23. PubMed PMID: 16847673.

3: Lu C, Perez-Soler R, Piperdi B, Walsh GL, Swisher SG, Smythe WR, Shin HJ, Ro JY, Feng L, Truong M, Yalamanchili A, Lopez-Berestein G, Hong WK, Khokhar AR, Shin DM. Phase II study of a liposome-entrapped cisplatin analog (L-NDDP) administered intrapleurally and pathologic response rates in patients with malignant pleural mesothelioma. J Clin Oncol. 2005 May 20;23(15):3495-501. PubMed PMID: 15908659.

4: Verschraegen CF, Kumagai S, Davidson R, Feig B, Mansfield P, Lee SJ, Maclean DS, Hu W, Khokhar AR, Siddik ZH. Phase I clinical and pharmacological study of intraperitoneal cis-bis-neodecanoato( trans- R, R-1, 2-diaminocyclohexane)-platinum II entrapped in multilamellar liposome vesicles. J Cancer Res Clin Oncol. 2003 Oct;129(10):549-55. Epub 2003 Aug 29. PubMed PMID: 14513369.

5: MacLean DS, Khokhar AR, Perez-Soler R. Neutron activation of NDDP, a liposomal platinum antitumor agent. Cancer Biother Radiopharm. 2000 Jun;15(3):253-9. PubMed PMID: 10941532.

6: Fox LE, Rosenthal RC, King RR, Levine PB, Vail DM, Helfand SC, MacEwen EG, Perez-Soler R, Calderwood-Mays M, Kurzman ID. Use of cis-bis-neodecanoato-trans-R,R-1,2-diaminocyclohexane platinum (II), a liposomal cisplatin analogue, in cats with oral squamous cell carcinoma. Am J Vet Res. 2000 Jul;61(7):791-5. PubMed PMID: 10895902.

7: Maclean DS, Khokhar AR, Tyle P, Perez-Soler R. Intraliposomal chemical activation patterns of liposomal cis-bis-neodecanoato-trans-R,R-1,2-diaminocyclohexane platinum (II) (L-NDDP)-a potential antitumour agent. J Microencapsul. 2000 May-Jun;17(3):307-22. PubMed PMID: 10819419.

8: Kelland LR. Meeting report on 8th International Symposium on Platinum and Other Metal Coordination Compounds in Cancer Chemotherapy. J Inorg Biochem. 1999 Oct;77(1-2):121-4. PubMed PMID: 10626364.

9: Fox LE, Toshach K, Calderwood-Mays M, Khokhar AR, Kubilis P, Perez-Soler R, MacEwen EG. Evaluation of toxicosis of liposome-encapsulated cis-bis-neodecanoato-trans-R,R-1,2-diaminocyclohexane platinum (II) in clinically normal cats. Am J Vet Res. 1999 Feb;60(2):257-63. PubMed PMID: 10048562.

10: Perez-Soler R, Shin DM, Siddik ZH, Murphy WK, Huber M, Lee SJ, Khokhar AR, Hong WK. Phase I clinical and pharmacological study of liposome-entrapped NDDP administered intrapleurally in patients with malignant pleural effusions. Clin Cancer Res. 1997 Mar;3(3):373-9. PubMed PMID: 9815694.

11: Han I, Khokhar AR, Perez-Soler R. Intraliposomal conversion of lipophilic cis-bis-carboxylato-trans-R,R-1,2-diaminocyclohexane-platinum (II) complexes into cis-bis-dichloro-trans-R,R-1,2-diaminocyclohexane-platinum (II). Cancer Chemother Pharmacol. 1996;39(1-2):17-24. PubMed PMID: 8995495.

12: Mori A, Wu SP, Han I, Khokhar AR, Perez-Soler R, Huang L. In vivo antitumor activity of cis-bis-neodecanoato-trans-R,R-1, 2-diaminocyclohexane platinum(II) formulated in long-circulating liposomes. Cancer Chemother Pharmacol. 1996;37(5):435-44. PubMed PMID: 8599866.

13: Li S, Khokhar AR, Perez-Soler R, Huang L. Improved antitumor activity of cis-Bis-neodecanoato-trans-R,R-1,2- diaminocyclohexaneplatinum (II) entrapped in long-circulating liposomes. Oncol Res. 1995;7(12):611-7. PubMed PMID: 8704278.

14: Han I, Ling YH, Khokhar AR, Perez-Soler R. Cell death and DNA fragmentation induced by liposomal platinum(II) complex, L-NDDP in A2780 and A2780/PDD cells. Anticancer Res. 1994 Mar-Apr;14(2A):421-6. PubMed PMID: 8017841.

15: Han I, Nguyen T, Yang LY, Khokhar AR, Perez-Soler R. Cellular accumulation and DNA damage induced by liposomal cis-bis-neodecanoato-trans-R,R-1,2-diaminocyclohexaneplatinum+ ++(II) in LoVo and LoVo/PDD cells. Anticancer Drugs. 1994 Feb;5(1):64-8. PubMed PMID: 8186432.

16: Perez-Soler R, Francis K, al-Baker S, Pilkiewicz F, Khokhar AR. Preparation and characterization of liposomes containing a lipophilic cisplatin derivative for clinical use. J Microencapsul. 1994 Jan-Feb;11(1):41-54. PubMed PMID: 8138874.

17: Han I, Ling YH, al-Baker S, Khokhar AR, Perez-Soler R. Cellular pharmacology of liposomal cis-bis-neodecanoato-trans-R,R-1,2-diaminocyclohexaneplatinum(II) in A2780/S and A2780/PDD cells. Cancer Res. 1993 Oct 15;53(20):4913-9. PubMed PMID: 8402681.

18: Christian MC. The current status of new platinum analogs. Semin Oncol. 1992 Dec;19(6):720-33. Review. PubMed PMID: 1462169.

19: Perez-Soler R, Khokhar AR. Lipophilic cisplatin analogues entrapped in liposomes: role of intraliposomal drug activation in biological activity. Cancer Res. 1992 Nov 15;52(22):6341-7. PubMed PMID: 1423280.

20: Khokhar AR, al-Baker S, Perez-Soler R. Toxicity and efficacy studies on a series of lipid-soluble dineodecanoato(trans-R,R- and trans-S,S-1,2-diaminocyclohexane) platinum (II) complexes entrapped in liposomes. Anticancer Drugs. 1992 Apr;3(2):95-100. PubMed PMID: 1525398.

21: Vadiei K, Siddik ZH, Khokhar AR, al-Baker S, Sampedro F, Perez-Soler R. Pharmacokinetics of liposome-entrapped cis-bis-neodecanoato-trans-R,R-1,2-diaminocyclohexane platinum(II) and cisplatin given i.v. and i.p. in the rat. Cancer Chemother Pharmacol. 1992;30(5):365-9. PubMed PMID: 1505075.

22: Sugarman SM, Perez-Soler R. Liposomes in the treatment of malignancy: a clinical perspective. Crit Rev Oncol Hematol. 1992;12(3):231-42. Review. PubMed PMID: 1497823.

23: Khokhar AR, al-Baker S, Brown T, Perez-Soler R. Chemical and biological studies on a series of lipid-soluble (trans-(R,R)- and -(S,S)-1,2-diaminocyclohexane)platinum(II) complexes incorporated in liposomes. J Med Chem. 1991 Jan;34(1):325-9. PubMed PMID: 1992134.

24: Perez-Soler R, Lopez-Berestein G, Lautersztain J, al-Baker S, Francis K, Macias-Kiger D, Raber MN, Khokhar AR. Phase I clinical and pharmacological study of liposome-entrapped cis-bis-neodecanoato-trans-R,R-1,2-diaminocyclohexane platinum(II). Cancer Res. 1990 Jul 15;50(14):4254-9. PubMed PMID: 2364384.

25: Perez-Soler R, Lautersztain J, Stephens LC, Wright K, Khokhar AR. Preclinical toxicity and pharmacology of liposome-entrapped cis-bis-neodecanoato-trans-R,R-1,2-diaminocyclohexane platinum(II). Cancer Chemother Pharmacol. 1989;24(1):1-8. PubMed PMID: 2720887.

26: Khokhar AR, al-Baker S, Krakoff IH, Perez-Soler R. Toxicity and antitumor activity of cis-bis-carboxylato(trans-R,R-1,2-diaminocyclohexane) platinum(II) complexes entrapped in liposomes. Cancer Chemother Pharmacol. 1989;23(4):219-24. PubMed PMID: 2647311.

27: Khokhar AR, Al-Baker S, Perez-Soler R. Toxicity and anti-tumor activity of hydrophobic diammine and diaminocyclohexane platinum complexes entrapped in multilamellar vesicles. Anticancer Drug Des. 1988 Dec;3(3):177-84. PubMed PMID: 3207465.

28: Perez-Soler R, Yang LY, Drewinko B, Lauterzstain J, Khokhar AR. Increased cytotoxicity and reversal of resistance to cis-diamminedichloro-platinum(II) with entrapment of cis-Bis-neodecanoato-trans-R,R-1,2-diaminocyclohexaneplatinum (II) in multilamellar lipid vesicles. Cancer Res. 1988 Aug 15;48(16):4509-12. PubMed PMID: 3396003.

29: Lautersztain J, Perez-Soler R, Turpin J, Khokhar AR, Siddik ZH, Schmidt K, Lopez-Berestein G. Cellular pharmacology of liposomal cis-bis-neodecanoato-trans-R,R-1,2-diaminocyclohexaneplatinum (II) in mouse resident peritoneal macrophages, Kupffer cells, and hepatocytes. Cancer Res. 1988 Mar 1;48(5):1300-6. PubMed PMID: 3342409.

30: Khokhar AR, Wright K, Siddik ZH, Perez-Soler R. Organ distribution and tumor uptake of liposome entrapped cis-bis-neodecanoato trans-R, R-1,2 diaminocyclohexane platinum (II) administered intravenously and into the proper hepatic artery. Cancer Chemother Pharmacol. 1988;22(3):223-7. PubMed PMID: 3409456.

31: Perez-Soler R, Khokhar AR, Lopez-Berestein G. Treatment and prophylaxis of experimental liver metastases of M5076 reticulosarcoma with cis-bis-neodecanoato-trans-R,R-1,2-diaminocyclohexaneplatinum (II) encapsulated in multilamellar vesicles. Cancer Res. 1987 Dec 15;47(24 Pt 1):6462-6. PubMed PMID: 3315188.

Aroplatin

10mg / Not available


Additional Information