A repayment of principal is never deductible. Interest on the loan may be deductible, depending on what you used the proceeds for. If you purchased securities, the interest is treated as investment interest deductible as an itemized deduction to the extent of net investment income. If you used the proceeds to buy a principal residence or second home and you are not a key employee, you can usually obtain a full interest deduction if the loan is secured by the home. But if you used the proceeds for personal reasons (e.g., paying medical or college expenses), no interest deduction is allowed.
Increase in value of property due to market conditions. When you sell appreciated property, you pay tax on the appreciation since the date of purchase. When you donate appreciated property held long term, you may generally deduct the appreciated value.